Ketorolac
Systematic (IUPAC) name
(±)-5-benzoyl-2,3-dihydro- 1H-pyrrolizine-1-carboxylic acid, 2-amino-2-(hydroxymethyl)-1,3-propanediol
Identifiers
CAS number	74103-06-3
ATC code	M01AB15
PubChem	3826
DrugBank	N/A
Chemical data
Formula	C15H13NO3
Mol. mass	376.4 g/mol
Pharmacokinetic data
Bioavailability	100% (All routes)
Metabolism	Hepatic
Half life	3.5-9.2 hrs, young adults; 4.7-8.6 hrs, elderly (mean age 72)
Excretion	Renal:91.4% (mean) Biliary:6.1% (mean)
Therapeutic considerations
Pregnancy cat.	C(AU) C(US) Image File history File links Ketorolac. ... 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. ... 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 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. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... For the bird, see Liver bird. ... 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 hour (symbol: h) is a unit of time. ... The kidneys are important excretory organs in vertebrates. ... The kidneys are the organs that filter wastes (such as urea) from the blood and excrete them, along with water, as urine. ... Bile (or gall) is a bitter, yellow or green alkaline fluid secreted by hepatocytes from the liver of most vertebrates. ... 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). ... For other uses of terms redirecting here, see US (disambiguation), USA (disambiguation), and United States (disambiguation) Motto In God We Trust(since 1956) (From Many, One; Latin, traditional) Anthem The Star-Spangled Banner Capital Washington, D.C. Largest city New York City National language English (de facto)1 Demonym American...
Legal status	℞ Prescription only The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ...
Routes	oral, I.M., I.V.

Ketorolac or ketorolac tromethamine (marketed as Toradol - generics have been approved) is a non-steroidal anti-inflammatory drug (NSAID) in the family of propionic acids, often used as an analgesic, antipyretic (fever reducer), and anti-inflammatory. Ketorolac acts by inhibiting bodily synthesis of prostaglandins. Ketorolac in its oral and intramuscular preparations is a racemic mixture of (S)-(−)-ketorolac, the active isomer, and (R)-(+)-ketorolac. An ophthalmic solution of ketorolac is available under the name Acular, and is used to treat eye pain and to relieve the itchiness and burning of seasonal allergies. 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. ... Intramuscular injection is an injection of a substance directly into a muscle. ... An intravenous drip in a hospital Intravenous therapy or IV therapy is the administration of liquid substances directly into a vein. ... Non-steroidal anti-inflammatory drugs, usually abbreviated to NSAIDs, are drugs with analgesic, antipyretic and anti-inflammatory effects - they reduce pain, fever and inflammation. ... Propionic acid (systematically named propanoic acid) is a naturally occurring carboxylic acid with chemical formula CH3CH2COOH. In the pure state, it is a colorless, corrosive liquid with a pungent odor. ... An analgesic (colloquially known as a painkiller) is any member of the diverse group of drugs used to relieve pain (achieve analgesia). ... Antipyretics are drugs that prevent or reduce fever by lowering the body temperature from a raised state. ... An analogue medical thermometer showing the temperature of 38. ... An abscess on the skin, showing the redness and swelling characteristic of inflammation. ... A prostaglandin is any member of a group of lipid compounds that are derived from fatty acids and have important functions in the animal body. ... In chemistry, a racemate is a mixture of equal amounts of left- and right-handed stereoisomers of a chiral molecule. ...

The brand name Toradol was coined by the Syntex company of the United States. Laboratorios Syntex SA was a pharmaceutical company formed in Mexico City in 1944 by Russell Marker to manufacture therapeutic steroids from the Mexican yam. ...

Chemistry

Ketorolac, like other 2-arylpropionate derivatives (including ketoprofen, flurbiprofen, naproxen, ibuprofen etc.) contains a chiral carbon in the α-position of the propionate moiety. As such there are two possible enantiomers of ketorolac with the potential for different biological effects and metabolism for each enantiomer. Ketoprofen, (RS)2-(3-benzoylphenyl)-propionic acid (chemical formula C16H14O3) is one of the propionic acid class of non-steroidal anti-inflammatory drug (NSAID) with analgesic and antipyretic effects. ... Flurbiprofen is an NSAID (non-steroidal anti-inflammatory drug) used to treat the inflammation and pain of arthritis. ... Naproxen (INN) (IPA: ) is a non-steroidal anti-inflammatory drug (NSAID) commonly used for the reduction of mild to moderate pain, fever, inflammation and stiffness caused by conditions such as osteoarthritis, rheumatoid arthritis, psoriatic arthritis, gout, ankylosing spondylitis, injury (like fractures), menstrual cramps, tendonitis, bursitis, and the treatment of primary... Ibuprofen (INN) (IPA: ) (from the earlier nomenclature iso-butyl-propanoic-phenolic acid) is a non-steroidal anti-inflammatory drug (NSAID) originally marketed as Nurofen and since under various trademarks including Act-3, Advil, Brufen, Dorival, Herron Blue, Panafen, Motrin, Nuprin and Ipren or Ibumetin (Sweden), Ibuprom (Poland), IbuHEXAL, Moment (Italy... The term chiral (pronounced ) is used to describe an object which is non-superimposable on its mirror image. ... In chemistry, enantiomers (from the Greek ἐνάντιος, opposite, and μέρος, part or portion) are stereoisomers that are nonsuperimposable complete mirror images of each other, much as ones left and right hands are the same but opposite. ...

NSAIDs are not recommended for use with other NSAIDs because of the potential for additive side effects. Non-steroidal anti-inflammatory drugs, usually abbreviated to NSAIDs, are drugs with analgesic, antipyretic and anti-inflammatory effects - they reduce pain, fever and inflammation. ...

The protein-binding effect of most non-aspirin NSAIDs is inhibited by the presence of aspirin in the blood. This article is about the drug. ...

Mechanism of action

The primary mechanism of action responsible for Ketorolac's anti-inflammatory/antipyretic/analgesic effects is the inhibition of prostaglandin synthesis by competitive blocking of the the enzyme cyclooxygenase (COX). Like most NSAIDs, Ketorolac is a non-selective cyclooxygenase inhibitor. Wikipedia does not yet have an article with this exact name. ... Anti-inflammatory refers to the property of a substance or treatment that reduces inflammation. ... Antipyretics are drugs that prevent or reduce fever by lowering the body temperature from a raised state. ... An analgesic (colloquially known as a painkiller) is any member of the diverse group of drugs used to relieve pain (achieve analgesia). ... Cyclooxygenase (COX) is an enzyme (EC 1. ... Non-steroidal anti-inflammatory drugs, usually abbreviated to NSAIDs, are drugs with analgesic, antipyretic and anti-inflammatory effects - they reduce pain, fever and inflammation. ... Cox may mean: hot man Coxswain. ...

As with other NSAIDs, the mechanism of the drug is associated with the chiral S form. Conversion of the R enantiomer into the S enantiomer has been shown to occur in the metabolism of ibuprofen; it is unknown whether it occurs in the metabolism of ketorolac. Non-steroidal anti-inflammatory drugs, usually abbreviated to NSAIDs, are drugs with analgesic, antipyretic and anti-inflammatory effects - they reduce pain, fever and inflammation. ... Structure of the coenzyme adenosine triphosphate, a central intermediate in energy metabolism. ...

Indications

Ketorolac is indicated for short-term management of pain (up to five days maximum).

Contraindications

Ketorolac is contraindicated against patients with a previously demonstrated hypersensitivity to ketorolac, and against patients with the complete or partial syndrome of nasal polyps, angioedema, bronchospastic reactivity or other allergic manifestations to aspirin or other non-steroidal anti-inflammatory drugs (due to possibility of severe anaphylaxis). As with all NSAIDs, ketorolac should be avoided in patients with renal dysfunction. (Prostaglandins are needed to dilate the afferent arteriole; NSAIDs effectively reverse this.) The patients at highest risk, especially in the elderly, are those with fluid imbalances or with compromised renal function (e.g., heart failure, diuretic use, cirrhosis, dehydration, and renal insufficiency). Angioedema (BE: angiooedema), also known by its eponym Quinckes edema, is the rapid swelling (edema) of the skin, mucosa and submucosal tissues. ... Bronchospasm is a difficulty in breathing caused by a sudden constriction of the muscles in the walls of the bronchioles. ... Allergy is an abnormal reaction to a substance foreign to the body that is acquired, predictable and rapid. ... Anaphylaxis is an acute systemic (multi-system) and severe Type I Hypersensitivity allergic reaction in humans and other mammals. ...

Adverse effects

Similar to other NSAIDs. See inset "Ketorolac adverse effects."

This page is about the condition called edema. ... The larynx (plural larynges), colloquially known as the voicebox, is an organ in the neck of mammals involved in protection of the trachea and sound production. ... For other uses, see Tongue (disambiguation). ... In physiology and medicine, hypotension refers to an abnormally low blood pressure. ... For a person to flush is to become markedly red in the face and often other areas of the skin, from various physiological conditions. ... This article or section should be merged with Birth control pill Weight Gain When Taking The Pill When starting to take the birth contol pill some people may expierence slight weight gain. ... An analogue medical thermometer showing the temperature of 38. ... Asthenia (Greek: ασθένεια, lit. ... For other forms of hypertension, see Hypertension (disambiguation). ... This article does not cite any references or sources. ... This article does not cite any references or sources. ... This article or section does not cite its references or sources. ... A rash is a change in skin which affects its color, appearance, or texture. ... An itch (Latin: pruritus) is a sensation felt on an area of skin that makes a person or animal want to scratch it. ... Toxic epidermal necrolysis is a life-threatening and usually drug-induced dermatological condition that occurs more often in women than in men. ... Stevens-Johnson syndrome (SJS) is a severe and life-threatening condition. ... For other uses, see Nausea (disambiguation). ... For the Physics term GUT, please refer to Grand unification theory The gastrointestinal or digestive tract, also referred to as the GI tract or the alimentary canal or the gut, is the system of organs within multicellular animals which takes in food, digests it to extract energy and nutrients, and... Pain redirects here. ... Constipation or irregularity, is a condition of the digestive system where a person (or animal) experiences hard feces that are difficult to egest; it may be extremely painful, and in severe cases (fecal impaction) lead to symptoms of bowel obstruction. ... 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... Flatulence is the presence of a mixture of gases known as flatus in the digestive tract of mammals expelled from the rectum. ... Vomiting (or emesis) is the forceful expulsion of the contents of ones stomach through the mouth. ... Stomatitis is an inflammation of the mucous lining of any of the structures in the mouth, which may involve the cheeks, gums, tongue, lips, and roof or floor of the mouth. ... A benign gastric ulcer (from the antrum) of a gastrectomy specimen. ... To meet Wikipedias quality standards, this article or section may require cleanup. ... In medicine, melena or melaena refers to the black, tarry feces that are associated with gastrointestinal hemorrhage. ... The rectum (from the Latin rectum intestinum, meaning straight intestine) is the final straight portion of the large intestine in some mammals, and the gut in others, terminating in the anus. ... Gastritis is inflammation of the gastric mucosa. ... The process of burping, also known as a belching or eructation, is an often audible release through the mouth of gas that has accumulated in the stomach or esophagus. ... Anorexia (deriving from the Greek α(ν)- (a(n)-, a prefix that denotes absence) + όρεξη (orexe) = appetite) is the decreased sensation of appetite. ... The appetite is the desire to eat food, felt as hunger. ... Pancreatitis is inflammation of the pancreas. ... Purple discolorations on the skin caused by bleeding underneath the skin. ... Thrombocytopenia (or -paenia, or thrombopenia in short) is the presence of relatively few platelets in blood. ... For the plant referred to as nosebleed plant, see Yarrow. ... This article discusses the medical condition. ... Leukopenia or leukocytopenia refers to a decrease in the number of circulating white blood cells (leukocytes) in the blood. ... Eosinophilia is the state of having high eosinophil granulocytes in the blood. ... Somnolence (or drowsiness, or hypersomnia) is a state of near-sleep, a strong desire for sleep, or sleeping unusually long periods. ... // Pre-syncope is a sensation of feeling faint. ... A headache (cephalgia in medical terminology) is a condition of pain in the head; sometimes neck or upper back pain may also be interpreted as a headache. ... Perspiration (also called sweating or sometimes transpiration) is the production and evaporation of a fluid, consisting primarily of water as well as a smaller amount of sodium chloride (the main constituent of table salt), that is excreted by the sweat glands in the skin of mammals. ... An injection is a method of putting liquid into the body with a hollow needle and a syringe which is pierced through the skin to a sufficient depth for the material to be forced into the body. ... This article is about the medical condition. ... For other uses, see Vertigo. ... Fred Ward as Earl Bassett in the 1990 film Tremors. ... Dreaming is the subjective experience of imaginary images, sounds/voices, thoughts or sensations during sleep, usually involuntarily. ... A hallucination is a false sensory perception in the absence of an external stimulus, as distinct from an illusion, which is a misperception of an external stimulus. ... Euphoria (Greek ) is a medically recognized emotional state related to happiness. ... Paresthesia or paraesthesia (in British English) is a sensation of tingling, pricking, or numbness of a persons skin with no apparent long-term physical effect, more generally known as the feeling of pins and needles or of a limb being asleep (but not directly related to the phenomenon of... In everyday language depression refers to any downturn in mood, which may be relatively transitory and perhaps due to something trivial. ... This article is about the sleeping disorder. ... Anxiety is a complex combination of the feeling of fear, apprehension and worry often accompanied by physical sensations such as palpitations, chest pain and/or shortness of breath. ... Hyperkinesis is a state of overactive restlesness in children. ... This article is being considered for deletion in accordance with Wikipedias deletion policy. ... Dyspnea (R06. ... The heart and lungs (from an older edition of Grays Anatomy) The lung is an organ belonging to the respiratory system and interfacing to the circulatory system of air-breathing vertebrates. ... Rhinitis is the medical term describing irritation and inflammation of the nose. ... Renal failure is the condition in which the kidneys fail to function properly. ... Polyuria is the passage of a large volume of urine in a given period. ... The urinary system is a system of organs, tubes, muscles, and nerves that work together to create, store, and carry, urine. ...

Warnings and precautions

The most serious risks associated with ketorolac are, as with other NSAIDs, gastrointestinal ulcerations, bleeding and perforation; renal events ranging from interstitial nephritis to complete renal failure; hemorrhage, and hypersensitivity reactions. The kidneys are the organs that filter wastes (such as urea) from the blood and excrete them, along with water, as urine. ... Nephritis is inflammation of the kidney. ... Renal failure is when the kidneys fail to function properly. ...

As with other NSAIDs, fluid and solute retention and edema have been reported with ketorolac; ketorolac elevated liver protein levels; it also inhibits platelet aggregation and may be associated with an increased risk of bleeding.

It should be noted that when administered intravenously through the same IV catheter as Morphine the two drugs have been known to sometimes combine to form a precipitate in the IV, which may block the line. Line flushing with a syringe of saline can push the blockage through.

Cautions

Ketorolac is not recommended for pre-operative analgesia or co-administration with anesthesia because it inhibits platelet aggregation. “Surgeon” redirects here. ... Anesthesia or anaesthesia (see spelling differences) has traditionally meant the condition of having the perception of pain and other sensations blocked. ...

Ketorolac is not recommended for obstetric analgesia because it has not been adequately tested for obstetrical administration and has demonstrable fetal toxicity in laboratory animals. Obstetrics (from the Latin obstare, to stand by) is the surgical specialty dealing with the care of a woman and her offspring during pregnancy, childbirth and the puerperium (the period shortly after birth). ...

Ketorolac has been co-administered with meperidine and morphine without apparent adverse effects. Pethidine (INN) or meperidine (USAN) (also referred to as: isonipecaine; lidol; operidine; pethanol; piridosal; Algil®; Alodan®; Centralgin®; Demerol®; Dispadol®; Dolantin®; Dolestine®; Dolosal®; Dolsin®; Mefedina®) is a fast-acting opioid analgesic drug. ... This article is about the drug. ...

Ketorolac is not recommended for long-term chronic pain patients.

Dosage, availability and price

Oral dosage is 10 mg; United States price for 30 tablets hovers around US$25. Australian pricing for 20 tablets is around AU$43.39.^[1]

Injected dosages are 15, 30 and 60 mg; United States price for 10 vials of 30 mg each is around US$45, making the intramuscular preparation considerably more expensive per dose. One 60-mg dose would require the administration by injection of two vials, at about $9 per dose. Australian pricing for 5 vials is around AU$57.90^[1], or $23.16 per dose. Ketorolac is not available on the Pharmaceutical Benefits Scheme.^[2] The Pharmaceutical Benefits Scheme or PBS is a programme of the Australian Government that provides heavily subsidised prescription drugs to residents of Australia. ...

In the United States^[3], United Kingdom^[4], Canada^[5] and Australia^[6] this drug cannot be sold over-the-counter and must be administered only with a prescription. The abbreviation OTC may refer to: an Office of Technology Commercialization, the intellectual property managing office of many American research universities (sometimes referred to as an Office of Technology Transfer or OTT). ... A medical prescription ) is an order (often in written form) by a qualified health care professional to a pharmacist or other therapist for a treatment to be provided to their patient. ...

SYNTEX (U.S.A.) L.L.C., Palo Alto, California, U.S.A. developed the ophthalmic solution Acular, and holds the registered trademark on that name. The brand name Acular product is manufactured and distributed by Allergan, Inc., under license from Syntex.^[7] Laboratorios Syntex SA was a pharmaceutical company formed in Mexico City in 1944 by Russell Marker to manufacture therapeutic steroids from the Mexican yam. ... Location in Santa Clara County and the state of California Coordinates: , Country State County Santa Clara Government  - Mayor Yoriko Kishimoto[1] Area  - City 25. ... Categories: Possible copyright violations ...

Apotex Products Group, a Canadian manufacturer, offers generic Ketorolac tromethamine 0.5% ophthalmic solution under the name "APO-KETOROLAC"^[8] in Canada and some other countries. Apotex is a Canadian pharmaceutical corporation. ... A generic drug (pl. ...

Syntex and Allergan sued Apotex for patent infringement of U.S. Patent No. 5,110,493 over the generic Ketorolac tomethamine product. In May, 2005, the United States court of appeals for the Federal Circuit handed Apotex a victory, ruling that a lower court upholding the Syntex patent misapplied the rules for judging whether an invention was obvious. Allergan claims the patent is valid until 2009.^[9] The examples and perspective in this article or section may not represent a worldwide view. ... For other uses, see Patent (disambiguation). ... Year 2005 (MMV) was a common year starting on Saturday (link displays full calendar) of the Gregorian calendar. ... The United States courts of appeals (or circuit courts) are the mid-level appellate courts of the United States federal court system. ... 2009 (MMIX) will be a common year starting on Thursday of the Gregorian calendar. ...

See also

• NSAID
• Analgesic

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 analgesic (colloquially known as a painkiller) is any member of the diverse group of drugs used to relieve pain (achieve analgesia). ...

External links

• rxlist.com monograph on ACULAR (ketorolac tromethamine ophthalmic solution) 0.5% Sterile
• allergan.com ACULAR product information
• medicinenet.com information on ketorolac tromethamine - ophthalmic (Acular)
• Druglib published studies related to Toradol (Ketorolac)

References

• Handley, D.A., P. Carvoni, J.E. McCray, J.R. McCullough (1998). "Preclinical Enantioselective Pharmacology of (R)- and (S)- Ketorolac.", J Clin Pharmacol 38, 25-35.
• 1993. Physicians' Desk Reference, Forty-seventh edition. Montvale, N.J., Medical Economics Co. Inc., 2411-2415.