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34444-01-4 molecular structure
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(6R,7R)-7-[(2R)-2-hydroxy-2-phenylacetamido]-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: 1160
Molecular Formular: C18H18N6O5S2
Molecular Mass: 462.50272
Monoisotopic Mass: 462.07800971
SMILES and InChIs

SMILES:
S1[C@H]2N(C(=O)[C@H]2NC(=O)[C@H](O)c2ccccc2)C(=C(C1)CSc1n(nnn1)C)C(=O)O
Canonical SMILES:
O[C@@H](C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)CSc1nnnn1C)c1ccccc1
InChI:
InChI=1S/C18H18N6O5S2/c1-23-18(20-21-22-23)31-8-10-7-30-16-11(15(27)24(16)12(10)17(28)29)19-14(26)13(25)9-5-3-2-4-6-9/h2-6,11,13,16,25H,7-8H2,1H3,(H,19,26)(H,28,29)/t11-,13-,16-/m1/s1
InChIKey:
OLVCFLKTBJRLHI-AXAPSJFSSA-N

Cite this record

CBID:1160 http://www.chembase.cn/molecule-1160.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(6R,7R)-7-[(2R)-2-hydroxy-2-phenylacetamido]-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
cefamandole
Brand Name
Mandol
Synonyms
Cefadole
Cefamandole nafate
Cefamandole
CAS Number
34444-01-4
PubChem SID
46508882
160964623
PubChem CID
456255

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 3.3241954  H Acceptors
H Donor LogD (pH = 5.5) -2.132789 
LogD (pH = 7.4) -3.3938322  Log P 0.027085615 
Molar Refractivity 126.6455 cm3 Polarizability 43.361332 Å3
Polar Surface Area 150.54 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -0.05  LOG S -2.9 
Solubility (Water) 5.81e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Hydrophobicity(logP)
0.50 [SANGSTER (1994)] expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB01326 external link
Item Information
Drug Groups approved
Description Cefamandole (INN, also known as cephamandole) is a broad-spectrum cephalosporin antibiotic. The clinically used form of cefamandole is the formate ester cefamandole nafate, a prodrug which is administered parenterally. Cefamandole is no longer available in the United States.
Indication For the treatment of serious infections caused by susceptible strains of microorganisms.
Pharmacology Cefamandole is a broad-spectrum cephalosporin antibiotic. The clinically used form of cefamandole is the formate ester cefamandole nafate, a prodrug which is administered parenterally. The bactericidal action of cefamandole results from inhibition of cell-wall synthesis. Cephalosporins have in vitro activity against a wide range of gram-positive and gram-negative organisms.
Toxicity Symptoms of overdose include blood in the urine, diarrhea, nausea, upper abdominal pain, and vomiting.
Affected Organisms
Enteric bacteria and other eubacteria
Half Life The half-life after an intravenous dose is 32 minutes; after intramuscular administration, the half-life is 60 minutes.
Protein Binding 75%
External Links
Wikipedia
RxList

REFERENCES

REFERENCES

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PATENTS

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