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Ketorolac
Cayman Chemical Item Number 9001148
Acular LS®; RS 37619; Acular PF®; Sprix® (CAS 74103-06-3)
Description
Ketorolac is a non-steroidal anti-inflammatory drug (NSAID) that belongs to the class of heteroaryl acetic acid derivatives. It is a non-selective cyclooxygenase (COX) inhibitor, being marketed as an analgesic to manage postoperative pain as well as an ophthalmic solution to treat ocular pain and inflammation.1↗ Ketorolac potently inhibits COX-1 and COX-2 (IC50s = 20 nM) in vivo. In a mouse model of acute pain, ketorolac 30 mg/kg suppressed both pain and peripheral PGE2 levels.2↗ As typical of many NSAIDs, ketorolac is a racemic mixture. (S)-Ketorolac exhibits potent COX1 and COX2 (IC50s = 0.1 and 2.7 μM) inhibition, whereas (R)-ketorolac is >100-fold less active on both COX subtypes.3↗
1 Gordon, S.M., Brahim, J.S., Rowan, J., et al. Pharmacodynamics and drug action. Peripheral prostanoid levels and nonsteroidal anti-inflammatory drug analgesia: Replicate clinical trials in a tissue injury model. Clin Pharmacol Ther 72(2) 175-183 (2002).
2 Zhang, Y., Shaffer, A., Portanova, J., et al. Inhibition of cyclooxygenase-2 rapidly reverses inflammatory hyperalgesia and prostaglandin E2 production. J Pharmacol Exp Ther 283 1069-1075 (1997).
3 Handley, D.A., Cervoni, P., McCray, J.E., et al. Preclinical enantioselective pharmacology of (R)- and (S)- ketorolac. J Clin Pharmacol 38 25S-35S (1998).
Synonyms Acular LS®
RS 37619
Acular PF®
Sprix®
Formal Name 5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid
CAS Number 74103-06-3
Molecular Formula C15H13NO3
Formula Weight 255.3
Formulation A crystalline solid
Purity ≥95%
λmax 245, 312 nm
Stability 2 years
Storage Room temperature
Shipping Room temperature in continental US; may vary elsewhere
SMILES Copy O=C(C1=CC=C2N1CCC2C(O)=O)C3=CC=CC=C3
InCHI Code Copy 1S/C15H13NO3/c17-14(10-4-2-1-3-5-10)13-7-6-12-11(15(18)19)8-9-16(12)13/h1-7,11H,8-9H2,(H,18,19)
InCHI Key Copy OZWKMVRBQXNZKK-UHFFFAOYSA-N |