Ketorolac

Title: Ketorolac
CAS Registry Number: 74103-06-3
CAS Name: 5-Benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid
Additional Names: 5-benzoyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid
Manufacturers' Codes: RS-37619
Molecular Formula: C15H13NO3
Molecular Weight: 255.27
Percent Composition: C 70.58%, H 5.13%, N 5.49%, O 18.80%
Literature References: Prostaglandin biosynthesis inhibitor. Prepn and separation of isomers: BE 856681; J. M. Muchowski, A. F. Kluge, US 4089969 (both 1978 to Syntex). Alternate processes: J. M. Muchowski, R. Greenhouse, US 4347186 (1982 to Syntex); F. Franco et al., J. Org. Chem. 47, 1682 (1982); J. B. Doherty, US 4496741 (1985 to Merck & Co.). Absolute configuration: A. Guzman et al., J. Med. Chem. 29, 589 (1986). Structure-activity relationships: J. M. Muchowski et al., ibid. 28, 1037 (1985). Pharmacology and analgesic, anti-inflammatory profile of ketorolac and its tromethamine salt: W. H. Rooks et al., Agents Actions 12, 684 (1982); eidem, Drugs Exp. Clin. Res. 11, 479 (1985). Clinical comparison with acetaminophen in post-operative pain: H. J. McQuay et al., Clin. Pharmacol. Ther. 39, 89 (1986).
Properties: Crystals from ethyl acetate + ether, mp 160-161°. uv max in methanol: 245, 312 nm (e 7080, 17400). pKa 3.49 ±0.02. LD50 orally in mice: ~200 mg/kg (Rooks).
Melting point: mp 160-161°
pKa: pKa 3.49 ±0.02
Absorption maximum: uv max in methanol: 245, 312 nm (e 7080, 17400)
Toxicity data: LD50 orally in mice: ~200 mg/kg (Rooks)
Derivative Type: (±)-Form tromethamine salt
CAS Registry Number: 74103-07-4
Trademarks: Acular (Allergan); Dolac (Syntex); Lixidol (Farmitalia); Tarasyn (Syntex); Toradol (Syntex); Toratex (Syntex)
Molecular Formula: C19H24N2O6
Molecular Weight: 376.40
Percent Composition: C 60.63%, H 6.43%, N 7.44%, O 25.50%
Derivative Type: (+)-Form
Properties: Crystals from hexane + ethyl acetate, mp 174° (Guzman); also reported as mp 154-156° (Muchowski, Kluge). [a]D +173° (c = 1 in methanol).
Melting point: mp 174° (Guzman); mp 154-156° (Muchowski, Kluge)
Optical Rotation: [a]D +173° (c = 1 in methanol)
Derivative Type: (-)-Form
Properties: Crystals from hexane + ethyl acetate, mp 169-170° (Guzman); also reported as mp 153-155° (Muchowski, Kluge). [a]D -176° (c = 1 in methanol).
Melting point: mp 169-170° (Guzman); mp 153-155° (Muchowski, Kluge)
Optical Rotation: [a]D -176° (c = 1 in methanol)
Therap-Cat: Analgesic; anti-inflammatory.
Keywords: Analgesic (Non-Narcotic); Anti-inflammatory (Nonsteroidal); Arylcarboxylic Acids.
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Ketorolac
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Systematic (IUPAC) name
(±)-5-benzoyl-2,3-dihydro-
1H-pyrrolizine-1-carboxylic acid,
2-amino-2-(hydroxymethyl)-1,3-propanediol
Clinical data
Trade names Toradol, Acular and Sprix
AHFS/Drugs.com monograph
MedlinePlus a693001
Licence data US Daily Med:link
Pregnancy cat. C (AU) C (US)
Legal status Prescription Only (S4) (AU) -only (US)
Routes Oral, I.M., I.V.
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)
Identifiers
CAS number 74103-06-3 N
ATC code M01AB15 S01BC05
PubChem CID 3826
DrugBank DB00465
ChemSpider 3694 YesY
UNII YZI5105V0L YesY
KEGG D08104 YesY
ChEBI CHEBI:6129 N
ChEMBL CHEMBL469 YesY
Chemical data
Formula C15H13NO3 
Mol. mass 255.27 g/mol
 N (what is this?)  (verify)

Ketorolac or ketorolac tromethamine is a non-steroidal anti-inflammatory drug (NSAID) in the family of heterocyclic acetic acid derivatives, used as an analgesic. Ketorolac was discovered in 1989 by Syntex Corp. (now Roche Bioscience, which is a wholly owned subsidiary of Roche holding Ltd., the parent company of Roche).[1] It was approved by FDA on 30 November 1989 and introduced as Toradol by Syntex.[2] The ophthalmic (i.e., eye-drop) form was approved by FDA on 9 November 1992 and was introduced as Acular eye drops by Allergan under license from Syntex.[3] An intranasal formulation of ketorolac tromethamine was approved by FDA on 14 May 2010 and introduced as Sprix Nasal Spray by Daiichi Sankyo[4] for short-term management of moderate to moderately severe pain requiring analgesia at the opioid level. In India it is available as Ketanov by Ranbaxy, which is owned by Daiichi Sankyo.

Ketorolac acts by inhibiting the bodily synthesis of prostaglandins. Ketorolac in its oral (tablet or capsule) and intramuscular (injected) preparations is a racemic mixture of both (S)-(−)-ketorolac, the active isomer, and (R)-(+)-ketorolac. An ophthalmic solution of ketorolac is available and is used to treat eye pain and to relieve the itchiness and burning of seasonal allergies.