Phenylbutazone
Systematic (IUPAC) name
4-butyl-1,2-diphenyl-pyrazolidine-3,5-dione
Identifiers
CAS number	50-33-9
ATC code	M01AA01 M02AA01
PubChem	4781
DrugBank	APRD00409
Chemical data
Formula	C19H20N2O2
Mol. mass	308. IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs It is controlled by the WHO Collaborating Centre for Drug A section of the Anatomical Therapeutic Chemical Classification System. A section of the Anatomical Therapeutic Chemical Classification System. PubChem is a Database of chemical Molecules The system is maintained by the National Center for Biotechnology Information (NCBI a component The DrugBank database available at the University of Alberta is a unique Bioinformatics and Cheminformatics resource that combines detailed drug (i A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Carbon (kɑɹbən is a Chemical element with the symbol C and its Atomic number is 6 Hydrogen (ˈhaɪdrədʒən is the Chemical element with Atomic number 1 Nitrogen (ˈnaɪtɹəʤɪn is a Chemical element that has the symbol N and Atomic number 7 and Atomic weight 14 Oxygen (from the Greek roots ὀξύς (oxys (acid literally "sharp" from the taste of acids and -γενής (-genēs (producer literally begetteris the The molecular mass (abbreviated m of a substance, more commonly referred to as molecular weight and abbreviated as MW, is the Mass of one 374 g/mol
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status
Routes	?

Phenylbutazone, often referred to as bute, is a crystalline substance having the structure shown at right. In Pharmacology, bioavailability is used to describe the fraction of an administered Dose of unchanged drug that reaches the Systemic circulation, one of Drug metabolism is the Metabolism of drugs, their Biochemical modification or degradation usually through specialized enzymatic systems The biological half-life of a substance is the time it takes for a substance (drug radioactive nuclide or other to lose half of its pharmacologic physiologic or radiologic activity Excretion is the process of eliminating waste products of Metabolism and other non-useful materials The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical if it is used as directed by the mother during The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction In Pharmacology and Toxicology, a route In Materials science, a crystal is a Solid in which the constituent Atoms Molecules or Ions are packed in a regularly ordered repeating A chemical substance is a Material with a definite chemical composition. Chemical structure refers to Molecular geometry, Electronic structure and Crystal structure.

• Structural name: 4-butyl-1,2-diphenyl-3,5-pyrazolidinedione
• Chemical formula: C₁₉H₂₀N₂O₂

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). Oxyphenbutazone is a Metabolite of Phenylbutazone. Scrabble "Oxyphenbutazone" holds the title for the highest known theoretically possible Metabolomics is the "systematic study of the unique chemical fingerprints that specific cellular processes leave behind" - specifically the study of their small-molecule metabolite Arene substitution patterns are part of Organic chemistry IUPAC nomenclature and pinpoint the position of Substituents other than Hydrogen in In Organic chemistry, the phenyl group or phenyl ring (often abbreviated as -Ph) is the Functional group with the formula - Hydrogen (ˈhaɪdrədʒən is the Chemical element with Atomic number 1 History See also Atomic theory, Atomism The concept that matter is composed of discrete units and cannot be divided into arbitrarily tiny Hydroxyl in Chemistry stands for a molecule consisting of an Oxygen atom and a Hydrogen atom connected by a Covalent bond.

Despite its name, phenylbutazone is chemically unrelated to the class of chemicals known as benzones (common examples include oxybenzone, dioxybenzone, avobenzone, and sulisobenzone), which are used as active ingredients in sunscreen formulations for protection against UVB rays. Chemical classification systems attempt to classify elements or compounds according to certain chemical functional or structural properties A chemical substance is a Material with a definite chemical composition. Phenylbutazone, often referred to as bute, is a Crystalline substance having the structure shown at right Oxybenzone ( Trade names Eusolex 4360 Escalol 567 is an Organic compound used in Sunscreens It is a derivative of Benzophenone. Dioxybenzone is an Organic compound used in Sunscreen to block UVB It is a derivative of Benzophenone. Avobenzone ( Trade names Parsol 1789, Eusolex 9020, Escalol 517 and others INCI Butyl Methoxydibenzoylmethane is an oil soluble Sunscreen (also known as sunblock or suntan lotion) is a Lotion, spray or other Topical product that absorbs or reflects the Sun 's Ultraviolet ( UV) light is Electromagnetic radiation with a Wavelength shorter than that of Visible light, but longer than X-rays

Phenylbutazone is used as a non-steroidal anti-inflammatory drug (NSAID) for the treatment of chronic pain, including the symptoms of arthritis. Non-steroidal anti-inflammatory drugs, usually abbreviated to NSAID s or NAID s, are drugs with Analgesic, Antipyretic and in higher Chronic pain is defined as Pain that persists longer than the temporal course of natural healing associated with a particular type of injury or disease process Arthritis (from Greek arthro-, joint + -itis, inflammation plural arthritides is a group of conditions involving damage to the Joints of the body Its use is limited by such severe side effects as suppression of white blood cell production and aplastic anemia. Side Effect were an influential Disco band that recorded between 1972 and 1995

The International Agency for Research on Cancer (IARC) places it in Group 3; i. The International Agency for Research on Cancer ( IARC, or CIRC in its French Acronym) is an intergovernmental agency forming part of the World Health e. , "not classifiable as to its carcinogenicity to humans. The term carcinogen refers to any substance Radionuclide or radiation that is an agent directly involved in the promotion of Cancer or in the fatation of its propagation "

Contents 1 Uses of phenylbutazone in horses 1.1 Dosage and administration 1.2 Side effects and disadvantages of phenylbutazone 1.3 History of phenylbutazone in racing 2 References 3 External links

Uses of phenylbutazone in horses

Phenylbutazone is an NSAID commonly used in horses for the following purposes:

• Analgesia: Pain relief from infections and musculoskeletal disorders including sprains, overuse injuries, tendinitis, arthralgias, arthritis, and laminitis. Non-steroidal anti-inflammatory drugs, usually abbreviated to NSAID s or NAID s, are drugs with Analgesic, Antipyretic and in higher The horse ( Equus caballus) is a hoofed ( Ungulate) Mammal, one of eight living species of the family Equidae. An infection is the detrimental Colonization of a host Organism by a foreign Species. Musculoskeletal disorders (MSDs can affect the body's Muscles Joints Tendons Ligaments and Nerves Most work-related MSDs develop over A sprain (from the French espraindre - to wring is an Injury which occurs to Ligaments caused by a sudden overtearing (for the Muscle Tendinitis /tendonitis is Inflammation of a Tendon. Many times the tendon tissue is torn Arthralgia (from Greek arthro-, joint + -algos, pain literally means joint pain; it is a symptom of injury infection illnesses -- in particular Arthritis (from Greek arthro-, joint + -itis, inflammation plural arthritides is a group of conditions involving damage to the Joints of the body Laminitis is a disease of the digital Laminae of the Hoof ( Foot of an Ungulate) Like other NSAIDs, acts directly on musculoskeletal tissue to control inflammation, thereby reducing secondary inflammatory damage, alleviating pain, and restoring range of motion. The musculoskeletal system (also known as the locomotor system is an organ system that gives Animals the ability to physically move using the Muscles and Tissue is a cellular organizational level intermediate between cells and a complete organism Inflammation ( Latin, inflamatio, to set on fire is the complex biological response of vascular tissues to harmful stimuli such as Pathogens Range of motion or ( ROM) as used in the Biomedical and Weightlifting communities is the measurement of the achievable distance between the flexed position Does not cure musculoskeletal ailments or work well on colic pain. A cure is a substance or procedure that makes a sick or diseased person well "Cholic" redirects here For cholic acid see Cholic acid.
• Antipyresis: Reduction of fevers. Antipyretics are Drugs that reduce body temperature in situations such as Fever. Antipyretic qualities may mask other symptoms; therefore, should not be administered for this purpose unless a veterinarian has concluded that the horse would not be able to eat or drink without its use or that the fever might hinder the horse's recovery. A symptom' (from Greek σύμπτωμα, "accident misfortune that which befalls" from συμπίπτω, "I befall" from A veterinarian ( American English) or a Veterinary surgeon ( British English) often shortened to vet, is a Physician

Dosage and administration

Phenylbutazone may be administered orally (via paste, powder or feed-in) or intravenously. Intravenous therapy or IV therapy is the giving of Liquid substances directly into a Vein. It should not be given intramuscularly or injected in any place other than a vein, as it can cause tissue damage. Intramuscular injection is the injection of a substance directly into a Muscle. In the Circulatory system, a vein is a Blood vessel that carries Blood back toward the Heart (as opposed to Artery, a blood vessel Tissue damage and edema may also occur if the drug is injected repetitively into the same vein. Oedema (or Edema in American English formerly known as dropsy or hydropsy, is the increase of Interstitial fluid in any organ &mdash swelling

The maximum oral dose recommended by manufacturers is 2 to 4 grams per 1000 pounds of body weight (4 to 9 mg/kg) per day. Manufacturers recommend that the dose be divided equally and given every 8 hours for maximum results, although most horse owners give it every 12 to 24 hours for convenience, usually giving 1 to 2 grams in the morning and at night.

Intravenously, the maximum daily dose recommended by manufacturers is 1 to 2 grams per 1000 pounds (2 to 4. 5 mg/kg). The maximum dose is usually given when the course of treatment is initiated, with the dosage subsequently being titrated down.

Phenylbutazone should be administered only under the advice of a veterinarian.

Side effects and disadvantages of phenylbutazone

Side effects of phenylbutazone are similar to that of other NSAIDs. Overdose or prolonged use can cause gastrointestinal ulcers, blood dyscrasia, kidney damage, oral lesions, and internal hemorrhage, especially pronounced in young, ill, or stressed horses. Ulcers are healing wounds that develop on the skin mucous membranes or eye Dyscrasia, is a concept from Ancient Greek Medicine with the word "dyskrasia" meaning bad mixture The kidneys are complicated organs that have numerous biological roles Bleeding, technically known as hemorrhaging / haemorrhaging (see American and British spelling differences) is the loss of Blood from 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 is obtained in straight forward manner 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

Phenylbutazone should not be used in combination with blood thinners (e. A lactam (the noun is a Portmanteau of the words Lactone + Amide) is a cyclic Amide. g. , Coumadin), as it amplifies the anticoagulant effects of these drugs; with other NSAIDs (all NSAIDs are additive); or in horses with known kidney or liver problems. Warfarin (also known under the brand names Coumadin, Jantoven, Marevan, and Waran) is an Anticoagulant. An anticoagulant is a substance that prevents coagulation; that is it stops Blood from clotting

Periodic blood tests are recommended when using phenylbutazone as Agranulocytosis can occur. Agranulocytosis is an acute condition involving a severe and dangerous Leukopenia particularly of neutrophils causing a Neutropenia in the circulating blood Periodically testing the blood may catch this issue before it is too late.

Phenylbutazone should be used cautiously in pregnant or nursing mares, as it may be toxic to the embryo and can be transferred via the umbilical cord and by milk. Pregnancy ( Latin graviditas) is the carrying of one or more offspring known as a Fetus or Embryo, inside the Uterus of a Female Nursing is a Profession focused on assisting individuals families, and communities in attaining maintaining and recovering optimal Health Toxicity is the degree to which a substance is able to damage an exposed organism An embryo (from Greek:, plural, lit "that which grows" from en- "in" + bryein "to swell be full" is a multicellular In placental Mammals the umbilical cord (also called the birth cord or funiculus umbilicalis) is the connecting cord from the developing Embryo Milk is an opaque white liquid produced by the Mammary glands of female Mammals (including Monotremes.

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. For the Roman class see Equestrian (Roman Equestrianism refers to the skill of riding or driving Horses This broad description This is an article about the rock music band "Circulatory System"

In humans, Phenylbutazone is very dangerous, as it can cause aplastic anemia. The medicine should be given in a paste form to avoid contact with the medicine. Never breathe powder from crushing tablets.

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 discovered in a post-race urinalysis. Year 1968 ( MCMLXVIII) was a Leap year starting on Monday (link will display full calendar of the Gregorian calendar. The Kentucky Derby is a Grade I stakes race for three year-old thoroughbred horses held annually in Louisville Kentucky, on the first Saturday in May Dancer's Image (1965-1992 an American Thoroughbred racehorse who is the only winner in the history of the Kentucky Derby to have been disqualified A urinalysis (or "UA" is an array of tests performed on Urine and one of the most common methods of Medical Diagnosis. Owned by prominent Massachusetts businessman Peter Fuller and jockeyed by Bobby Ussery, Dancer's Image remains the only horse in history to win the Kentucky Derby and then be disqualified. The Commonwealth of Massachusetts ( is a state located in the New England region of the northeastern United States. Peter Michael Fuller (born 31st August 1947 in Damascus, Syria &mdash 1990 was a British art critic and magazine editor who was educated at Epsom College In Sport, a jockey is one who rides Horses in Horse racing or steeplechase racing primarily as a profession Robert N "Bobby" Ussery (born 1935 in Vian Oklahoma) is an American Thoroughbred Horse racing Hall of Fame Jockey. Phenylbutazone was legal on most tracks around the country in 1968 but had not yet been approved by Churchill Downs. History The track is named for John and Henry Churchill who leased 80 acres (320000 m² of land to their nephew Colonel Meriwether Lewis Clark Jr Also, in the weeks prior to the race Peter Fuller had given his purse to Coretta Scott King, the widow of slain Civil Rights activist Martin Luther King Jr., an act that brought him both praise from Civil Rights supporters and criticism from racists. Coretta Scott King (April 27 1927 January 30 2006 was an American Author and Activist, perhaps most recognized as the wife of Martin WIDOW is a full-length Album recorded by British rock band Ritual released in 1983 Martin Luther King Jr ( January 15, 1929 April 4, 1968) was an American clergyman, Activist and prominent leader List of racism-related topics|Racism by country Racism, by its simplest definition is the belief that race is the primary determinant of human traits and capacities and that Martin Luther King Jr. had helped plan a sit-in on the Kentucky Derby the year before but did not allow it to proceed. A sit-in or sit-down is a form of direct action that involves one or more persons nonviolently occupying an area for a Protest, often to promote political social ^[1]

Controversy and speculation still surrounds the incident. Although after many appeals, Forward Pass was named the winner, the Kentucky Derby official website lists both Dancer's Image and Forward Pass as the winner. In several forms of Football a forward pass is when the ball is thrown in the direction of the opponent's end line 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. History The track is named for John and Henry Churchill who leased 80 acres (320000 m² of land to their nephew Colonel Meriwether Lewis Clark Jr ^[2]

References

External links

• IARC monograph on carcinogenicity of phenylbutazone
• Phenylbutazone For Veterinary Use
• Resource on Equine Joint Health

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