Structure via PubChem · Public domain (PubChem)
cefapirin
Sign in to saveAlso known as Cefadyl, Cefa-Lak, (6R,7R)-3-(Acetoxymethyl)-8-oxo-7-{[(pyridin-4-ylsulfanyl)acetyl]amino}-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, CEPR, Cefaprin, Cephapirine, Cephapirin, Cefapirina
Cefapirin (INN, also spelled cephapirin) is an injectable, first-generation cephalosporin antibiotic. It is marketed under the trade name Cefadyl. Production for use in humans has been discontinued in the United States.
Chemical data
- Formula
- C17H17N3O6S2
- Molecular weight
- 423.5 g/mol
- IUPAC name
- (6R,7R)-3-(acetyloxymethyl)-8-oxo-7-[(2-pyridin-4-ylsulfanylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- SMILES
- CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)CSC3=CC=NC=C3)SC1)C(=O)O
- InChIKey
- UQLLWWBDSUHNEB-CZUORRHYSA-N
- XLogP
- -1.1
- Polar surface area
- 177 Ų
- H-bond donors
- 2
- H-bond acceptors
- 9
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1974
- Admin. routes
- parenteral
- Indications
- bacterial disease
via ChEMBL · EBI
Research
680 papers- Assessment of the Usefulness of Cefapirin and Cefalonium Disks for Susceptibility Testing of Staphylococcus aureus Isolates from Bovine Mastitis.Antibiotics (Basel, Switzerland) · 2020
- Prednisolone and cefapirin act synergistically in resolving experimental Escherichia coli mastitis.Journal of dairy science · 2013
- BestBETs for Vets.The Veterinary record · 2017
- [Cephalosporins].Nederlands tijdschrift voor geneeskunde · 1975
- Ecotoxicity of the two veterinarian antibiotics ceftiofur and cefapirin before and after photo-transformation.The Science of the total environment · 2018
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 423.055877
- Has use
- medication
Show 7 more facts
- defined daily dose
- 4
- chemical formula
- C₁₇H₁₇N₃O₆S₂
- subject has role
- bactericide
- canonical SMILES
- CC(=O)OCC1=C(N2C(C(C2=O)NC(=O)CSC3=CC=NC=C3)SC1)C(=O)O
- isomeric SMILES
- CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)CSC3=CC=NC=C3)SC1)C(=O)O
- medical condition treated
- staphylococcal infection
- Commons category
- Cefapirin
Sources (3)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- Synthesis
- References
Cefapirin (INN, also spelled cephapirin) is an injectable, first-generation cephalosporin antibiotic. It is marketed under the trade name Cefadyl. Production for use in humans has been discontinued in the United States.
It also has a role in veterinary medicine as Metricure, an intrauterine preparation, and combined with prednisolone in Mastiplan, an intramammary preparation. Both are licensed in cattle.
Excerpted from Wikipedia’s “cefapirin” article, available under the CC BY-SA 4.0 licence.