Drug Information

General Information
Drug ID
DR00539
Drug Name
Cefmetazole
Synonyms
(6R,7S)-7-(2-((Cyanomethyl)thio)acetamido)-7-methoxy-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid; (6R,7S)-7-(2-((Cyanomethyl)thio)acetamido)-7-methoxy-3-(((1-methyl-1H-tetrazol-5-yl)thiomethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, sodium salt; (6R,7S)-7-({[(cyanomethyl)sulfanyl]acetyl}amino)-7-methoxy-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7S)-7-({[(cyanomethyl)thio]acetyl}amino)-7-(methyloxy)-3-{[(1-methyl-1H-tetrazol-5-yl)thio]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7S)-7-[[2-(cyanomethylsulfanyl)acetyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; 6beta-{[(cyanomethyl)sulfanyl]acetamido}-6alpha-methoxy-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}ceph-3-em-4-carboxylic acid; CMZ; CS 1170; CS-1170; Cefmetazole (USP/INN); Cefmetazole Monosodium Salt; Cefmetazole [USAN:INN]; Cefmetazolo; Cefmetazolo [INN-Spanish]; Cefmetazolum; Cefmetazolum [INN-Latin]; SKF 83088; U 72791; U-72791A
Drug Type
Small molecular drug
Indication Urinary tract and skin bacteria infections [ICD11:GC08] Approved [1]
Therapeutic Class
Antibiotics
Structure
3D MOL 2D MOL
Formula
C15H17N7O5S3
Canonical SMILES
CN1C(=NN=N1)SCC2=C(N3C(C(C3=O)(NC(=O)CSCC#N)OC)SC2)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
InChIKey
SNBUBQHDYVFSQF-HIFRSBDPSA-N
CAS Number
CAS 56796-20-4
Pharmaceutical Properties Molecular Weight 471.5 Topological Polar Surface Area 239
Heavy Atom Count 30 Rotatable Bond Count 9
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 12
XLogP
-0.6
PubChem CID
42008
PubChem SID
10303 ,104338473 ,11466728 ,11467848 ,11486516 ,123087792 ,124766309 ,126625684 ,126686221 ,131319170 ,134224281 ,134338424 ,135002546 ,135882605 ,136357157 ,137006381 ,140396436 ,152035638 ,15479323 ,160963622 ,162173144 ,164788224 ,175442148 ,179150673 ,184544918 ,198970111 ,223674319 ,226513671 ,251916490 ,251917837 ,252347145 ,252449370 ,34707577 ,46504461 ,47217057 ,47217058 ,47440545 ,47440546 ,48259496 ,48415716 ,50050974 ,50294685 ,57312636 ,58106756 ,632166 ,7847973 ,7978876 ,8177398 ,92251462 ,92712300
ChEBI ID
ChEBI:3489
TTD Drug ID
D05UBX
DT(s) Transporting This Drug OATP1B3 Transporter Info Organic anion transporting polypeptide 1B3 Substrate [2]
PEPT1 Transporter Info Peptide transporter 1 Substrate [3]
References
1 Cefmetazole was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 Screening of antibiotics that interact with organic anion-transporting polypeptides 1B1 and 1B3 using fluorescent probes. Biol Pharm Bull. 2011;34(3):389-95.
3 Intestinal transport of beta-lactam antibiotics: analysis of the affinity at the H+/peptide symporter (PEPT1), the uptake into Caco-2 cell monolayers and the transepithelial flux. Pharm Res. 1999 Jan;16(1):55-61.

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