Cefapirin: Difference between revisions

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			{{Short description\|Chemical compound}}
	{{Drugbox		{{Drugbox
	\| Watchedfields = changed		\| Watchedfields = changed
	\| verifiedrevid = ~~443508168~~		\| verifiedrevid = 460022704
	\| IUPAC_name =		\| IUPAC_name =
	\| image = Cefapirin.svg		\| image = Cefapirin.svg

	<!--Clinical data-->		<!--Clinical data-->
	\| tradename =		\| tradename =
	\| Drugs.com = {{drugs.com\|international\|cefapirin}}		\| Drugs.com = {{drugs.com\|international\|cefapirin}}
	\| MedlinePlus = a601206		\| MedlinePlus = a601206
	\| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->		\| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
	\| pregnancy_US = B		\| pregnancy_US = B
	\| pregnancy_category =		\| pregnancy_category =
	\| legal_AU = <!-- Unscheduled / S2 / S4 / S8 -->		\| legal_AU = <!-- Unscheduled / S2 / S4 / S8 -->
	\| legal_UK = <!-- GSL / P / POM / CD -->		\| legal_UK = <!-- GSL / P / POM / CD -->
	\| legal_US = Rx-only		\| legal_US = Rx-only
	\| legal_status =		\| legal_status =
	\| routes_of_administration = ], ]		\| routes_of_administration = ], ]

	<!--Pharmacokinetic data-->		<!--Pharmacokinetic data-->
	\| bioavailability =		\| bioavailability =
	\| protein_bound =		\| protein_bound =
	\| metabolism =		\| metabolism =
	\| elimination_half-life =		\| elimination_half-life =
	\| excretion =		\| excretion =

	<!--Identifiers-->		<!--Identifiers-->
	\| ~~CASNo_Ref~~ = {{cascite\|correct\|~~CAS~~}}		\| CAS_number_Ref = {{cascite\|correct\|??}}
	\| CAS_number = 21593-23-7		\| CAS_number = 21593-23-7
	\| ATC_prefix = J01		\| ATC_prefix = J01
	\| ATC_suffix = DB08		\| ATC_suffix = DB08
	\| ATC_supplemental = {{ATCvet\|J51\|~~DA30~~}}		\| ATC_supplemental = {{ATCvet\|G51\|AA05}} {{ATCvet\|J51\|DB08}}
	\| PubChem = 30699		\| PubChem = 30699
	\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}		\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}
	\| DrugBank = ~~APRD00860~~		\| DrugBank = DB01139
	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}		\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
	\| ChemSpiderID = 28486		\| ChemSpiderID = 28486
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	\| ChEMBL_Ref = {{ebicite\|correct\|EBI}}		\| ChEMBL_Ref = {{ebicite\|correct\|EBI}}
	\| ChEMBL = 1599		\| ChEMBL = 1599

	<!--Chemical data-->		<!--Chemical data-->
	\| C=17 \| H=17 \| N=3 \| O=6 \| S=2		\| C=17 \| H=17 \| N=3 \| O=6 \| S=2
	\| molecular_weight = 423.466 g/mol
	\| smiles = O=C2N1/C(=C(\CS12NC(=O)CSc3ccncc3)COC(=O)C)C(=O)O		\| smiles = O=C2N1/C(=C(\CS12NC(=O)CSc3ccncc3)COC(=O)C)C(=O)O
	\| InChI = 1/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
	\| InChIKey = UQLLWWBDSUHNEB-CZUORRHYBF
	\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}		\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChI = 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		\| StdInChI = 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
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	\| StdInChIKey = UQLLWWBDSUHNEB-CZUORRHYSA-N		\| StdInChIKey = UQLLWWBDSUHNEB-CZUORRHYSA-N
	}}		}}
	'''Cefapirin''' (], also spelled '''cephapirin''') is an injectable, first-generation ] ]. It is marketed under the trade name ~~'''~~Cefadyl~~'''~~. Production for use in humans has been discontinued in the United States.<ref>http://www.accessdata.fda.gov/scripts/cder/drugsatfda/index.cfm?fuseaction=Search.Overview&DrugName=CEFADYL</ref>		'''Cefapirin''' (], also spelled '''cephapirin''') is an injectable, first-generation ] ]. It is marketed under the trade name Cefadyl. Production for use in humans has been discontinued in the United States.<ref>{{cite web \| title = CEFADYL \| url = http://www.accessdata.fda.gov/scripts/cder/drugsatfda/index.cfm?fuseaction=Search.Overview&DrugName=CEFADYL \| publisher = U.S. Food and Drug Administration }}</ref>

	It also has a role in ] as ~~'''~~Metricure~~'''~~, an intrauterine preparation and combined with ] in ~~'''~~Mastiplan~~'''~~, an intramammary preparation. Both are ~~licenced~~ in ].		It also has a role in ] as Metricure, an intrauterine preparation, and combined with ] in Mastiplan, an intramammary preparation. Both are licensed in ].{{cn\|date=March 2023}}

	==~~References~~==		==Synthesis==
			]
			In one of the syntheses, ] (]) is reacted with bromoacetyl chloride to give the amide. The halo group is then displaced by 4-thiopyridine.<ref name=Crast/>

			== References ==
	{{reflist}}		{{reflist}}

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	]		]
	]		]
	]		]
	]		]


	{{antibiotic-stub}}		{{antibiotic-stub}}

	]
	]
	]
	]

Latest revision as of 15:05, 13 March 2023

Chemical compound Pharmaceutical compound

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
PubChem CID	30699
DrugBank	DB01139
ChemSpider	28486
UNII	89B59H32VN
KEGG	D07636
ChEBI	CHEBI:554446
ChEMBL	ChEMBL1599
CompTox Dashboard (EPA)	DTXSID9022784
ECHA InfoCard	100.040.409
Chemical and physical data
Formula	C₁₇H₁₇N₃O₆S₂
Molar mass	423.46 g·mol
3D model (JSmol)	Interactive image
SMILES O=C2N1/C(=C(\CS12NC(=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 Key:UQLLWWBDSUHNEB-CZUORRHYSA-N
(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.

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.

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.

References

"CEFADYL". U.S. Food and Drug Administration.
^ 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)

β-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)	Benzylpenicillin (G) Benzathine benzylpenicillin Procaine benzylpenicillin Phenoxymethylpenicillin (V) Propicillin Pheneticillin Azidocillin Clometocillin Penamecillin
β-lactamase resistant (2nd generation)	Cloxacillin (Dicloxacillin Flucloxacillin) Oxacillin Nafcillin Methicillin

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

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