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Encyclopedia > Indometacin
Indometacin
Systematic (IUPAC) name
1-(4-chlorobenzoyl)-5-methoxy-
2-methyl-1-H-indole-3-acetic acid
Identifiers
CAS number 53-86-1
ATC code C01EB03 M01AB01, M02AA23, S01BC01
PubChem 3715
DrugBank APRD00109
Chemical data
Formula C19H16ClNO4 
Mol. mass 357.79 g.mol-1
Pharmacokinetic data
Bioavailability ~100% (oral), 80–90% (rectal)
Protein binding 99%
Metabolism Hepatic
Half life 4.5 hours
Excretion Renal 60%, faecal 33%
Therapeutic considerations
Pregnancy cat.

C (Au), C/D (US) Image File history File links This is a lossless scalable vector image. ... 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. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A section of the Anatomical Therapeutic Chemical Classification System. ... A section of the Anatomical Therapeutic Chemical Classification System. ... 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 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 concise way of expressing information about the atoms that constitute a particular chemical compound. ... For other uses, see Carbon (disambiguation). ... This article is about the chemistry of hydrogen. ... General Name, symbol, number chlorine, Cl, 17 Chemical series halogens Group, period, block 17, 3, p Appearance yellowish green Standard atomic weight 35. ... General Name, symbol, number nitrogen, N, 7 Chemical series nonmetals Group, period, block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... General Name, symbol, number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, period, block 16, 2, p Appearance colorless (gas) pale blue (liquid) Standard atomic weight 15. ... The molecular mass (abbreviated Mr) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... A drugs efficacy may be affected by the degree to which it binds to the proteins within blood plasma. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... The liver is an organ in vertebrates including humans. ... The biological half-life of a substance is the time required for half of that substance to be removed from an organism by either a physical or a chemical process. ... The kidneys are important excretory organs in vertebrates. ... Kidneys viewed from behind with spine removed The kidneys are bean-shaped excretory organs in vertebrates. ... Horse feces Feces, faeces, or fæces (see spelling differences) is a waste product from an animals digestive tract expelled through the anus (or cloaca) during defecation. ... 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 pregnancy. ... For other uses, see Australia (disambiguation). ...

Legal status

Prescription only The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ...

Routes Oral, rectal, IV, topical

Indometacin (INN) or Indomethacin (USAN and former BAN) is a non-steroidal anti-inflammatory drug commonly used to reduce fever, pain, stiffness, and swelling. It works by inhibiting the production of prostaglandins, molecules known to cause these symptoms. It is marketed under many trade names, including Indocin, Indocid, Indochron E-R, and Indocin-SR. In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body. ... Four 500mg acetaminophen/paracetamol suppositories A suppository is a medicine that is inserted either into the rectum (rectal suppository) or into the vagina (vaginal suppository) where it melts. ... An intravenous drip in a hospital Intravenous therapy or IV therapy is the administration of liquid substances directly into a vein. ... An International Nonproprietary Name (INN) is the official non-proprietary or generic name given to a pharmaceutical substance, as designated by the World Health Organization. ... A United States Adopted Name (USAN) is the official non-proprietary or generic name given to a pharmaceutical substance, as defined in the United States Pharmacopeia (USP). ... A British Approved Name (BAN) is the official non-proprietary or generic name given to a pharmaceutical substance, as defined in the British Pharmacopoeia (BP). ... Non-steroidal anti-inflammatory drugs, usually abbreviated to NSAIDs, are drugs with analgesic, antipyretic and anti-inflammatory effects - they reduce pain, fever and inflammation. ... An analogue medical thermometer showing the temperature of 38. ... Pain redirects here. ... An abscess on the skin, showing the redness and swelling characteristic of inflammation. ... E1 - Alprostadil I2 - Prostacyclin A prostaglandin is any member of a group of lipid compounds that are derived enzymatically from fatty acids and have important functions in the animal body. ...

Contents

Chemical properties

Indometacin is a methylated indole derivative and a member of the arylalkanoic acid class of NSAIDs, which includes diclofenac. Methylation is a term used in the chemical sciences to denote the attachment or substitution of a methyl group on various substrates. ... Indole is an aromatic heterocyclic organic compound. ... my sister died form overdose!!! Diclofenac (marketed as Voltaren, Voltarol, Diclon, Dicloflex Difen, Difene, Cataflam, Pennsaid, Rhumalgan, Modifenac, Abitren and Zolterol) is a non-steroidal anti-inflammatory drug (NSAID) taken to reduce inflammation and an analgesic reducing pain in conditions such as in arthritis or acute injury. ...


Indications

Clinical indications for indometacin include:

Indometacin has also been used clinically to delay premature labor, reduce amniotic fluid in polyhydramnios, and to treat patent ductus arteriosus. Rheumatoid arthritis (RA) is traditionally considered a chronic, inflammatory autoimmune disorder that causes the immune system to attack the joints. ... Gout (also called gouty arthritis, Greek name: podagra, from pod - foot and agra - trap) is a form of arthritis caused by the accumulation of uric acid crystals in joints. ... Osteoarthritis (OA, also known as degenerative arthritis, degenerative joint disease, or in more colloquial terms wear and tear), is a condition in which low-grade inflammation results in pain in the joints, caused by wearing of the cartilage that covers and acts as a cushion inside joints and destruction or... Psoriatic arthritis (or Arthropathic psoriasis) is a type of inflammatory arthritis that affects around 20% of people suffering from the chronic skin condition Psoriasis. ... It has been suggested that this article or section be merged with Reactive arthritis. ... Bold text X-ray of Pagets disease Pagets disease, otherwise known as osteitis deformans, is a chronic disorder that typically results in enlarged and deformed bones. ... Bartter syndrome is a rare genetic disease characterized by low potassium levels (hypokalemia), decreased acidity of blood (alkalosis), and normal to low blood pressure. ... It has been suggested that this article or section be merged with Calcium pyrophosphate deposition disease. ... Dysmenorrhea (or dysmenorrhoea), cramps or painful menstruation, involves menstrual periods that are accompanied by either sharp, intermittent pain or dull, aching pain, usually in the pelvis or lower abdomen. ... Pericarditis is inflammation of the sac surrounding the heart, the pericardium. ... Bursitis is the inflammation of one or more bursae, or small sacs of synovial fluid, in the body. ... Tendonitis (also tenonitis or tendinitis) is an inflammation of a tendon. ... Diabetes insipidus (DI) is a disease characterized by excretion of large amounts of severely diluted urine, which cannot be reduced when fluid intake is reduced. ... Arginine vasopressin (AVP), also known as argipressin or antidiuretic hormone (ADH), is a human hormone that is released when the body is low on water; it causes the kidneys to conserve water, but not salt, by concentrating the urine and reducing urine volume. ... The kidneys are the organs that filter wastes (such as urea) from the blood and excrete them, along with water, as urine. ... An analogue medical thermometer showing the temperature of 38. ... Pain redirects here. ... Chronic paroxysmal hemicrania (CPH), also known as Sjaastad syndrome, is a cluster-like headache that normally affects females. ... Hemicrania continua (HC) is a persistent unilateral headache that responds to indomethacin. ... Renal colic is a type of pain commonly caused by kidney stones. ... Kidney stones are solid accretions (crystals) of dissolved minerals in urine found inside the kidneys or ureters. ... Premature birth is defined medically as a birth occurring earlier than 37 weeks. ... The amniotic sac is a tough but thin transparent pair of membranes which holds a developing embryo (and later fetus) until shortly before birth. ... Polyhydramnios (polyhydramnion, hydramnios) is the medical condition of too much amniotic fluid in the amniotic sac. ... Patent ductus arteriosus (PDA) is a congenital heart defect wherein a childs ductus arteriosus fails to close after birth. ...


Indometacin is a potent drug with many serious side effects and should not be considered an analgesic for minor aches and pains or fever. The drug is more potent than aspirin, but is not a better analgesic. In mild to moderate pain a standard oral dose of indometacin proved as effective as 600mg aspirin. This article is about the drug. ...


Contraindications

  • concurrent peptic ulcer, or history of ulcer disease
  • allergy to indometacin, aspirin, or other NSAIDs
  • patients with nasal polyps reacting with an angioedema to other NSAIDs
  • children under 2 years of age (with the exception of neonates with patent ductus arteriosus)
  • severe pre-existing renal and liver damage
  • caution : pre-existing bone marrow damage (frequent blood cell counts are indicated)
  • caution : bleeding tendencies of unknown origin (indometacin inhibits platelet aggregation)
  • caution : Parkinson's disease, epilepsy, psychotic disorders (indometacin may worsen these conditions)

A benign gastric ulcer (from the antrum) of a gastrectomy specimen. ... This article is about the cnidarian polyps. ... Angioedema (BE: angiooedema), also known by its eponym Quinckes edema, is the rapid swelling (edema) of the skin, mucosa and submucosal tissues. ... A 250 ml bag of newly collected platelets. ...

Mechanism of action

{{main|Non-steroidal anti-inflammatory drug


Indomethacin is a nonselective inhibitor of cyclooxygenase (COX) 1 and 2, enzymes that participate in prostaglandin synthesis from arachidonic acid. Prostaglandins are hormone-like molecules normally found in the body, where they have a wide variety of effects, some of which lead to pain, fever, and inflammation. Cyclooxygenase (COX) is an enzyme (EC 1. ... Arachidonic acid (AA) is an omega-6 fatty acid 20:4(ω-6). ... For other uses, see Hormone (disambiguation). ...


Prostaglandins also cause uterine contractions in pregnant women. Indometacin is an effective tocolytic agent, able to delay premature labor by reducing uterine contractions through inhibition of PG synthesis in the uterus and possibly through calcium channel blockade. In medicine (obstetrics), a contraction is a forceful motion of the uterus, generated by the release of oxytocin (quick labor) by the pituitary gland, culminating in childbirth. ... Ion channels are present in the membranes that surround all biological cells. ...


Indometacin has two additional modes of actions with clinical importance:

  • It inhibits motility of polymorphonuclear leukocytes, similar to colchicine.
  • It uncouples oxidative phosphorylation in cartilaginous (and hepatic) mitochondria, like salicylates.

These additional effects account as well for the analgesic and the anti-inflammatory properties. Colchicine is a highly deadly poisonous alkaloid, originally extracted from plants of the genus Colchicum (Autumn crocus, also known as the Meadow saffron). Originally used to treat rheumatic complaints and especially gout, it was also prescribed for its cathartic and emetic effects. ...


Indometacin readily crosses the placenta, and can reduce fetal urine production to treat polyhydramnios. It does so by reducing renal blood flow and increasing renal vascular resistance, possibly by enhancing the effects of vasopressin on the fetal kidneys. The placenta is a sack of fat present in placental vertebrates, such as some mammals and sharks during gestation (pregnancy). ... For other uses, see Fetus (disambiguation). ... This article is about the urine of animals generally. ... Arginine vasopressin (AVP), also known as argipressin or antidiuretic hormone (ADH), is a human hormone that is released when the body is low on water; it causes the kidneys to conserve water, but not salt, by concentrating the urine and reducing urine volume. ...


Adverse effects

Since indomethacin inhibits both COX-1 and COX-2, it inhibits the production of prostaglandins in the stomach and intestines which maintain the mucous lining of the gastrointestinal tract. Indometacin, therefore, like other nonselective COX inhibitors, can cause peptic ulcers. The ulcers can result in serious bleeding and/or perforation requiring hospitalization of the patient. Some even die from these complications. To reduce the possibility of peptic ulcers, indometacin should be prescribed at the lowest dosage needed to achieve a therapeutic effect, usually between 50–200 mg/day. It should always be taken with food. Nearly all patients benefit from an ulcer protective drug (e.g. highly dosed antacids, ranitidine 150mg at bedtime, or omeprazole 20mg at bedtime). Other common gastrointestinal complaints, including dyspepsia, heartburn and mild diarrhea are less serious and rarely require discontinuation of indometacin. Cyclooxygenase (COX) is an enzyme (EC 1. ... Cyclooxygenase (COX) is an enzyme that is responsible for formation of important biological mediators called prostanoids (including prostaglandins, prostacyclin and thromboxane). ... In anatomy, the stomach is a bean-shaped hollow muscular organ of the gastrointestinal tract involved in the second phase of digestion, following mastication. ... The intestine is the portion of the alimentary canal extending from the stomach to the anus and, in humans and other mammals, consists of two segments, the small intestine and the large intestine. ... Mucus cells. ... Gut redirects here. ... A benign gastric ulcer (from the antrum) of a gastrectomy specimen. ... Ranitidine (INN) (IPA: ) is a histamine H2-receptor antagonist that inhibits stomach acid production, and commonly used in the treatment of peptic ulcer disease (PUD) and gastroesophageal reflux disease (GERD). ... Omeprazole (INN) (IPA: ) is a proton pump inhibitor used in the treatment of dyspepsia, peptic ulcer disease (PUD), gastroesophageal reflux disease (GORD/GERD) and Zollinger-Ellison syndrome. ... Diarrhea, also spelled diarrhoea (see spelling differences), is a condition in which the sufferer has frequent watery, loose bowel movements (from the Greek word διάρροια; literally meaning through-flowing). Acute infectious diarrhea is a common cause of death in developing countries (particularly among infants), accounting for 5 to 8 million deaths...


Many NSAIDs, but particularly indometacin, cause lithium retention by reducing its excretion by the kidneys. Thus indometacin users have an elevated risk of lithium toxicity. For patients taking lithium supplements (e.g. for treatment of depression or bipolar disorder), less toxic NSAIDs such as sulindac or aspirin, are preferred. This article is about the chemical element named Lithium. ... The kidneys are the organs that filter wastes (such as urea) from the blood and excrete them, along with water, as urine. ... On the Threshold of Eternity. ... For other uses, see Bipolar. ... Sulindac is a non-steroidal anti-inflammatory drug of the arylalkanoic acid class that is marketed in the U.S. as Clinoril. ... This article is about the drug. ...


Indometacin also reduces plasma renin activity and aldosterone levels, and increases sodium and potassium retention. It also enhances the effects of vasopressin. Together these may lead to: Not to be confused with rennin, the active enzyme in rennet. ... Aldosterone is a steroid hormone (mineralocorticoid family) produced by the outer-section (zona glomerulosa) of the adrenal cortex in the adrenal gland to regulate sodium and potassium balance in the blood. ... For sodium in the diet, see Edible salt. ... General Name, symbol, number potassium, K, 19 Chemical series alkali metals Group, period, block 1, 4, s Appearance silvery white Standard atomic weight 39. ... Arginine vasopressin (AVP), also known as argipressin or antidiuretic hormone (ADH), is a human hormone that is released when the body is low on water; it causes the kidneys to conserve water, but not salt, by concentrating the urine and reducing urine volume. ...

The drug may also cause elevations of serum creatinine and more serious renal damage such as acute renal failure, chronic nephritis and nephrotic syndrome. These conditions also often begin with edema and hyperkalema. This page is about the condition called edema. ... Hyperkalemia is an elevated blood level (above 5. ... Hypernatremia is an electrolyte disturbance consisting of an elevated sodium level in the blood (compare to hyponatremia, meaning a low sodium level). ... For other forms of hypertension, see Hypertension (disambiguation). ... Creatinine is a breakdown product of creatine phosphate in muscle, and is usually produced at a fairly constant rate by the body (depending on muscle mass). ... Nephritis is inflammation of the kidney. ...


Additionally, indometacin quite often causes headache (10 to 20%), sometimes with vertigo and dizziness, hearing loss, tinnitus, blurred vision (with or without retinal damage) and worsens Parkinson's disease, epilepsy, and psychiatric disorders. Cases of life-threatening shock (including angioedema, sweating, severe hypotension and tachycardia as well as acute bronchospasm), severe or lethal hepatitis and severe bone marrow damage have all been reported. Skin reactions and photosensitivity are also possible side effects. Angioedema (BE: angiooedema), also known by its eponym Quinckes edema, is the rapid swelling (edema) of the skin, mucosa and submucosal tissues. ... In physiology and medicine, hypotension refers to an abnormally low blood pressure. ... This article or section does not cite any references or sources. ... Bronchospasm is a difficulty in breathing caused by a sudden constriction of the muscles in the walls of the bronchioles. ... Hepatitis (plural hepatitides) implies injury to liver characterised by presence of inflammatory cells in the liver tissue. ... Photosensitivity is the amount to which an object reacts upon receiving photons of light. ...


Due to its strong antipyretic activity indometacin may obscure the clinical course of serious infections. Antipyretics are drugs that prevent or reduce fever by lowering the body temperature from a raised state. ...


The frequency and severity of side effects and the availability of better tolerated alternatives make indometacin today a drug of second choice. Its use in acute gout attacks and in dysmenorrhea is well-established because in these indications the duration of treatment is limited to a few days only, therefore serious side effects are not likely to occur. Dysmenorrhea (or dysmenorrhoea), cramps or painful menstruation, involves menstrual periods that are accompanied by either sharp, intermittent pain or dull, aching pain, usually in the pelvis or lower abdomen. ...


Necessary Examinations during Longterm Treatment

Patients should undergo regular physical examination to detect edema and signs of central nervous side effects. Blood pressure checks will reveal development of hypertension. Periodic serum electrolyte (sodium, potassium, chloride) measurements, complete blood cell counts and assessment of liver enzymes as well as of creatinine (renal function) should be performed. This is particularly important if indometacin is given together with an ACE inhibitor or with potassium-sparing diuretics, because these combinations can lead to hyperkalemia and/or serious kidney failure. No examinations are necessary if only the topical preparations (spray or gel) are applied. Captopril, the first ACE inhibitor ACE inhibitors, or inhibitors of Angiotensin-Converting Enzyme, are a group of pharmaceuticals that are used primarily in treatment of hypertension and congestive heart failure, in most cases as the drugs of first choice. ... This illustration shows where some types of diuretics act, and what they do. ...


Animal Toxicity and Human Overdose

Indomethacin has a high acute toxicity both for animals (12 mg/kg in rats and 50 mg/kg in mice) and for humans. Exact human data does not exist, but some fatal human cases, particularly in children and adolescents, have been seen.


Generally, overdose in humans causes drowsiness, dizziness, severe headache, mental confusion, paresthesia, numbness of limbs, nausea and vomiting. Severe gastrointestinal bleeding is also possible. Cerebral edema, and cardiac arrest with fatal outcome have been seen in children.


The treatment is symptomatic and largely the same as with diclofenac. However, the possibility of severe GI tract symptoms should be particularly noted. my sister died form overdose!!! Diclofenac (marketed as Voltaren, Voltarol, Diclon, Dicloflex Difen, Difene, Cataflam, Pennsaid, Rhumalgan, Modifenac, Abitren and Zolterol) is a non-steroidal anti-inflammatory drug (NSAID) taken to reduce inflammation and an analgesic reducing pain in conditions such as in arthritis or acute injury. ...


The risk of overdose after exaggerated local treatment with gel or spray is very limited.


Usual Dosage Forms

  • Tablets or Capsules 25 and 50mg
  • Suppositories 50 and 100mg
  • Modified-release Capsules 75mg
  • Syrup (25mg/5ml)
  • Injectable concentrate 50mg for i.m. injection
  • Spray or Gel
  • Patches containing 0.5% by weight
  • 1% topical liquid

History

Indometacin was discovered in 1963 and it was first approved for use in the U.S. by the Food and Drug Administration in 1965. Its mechanism of action, along with several other NSAIDs that inhibit COX, was described in 1971. For other uses, see 1963 (disambiguation). ... “FDA” redirects here. ... Year 1965 (MCMLXV) was a common year starting on Friday (link will display full calendar) of the 1965 Gregorian calendar. ... Year 1971 (MCMLXXI) was a common year starting on Friday (link will display full calendar) of the 1971 Gregorian calendar. ...


References

  • Lum G, Aisenbrey G, Dunn M, Berl T, Schrier R, McDonald K (Jan 1977). "In vivo effect of indomethacin to potentiate the renal medullary cyclic AMP response to vasopressin." (PDF or scanned copy). J Clin Invest 59 (1): 8-13. PMID 187624. 
  • Akbarpour F, Afrasiabi A, Vaziri N (1985). "Severe hyperkalemia caused by indomethacin and potassium supplementation.". South Med J 78 (6): 756-7. PMID 4002013. 
  • Ragheb M (Oct 1990). "The clinical significance of lithium-nonsteroidal anti-inflammatory drug interactions.". J Clin Psychopharmacol 10 (5): 350-4. PMID 2258452. 
  • Phelan K, Mosholder A, Lu S (Nov 2003). "Lithium interaction with the cyclooxygenase 2 inhibitors rofecoxib and celecoxib and other nonsteroidal anti-inflammatory drugs.". J Clin Psychiatry 64 (11): 1328-34. PMID 14658947. 
  • Hart F, Boardman P (Oct 1963). "Indomethacin: A new non-steroid anti-inflammatory agent.". Br Med J 5363: 965-70. PMID 14056924. 
  • Ferreira S, Moncada S, Vane J (Jun 23 1971). "Indomethacin and aspirin abolish prostaglandin release from the spleen.". Nat New Biol 231 (25): 237-9. PMID 5284362. 
  • Scherzer P, Wald H, Rubinger D, Popovtzer M (sep 1992). "Indomethacin and sodium retention in the rat: role of inhibition of prostaglandin E2 synthesis.". Clin Sci (Lond) 83 (3): 307-11. PMID 1327647. 

External links


  Results from FactBites:
 
Indometacin, Indomethacin (456 words)
Indometacin reduces the renal clearance of lithium preparation; inhibits the vasodilating effect of nitroglycerin; increases toxicity of the aminoglycoside antibiotics.
Indometacin is a derivative of indol, possessing prominent anti-inflammatory action, significantly exceeding the antiinflammatory effect of the salicyllates and phenylbutazone.
6 Indometacin suppositories of 50 mg or 100 mg.
  More results at FactBites »

 
 

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