Structure via PubChem · Public domain (PubChem)
cefamandole
Sign in to saveAlso 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.
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 Ų
- 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
via Wikidata · CC0
~3 min read
Encyclopedic overview
2 sectionsContents
- 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
| tradename = former Mandol | Drugs.com = | MedlinePlus = a601206 | pregnancy_AU = B1 | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = POM | legal_US = | legal_US_comment = Discontinued | routes_of_administration = Intramuscular, intravenous
Excerpted from Wikipedia’s “cefamandole” article, available under the CC BY-SA 4.0 licence.