Structure via PubChem · Public domain (PubChem)
سفاپیرین
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