(6R,7R)-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-7-[2-(1H-1,2,3,4-tetrazol-1-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 126462
• Molecular Formular: C14H14N8O4S3
• Molecular Mass: 454.50716
• Monoisotopic Mass: 454.03001397
• SMILES: O=C1N2C(=C(CS[C@@H]2[C@@H]1NC(=O)Cn1nnnc1)CSc1nnc(s1)C)C(=O)O
• Canonical SMILES: O=C(N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)CSc1nnc(s1)C)Cn1cnnn1
• InChI: InChI=1S/C14H14N8O4S3/c1-6-17-18-14(29-6)28-4-7-3-27-12-9(11(24)22(12)10(7)13(25)26)16-8(23)2-21-5-15-19-20-21/h5,9,12H,2-4H2,1H3,(H,16,23)(H,25,26)/t9-,12-/m1/s1
• InChIKey: MLYYVTUWGNIJIB-BXKDBHETSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-7-[2-(1H-1,2,3,4-tetrazol-1-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: cefazolin; (6R,7R)-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-7-[2-(1H-1,2,3,4-tetrazol-1-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• Brand Name: Ancef, Kefzol
• Synonyms: Cefazolin; Cephamezine; Cefazolin

Database IDs

• CAS Number: 25953-19-9
• PubChem SID: 162220796
• PubChem CID: 33255
• CHEBI ID: 474053
• ATC CODE: J01DB04; QJ51DB04
• CHEMBL: 1435
• Chemspider ID: 30723
• DrugBank ID: DB01327
• KEGG ID: D02299
• Unique Ingredient Identifier: IHS69L0Y4T
• Wikipedia Title: Cefazolin

CALCULATED PROPERTIES

• Acid pKa: 3.0265586
• H Acceptors: 9
• H Donor: 2
• LogD (pH = 5.5): -3.9590034
• LogD (pH = 7.4): -4.991068
• Log P: -1.5194101
• Molar Refractivity: 119.8562 cm^3
• Polarizability: 39.86288 Å^3
• Polar Surface Area: 156.09 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Admin Routes: Intravenous, intramuscular
• Bioavailability: NA
• Excretion: Renal, unchanged
• Half Life: 1.8 hours (given IV); 2 hours (given IM)
• Legal Status: Rx-only
• Pregnancy Category: B (US); B1 (Australia)
• Mechanism of Action: Mucopeptide synthesis inhibitor

Product Information

• Application(s): Antibiotic

REFERENCES

• Shibata, H. et al., Antimicrob. Agents Chemother., 1970, 467, (props)
• Kariyone, K. et al., J. Antibiot., 1970, 23, 131, (synth, props)
• Zappala, A.E., Anal. Profiles Drug Subst., 1975, 4, 1, (rev)
• Nakano, H., Pharmacol. Biochem. Prop. Drug Subst., 1977, 1, 155, (rev)
• Van Meerssche, M. et al., Cryst. Struct. Commun., 1979, 8, 281, (cryst struct)
• Muneyuki, R. et al., Chem. Ind. (London), 1981, 159, (synth)
• Tori, K. et al., Tet. Lett., 1981, 22, 2793, (cmr)
• Palomo-Coll, A. et al., Tetrahedron, 1985, 41, 5133, (synth)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 3103, (synonyms)
• Kirk-Othmer Encycl. Chem. Technol., 4th edn., Wiley, 1991, 3, 28, (rev)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 140
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, CCS250