Basic information
- CAS
66635-92-5- Standard SMILES
O=C(c1ccccc1)c1ccc2n1CC[C@@H]2C(=O)O- InChIKey
OZWKMVRBQXNZKK-NSHDSACASA-N- Molecular formula
- C15H13NO3
- Average molar mass
- 255.27 g/mol
- Monoisotopic mass
- 255.08954328
Overview
(S)-ketorolac is a 5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid that has S configuration. While (S)-ketorolac is a COX1 and COX2 inhibitor, both enantiomers exhibit analgesic effects. Racemic ketorolac, known simply as ketorolac, is used (mainly as the 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. It has a role as a non-steroidal anti-inflammatory drug, an analgesic, a cyclooxygenase 2 inhibitor and a cyclooxygenase 1 inhibitor. It is an enantiomer of a (R)-ketorolac.
Names & identifiers
- Preferred name
- (-)-Ketorolac
- IUPAC
- (1S)-5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid
- English name
- (S)-Ketorolac
- Molecular formula
- C15H13NO3
- Molecular weight
- 255.27
Names & synonyms
(S)-Ketorolac(-)-KetorolacKetorolac, (S)-S-(-)-Ketorolac(S)-(-)-ketorolacUNII-5H3TJ0A81K5H3TJ0A81KCHEBI:762281H-Pyrrolizine-1-carboxylic acid, 5-benzoyl-2,3-dihydro-, (1S)-RefChem:19635766635-92-5(1S)-5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid
Show more names
Ketorolac S-IsoMer(S)-Ketorolac ISO 9001：2015 REACHKetorolac impurity 2/Ketorolac S-IsomerPhosphorousacid,tris(1,5-dimethylethyl)ester
(S)-5-Benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acidCHEMBL4962401H-Pyrrolizine-1-carboxylicacid, 5-benzoyl-2,3-dihydro-, (1S)-1H-Pyrrolizine-1-carboxylic acid, 5-benzoyl-2,3-dihydro-, (S)-S-KetorolacSCHEMBL14892orb1708613HY-B0580A
Database identifiers
- CAS
66635-92-5- PubChem CID
- 181817
- DTXSID
DTXSID901317534- ChEMBL
CHEMBL496240
Properties
Computed structural properties
- XLogP
- 1.9
- Topological polar surface area
- 59.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 3
- Heavy atoms
- 19
- Formal charge
- 0
- Complexity
- 376
Physicochemical properties
- Melting point
- 160 · 160-167C
- Boiling point
- 493.2 · 493.2±40.0 °C(Predicted)
- Density
- 1.33 · 1.33±0.1 g/cm3(Predicted)
- storage temp.
- Refrigerator
- solubility
- 1 mg/ml; · Chloroform: Slightly; Ethanol: >1mg/ml; Methanol: Slightly
- form
- A crystalline solid
- pka
- 4.29 · 4.29±0.20(Predicted)
- color
- White to off-white
- optical activity
- -165 to · [α]/D -165 to -185°, c =0.5 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-/m0/s1
- InChIKey
- OZWKMVRBQXNZKK-NSHDSACASA-N
- SMILES
- [n]21c(ccc2C(=O)c3ccccc3)[C@H](CC1)C(=O)O
- FDA UNII
- 5 H3TJ0A81K · 5H3TJ0A81K
- UNSPSC Code
- 51111800 · 51111800
- NACRES
- 77 · NA.77
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 3 (100%)
Safety data
- wgk
- WGK 3
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard statements
- H301
- Hazard Classifications
- Acute Tox. 3 Oral
- Precautionary statements
- P264-P270-P301+P310-P405-P501
Chemistry & industry
Applications
Description(S)-Ketorolac is a non-selective COX inhibitor and non-steroidal anti-inflammatory drug (NSAID; IC50s = 0.1 and 2.7 μM for COX-1 and COX-2, respectively). (S)-Ketorolac is approximately twice as potent as the racemic mixture and 60 times more potent than (R)-ketorolac in a rat pain assay. (S)-Ketorolac is cleared from rat kidney and liver more quickly than (R)-ketorolac. Formulations containing ketorolac have been used to manage postoperative pain as well as an ophthalmic solution to treat ocular pain and inflammation.
UsesThe R-enantiomer of Ketorolac. The (S)-enantiomer is about 60 times more potent than (R)-enantiomer. Prostaglandin biosynthesis inhibitor. Analgesic; anti-inflammatory.
Uses(S)-Ketorolac is the S-enantiomer of Ketorolac. The (S)-enantiomer is about 60 times more potent than (R)-enantiomer. Prostaglandin biosynthesis inhibitor. Analgesic; anti-inflammatory.
Suppliers48 total
上海策嵘生物科技有限公司[email protected]
济南百隆化学有限公司[email protected] · [email protected]
武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]
广州隽沐生物科技股份有限公司020-36607679; 13502246435 · [email protected]
陕西缔都化学有限公司029-029-81123119 17391733320 · [email protected]
南京望知星医药科技有限公司18569809817 · [email protected]
Sinco Pharmachem (ShenZhen) R&D Co., Ltd.+86-18603013401 · [email protected]
上海波以尔化工有限公司
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…