Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR2503)
Drug Name
Cefazolin
Synonyms
Cefamezin; Cefazolin acid; Cefazolin sodium salt; Cefazolina; Cefazolina [INN-Spanish]; Cefazoline; Cefazoline [INN-French]; Cefazolinum; Cefazolinum [INN-Latin]; Cephamezine; Cephazolidin; Cephazolin; Cephazoline; Elzogram; Etchlorvinolo; Aethyl-chlorvynol; Alvinol; Arvynol; Etclorvinol; Etclorvinol [INN-Spanish]; Ethchlorovynol; Ethchlorvinol; Ethchlorvinyl; Ethchlorvynolum; Ethclorvynol; Ethochlorvynol; Ethychlorvynol; IHS69L0Y4T; Kefzol; Normonson; Normosan; Normoson; Nostel; Nromoson; Placidil; Placidyl; Roeridorm; Serenesil; Serenil; Serensil; Serensiloline; cefazolin; ethchlorvynol; 1-Chloro-3-ethyl-1-penten-4-yn-3-ol; 1-Penten-4-yn-3-ol, 1-chloro-3-ethyl-; 25953-19-9; 3-(beta-Chlorovinyl)-1-pentyn-3-ol; 7-(1-(1H-)-Tetrazolylacetamido)-3-(2-(5-methyl-1,3,4-thiadiazolyl)thiomethyl)delta3-cephem-4-carboxylic acid; BRN 4169371; CEZ; CHEBI:474053; EINECS 247-362-8; Ethyl beta-chlorovinyl ethynyl carbinol; HSDB 3213; UNII-IHS69L0Y4T; beta-Chlorovinyl ethyl ethynyl carbinol
Indication Infectious cystitis [ICD11: GC00] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 454.5 Topological Polar Surface Area 235
Heavy Atom Count 29 Rotatable Bond Count 7
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 12
Cross-matching ID
PubChem CID
33255
PubChem SID
9097 ; 602960 ; 7849358 ; 7978873 ; 8173059 ; 11335189 ; 11360428 ; 11362960 ; 11365522 ; 11368084 ; 11371259 ; 11373873 ; 11376246 ; 11461400 ; 11466764 ; 11467884 ; 11484775 ; 11486367 ; 11488956 ; 11490146 ; 11492082 ; 11493920 ; 14833488 ; 15008581 ; 29215418 ; 34675123 ; 46506123 ; 47193754 ; 47290958 ; 47440062 ; 47440063 ; 47440064 ; 47810578 ; 48110278 ; 48259043 ; 48334299 ; 48415713 ; 50051012 ; 56314760 ; 57311487 ; 75509242 ; 81093146 ; 85663279 ; 92714647 ; 103510684 ; 104133789 ; 104231690 ; 104315593 ; 117600526 ; 124766146
ChEBI ID
CHEBI:474053
CAS Number
25953-19-9
TTD Drug ID
D09KDN
Formula
C14H14N8O4S3
Canonical SMILES
CC1=NN=C(S1)SCC2=C(N3C(C(C3=O)NC(=O)CN4C=NN=N4)SC2)C(=O)O
InChI
1S/C14H14N8O4S3/c1-6-17-18-14(29-6)28-4-7-3-27-12-9(11(24)22(12)10(7)13(25)26)16-8(23)2-21-5-15-19-20-21/h5,9,12H,2-4H2,1H3,(H,16,23)(H,25,26)/t9-,12-/m1/s1
InChIKey
MLYYVTUWGNIJIB-BXKDBHETSA-N
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Beta-lactamase (blaB) DME1094 Citrobacter freundii
AMPC_CITFR
3.5.2.6
[2] , [3]
Beta-lactamase (blaB) DME1023 Klebsiella pneumoniae
A0A378EHS6_KLEPR
3.5.2.6
[4]
Beta-lactamase (blaB) DME1095 Bacteroides fragilis
BLAB_BACFG
3.5.2.6
[5] , [6]
Thiopurine methyltransferase (TPMT) DME0014 Homo sapiens
TPMT_HUMAN
2.1.1.67
[7]
References
1 Cefazolin was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Citrobacter freundii bacteremia: Risk factors of mortality and prevalence of resistance genes. J Microbiol Immunol Infect. 2018 Aug;51(4):565-572.
3 Identification and functional characterization of arylamine N-acetyltransferases in eubacteria: evidence for highly selective acetylation of 5-aminosalicylic acid. J Bacteriol. 2001 Jun;183(11):3417-27.
4 Analysis of the drug-resistant characteristics of Klebsiella pneumoniae isolated from the respiratory tract and CTX-M ESBL genes. Genet Mol Res. 2015 Oct 5;14(4):12043-8.
5 Prevalence of antimicrobial resistance genes in Bacteroides spp. and Prevotella spp. Dutch clinical isolates. Clin Microbiol Infect. 2019 Sep;25(9):1156.e9-1156.e13.
6 Antibacterial activity of cefoperazone against anaerobic bacteria (author's transl). Jpn J Antibiot. 1980 Nov;33(11):1171-82.
7 Cefazolin administration and 2-methyl-1,3,4-thiadiazole-5-thiol in human tissue: possible relationship to hypoprothrombinemia. Drug Metab Dispos. 2002 Oct;30(10):1123-8.

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