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

• ChemBase ID: 114
• Molecular Formular: C18H23N9O4S3
• Molecular Mass: 525.62812
• Monoisotopic Mass: 525.10351326
• SMILES: S1[C@H]2N(C(=O)[C@H]2NC(=O)Cc2nc(sc2)N)C(=C(C1)CSc1n(nnn1)CCN(C)C)C(=O)O
• Canonical SMILES: CN(CCn1nnnc1SCC1=C(C(=O)O)N2[C@H](SC1)[C@@H](C2=O)NC(=O)Cc1csc(n1)N)C
• InChI: InChI=1S/C18H23N9O4S3/c1-25(2)3-4-26-18(22-23-24-26)34-7-9-6-32-15-12(14(29)27(15)13(9)16(30)31)21-11(28)5-10-8-33-17(19)20-10/h8,12,15H,3-7H2,1-2H3,(H2,19,20)(H,21,28)(H,30,31)/t12-,15-/m1/s1
• InChIKey: QYQDKDWGWDOFFU-IUODEOHRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-[2-(2-amino-1,3-thiazol-4-yl)acetamido]-3-[({1-[2-(dimethylamino)ethyl]-1H-1,2,3,4-tetrazol-5-yl}sulfanyl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: cefotiam
• Brand Name: Ceradon
• Synonyms: Abbott 48999; Spizef; Sporidyn; Cefotiam Dihydrochloride; (6R,7R)-7-[[2-(2-Amino-4-thiazolyl)acetyl]amino]-3-[[[1-[2-(dimethylamino)ethyl]-1H-tetrazol-5-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Hydrochloride; Cefotiam hydrochloride; Cefotiamum [INN-Latin]; CTM; Cefotiam

Database IDs

• CAS Number: 66309-69-1; 61622-34-2
• PubChem SID: 46506679; 160963577
• PubChem CID: 43708

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.794902
• H Acceptors: 10
• H Donor: 3
• LogD (pH = 5.5): -3.1281393
• LogD (pH = 7.4): -3.1065228
• Log P: -3.0857437
• Molar Refractivity: 142.3365 cm^3
• Polarizability: 48.78519 Å^3
• Polar Surface Area: 172.46 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -0.33
• LOG S: -2.61
• Solubility (Water): 1.29e+00 g/l

PROPERTIES

Physical Property

• Solubility: Soluble
• Hydrophobicity(logP): -2.1

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

DrugBank - DB00229

• Drug Groups: approved
• Description: One of the cephalosporins that has a broad spectrum of activity against both gram-positive and gram-negative microorganisms. [PubChem]
• Indication: For treatment of severe infections caused by susceptible bacteria.
• Pharmacology: Cefotiam is a third generation beta-lactam cephalosporin antibiotic. It has broad spectrum activity against Gram positive and Gram negative bacteria. It does not have activity against Pseudomonas aeruginosa. Cefotiam works by inhibiting bacterial cell wall biosynthesis.
• Toxicity: Adverse effects following overdosage include nausea, vomiting, epigastric distress, diarrhea, and convulsions.
• Affected Organisms: Enteric bacteria and other eubacteria
• Absorption: Rapidly absorbed following intramuscular injection. Bioavailability is 60% following intramuscular injection.
• Half Life: Approximately 1 hour.
• Protein Binding: 40%
• References: Muller R, Bottger C, Wichmann G: Suitability of cefotiam and cefuroxime axetil for the perioperative short-term prophylaxis in tonsillectomy patients. Arzneimittelforschung. 2003;53(2):126-32. [Pubmed] ; Kolben M, Mandoki E, Ulm K, Freitag K: Randomized trial of cefotiam prophylaxis in the prevention of postoperative infectious morbidity after elective cesarean section. Eur J Clin Microbiol Infect Dis. 2001 Jan;20(1):40-2. [Pubmed] ; Shimizu S, Chen KR, Miyakawa S: Cefotiam-induced contact urticaria syndrome: an occupational condition in Japanese nurses. Dermatology. 1996;192(2):174-6. [Pubmed]
• External Links: Wikipedia

Toronto Research Chemicals - C243005

Cephalosporin Antibiotic.

REFERENCES

• Muller R, Bottger C, Wichmann G: Suitability of cefotiam and cefuroxime axetil for the perioperative short-term prophylaxis in tonsillectomy patients. Arzneimittelforschung. 2003;53(2):126-32. Pubmed
• Kolben M, Mandoki E, Ulm K, Freitag K: Randomized trial of cefotiam prophylaxis in the prevention of postoperative infectious morbidity after elective cesarean section. Eur J Clin Microbiol Infect Dis. 2001 Jan;20(1):40-2. Pubmed
• Shimizu S, Chen KR, Miyakawa S: Cefotiam-induced contact urticaria syndrome: an occupational condition in Japanese nurses. Dermatology. 1996;192(2):174-6. Pubmed
• Murata, H., et al.: J. Hepatol., 38, 573 (2003)
• Osawa, M., et al.: Legal Med., 10, 143 (2003)
• Fliri, A., et al.: J. Med. Chem., 52, 8038 (2003)