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Phenylbutazone

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Phenylbutazone
Skeletal formula
Ball-and-stick model
Clinical data
Trade namesButazolidine
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • 4-Butyl-1,2-diphenyl-pyrazolidine-3,5-dione
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.027 Edit this at Wikidata
Chemical and physical data
FormulaC19H20N2O2
Molar mass308.381 g·mol−1
3D model (JSmol)
  • O=C2N(c1ccccc1)N(C(=O)C2CCCC)c3ccccc3
  • InChI=1S/C19H20N2O2/c1-2-3-14-17-18(22)20(15-10-6-4-7-11-15)21(19(17)23)16-12-8-5-9-13-16/h4-13,17H,2-3,14H2,1H3 checkY
  • Key:VYMDGNCVAMGZFE-UHFFFAOYSA-N checkY
  (verify)

Phenylbutazone, often referred to as "bute",[1] is a nonsteroidal anti-inflammatory drug (NSAID) for the short-term treatment of pain and fever in animals.

In the United States and United Kingdom, it is no longer approved for human use (except in the United Kingdom for ankylosing spondylitis), as it can cause severe adverse effects such as suppression of white blood cell production and aplastic anemia. This drug was implicated in the 2013 meat adulteration scandal. Positive phenylbutazone tests in horse meat were uncommon in the UK, however.[2]

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Nonsteroidal anti-inflammatory drug

Nonsteroidal anti-inflammatory drug

Non-steroidal anti-inflammatory drugs (NSAID) are members of a therapeutic drug class which reduces pain, decreases inflammation, decreases fever, and prevents blood clots. Side effects depend on the specific drug, its dose and duration of use, but largely include an increased risk of gastrointestinal ulcers and bleeds, heart attack, and kidney disease.

Ankylosing spondylitis

Ankylosing spondylitis

Ankylosing spondylitis (AS) is a type of arthritis characterized by long-term inflammation of the joints of the spine typically where the spine joins the pelvis. Occasionally areas affected may include other joints such as the shoulders or hips. Eye and bowel problems may occur as well as back pain. Joint mobility in the affected areas generally worsens over time.

White blood cell

White blood cell

White blood cells, also called leukocytes or leucocytes, are the cells of the immune system that are involved in protecting the body against both infectious disease and foreign invaders. All white blood cells are produced and derived from multipotent cells in the bone marrow known as hematopoietic stem cells. Leukocytes are found throughout the body, including the blood and lymphatic system.

Aplastic anemia

Aplastic anemia

Aplastic anemia is a severe hematologic condition in which the body fails to make blood cells in sufficient numbers. Aplastic anemia is associated with cancer and various cancer syndromes. Blood cells are produced in the bone marrow by stem cells that reside there. Aplastic anemia causes a deficiency of all blood cell types: red blood cells, white blood cells, and platelets.

Uses

In humans

Phenylbutazone was originally made available for use in humans for the treatment of rheumatoid arthritis and gout in 1949. However, it is no longer approved, and therefore not marketed, for any human use in the United States.[3] In the UK it is used to treat ankylosing spondylitis, but only when other therapies are unsuitable.[4]

In horses

Phenylbutazone is the most commonly used NSAID for horses in the United States.[5] It is used for the following purposes:

History of phenylbutazone in racing

In the 1968 Kentucky Derby, Dancer's Image, the winner of the race, was disqualified after traces of phenylbutazone were allegedly discovered in a post-race urinalysis. Owned by prominent Massachusetts businessman Peter D. Fuller and ridden by jockey Bobby Ussery, Dancer's Image was the first horse to win the Kentucky Derby and then be disqualified. Phenylbutazone was legal on most tracks around the United States in 1968, but had not yet been approved by Churchill Downs.

Controversy and speculation still surround the incident. In the weeks prior to the race, Fuller had given previous winnings to Coretta Scott King, the widow of slain civil rights activist Martin Luther King Jr., which brought both praise and criticism. The previous year, King held a sit-in against housing discrimination which disrupted Derby week. Forty years later, Fuller still believed Dancer's Image was disqualified due to these events.[6][7]

Although Forward Pass had been named the winner, after many appeals the Kentucky Derby official website lists both Dancer's Image and Forward Pass as the winner. The website's race video commentary states that on the winner's plaque at Churchill Downs, both Dancer's Image and Forward Pass are listed as the 1968 winner of the Kentucky Derby.[8]

In dogs

Phenylbutazone is occasionally used in dogs for the longer-term management of chronic pain, particularly due to osteoarthritis. About 20% of adult dogs are affected with osteoarthritis, which makes the management of musculoskeletal pain a major component of companion animal practice. The margin of safety for all NSAIDs is narrow in the dog, and other NSAIDs are more commonly used (etodolac, and carprofen). Gastrointestinal-protectant drugs, such as misoprostol, cimetidine, omeprazole, ranitidine, or sucralfate, are frequently included as a part of treatment with any NSAID. Dogs receiving chronic phenylbutazone therapy should be followed with regular blood work and renal monitoring.[9]

Side effects of phenylbutazone in dogs include gastrointestinal (GI) ulceration, bone marrow depression, rashes, malaise, blood dyscrasias, and diminished renal blood flow.

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Gout

Gout

Gout is a form of inflammatory arthritis characterized by recurrent attacks of a red, tender, hot and swollen joint, caused by the deposition of needle-like crystals of uric acid known as monosodium urate crystals. Pain typically comes on rapidly, reaching maximal intensity in less than 12 hours. The joint at the base of the big toe is affected (Podagra) in about half of cases. It may also result in tophi, kidney stones, or kidney damage.

Ankylosing spondylitis

Ankylosing spondylitis

Ankylosing spondylitis (AS) is a type of arthritis characterized by long-term inflammation of the joints of the spine typically where the spine joins the pelvis. Occasionally areas affected may include other joints such as the shoulders or hips. Eye and bowel problems may occur as well as back pain. Joint mobility in the affected areas generally worsens over time.

Horse

Horse

The horse is a domesticated, one-toed, hoofed mammal. It belongs to the taxonomic family Equidae and is one of two extant subspecies of Equus ferus. The horse has evolved over the past 45 to 55 million years from a small multi-toed creature, Eohippus, into the large, single-toed animal of today. Humans began domesticating horses around 4000 BCE, and their domestication is believed to have been widespread by 3000 BCE. Horses in the subspecies caballus are domesticated, although some domesticated populations live in the wild as feral horses. These feral populations are not true wild horses, as this term is used to describe horses that have never been domesticated. There is an extensive, specialized vocabulary used to describe equine-related concepts, covering everything from anatomy to life stages, size, colors, markings, breeds, locomotion, and behavior.

Bowed tendon

Bowed tendon

Tendinitis/tendonitis is inflammation of a tendon, often involving torn collagen fibers. A bowed tendon is a horseman's term for a tendon after a horse has sustained an injury that causes swelling in one or more tendons creating a "bowed" appearance.

Arthralgia

Arthralgia

Arthralgia literally means joint pain. Specifically, arthralgia is a symptom of injury, infection, illness, or an allergic reaction to medication.

Arthritis

Arthritis

Arthritis is a term often used to mean any disorder that affects joints. Symptoms generally include joint pain and stiffness. Other symptoms may include redness, warmth, swelling, and decreased range of motion of the affected joints. In some types of arthritis, other organs are also affected. Onset can be gradual or sudden.

Laminitis

Laminitis

Laminitis is a disease that affects the feet of ungulates and is found mostly in horses and cattle. Clinical signs include foot tenderness progressing to inability to walk, increased digital pulses, and increased temperature in the hooves. Severe cases with outwardly visible clinical signs are known by the colloquial term founder, and progression of the disease will lead to perforation of the coffin bone through the sole of the hoof or being unable to stand up, requiring euthanasia.

Inflammation

Inflammation

Inflammation is part of the complex biological response of body tissues to harmful stimuli, such as pathogens, damaged cells, or irritants, and is a protective response involving immune cells, blood vessels, and molecular mediators. The function of inflammation is to eliminate the initial cause of cell injury, clear out necrotic cells and tissues damaged from the original insult and the inflammatory process, and initiate tissue repair.

Range of motion

Range of motion

Range of motion, is the linear or angular distance that a moving object may normally travel while properly attached to another. It is also called range of travel, particularly when talking about mechanical devices and in mechanical engineering fields. For example, a sound volume control knob.

Cure

Cure

A cure is a substance or procedure that ends a medical condition, such as a medication, a surgical operation, a change in lifestyle or even a philosophical mindset that helps end a person's sufferings; or the state of being healed, or cured. The medical condition could be a disease, mental illness, genetic disorder, or simply a condition a person considers socially undesirable, such as baldness or lack of breast tissue.

Colic

Colic

Colic or cholic is a form of pain that starts and stops abruptly. It occurs due to muscular contractions of a hollow tube in an attempt to relieve an obstruction by forcing content out. It may be accompanied by sweating and vomiting. Types include:Baby colic, a condition, usually in infants, characterized by incessant crying Biliary colic, blockage by a gallstone of the common bile duct or cystic duct Devon colic or painter's colic, an affliction caused by lead poisoning Horse colic, a potentially fatal condition experienced by horses, caused by intestinal displacement or blockage Renal colic, a pain in the flank, characteristic of kidney stones

Antipyretic

Antipyretic

An antipyretic is a substance that reduces fever. Antipyretics cause the hypothalamus to override a prostaglandin-induced increase in temperature. The body then works to lower the temperature, which results in a reduction in fever.

Dosage and administration in horses

Phenylbutazone has a plasma elimination half-life of 4–8 hours, however the inflammatory exudate half life is 24 hours,[10] so single daily dosing can be sufficient, although it is often used twice per day.[5] The drug is considered fairly non-toxic when given at appropriate doses (2.2-4.4 mg/kg/day), even when used repeatedly.[11] This dose has been doubled for diseases that cause severe pain, such as laminitis, but is toxic if repeated long-term, and exceptionally high doses (15 mg/kg/d or higher) can kill the animal in less than a week.[12]

Phenylbutazone can be administered orally (via paste, powder or feed-in) or intravenously. It should not be given intramuscularly or injected in any place other than a vein, as it can cause tissue damage. Tissue damage and edema may also occur if the drug is injected repetitively into the same vein.

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Biological half-life

Biological half-life

Biological half-life is the time taken for concentration of a biological substance to decrease from its maximum concentration (Cmax) to half of Cmax in the blood plasma, and is denoted by the abbreviation .

Exudate

Exudate

An exudate is a fluid emitted by an organism through pores or a wound, a process known as exuding or exudation. Exudate is derived from exude 'to ooze' from Latin exsūdāre 'to sweat'.

Laminitis

Laminitis

Laminitis is a disease that affects the feet of ungulates and is found mostly in horses and cattle. Clinical signs include foot tenderness progressing to inability to walk, increased digital pulses, and increased temperature in the hooves. Severe cases with outwardly visible clinical signs are known by the colloquial term founder, and progression of the disease will lead to perforation of the coffin bone through the sole of the hoof or being unable to stand up, requiring euthanasia.

Injection (medicine)

Injection (medicine)

An injection is the act of administering a liquid, especially a drug, into a person's body using a needle and a syringe. An injection is considered a form of parenteral drug administration; it does not involve absorption in the digestive tract. This allows the medication to be absorbed more rapidly and avoid the first pass effect. There are many types of injection, which are generally named after the body tissue the injection is administered into. This includes common injections such as subcutaneous, intramuscular, and intravenous injections, as well as less common injections such as intraperitoneal, intraosseous, intracardiac, intraarticular, and intracavernous injections.

Vein

Vein

Veins are blood vessels in the circulatory system of humans and most other animals that carry blood toward the heart. Most veins carry deoxygenated blood from the tissues back to the heart; exceptions are those of the pulmonary and fetal circulations which carry oxygenated blood to the heart. In the systemic circulation arteries carry oxygenated blood away from the heart, and veins return deoxygenated blood to the heart.

Edema

Edema

Edema, also spelled oedema, and also known as fluid retention, dropsy, hydropsy and swelling, is the build-up of fluid in the body's tissue. Most commonly, the legs or arms are affected. Symptoms may include skin which feels tight, the area may feel heavy, and joint stiffness. Other symptoms depend on the underlying cause.

Side effects and disadvantages

Side effects of phenylbutazone are similar to those of other NSAIDs. Overdose or prolonged use can cause gastrointestinal ulcers, blood dyscrasia, kidney damage (primarily dose-dependant renal papillary necrosis), oral lesions if given by mouth, and internal hemorrhage.[12] This is especially pronounced in young, ill, or stressed horses which are less able to metabolize the drug.[13] Effects of gastrointestinal damage include edema of the legs and belly secondary to leakage of blood proteins into the intestines, resulting in decreased appetite, excessive thirst, weight loss, weakness, and in advanced stages, kidney failure and death. Phenylbutazone can also cause agranulocytosis.

Phenylbutazone amplifies the anticoagulant effect of vitamin K antagonists such as warfarin or phenprocoumon. Phenylbutazone displaces warfarin from plasma binding sites, and toxic blood levels leading to haemorrhage can occur. It may aggravate kidney or liver problems.

Phenylbutazone may be toxic to the embryo and can be transferred via the umbilical cord and by milk.

Phenylbutazone can be used in foals. Premature foals, septicemic foals, foals with questionable kidney or liver function and foals with diarrhea require careful monitoring. Drugs to protect the GI tract such as omeprazole, cimetidine, and sucralfate are frequently used with phenylbutazone.

High doses of phenylbutazone may be considered a rules violation under some equestrian organizations, as the drug may remain in the bloodstream four to five days after administration.

The International Agency for Research on Cancer places it in Group 3; i.e., "not classifiable as to its carcinogenicity to humans".

Use in horses is limited to those not intended for food. Metabolites of phenylbutazone can cause aplastic anaemia in humans.[14][15]

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Equine gastric ulcer syndrome

Equine gastric ulcer syndrome

Equine gastric ulcer syndrome (EGUS) is a common cause of colic and decreased performance in horses. Horses form ulcers in the mucosa of the stomach, leading to pain, decreased appetite, weight loss, and behavioral changes. Treatment generally involves reducing acid production of the stomach and dietary management. Unlike some animals, however, stomach rupture is rare, and the main goal of treating is to reduce pain and improve performance of animals used for showing or racing.

Kidney

Kidney

The kidneys are two reddish-brown bean-shaped organs found in vertebrates. They are located on the left and right in the retroperitoneal space, and in adult humans are about 12 centimetres in length. They receive blood from the paired renal arteries; blood exits into the paired renal veins. Each kidney is attached to a ureter, a tube that carries excreted urine to the bladder.

Agranulocytosis

Agranulocytosis

Agranulocytosis, also known as agranulosis or granulopenia, is an acute condition involving a severe and dangerous lowered white blood cell count and thus causing a neutropenia in the circulating blood. It is a severe lack of one major class of infection-fighting white blood cells. People with this condition are at very high risk of serious infections due to their suppressed immune system.

Anticoagulant

Anticoagulant

Anticoagulants, commonly known as blood thinners, are chemical substances that prevent or reduce coagulation of blood, prolonging the clotting time. Some of them occur naturally in blood-eating animals such as leeches and mosquitoes, where they help keep the bite area unclotted long enough for the animal to obtain some blood. As a class of medications, anticoagulants are used in therapy for thrombotic disorders. Oral anticoagulants (OACs) are taken by many people in pill or tablet form, and various intravenous anticoagulant dosage forms are used in hospitals. Some anticoagulants are used in medical equipment, such as sample tubes, blood transfusion bags, heart–lung machines, and dialysis equipment. One of the first anticoagulants, warfarin, was initially approved as a rodenticide.

Phenprocoumon

Phenprocoumon

Phenprocoumon is a long-acting blood thinner drug to be taken by mouth, and a derivative of coumarin. It acts as a vitamin K antagonist and inhibits blood clotting (coagulation) by blocking synthesis of coagulation factors II, VII, IX and X. It is used for the prophylaxis and treatment of thromboembolic disorders such as heart attacks and pulmonary (lung) embolism. The most common adverse effect is bleeding. The drug interacts with a large number of other medications, including aspirin and St John's Wort. It is the standard coumarin used in Germany, Austria, and other European countries.

Embryo

Embryo

An embryo is an initial stage of development of a multicellular organism. In organisms that reproduce sexually, embryonic development is the part of the life cycle that begins just after fertilization of the female egg cell by the male sperm cell. The resulting fusion of these two cells produces a single-celled zygote that undergoes many cell divisions that produce cells known as blastomeres. The blastomeres are arranged as a solid ball that when reaching a certain size, called a morula, takes in fluid to create a cavity called a blastocoel. The structure is then termed a blastula, or a blastocyst in mammals.

Milk

Milk

Milk is a white liquid food produced by the mammary glands of mammals. It is the primary source of nutrition for young mammals before they are able to digest solid food. Immune factors and immune-modulating components in milk contribute to milk immunity. Early-lactation milk, which is called colostrum, contains antibodies that strengthen the immune system, and thus reduces the risk of many diseases. Milk contains many nutrients, including protein and lactose.

Sepsis

Sepsis

Sepsis, formerly known as septicemia or blood poisoning, is a life-threatening condition that arises when the body's response to infection causes injury to its own tissues and organs. This initial stage is followed by suppression of the immune system. Common signs and symptoms include fever, increased heart rate, increased breathing rate, and confusion. There may also be symptoms related to a specific infection, such as a cough with pneumonia, or painful urination with a kidney infection. The very young, old, and people with a weakened immune system may have no symptoms of a specific infection, and the body temperature may be low or normal instead of having a fever. Severe sepsis causes poor organ function or blood flow. The presence of low blood pressure, high blood lactate, or low urine output may suggest poor blood flow. Septic shock is low blood pressure due to sepsis that does not improve after fluid replacement.

Gastrointestinal tract

Gastrointestinal tract

The gastrointestinal tract is the tract or passageway of the digestive system that leads from the mouth to the anus. The GI tract contains all the major organs of the digestive system, in humans and other animals, including the esophagus, stomach, and intestines. Food taken in through the mouth is digested to extract nutrients and absorb energy, and the waste expelled at the anus as feces. Gastrointestinal is an adjective meaning of or pertaining to the stomach and intestines.

Equestrianism

Equestrianism

Equestrianism, commonly known as horse riding or horseback riding, includes the disciplines of riding, driving, and vaulting. This broad description includes the use of horses for practical working purposes, transportation, recreational activities, artistic or cultural exercises, and competitive sport.

International Agency for Research on Cancer

International Agency for Research on Cancer

The International Agency for Research on Cancer is an intergovernmental agency forming part of the World Health Organization of the United Nations. Its role is to conduct and coordinate research into the causes of cancer. It also collects and publishes surveillance data regarding the occurrence of cancer worldwide.

Carcinogen

Carcinogen

A carcinogen is any substance, radionuclide, or radiation that promotes carcinogenesis. This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes. Several radioactive substances are considered carcinogens, but their carcinogenic activity is attributed to the radiation, for example gamma rays and alpha particles, which they emit. Common examples of non-radioactive carcinogens are inhaled asbestos, certain dioxins, and tobacco smoke. Although the public generally associates carcinogenicity with synthetic chemicals, it is equally likely to arise from both natural and synthetic substances. Carcinogens are not necessarily immediately toxic; thus, their effect can be insidious.

Investigations into potential carcinogenicity

Opinions are conflicting regarding the carcinogenicity of phenylbutazone in animals; no evidence indicates it causes cancer in humans at therapeutic doses. Maekawa et al. (1987) found no increased cancer incidence in DONRYU rats fed a diet containing 0.125% or 0.25% phenylbutazone over two years.[16] On the other hand, Kari et al. (1995) found a rare type of kidney cancer in rats (13 of 100) and an increased rate of liver cancer in male rats fed 150 and 300 mg/kg body weight of phenylbutazone for two years.[17] Tennant (1993) listed phenylbutazone as a non-mutagenic carcinogen.[18] Kirkland and Fowler (2010) acknowledged that, while phenylbutazone is not predicted to be a mutagen by computer software that simulates the chemicals interaction with DNA,[19] one laboratory study indicated phenylbutazone subtly altered the structure of chromosomes of bone marrow cells of mice.[20] Kirkland and Fowler (2010) furthermore explained that the theoretical carcinogenic effects of phenylbutazone in humans cannot be studied because patients prescribed the drug were given doses far below the level any effect may become apparent (mM).[19] The World Health Organization's International Agency For Research On Cancer (IARC) stated in 1987 that there was inadequate evidence for a carcinogenic effect in humans.[21]

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Cancer

Cancer

Cancer is a group of diseases involving abnormal cell growth with the potential to invade or spread to other parts of the body. These contrast with benign tumors, which do not spread. Possible signs and symptoms include a lump, abnormal bleeding, prolonged cough, unexplained weight loss, and a change in bowel movements. While these symptoms may indicate cancer, they can also have other causes. Over 100 types of cancers affect humans.

Kidney

Kidney

The kidneys are two reddish-brown bean-shaped organs found in vertebrates. They are located on the left and right in the retroperitoneal space, and in adult humans are about 12 centimetres in length. They receive blood from the paired renal arteries; blood exits into the paired renal veins. Each kidney is attached to a ureter, a tube that carries excreted urine to the bladder.

Mutagen

Mutagen

In genetics, a mutagen is a physical or chemical agent that permanently changes genetic material, usually DNA, in an organism and thus increases the frequency of mutations above the natural background level. As many mutations can cause cancer in animals, such mutagens can therefore be carcinogens, although not all necessarily are. All mutagens have characteristic mutational signatures with some chemicals becoming mutagenic through cellular processes.

Chromosome

Chromosome

A chromosome is a long DNA molecule with part or all of the genetic material of an organism. In most chromosomes the very long thin DNA fibers are coated with packaging proteins; in eukaryotic cells the most important of these proteins are the histones. These proteins, aided by chaperone proteins, bind to and condense the DNA molecule to maintain its integrity. These chromosomes display a complex three-dimensional structure, which plays a significant role in transcriptional regulation.

Bone marrow

Bone marrow

Bone marrow is a semi-solid tissue found within the spongy portions of bones. In birds and mammals, bone marrow is the primary site of new blood cell production. It is composed of hematopoietic cells, marrow adipose tissue, and supportive stromal cells. In adult humans, bone marrow is primarily located in the ribs, vertebrae, sternum, and bones of the pelvis. Bone marrow comprises approximately 5% of total body mass in healthy adult humans, such that a man weighing 73 kg (161 lbs) will have around 3.7 kg (8 lbs) of bone marrow.

World Health Organization

World Health Organization

The World Health Organization (WHO) is a specialized agency of the United Nations responsible for international public health. Headquartered in Geneva, Switzerland, it has six regional offices and 150 field offices worldwide.

International Agency for Research on Cancer

International Agency for Research on Cancer

The International Agency for Research on Cancer is an intergovernmental agency forming part of the World Health Organization of the United Nations. Its role is to conduct and coordinate research into the causes of cancer. It also collects and publishes surveillance data regarding the occurrence of cancer worldwide.

Interactions

Other anti-inflammatory drugs that tend to cause GI ulcers, such as corticosteroids and other NSAIDs, can potentiate the bleeding risk. Combination with anticoagulant drugs, particularly coumarin derivatives, also increases the risk of bleeding. Avoid combining with other hepatotoxic drugs.

Phenylbutazone may affect blood levels and duration of action of phenytoin, valproic acid, sulfonamides, sulfonylurea antidiabetic agents, barbiturates, promethazine, rifampicin, chlorpheniramine, diphenhydramine, and penicillin G.[22]

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Phenytoin

Phenytoin

Phenytoin (PHT), sold under the brand name Dilantin among others, is an anti-seizure medication. It is useful for the prevention of tonic-clonic seizures and focal seizures, but not absence seizures. The intravenous form, fosphenytoin, is used for status epilepticus that does not improve with benzodiazepines. It may also be used for certain heart arrhythmias or neuropathic pain. It can be taken intravenously or by mouth. The intravenous form generally begins working within 30 minutes and is effective for roughly 24 hours. Blood levels can be measured to determine the proper dose.

Sulfonamide (medicine)

Sulfonamide (medicine)

Sulfonamide is a functional group that is the basis of several groups of drugs, which are called sulphonamides, sulfa drugs or sulpha drugs. The original antibacterial sulfonamides are synthetic (nonantibiotic) antimicrobial agents that contain the sulfonamide group. Some sulfonamides are also devoid of antibacterial activity, e.g., the anticonvulsant sultiame. The sulfonylureas and thiazide diuretics are newer drug groups based upon the antibacterial sulfonamides.

Sulfonylurea

Sulfonylurea

Sulfonylureas are a class of organic compounds used in medicine and agriculture, for example as antidiabetic drugs widely used in the management of diabetes mellitus type 2. They act by increasing insulin release from the beta cells in the pancreas. A number of sulfonylureas are also used as herbicides, because they can interfere with plant biosynthesis of certain amino acids. Sulfonylureas are also used experimentally to inhibit interleukin 1 beta release from the NALP3 inflammasome.

Barbiturate

Barbiturate

Barbiturates are a class of depressant drugs that are chemically derived from barbituric acid. They are effective when used medically as anxiolytics, hypnotics, and anticonvulsants, but have physical and psychological addiction potential as well as overdose potential among other possible adverse effects. They have been used recreationally for their anxiolytic and sedative effects, and are thus controlled in most countries due to the risks associated with such use.

Promethazine

Promethazine

Promethazine, sold under the brand name Phenergan among others, is a first-generation antihistamine, antipsychotic, sedative, and antiemetic used to treat allergies, insomnia, and nausea. It may also help with some symptoms associated with the common cold and may also be used for sedating people who are agitated or anxious, an effect that has led to some recreational use. Promethazine is taken by mouth, as a rectal suppository, or by injection into a muscle.

Rifampicin

Rifampicin

Rifampicin, also known as rifampin, is an ansamycin antibiotic used to treat several types of bacterial infections, including tuberculosis (TB), Mycobacterium avium complex, leprosy, and Legionnaires’ disease. It is almost always used together with other antibiotics with two notable exceptions: when given as a "preferred treatment that is strongly recommended" for latent TB infection; and when used as post-exposure prophylaxis to prevent Haemophilus influenzae type b and meningococcal disease in people who have been exposed to those bacteria. Before treating a person for a long period of time, measurements of liver enzymes and blood counts are recommended. Rifampicin may be given either by mouth or intravenously.

Diphenhydramine

Diphenhydramine

Diphenhydramine (DPH) is an antihistamine and sedative mainly used to treat allergies, insomnia, and symptoms of the common cold. It is also less commonly used for tremor in parkinsonism, and nausea. It is taken by mouth, injected into a vein, injected into a muscle, or applied to the skin. Maximal effect is typically around two hours after a dose, and effects can last for up to seven hours.

Overdose

Overdoses of phenylbutazone can cause kidney failure, liver injury, bone marrow suppression, and gastric ulceration or perforation. Early signs of toxicity include loss of appetite, and depression.[22]

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Kidney failure

Kidney failure

Kidney failure, also known as end-stage kidney disease, is a medical condition in which the kidneys can no longer adequately filter waste products from the blood, functioning at less than 15% of normal levels. Kidney failure is classified as either acute kidney failure, which develops rapidly and may resolve; and chronic kidney failure, which develops slowly and can often be irreversible. Symptoms may include leg swelling, feeling tired, vomiting, loss of appetite, and confusion. Complications of acute and chronic failure include uremia, high blood potassium, and volume overload. Complications of chronic failure also include heart disease, high blood pressure, and anemia.

Peptic ulcer disease

Peptic ulcer disease

Peptic ulcer disease (PUD) is a break in the inner lining of the stomach, the first part of the small intestine, or sometimes the lower esophagus. An ulcer in the stomach is called a gastric ulcer, while one in the first part of the intestines is a duodenal ulcer. The most common symptoms of a duodenal ulcer are waking at night with upper abdominal pain and upper abdominal pain that improves with eating. With a gastric ulcer, the pain may worsen with eating. The pain is often described as a burning or dull ache. Other symptoms include belching, vomiting, weight loss, or poor appetite. About a third of older people have no symptoms. Complications may include bleeding, perforation, and blockage of the stomach. Bleeding occurs in as many as 15% of cases.

Anorexia (symptom)

Anorexia (symptom)

Anorexia is a medical term for a loss of appetite. While the term outside of the scientific literature is often used interchangeably with anorexia nervosa, many possible causes exist for a loss of appetite, some of which may be harmless, while others indicate a serious clinical condition or pose a significant risk.

Depression (mood)

Depression (mood)

Depression is a mental state of low mood and aversion to activity. It affects more than 280 million people of all ages. Classified medically as a mental and behavioral disorder, the experience of depression affects a person's thoughts, behavior, motivation, feelings, and sense of well-being. The core symptom of depression is said to be anhedonia, which refers to loss of interest or a loss of feeling of pleasure in certain activities that usually bring joy to people. Depressed mood is a symptom of some mood disorders such as major depressive disorder and dysthymia; it is a normal temporary reaction to life events, such as the loss of a loved one; and it is also a symptom of some physical diseases and a side effect of some drugs and medical treatments. It may feature sadness, difficulty in thinking and concentration and a significant increase or decrease in appetite and time spent sleeping. People experiencing depression may have feelings of dejection, hopelessness and suicidal thoughts. It can either be short term or long term.

Chemistry

Phenylbutazone is a crystalline substance. It is obtained by condensation of diethyl n-butylmalonate with hydrazobenzene in the presence of base. In effect, this represents the formation of the heterocyclic system by simple lactamization.

Oxyphenbutazone, the major metabolite of phenylbutazone, differs only in the para location of one of its phenyl groups, where a hydrogen atom is replaced by a hydroxyl group (making it 4-butyl-1-(4-hydroxyphenyl)-2-phenyl-3,5-pyrazolidinedione).

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Crystal

Crystal

A crystal or crystalline solid is a solid material whose constituents are arranged in a highly ordered microscopic structure, forming a crystal lattice that extends in all directions. In addition, macroscopic single crystals are usually identifiable by their geometrical shape, consisting of flat faces with specific, characteristic orientations. The scientific study of crystals and crystal formation is known as crystallography. The process of crystal formation via mechanisms of crystal growth is called crystallization or solidification.

Chemical substance

Chemical substance

A chemical substance is a form of matter having constant chemical composition and characteristic properties. Some references add that chemical substance cannot be separated into its constituent elements by physical separation methods, i.e., without breaking chemical bonds. Chemical substances can be simple substances, chemical compounds, or alloys.

Hydrazobenzene

Hydrazobenzene

Hydrazobenzene (1,2-diphenylhydrazine) is an aromatic organic compound consisting of two aniline groups joined via their nitrogen atoms. It is an important industrial chemical used in the manufacture of dyes, pharmaceuticals, and hydrogen peroxide.

Oxyphenbutazone

Oxyphenbutazone

Oxyphenbutazone is a nonsteroidal anti-inflammatory drug (NSAID). It is a metabolite of phenylbutazone.

Metabolite

Metabolite

In biochemistry, a metabolite is an intermediate or end product of metabolism. The term is usually used for small molecules. Metabolites have various functions, including fuel, structure, signaling, stimulatory and inhibitory effects on enzymes, catalytic activity of their own, defense, and interactions with other organisms.

Phenyl group

Phenyl group

In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula C6H5, and is often represented by the symbol Ph. Phenyl group is closely related to benzene and can be viewed as a benzene ring, minus a hydrogen, which may be replaced by some other element or compound to serve as a functional group. Phenyl group has six carbon atoms bonded together in a hexagonal planar ring, five of which are bonded to individual hydrogen atoms, with the remaining carbon bonded to a substituent. Phenyl groups are commonplace in organic chemistry. Although often depicted with alternating double and single bonds, phenyl group is chemically aromatic and has equal bond lengths between carbon atoms in the ring.

Hydrogen

Hydrogen

Hydrogen is the chemical element with the symbol H and atomic number 1. Hydrogen is the lightest element. At standard conditions hydrogen is a gas of diatomic molecules having the formula H2. It is colorless, odorless, tasteless, non-toxic, and highly combustible. Hydrogen is the most abundant chemical substance in the universe, constituting roughly 75% of all normal matter. Stars such as the Sun are mainly composed of hydrogen in the plasma state. Most of the hydrogen on Earth exists in molecular forms such as water and organic compounds. For the most common isotope of hydrogen each atom has one proton, one electron, and no neutrons.

Atom

Atom

An atom is a particle that consists of a nucleus of protons and neutrons surrounded by a cloud of electrons. The atom is the basic particle of the chemical elements, and the chemical elements are distinguished from each other by the number of protons that are in their atoms. For example, any atom that contains 11 protons is sodium, and any atom that contains 29 protons is copper. The number of neutrons defines the isotope of the element.

Source: "Phenylbutazone", Wikipedia, Wikimedia Foundation, (2023, January 25th), https://en.wikipedia.org/wiki/Phenylbutazone.

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References
  1. ^ Bogdanich W, Drape J (24 March 2012). "Death and Disarray at America's Racetracks". The New York Times.
  2. ^ "Horse meat investigation. Advice for consumers". Enforcement and regulation. Food Standards Agency. Retrieved 19 May 2013.
  3. ^ "FDA Order Prohibits Extralabel Use of Phenylbutazone in Certain Dairy Cattle". Food and Drug Administration. 28 February 2003.
  4. ^ NHS: Drugs used in Rheumatic Diseases and Gout Archived 2013-04-29 at the Wayback Machine
  5. ^ a b McIlwraith CW, Frisbie DD, Kawcak CE. Nonsteroidal Anti-Inflammatory Drugs. Proc. AAEP 2001 (47): 182-187.
  6. ^ Boston Globe article about the 40th Anniversary of the Race
  7. ^ "Sports: Dancer's tainted image". Archived from the original on 2007-01-01. Retrieved 2007-10-07.
  8. ^ "Kentucky Derby 132". 2006. Retrieved 2007-10-07.
  9. ^ "Wedgewood Pharmaceuticals-Phenylbutazol".
  10. ^ Lees P, Taylor JB, Higgins AJ, Sharma SC (June 1986). "Phenylbutazone and oxyphenbutazone distribution into tissue fluids in the horse". Journal of Veterinary Pharmacology and Therapeutics. 9 (2): 204–12. doi:10.1111/j.1365-2885.1986.tb00031.x. PMID 3723663.
  11. ^ Collins LG, Tyler DE (March 1984). "Phenylbutazone toxicosis in the horse: a clinical study". Journal of the American Veterinary Medical Association. 184 (6): 699–703. PMID 6725103.
  12. ^ a b MacKay RJ, French TW, Nguyen HT, Mayhew IG (May 1983). "Effects of large doses of phenylbutazone administration to horses". American Journal of Veterinary Research. 44 (5): 774–80. PMID 6869982.
  13. ^ Lees P, Higgins AJ. Clinical pharmacology in therapeutic uses of non-steroidal anti-inflammatory drugs in the horse. Equine Vet J 1985;17:83–96.
  14. ^ Scanaill PÓ. "Phenylbutazone and its availability in ireland – prudent prescribing and dispensing" (PDF). Irish Veterinary Journal. 63 (12): 766–8. Archived from the original (PDF) on 2012-04-02.
  15. ^ "Ante and Post-mortem Procedures, Dispositions, Monitoring and Controls - Red Meat Species, Ostriches, Rheas and Emus". Canadian Food Inspection Agency. 2013-05-31.
  16. ^ Meakawa A, Onodera H, Tanigawa H, Furuta K, Kanno J, Matsuoka C, et al. (September 1987). "Long-term studies on carcinogenicity and promoting effect of phenylbutazone in DONRYU rats". Journal of the National Cancer Institute. 79 (3): 577–84. doi:10.1093/jnci/79.3.577. PMID 3476793.
  17. ^ Kari F, Bucher J, Haseman J, Eustis S, Huff J (March 1995). "Long-term exposure to the anti-inflammatory agent phenylbutazone induces kidney tumors in rats and liver tumors in mice". Japanese Journal of Cancer Research. 86 (3): 252–63. doi:10.1111/j.1349-7006.1995.tb03048.x. PMC 5920813. PMID 7744695.
  18. ^ Tennant RW (October 1993). "A perspective on nonmutagenic mechanisms in carcinogenesis". Environmental Health Perspectives. 101 Suppl 3 (Suppl 3): 231–6. doi:10.1289/ehp.93101s3231. PMC 1521175. PMID 8143623.
  19. ^ a b Kirkland D, Fowler P (November 2010). "Further analysis of Ames-negative rodent carcinogens that are only genotoxic in mammalian cells in vitro at concentrations exceeding 1 mM, including retesting of compounds of concern". Mutagenesis. 25 (6): 539–53. doi:10.1093/mutage/geq041. PMID 20720197.
  20. ^ Giri AK, Mukhopadhyay A (December 1998). "Mutagenicity assay in Salmonella and in vivo sister chromatid exchange in bone marrow cells of mice for four pyrazolone derivatives". Mutation Research. 420 (1–3): 15–25. doi:10.1016/S1383-5718(98)00138-7. PMID 9838026.
  21. ^ IARC (1987). IARC monographs on the evaluation of the carcinogenic risk of chemicals to man. International Agency for Research on Cancer. p. 316.
  22. ^ a b "Phenylbutazol for veterinary use". Wedgewood Pharmacy.

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