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(R)-(+)-Ketorolac

Product Name(R)-(+)-Ketorolac
CAS66635-93-6
MFC15H13NO3
MW255.27
EINECS
MOL File66635-93-6.mol

Chemical Properties

Melting point	163-170°C
storage temp.	-20°C
solubility	Chloroform (Slightly), Methanol (Slightly)
form	powder
color	white to beige
optical activity	[α]/D +162 to +178°, c = 1 in methanol
InChI	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)/t11-/m1/s1
InChIKey	OZWKMVRBQXNZKK-LLVKDONJSA-N
SMILES	O=C(O)[C@H]1C2=CC=C(C(C3=CC=CC=C3)=O)N2CC1

Safety Information

WGK Germany	WGK 3
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

Usage And Synthesis

Chemical Properties

Off-White Solid

Uses

(R)-Ketorolac is the R-enantiomer of Ketorolac. The (S)-enantiomer is about 60 times more potent than (R)-enantiomer. Prostaglandin biosynthesis inhibitor. Analgesic; anti-inflammatory.

Definition

ChEBI: A 5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid that has R configuration. Unlike the S-enantiomer, it does not exhibit COX1 and COX2 inhibition, but does exhibit analgesic activity. Racemic keto olac, known simply as ketorolac, is used (mainly as a tromethamine salt) as a potent analgesic for the short-term management of post-operative pain, and in eye drops to relieve the ocular itching associated with seasonal allergic conjunctivitis.

Biochem/physiol Actions

R-Ketorolac is potent and selective Rho-family GTPases Cdc42 (cell division control protein 42) and Rac1 (Ras-related C3 botulinum toxin substrate 1) allosteric inhibitor that modulates downstream GTPase-dependent physiologic responses critical to tumor metastasis. R-ketorolac significantly inhibits ovarian cancer cell adhesion, migration, and invasion.

in vivo

(R)-Ketorolac (2 mg/kg, p.o., daily) ameliorates cancer-associated cachexia and prolongs survival of C26 tumour-bearing mice^[3].

Animal Model:	C26 tumour-bearing mice^[3]
Dosage:	2 mg/kg
Administration:	Oral gavage (p.o.), every day after cachexia onset
Result:	Prolonged survival and alleviates C26-induced weight loss independent of tumour growth and food intake. Showed a tumour weight of 0.7 g and a weight loss of 0.61 g. Did not affect C26-associated hepatosplenomegaly and splenic lymphocyte numbers. Prevented C26-induced T-lymphopenia.

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