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

General Information of Drug (ID: DR2178)
Drug Name
Cephalothin
Synonyms
Cefalothin; Cefalotin (BAN); Cefalotina; Cefalotina [INN-Spanish]; Cefalotina fabra; Cefalotina fabra (TN); Cefalotine; Cefalotine [INN-French]; Cefalotinum; Cefalotinum [INN-Latin]; Cemastin; Cephalothin Monosodium Salt; Cephalothinum; Cephalotin; Coaxin; Keflin (TN); Averon-1; (6R,7R)-3-(acetyloxymethyl)-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-3-[(acetyloxy)methyl]-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; 3-(Acetoxymethyl)-8-oxo-7-(2-(2-thienyl)acetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid; 3-(Hydroxymethyl)-8-oxo-7-(2-(2-thienyl)acetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid acetate; 3-ACETOXYMETHYL-8-OXO-7-(2-THIOPHEN-2-YL-ACETYLAMINO)-5-THIA-1-AZA-BICYCLO[4.2.0]OCT-2-ENE-2-CARBOXYLIC ACID; 3-Acetoxymethyl-7-(2-thienylacetamido)-3-cephem-4-carboxylic acid; 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-(hydroxymethyl)-8-oxo-7-(2-(2-thienyl)acetamido)-, acetate (ester); 6R-trans-3-((Acetyloxy)methyl)-8-oxo-7-((2-thienylacetyl)amino)-5-thia-1-azabicyclo(4.2.0)-oct-2-ene-2-carboxylic acid; 7-(2-(2-Thienyl)acetylamido)cephalosporanic acid; 7-(2-Thienylacetamido)cephalosporanic acid; 7-(Thiophene-2-acetamido)cephalosporanic acid; 7-(Thiophene-2-acetamido)cephalosporin; 7beta-(thiophen-2-ylacetamido)-3-acetoxymethyl-3,4-didehydrocepham-4-carboxylic acid
Indication Infectious cystitis [ICD11: GC00] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 396.4 Topological Polar Surface Area 167
Heavy Atom Count 26 Rotatable Bond Count 7
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 8
Cross-matching ID
PubChem CID
6024
PubChem SID
9963 ; 602881 ; 824703 ; 7886646 ; 7978894 ; 8153752 ; 11335272 ; 11360511 ; 11362964 ; 11365526 ; 11368088 ; 11371283 ; 11373877 ; 11376250 ; 11461483 ; 11466747 ; 11467867 ; 11483898 ; 11486594 ; 11487937 ; 11490148 ; 11492084 ; 11493924 ; 14781066 ; 16794138 ; 29215241 ; 29225038 ; 46509079 ; 47193756 ; 47588840 ; 47662113 ; 47736307 ; 47810601 ; 47885259 ; 48110301 ; 48334326 ; 48334327 ; 48415743 ; 50050997 ; 50716459 ; 51091939 ; 57323124 ; 81093187 ; 84981763 ; 85788476 ; 87322650 ; 103186843 ; 104097230 ; 104310899 ; 124766006
ChEBI ID
ChEBI:50895
CAS Number
153-61-7
TTD Drug ID
D01PLN
Formula
C16H16N2O6S2
Canonical SMILES
CC(=O)OCC1=C(N2C(C(C2=O)NC(=O)CC3=CC=CS3)SC1)C(=O)O
InChI
1S/C16H16N2O6S2/c1-8(19)24-6-9-7-26-15-12(14(21)18(15)13(9)16(22)23)17-11(20)5-10-3-2-4-25-10/h2-4,12,15H,5-7H2,1H3,(H,17,20)(H,22,23)/t12-,15-/m1/s1
InChIKey
XIURVHNZVLADCM-IUODEOHRSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Deacetylcephalothin DM001793
93015
Oxidation - Deacetylation 1 [6]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000600 Cephalothin Deacetylcephalothin Oxidation - Deacetylation Unclear [6]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
AmpC beta-lactamase (ampC) DME1192 Burkholderia multivorans
A0A0H3KQ39_BURM1
3.5.2.6
[2]
Beta-lactamase (blaB) DME1026 Bacteroides uniformis
BLAC_BACUN
3.5.2.6
[3]
Beta-lactamase (blaB) DME1095 Bacteroides fragilis
BLAB_BACFG
3.5.2.6
[4]
Unclear metabolic mechanism (DME-unclear) DME1533 Helicobacter rodentium Not Available Not Available [5]
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
Beta-lactamase (blaB) DME1026 Km = 113 microM
BLAC_BACUN
[3]
References
1 Cephalothin was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Characterization of the AmpC beta-Lactamase from Burkholderia multivorans. Antimicrob Agents Chemother. 2018 Sep 24;62(10). pii: e01140-18.
3 Purification and characterization of a new beta-lactamase from Bacteroides uniformis. Antimicrob Agents Chemother. 1995 Jul;39(7):1458-61.
4 Antibacterial activity of cefoperazone against anaerobic bacteria (author's transl). Jpn J Antibiot. 1980 Nov;33(11):1171-82.
5 Helicobacter rodentium sp. nov., a urease-negative Helicobacter species isolated from laboratory mice. Int J Syst Bacteriol. 1997 Jul;47(3):627-34.
6 Effects of rate of infusion and probenecid on serum levels, renal excretion, and tolerance of intravenous doses of cefoxitin in humans: comparison with cephalothin Antimicrob Agents Chemother. 1974 Sep;6(3):338-46. doi: 10.1128/AAC.6.3.338.

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