cefamandole

Also known as Cefamandolum, Cephadole, Cefadole, Cephamandole, Cefamandole nafate, L-Cefamandole, Cefamandol, (6R,7R)-7-(R)-Mandelamido-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-carboxylic acid

Cefamandole (INN, also known as cephamandole) is a second-generation 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.

In the Vinony graph

Within Vinony's link graph, cefamandole is referenced by 196 other articles, and connects out to antibiotic, ceftolozane/tazobactam and International Standard Book Number.

It is catalogued under topics including Acetaldehyde dehydrogenase inhibitors, Cephalosporin antibiotics and Drugboxes which contain changes to watched fields.

Its subject is documented across 19 Wikipedia language editions.

Chemical data

Formula: C18H18N6O5S2
Molecular weight: 462.5 g/mol
IUPAC name: (6R,7R)-7-[[(2R)-2-hydroxy-2-phenylacetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
SMILES: CN1C(=NN=N1)SCC2=C(N3[C@@H]([C@@H](C3=O)NC(=O)[C@@H](C4=CC=CC=C4)O)SC2)C(=O)O
InChIKey: OLVCFLKTBJRLHI-AXAPSJFSSA-N
XLogP: -0.9
Polar surface area: 201 Å²
H-bond donors: 3
H-bond acceptors: 10
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
Indications: osteomyelitis, bacterial disease

via ChEMBL · EBI

Research

2,979 papers

Cefamandole and cefoxitin.Annals of internal medicine · 1985
[Cefamandole-induced acute kidney failure].Orvosi hetilap · 1988
Cefamandole and beta-lactamases.British medical journal · 1978
Cefamandole pharmacokinetics during standard and pulsatile cardiopulmonary bypass.Journal of clinical pharmacology · 1988
Cefamandole and cefoxitin.The Medical letter on drugs and therapeutics · 1979

via PubMed

Wikidata facts

Mass: 462.078
Has use: medication

Show 8 more facts

chemical formula: C₁₈H₁₈N₆O₅S₂
medical condition treated: staphylococcal infection
isomeric SMILES: CN1C(=NN=N1)SCC2=C(N3[C@@H]([C@@H](C3=O)NC(=O)[C@@H](C4=CC=CC=C4)O)SC2)C(=O)O
canonical SMILES: CN1C(=NN=N1)SCC2=C(N3C(C(C3=O)NC(=O)C(C4=CC=CC=C4)O)SC2)C(=O)O
World Health Organisation international non-proprietary name: cefamandole
defined daily dose: 6
subject has role: bactericide
Commons category: Cefamandole

Sources (5)

via Wikidata · CC0

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Encyclopedic overview

2 sections

Contents

See also
References

{{Drugbox | Watchedfields = changed | verifiedrevid = 443508077 | IUPAC_name = (6R,7R)-7-{[(2R)-2-hydroxy-2-phenylacetyl]amino}-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | image = Cefamandole.svg | image_class = skin-invert-image

Excerpted from Wikipedia’s “cefamandole” article, available under the CC BY-SA 4.0 licence.