Cefapirin
Chemical compound
- J01DB08 (WHO) QG51AA05 (WHO) QJ51DB08 (WHO)
- US: ℞-only
- 21593-23-7 Y
- 30699
- DB01139 Y
- 28486 Y
- 89B59H32VN
- D07636 Y
- CHEBI:554446 Y
- ChEMBL1599 Y
- DTXSID9022784
- Interactive image
- O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)CSc3ccncc3)COC(=O)C)C(=O)O
InChI
- InChI=1S/C17H17N3O6S2/c1-9(21)26-6-10-7-28-16-13(15(23)20(16)14(10)17(24)25)19-12(22)8-27-11-2-4-18-5-3-11/h2-5,13,16H,6-8H2,1H3,(H,19,22)(H,24,25)/t13-,16-/m1/s1 Y
- Key:UQLLWWBDSUHNEB-CZUORRHYSA-N Y
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.[1]
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.[citation needed]
Synthesis
In one of the syntheses, 7-aminocephalosporanic acid (7-ACA) is reacted with bromoacetyl chloride to give the amide. The halo group is then displaced by 4-thiopyridine.[2]
References
- ^ "CEFADYL". U.S. Food and Drug Administration.
- ^ a b Crast LB, Graham RG, Cheney LC (December 1973). "Synthesis of cephapirin and related cephalosporins from 7-(alpha-bromoacetamido)cephalosporanic acid". Journal of Medicinal Chemistry. 16 (12): 1413–5. doi:10.1021/jm00270a025. PMID 4148798.
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(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
transpeptidases)
Lipopeptides |
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Other |
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- Inhibit PG subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin)
- DADAL/AR inhibitors (Cycloserine)
- bactoprenol inhibitors (Bacitracin)
- Hydrolyze NAM-NAG
- Tyrothricin
- Isoniazid#
- Teixobactin
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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