(1S)-5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid

• ChemBase ID: 172112
• Molecular Formular: C15H13NO3
• Molecular Mass: 255.26862
• Monoisotopic Mass: 255.08954328
• SMILES: c12n(c(cc1)C(=O)c1ccccc1)CC[C@@H]2C(=O)O
• Canonical SMILES: OC(=O)[C@H]1CCn2c1ccc2C(=O)c1ccccc1
• InChI: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S)-5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid
• IUPAC Traditional name: (1S)-5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid
• Synonyms: (1S)-5-Benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic Acid; (-)-Ketorolac; S-(-)-Ketorolac; (S)-Ketorolac; (1R)-5-Benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic Acid; (+)-Ketorolac; R-(+)-Ketorolac; (R)-Ketorolac

Database IDs

• CAS Number: 66635-93-6; 66635-92-5
• PubChem SID: 164228022
• PubChem CID: 181817

CALCULATED PROPERTIES

• Acid pKa: 3.8351793
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.6151371
• LogD (pH = 7.4): -0.9625098
• Log P: 2.2833629
• Molar Refractivity: 70.1945 cm^3
• Polarizability: 26.83597 Å^3
• Polar Surface Area: 59.3 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White Solid
• Melting Point: 160-167°C; 163-170°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - K235605

(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.

Toronto Research Chemicals - K235600

(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.

REFERENCES

• Rooks, W.H., et al.: Agents Actions, 12, 684 (1982)
• Guzman, A., et al.: J. Med. Chem., 29, 589 (1982)
• McQuary, H.J., et al.: Clin. Pharmacol. Ther., 39, 89 (1982)
• Rooks, W.H., et al.: Agents Actions, 12, 684 (1982)
• Guzman, A., et al.: J. Med. Chem., 29, 589 (1982)
• McQuary, H.J., et al.: Clin. Pharmacol. Ther., 39, 89 (1982)