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SML1654

Sigma-Aldrich

R-Ketorolac

≥95% (HPLC)

Synonym(s):

(+)-Ketorolac, (1R)-5-Benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid;, (R)-(+)-ketorolac, (R)-Ketorolac

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About This Item

Empirical Formula (Hill Notation):
C15H13NO3
CAS Number:
66635-93-6
Molecular Weight:
255.27
MDL number:
MFCD00871492
UNSPSC Code:
12352200
PubChem Substance ID:
329825993

Quality Level

100

Assay

≥95% (HPLC)

form

powder

optical activity

[α]/D +162 to +178°, c = 1 in methanol

color

white to beige

solubility

DMSO: 25 mg/mL, clear

storage temp.

−20°C

SMILES string

O=C(O)[C@H]1C2=CC=C(C(C3=CC=CC=C3)=O)N2CC1

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

InChI key

OZWKMVRBQXNZKK-LLVKDONJSA-N

Biochem/physiol Actions

Ketorolac ((rac)-5-benzoyl-1,2-3H-pyrrolo[1,2a] pyrrole1-carboxylic acid) is a non-steroidal anti-inflammatory drug (NSAID). It is used as a racemic mixture that contains a 1:1 ratio of the R(+) and S(−) stereoisomers. It is broadly used off-label as a parenteral analgesic in children. Ketorolac serves as a non-narcotic analgesic. It prevents the synthesis of prostaglandins, peripheral to the central nervous system.
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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315 - H319 - H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Tudor I Oprea et al.
Drug discovery today. Therapeutic strategies, 8(3-4), 61-69 (2012-03-01)
Academia and small business research units are poised to play an increasing role in drug discovery, with drug repurposing as one of the major areas of activity. Here we summarize project status for a number of drugs or classes of
Enantiomer?selective pharmacokinetics and metabolism of ketorolac in children.
Kauffman RE, et al.
Clinical Pharmacology and Therapeutics, 65(4), 382-388 (1999)
The pharmacokinetics of ketorolac enantiomers following intramuscular administration of the racemate.
Hayball PJ, et al.
British Journal of Clinical Pharmacology, 37(1), 75-78 (1994)
Yuna Guo et al.
Molecular cancer therapeutics, 14(10), 2215-2227 (2015-07-25)
Cdc42 (cell division control protein 42) and Rac1 (Ras-related C3 botulinum toxin substrate 1) are attractive therapeutic targets in ovarian cancer based on established importance in tumor cell migration, adhesion, and invasion. Despite a predicted benefit, targeting GTPases has not
Tudor I Oprea et al.
PloS one, 10(11), e0142182-e0142182 (2015-11-13)
Rho family GTPases (including Rac, Rho and Cdc42) collectively control cell proliferation, adhesion and migration and are of interest as functional therapeutic targets in numerous epithelial cancers. Based on high throughput screening of the Prestwick Chemical Library® and cheminformatics we
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