Cefmetazole: Difference between revisions

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Cefmetazole
	File:Cefmetazole.svg
Clinical data
AHFS/Drugs.com	International Drug Names
MedlinePlus	a601206
ATC code	J01DC09 (WHO) ;
Identifiers
	IUPAC name (6R,7S)-7-(2-(cyanomethylthio)acetamido)-7-methoxy-3-((1-methyl-1H-tetrazol-5-ylthio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;
CAS Number	56796-20-4 ;
PubChem CID	42008;
DrugBank	DB00274 ;
ChemSpider	38311 ;
UNII	3J962UJT8H;
KEGG	D00910 ;
ChEBI	CHEBI:3489 ;
ChEMBL	ChEMBL1201195 ;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C15H17N7O5S3
Molar mass	471.538 g/mol
3D model (JSmol)	Interactive image;
	SMILES O=C2N1/C(=C(\CS[C@@H]1[C@]2(OC)NC(=O)CSCC#N)CSc3nnnn3C)C(=O)O;
	InChI InChI=1S/C15H17N7O5S3/c1-21-14(18-19-20-21)30-6-8-5-29-13-15(27-2,17-9(23)7-28-4-3-16)12(26)22(13)10(8)11(24)25/h13H,4-7H2,1-2H3,(H,17,23)(H,24,25)/t13-,15+/m1/s1 ; Key:SNBUBQHDYVFSQF-HIFRSBDPSA-N ;
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VisualWikitext

Revision as of 15:32, 13 April 2015

Editor-In-Chief: George M. Garrity, Sc.D. [1]

Overview

Cefmetazole is a cephamycin antibiotic, usually grouped with the second-generation cephalosporins.

Adverse effects

The chemical structure of cefmetazole, like that of several other cephalosporins, contains an N-methylthiotetrazole (NMTT or 1-MTT) side chain. As the antibiotic is broken down in the body, it releases free NMTT, which can cause hypoprothrombinemia (likely due to inhibition of the enzyme vitamin K epoxide reductase) and a reaction with ethanol similar to that produced by disulfiram (Antabuse), due to inhibition of aldehyde dehydrogenase.^[1]

Spectrum of bacterial susceptibility

Cefmetazole is a broad-spectrum cephalosporin antimicrobial and has been effective in treating bacteria responsible for causing urinary tract and skin infections. The following represents MIC susceptibility data for a few medically significant microorganisms.

Bacteroides fragilis: 0.06 - >256 µg/ml
Clostridium difficile: 8 - >128 µg/ml
Staphylococcus aureus: 0.5 - 256 µg/ml (includes MRSA)

^[2]

References

↑ Stork CM (2006). "Antibiotics, antifungals, and antivirals". In Nelson LH, Flomenbaum N, Goldfrank LR, Hoffman RL, Howland MD, Lewin NA (eds.). Goldfrank's toxicologic emergencies. New York: McGraw-Hill. p. 847. ISBN 0-07-143763-0. Retrieved 2009-07-03.
↑ http://www.toku-e.com/Assets/MIC/Cefmetazole%20free%20acid.pdf

Template:Antibiotic-stub

[Goldfrank-1] Stork CM (2006). "Antibiotics, antifungals, and antivirals". In Nelson LH, Flomenbaum N, Goldfrank LR, Hoffman RL, Howland MD, Lewin NA (eds.). Goldfrank's toxicologic emergencies. New York: McGraw-Hill. p. 847. ISBN 0-07-143763-0. Retrieved 2009-07-03.

[2] ttp://www.toku-e.com/Assets/MIC/Cefmetazole%20free%20acid.pdf

[1]

[2]

@@ Line 1: / Line 1: @@
 {{Drugbox
-| IUPAC_name        = (6''R'',7''S'')-7-{[2-(cyanomethylsulfanyl)acetyl]amino}-<br>7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-<br>8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic&nbsp;acid
+| Verifiedfields = changed
-| image             = Cefmetazole.png
+| Watchedfields = changed
-| CAS_number        =
+| verifiedrevid = 460023468
-| ATC_prefix        = J01
+| IUPAC_name = (6''R'',7''S'')-7-(2-(cyanomethylthio)acetamido)-7-methoxy-3-((1-methyl-1''H''-tetrazol-5-ylthio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
-| ATC_suffix        = DC09
+| image = Cefmetazole.svg
-| PubChem           = 42008
-| DrugBank          =
+<!--Clinical data-->
-| C=15|H=17|N=7|O=5|S=3
+| tradename =
-| molecular_weight  = 471.538 g/mol
+| Drugs.com = {{drugs.com|international|cefmetazole}}
-| bioavailability   =
+| MedlinePlus = a601206
-| protein_bound     =
+| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
-| metabolism        =
+| pregnancy_US = <!-- A / B            / C / D / X -->
-| elimination_half-life =
+| pregnancy_category =
-| excretion         =
+| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
-| pregnancy_AU      =  <!-- A / B1 / B2 / B3 / C / D / X -->
+| legal_CA = <!--             / Schedule I, II, III, IV, V, VI, VII, VIII -->
-| pregnancy_US      =  <!-- A / B            / C / D / X -->
+| legal_UK = <!-- GSL         / P       / POM / CD / Class A, B, C -->
-| pregnancy_category=
+| legal_US = <!-- OTC                   / Rx-only  / Schedule I, II, III, IV, V -->
-| legal_AU          =  <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
+| legal_status =
-| legal_CA          =  <!--             / Schedule I, II, III, IV, V, VI, VII, VIII -->
+| routes_of_administration =
-| legal_UK          =  <!-- GSL         / P       / POM / CD / Class A, B, C -->
-| legal_US          =  <!-- OTC                   / Rx-only  / Schedule I, II, III, IV, V -->
+<!--Pharmacokinetic data-->
-| legal_status      =
+| bioavailability =
-| routes_of_administration =
+| protein_bound =
+| metabolism =
+| elimination_half-life =
+| excretion =
+<!--Identifiers-->
+| CASNo_Ref = {{cascite|correct|CAS}}
+| CAS_number_Ref = {{cascite|correct|??}}
+| CAS_number = 56796-20-4
+| ATC_prefix = J01
+| ATC_suffix = DC09
+| PubChem = 42008
+| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
+| DrugBank = DB00274
+| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
+| ChemSpiderID = 38311
+| UNII_Ref = {{fdacite|correct|FDA}}
+| UNII = 3J962UJT8H
+| KEGG_Ref = {{keggcite|correct|kegg}}
+| KEGG = D00910
+| ChEBI_Ref = {{ebicite|correct|EBI}}
+| ChEBI = 3489
+| ChEMBL_Ref = {{ebicite|changed|EBI}}
+| ChEMBL = 1201195
+<!--Chemical data-->
+| C=15 | H=17 | N=7 | O=5 | S=3
+| molecular_weight = 471.538 g/mol
+| smiles = O=C2N1/C(=C(\CS[C@@H]1[C@]2(OC)NC(=O)CSCC#N)CSc3nnnn3C)C(=O)O
+| InChI = 1/C15H17N7O5S3/c1-21-14(18-19-20-21)30-6-8-5-29-13-15(27-2,17-9(23)7-28-4-3-16)12(26)22(13)10(8)11(24)25/h13H,4-7H2,1-2H3,(H,17,23)(H,24,25)/t13-,15+/m1/s1
+| InChIKey = SNBUBQHDYVFSQF-HIFRSBDPBM
+| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
+| StdInChI = 1S/C15H17N7O5S3/c1-21-14(18-19-20-21)30-6-8-5-29-13-15(27-2,17-9(23)7-28-4-3-16)12(26)22(13)10(8)11(24)25/h13H,4-7H2,1-2H3,(H,17,23)(H,24,25)/t13-,15+/m1/s1
+| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
+| StdInChIKey = SNBUBQHDYVFSQF-HIFRSBDPSA-N
 }}
+__Notoc__
 {{SI}}
+{{GMG}}
+==Overview==
+'''Cefmetazole''' is a [[cephamycin]] [[antibiotic]], usually grouped with the second-generation cephalosporins.
-'''Cefmetazole''' is a [[cephalosporin]].
+==Adverse effects==
+The chemical structure of cefmetazole, like that of several other cephalosporins, contains an ''N''-methylthiotetrazole (NMTT or 1-MTT) [[side chain]]. As the antibiotic is broken down in the body, it releases free NMTT, which can cause [[hypoprothrombinemia]] (likely due to [[enzyme inhibitor|inhibition]] of the [[enzyme]] [[vitamin K epoxide reductase]]) and a reaction with ethanol similar to that produced by [[disulfiram]] (Antabuse), due to inhibition of [[aldehyde dehydrogenase]].<ref name=Goldfrank>{{cite book |author=Stork CM |editor=Nelson LH, Flomenbaum N, Goldfrank LR, Hoffman RL, Howland MD, Lewin NA (eds.) |title=Goldfrank's toxicologic emergencies |chapter=Antibiotics, antifungals, and antivirals |chapterurl=http://books.google.com/books?id=cvJuLqBxGUcC&pg=PA847 |publisher=McGraw-Hill |location=New York |year=2006 |pages=847 |isbn=0-07-143763-0 |accessdate=2009-07-03}}</ref>
-Side Effects - The N-methyl-thiotetrazole side chain causes many bleeding problems and disulfaram-like reactions with substances such as alcohol.
+==Spectrum of bacterial susceptibility==
+Cefmetazole is a broad-spectrum cephalosporin antimicrobial and has been effective in treating bacteria responsible for causing urinary tract and skin infections. The following represents MIC susceptibility data for a few medically significant microorganisms.
+* ''Bacteroides fragilis'': 0.06 - >256 µg/ml
+* ''Clostridium difficile'': 8 - >128 µg/ml
+* ''Staphylococcus aureus'': 0.5 - 256 µg/ml (includes [[MRSA]])
+<ref>http://www.toku-e.com/Assets/MIC/Cefmetazole%20free%20acid.pdf</ref>
+==References==
+{{Reflist|2}}
+{{antibiotic-stub}}
 {{CephalosporinAntiBiotics}}
 [[Category:Cephalosporin antibiotics]]
-{{WikiDoc Help Menu}}
+[[Category:Tetrazoles]]
-{{WS}}
+[[Category:Nitriles]]
+[[Category:Drug]]

v t e Antibacterials: cell wall disruption (J01C-J01D)
Internal to membrane/ (inhibit peptidoglycan subunit synthesis and transport)	Template:Navbox subgroup
Glycopeptide/ (inhibit PG chain elongation)	Vancomycin # (Oritavancin, Telavancin) · Teicoplanin (Dalbavancin) · Ramoplanin
Beta-lactams/ (inhibit cross-links with PBP)	Template:Navbox subgroup
Other	Template:Navbox subgroup
# = WHO-EM