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(Top) 1 Synthesis 2 References

Cefapirin

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Cefapirin
Clinical data

AHFS/Drugs.com	International Drug Names
MedlinePlus	a601206
Routes of administration	Intravenous, intramuscular
ATC code	J01DB08 (WHO) QG51AA05 (WHO) QJ51DB08 (WHO)
Legal status
Legal status	US: ℞-only
Identifiers
CAS Number	21593-23-7^Y
PubChem CID	30699
DrugBank	DB01139^Y
ChemSpider	28486^Y
UNII	89B59H32VN
KEGG	D07636^Y
ChEBI	CHEBI:554446^Y
ChEMBL	ChEMBL1599^Y
CompTox Dashboard (EPA)	DTXSID9022784
ECHA InfoCard	100.040.409
Chemical and physical data
Formula	C₁₇H₁₇N₃O₆S₂
Molar mass	423.46 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES 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
(verify)

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

[edit]

Cephapirin synthesis:^[2] U.S. patent 3,422,100 U.S. patent 3,503,967 U.S. patent 3,578,661

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

[edit]

^ "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.

Antibacterials active on the cell wall and envelope (J01C-J01D)

Beta-lactams
(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
transpeptidases)

Penicillins (Penams)

Narrow
spectrum

β-lactamase sensitive
(1st generation)

β-lactamase resistant
(2nd generation)

Extended
spectrum

Aminopenicillins (3rd generation)	Amoxicillin^# Ampicillin^# (Pivampicillin Hetacillin^‡ Bacampicillin^‡ Lenampicillin Metampicillin^‡ Talampicillin^‡) Epicillin^‡
Carboxypenicillins (4th generation)	Ticarcillin Carbenicillin^‡ / Carindacillin^‡ Temocillin^‡
Ureidopenicillins (4th generation)	Piperacillin Azlocillin^‡ Mezlocillin^‡
Other	Mecillinam (Pivmecillinam) Sulbenicillin^‡

Carbapenems / Penems

Cephems
Cephalosporins
Cephamycins
Carbacephems

1st generation	Cefazolin^# Cefalexin ^# Cefadroxil Cefapirin Cefazedone^‡ Cefazaflur^‡ Cefradine^‡ Cefroxadine^‡ Ceftezole^‡ Cefaloglycin^‡ Cefacetrile^‡ Cefalonium^‡ Cefaloridine^‡ Cefalotin Cefatrizine^‡
2nd generation	Cefaclor Cefprozil Cefuroxime Cefuroxime axetil Cefamandole^‡ Cefonicid^‡ Ceforanide^‡ Cefuzonam^‡ Cephamycin (Cefoxitin Cefotetan Cefminox^‡ Cefbuperazone^‡ Cefmetazole^‡) Carbacephem (Loracarbef^‡)
3rd generation	Cefixime^# Ceftriaxone^# Cefotaxime^# Antipseudomonal (Ceftazidime^# Cefoperazone) Cefdinir Cefcapene Cefdaloxime Ceftizoxime Cefmenoxime Cefpiramide Cefpodoxime Ceftibuten Cefditoren Cefotiam^‡ Cefetamet^‡ Cefodizime^‡ Cefpimizole^‡ Cefsulodin^‡ Cefteram^‡ Ceftiolene^‡ Oxacephem (Flomoxef Latamoxef^‡)
4th generation	Cefepime Cefozopran^‡ Cefpirome Cefquinome^‡
5th generation	Ceftaroline fosamil Ceftolozane Ceftobiprole
Siderophore	Cefiderocol^#
Veterinary	Ceftiofur Cefquinome Cefovecin

Monobactams

β-lactamase inhibitors

Combinations

Polypeptides

Lipopeptides

Insert into bacterial cell wall causing perforation and depolarization: Daptomycin
Surfactin

Other

Inhibits PG elongation and crosslinking: Ramoplanin^§

Intracellular

Inhibit PG subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin)
DADAL/AR inhibitors (Cycloserine)
bactoprenol inhibitors (Bacitracin)

Other

^#WHO-EM

^‡Withdrawn from market

Clinical trials:

^†Phase III
^§Never to phase III

This systemic antibiotic-related article is a stub. You can help Wikipedia by expanding it.

Retrieved from "https://en.wikipedia.org/w/index.php?title=Cefapirin&oldid=1144398038" Categories: ●Cephalosporin antibiotics ●Enantiopure drugs ●4-Pyridyl compounds ●Acetate esters ●Antibiotic stubs Hidden categories: ●Articles with short description ●Short description matches Wikidata ●ECHA InfoCard ID from Wikidata ●Drugboxes which contain changes to watched fields ●All articles with unsourced statements ●Articles with unsourced statements from March 2023 ●All stub articles ●This page was last edited on 13 March 2023, at 15:05 (UTC). ●Text is available under the Creative Commons Attribution-ShareAlike License 4.0; additional terms may apply. By using this site, you agree to the Terms of Use and Privacy Policy. Wikipedia® is a registered trademark of the Wikimedia Foundation, Inc., a non-profit organization. ●Privacy policy ●About Wikipedia ●Disclaimers ●Contact Wikipedia ●Code of Conduct ●Developers ●Statistics ●Cookie statement ●Mobile view