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

General Information of Drug (ID: DR5510)
Drug Name
Penicillin G Sodium
Synonyms
Penicillin G sodium salt; 69-57-8; Benzylpenicillin sodium; Crystapen; American penicillin; Pencillin G sodium; Sodium penicillin G; BENZYLPENICILLIN SODIUM SALT; Sodium penicillin; Sodium benzylpenicillinate; Sodium penicillin II; Veticillin; Penilaryn; Mycofarm; Novocillin; Sodium benzylpenicillin; Kesso-Pen; Pen-A-Brasive; Sodium benzylpenicillin G; Monosodium benzylpenicillin; Benzylpenicillinic acid sodium salt; Sugracillin sodium salt; Penicillin G Sodium, Crystalline; Sodium benzylp
Indication Bacterial infection [ICD11: 1A00-1C4Z] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 356.4 Topological Polar Surface Area 115
Heavy Atom Count 24 Rotatable Bond Count 4
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
23668834
ChEBI ID
CHEBI:51765
CAS Number
69-57-8
TTD Drug ID
D0K5OT
Formula
C16H17N2NaO4S
Canonical SMILES
CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)CC3=CC=CC=C3)C(=O)[O-])C.[Na+]
InChI
InChI=1S/C16H18N2O4S.Na/c1-16(2)12(15(21)22)18-13(20)11(14(18)23-16)17-10(19)8-9-6-4-3-5-7-9;/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22);/q;+1/p-1/t11-,12+,14-;/m1./s1
InChIKey
FCPVYOBCFFNJFS-LQDWTQKMSA-M
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
6-APA DM001190
11082
Hydrolysis - Hydrolysis 1 [6]
Penicillin G Sodium metabolite M3 DM017098 N. A. Unclear - Unclear 1 [7]
Penicillin G Sodium metabolite M7 DM016502
102263598
Unclear - Unclear 1 [7]
Penicilloic acid DM001188
52921568
Oxidation - Oxidation 1 [7]
Phenyl acetic acid DM001228
999
Hydrolysis - Hydrolysis 1 [4]
Phenylacetyl-7-aminodeacetoxycephalosporanic acid (G-7-ADCA) DM015380
2956817
Unclear - Unclear 1 [3]
Penicillin G Sodium metabolite M4 DM016501
102263594
Reduction - Reduction 2 [7]
Penicillin G Sodium metabolite M5 DM017097 N. A. Oxidation - Hydroxylation 2 [7]
Penicillin G Sodium metabolite M6 DM017096 N. A. Conjugation - Glucuronidation 2 [7]
Penilloic acid DM015262
255293
Reduction - Decarboxylation 2 [7]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR008099 Penicillin G Sodium Penicilloic acid Oxidation - Oxidation Unclear [7]
MR008103 Penicillin G Sodium Penicillin G Sodium metabolite M3 Unclear - Unclear Unclear [7]
MR008105 Penicillin G Sodium Penicillin G Sodium metabolite M7 Unclear - Unclear Unclear [7]
MR008106 Penicillin G Sodium 6-aminopenicillanic acid Hydrolysis - Hydrolysis Unclear [6]
MR008107 Penicillin G Sodium Phenylacetyl-7-aminodeacetoxycephalosporanic acid (G-7-ADCA) Unclear - Unclear cefE [3]
MR008108 Penicillin G Sodium Phenyl acetic acid Hydrolysis - Hydrolysis PA [4]
MR008104 Penicillin G Sodium metabolite M3 Penicillin G Sodium metabolite M4 Reduction - Reduction Unclear [7]
MR008100 Penicilloic acid Penilloate Reduction - Decarboxylation Unclear [7]
MR008101 Penicilloic acid Penicillin G Sodium metabolite M6 Conjugation - Glucuronidation Unclear [7]
MR008102 Penicilloic acid Penicillin G Sodium metabolite M5 Oxidation - Hydroxylation Unclear [7]
⏷ Show the Full List of 10 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Beta-lactamase OtLac (bla OtLac) DMEN872 . Not Available Not Available [2]
Deacetoxycephalosporin C synthetase (cefE) DMEN746 Streptomyces clavuligerus
B5GLB0_STRCL
1.14.20.1
[3]
penicillin amidase (PA) DMEN747 Homo sapiens Not Available Not Available [4]
Streptomyces R61 DD-peptidase (ddp) DMEN873 . Not Available Not Available [5]
References
1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 Enzyme-catalyzed biodegradation of penicillin fermentation residues by -lactamase OtLac from Ochrobactrum tritici
3 Whole-Cell Biotransformation of Penicillin G by a Three-Enzyme Co-expression System with Engineered Deacetoxycephalosporin?C Synthase
4 A breakthrough in enzyme technology to fight penicillin resistance-industrial application of penicillin amidase
5 Acylation and deacylation mechanism and kinetics of penicillin G reaction with Streptomyces R61 DD-peptidase
6 Metabolism of penicillins to penicilloic acids and 6-aminopenicillanic acid in man and its significance in assessing penicillin absorption
7 Identification of new minor metabolites of penicillin G in human serum by multiple-stage tandem mass spectrometry

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