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65085-01-0 molecular structure
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(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

ChemBase ID: 152
Molecular Formular: C16H17N9O5S3
Molecular Mass: 511.55848
Monoisotopic Mass: 511.05147769
SMILES and InChIs

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

Cite this record

CBID:152 http://www.chembase.cn/molecule-152.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
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
Brand Name
Cefmax
Tacef
Bestcall
Synonyms
Cefmenoxima [INN-Spanish]
Cefmenoxime hydrochloride
Cefmenoximum [INN-Latin]
Cefmenoxime
(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
CAS Number
65085-01-0
MDL Number
MFCD00864851
PubChem SID
160963615
PubChem CID
5361486

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Enamine
EN300-122381 external link Add to cart Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 3.0366993  H Acceptors 11 
H Donor LogD (pH = 5.5) -2.4868429 
LogD (pH = 7.4) -3.553978  Log P -1.4007788 
Molar Refractivity 133.5115 cm3 Polarizability 45.1463 Å3
Polar Surface Area 190.81 Å2 Rotatable Bonds
Lipinski's Rule of Five false 
Log P -0.13  LOG S -3.06 
Solubility (Water) 4.46e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Product Information Bioassay(PubChem)
Melting Point
159 - 161°C expand Show data source
Hydrophobicity(logP)
0.252 expand Show data source
-1.3 expand Show data source
Purity
95% expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00267 external link
Item Information
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

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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
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