CAS 65085-01-0|Tacef|Cefmenoxima [INN-Spanish]|bestcall|Cefmax|Cefmenoxime hydrochloride|(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-y...

General Information

Structure

Molecular Formula

C₁₆H₁₇N₉O₅S₃

Molecular Mass

511.55848

Exact Mass

511.05147769

Charge

0

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

Canonic Smiles

CO/N=C(/C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)CSc1nnnn1C)\c1csc(n1)N

Isomeric 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

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

Polarizability

45.1463

Polar Surface Area

190.81

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

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

Brand Name

CefmaxBestcallTacef

Synonyms

CefmenoximeCefmenoxime hydrochlorideCefmenoximum [INN-Latin]Cefmenoxima [INN-Spanish](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

IUPAC Traditional name

bestcall (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

IUPAC name

(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 (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

Names and Identifiers

Registration numbers

CAS Number

PubChem SID

MDL Number

PubChem CID

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

-1.3

0.252

Melting Point

159 - 161°C

Product Information

Purity

95%

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule 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]

Molecule Details

References

PubChem Literature

From Data Sources

• 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

• 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

• 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

• Duncker GI, Reich U, Krausse R: Cefmenoxime in corneal organ culture. Ophthalmologica. 1994;208(5):262-6. Pubmed

References

Bioactivity

PubChem BioAssay

Bioactivity

Molecule

ID:152