(6R,7R)-7-[2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-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: 152
• Molecular Formular: C16H17N9O5S3
• Molecular Mass: 511.55848
• Monoisotopic Mass: 511.05147769
• SMILES: S1[C@H]2N(C(=O)[C@H]2NC(=O)/C(=N/OC)/c2nc(sc2)N)C(=C(C1)CSc1n(nnn1)C)C(=O)O
• Canonical SMILES: CO/N=C(/C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)CSc1nnnn1C)\c1csc(n1)N
• InChI: InChI=1S/C16H17N9O5S3/c1-24-16(20-22-23-24)33-4-6-3-31-13-9(12(27)25(13)10(6)14(28)29)19-11(26)8(21-30-2)7-5-32-15(17)18-7/h5,9,13H,3-4H2,1-2H3,(H2,17,18)(H,19,26)(H,28,29)/b21-8+/t9-,13-/m1/s1
• InChIKey: HJJDBAOLQAWBMH-DKQCJYJNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-[2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-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; (6R,7R)-7-[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-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: (6R,7R)-7-[2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-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; bestcall
• Brand Name: Cefmax; Tacef; Bestcall
• Synonyms: (6R,7R)-7-[2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-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; Cefmenoxima [INN-Spanish]; Cefmenoxime hydrochloride; Cefmenoximum [INN-Latin]; Cefmenoxime

Database IDs

• CAS Number: 65085-01-0
• MDL Number: MFCD00864851
• PubChem SID: 160963615
• PubChem CID: 5361486

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.0366993
• H Acceptors: 11
• H Donor: 3
• LogD (pH = 5.5): -2.4868429
• LogD (pH = 7.4): -3.553978
• Log P: -1.4007788
• Molar Refractivity: 133.5115 cm^3
• Polarizability: 45.1463 Å^3
• Polar Surface Area: 190.81 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -0.13
• LOG S: -3.06
• Solubility (Water): 4.46e-01 g/l

PROPERTIES

Physical Property

• Melting Point: 159 - 161°C
• Hydrophobicity(logP): 0.252; -1.3

Product Information

• Purity: 95%

DETAILS

DrugBank - DB00267

• Drug Groups: approved
• Description: Cefmenoxime is a third-generation cephalosporin antibiotic. [Wikipedia]
• Indication: Used to treat female gynecologic and obstetric infections caused by susceptible aerobic (including the gonococcus) and anaerobic bacteria.
• Pharmacology: Cefmenoxime is a semisynthetic beta-lactam cephalosporin antibiotic with activity similar to that of cefotaxime. It has broad spectrum activity against Gram positive and Gram negative bacteria.
• Toxicity: Information on cefmenoxime overdosage in humans is not available. However, with other b-lactam antibiotics, adverse effects following overdosage have included nausea, vomiting, epigastric distress, diarrhea, and convulsions.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: Not appreciably metabolized.
• Absorption: Bioavailability is approximately 100% following intramuscular injection.
• Half Life: 1 hour
• Protein Binding: 50-70%
• References: Yokota N, Koguchi M, Suzuki Y, Fukayama S, Ishihara R, Deguchi K, Oda S, Tanaka S, Nakane Y, Fukumoto T: [Antibacterial activities of cefmenoxime against recent fresh clinical isolates from patients in sinusitis] Jpn J Antibiot. 1995 May;48(5):602-9. [Pubmed] ; Paladino JA, Fell RE: Pharmacoeconomic analysis of cefmenoxime dual individualization in the treatment of nosocomial pneumonia. Ann Pharmacother. 1994 Mar;28(3):384-9. [Pubmed] ; Duncker GI, Reich U, Krausse R: Cefmenoxime in corneal organ culture. Ophthalmologica. 1994;208(5):262-6. [Pubmed] ; Tsuchiya K, Kondo M, Kida M, Nakao M, Iwahi T, Nishi T, Noji Y, Takeuchi M, Nozaki Y: Cefmenoxime (SCE-1365), a novel broad-spectrum cephalosporin: in vitro and in vivo antibacterial activities. Antimicrob Agents Chemother. 1981 Jan;19(1):56-65. [Pubmed]
• External Links: Wikipedia

REFERENCES

• Yokota N, Koguchi M, Suzuki Y, Fukayama S, Ishihara R, Deguchi K, Oda S, Tanaka S, Nakane Y, Fukumoto T: [Antibacterial activities of cefmenoxime against recent fresh clinical isolates from patients in sinusitis] Jpn J Antibiot. 1995 May;48(5):602-9. Pubmed
• Paladino JA, Fell RE: Pharmacoeconomic analysis of cefmenoxime dual individualization in the treatment of nosocomial pneumonia. Ann Pharmacother. 1994 Mar;28(3):384-9. Pubmed
• Duncker GI, Reich U, Krausse R: Cefmenoxime in corneal organ culture. Ophthalmologica. 1994;208(5):262-6. Pubmed
• Tsuchiya K, Kondo M, Kida M, Nakao M, Iwahi T, Nishi T, Noji Y, Takeuchi M, Nozaki Y: Cefmenoxime (SCE-1365), a novel broad-spectrum cephalosporin: in vitro and in vivo antibacterial activities. Antimicrob Agents Chemother. 1981 Jan;19(1):56-65. Pubmed