Cefalotin (original) (raw)
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Chemical compound
Cefalotin
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|---|---|
| Clinical data | |
| AHFS/Drugs.com | International Drug Names |
| MedlinePlus | a682860 |
| Pregnancy category | AU: A |
| Routes of administration | Intravenous |
| ATC code | J01DB03 (WHO) |
| Legal status | |
| Legal status | AU: S4 (Prescription only) UK: POM (Prescription only) |
| Pharmacokinetic data | |
| Bioavailability | n/a |
| Protein binding | 65 to 80% |
| Metabolism | Hepatic |
| Elimination half-life | 30 minutes to 1 hour |
| Excretion | Renal |
| Identifiers | |
| IUPAC name (6_R_,7_R_)-3-[(acetoxy)methyl]-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | |
| CAS Number | 153-61-7  Y |
| PubChem CID | 6024 |
| DrugBank | DB00456 Y |
| ChemSpider | 5802 Y |
| UNII | R72LW146E6 |
| KEGG | D07635 Y |
| ChEBI | CHEBI:124991 Y |
| ChEMBL | ChEMBL617 Y |
| CompTox Dashboard (EPA) | DTXSID4022783  |
| ECHA InfoCard | 100.005.288 |
| Chemical and physical data | |
| Formula | C16H16N2O6S2 |
| Molar mass | 396.43 g·mol−1 |
| 3D model (JSmol) | Interactive image |
| Melting point | 160 to 160.5 °C (320.0 to 320.9 °F) |
| SMILES O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)Cc3sccc3)COC(=O)C)C(=O)O | |
| InChI InChI=1S/C16H16N2O6S2/c1-8(19)24-6-9-7-26-15-12(14(21)18(15)13(9)16(22)23)17-11(20)5-10-3-2-4-25-10/h2-4,12,15H,5-7H2,1H3,(H,17,20)(H,22,23)/t12-,15-/m1/s1 YKey:XIURVHNZVLADCM-IUODEOHRSA-N Y |
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Cefalotin (INN) or cephalothin (USAN) is a first-generation cephalosporin antibiotic with broad spectrum antibiotic activity.[1][2] It was the first cephalosporin marketed (1964) and continues to be widely used.[3] Cefalotin is used for bacterial infections of the respiratory tract, urinary tract, skin, soft tissues, bones and joints, sepsis, peritonitis, osteomyelitis, mastitis, infected wounds, and post-operational infections.[2]
It is an intravenously administered agent with a similar antimicrobial spectrum to cefazolin and the oral agents cefalexin and cefadroxil. Cefalotin sodium is marketed as Keflin (Lilly) and under other trade names.[4]
The compound is a derivative of thiophene-2-acetic acid.[5]
- ^ Hameed TK, Robinson JL (July 2002). "Review of the use of cephalosporins in children with anaphylactic reactions from penicillins". The Canadian Journal of Infectious Diseases. 13 (4): 253–8. doi:10.1155/2002/712594. PMC 2094874. PMID 18159398.
- ^ a b "Cefalotin - an overview | ScienceDirect Topics". www.sciencedirect.com. Retrieved 2024-01-26.
- ^ Greenwood D (21 February 2008). Antimicrobial Drugs: Chronicle of a Twentieth Century Medical Triumph. OUP Oxford. pp. 128–. ISBN 978-0-19-953484-5.
- ^ International Drug Names: Cefalotin
- ^ Swanston, Jonathan (2006). "Thiophene". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a26_793.pub2. ISBN 3527306730..