(7S)-7-{4-[carbamoyl(carboxy)methylidene]-1,3-dithietane-2-amido}-7-methoxy-3-{[(1-methyl-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: 1164
• Molecular Formular: C17H17N7O8S4
• Molecular Mass: 575.61898
• Monoisotopic Mass: 575.00214454
• SMILES: S1C2N(C(=O)[C@@]2(OC)NC(=O)C2S/C(=C(\C(=O)N)/C(=O)O)/S2)C(=C(C1)CSc1n(nnn1)C)C(=O)O
• Canonical SMILES: CO[C@@]1(NC(=O)C2S/C(=C(\C(=O)O)/C(=O)N)/S2)C(=O)N2C1SCC(=C2C(=O)O)CSc1nnnn1C
• InChI: InChI=1S/C17H17N7O8S4/c1-23-16(20-21-22-23)34-4-5-3-33-15-17(32-2,14(31)24(15)7(5)11(29)30)19-9(26)13-35-12(36-13)6(8(18)25)10(27)28/h13,15H,3-4H2,1-2H3,(H2,18,25)(H,19,26)(H,27,28)(H,29,30)/b12-6-/t13?,15?,17-/m0/s1
• InChIKey: SRZNHPXWXCNNDU-PWIJFWJWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (7S)-7-{4-[carbamoyl(carboxy)methylidene]-1,3-dithietane-2-amido}-7-methoxy-3-{[(1-methyl-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: (7S)-7-{4-[carbamoyl(carboxy)methylidene]-1,3-dithietane-2-amido}-7-methoxy-3-{[(1-methyl-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• Brand Name: Cefotan; Yamatetan
• Synonyms: Cefotetanum [inn-latin]; Cefotetan

Database IDs

• CAS Number: 69712-56-7
• PubChem SID: 160964627
• PubChem CID: 50614

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.2314074
• H Acceptors: 11
• H Donor: 4
• LogD (pH = 5.5): -4.074055
• LogD (pH = 7.4): -6.970815
• Log P: -0.37600145
• Molar Refractivity: 153.5523 cm^3
• Polarizability: 50.305107 Å^3
• Polar Surface Area: 219.93 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -0.65
• LOG S: -3.04
• Solubility (Water): 5.21e-01 g/l

DETAILS

DrugBank - DB01330

• Drug Groups: approved
• Description: A semisynthetic cephamycin antibiotic that is administered intravenously or intramuscularly. The drug is highly resistant to a broad spectrum of beta-lactamases and is active against a wide range of both aerobic and anaerobic gram-positive and gram-negative microorganisms. [PubChem]
• Indication: For prophylaxis and treatment of bacterial infections.
• Pharmacology: Cefotetan is a semisynthetic cephamycin antibiotic that is administered intravenously or intramuscularly. The drug is highly resistant to a broad spectrum of beta-lactamases and is active against a wide range of both aerobic and anaerobic gram-positive and gram-negative microorganisms.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: No active metabolites of cefotetan have been detected; however, small amounts (less than 7%) of cefotetan in plasma and urine may be converted to its tautomer, which has antimicrobial activity similar to the parent drug.
• Half Life: In volunteers with reduced renal function, the plasma half-life of cefotetan is prolonged
• Protein Binding: Cefotetan is 88% plasma protein bound.
• Elimination: No active metabolites of cefotetan have been detected; however, small amounts (less than 7%) of cefotetan in plasma and urine may be converted to its tautomer, which has antimicrobial activity similar to the parent drug. In normal patients, from 51% to 81% of an administered dose of Cefotetan is excreted unchanged by the kidneys over a 24 hour period, which results in high and prolonged urinary concentrations.
• Distribution: * 10.4 L [elderly patients (greater than 65 years) with normal renal function]; * 10.3 L [healthy volunteers (aged 25 to 28 years)]
• Clearance: * 1.8 +/- 0.1 L/h [elderly patients with normal renal function (.65 years)]; * 1.8 +/- 0.3 L/h [healthy volunteers (aged 25 to 28 years)]
• External Links: Wikipedia; RxList; Drugs.com