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

General Information of Drug (ID: DR2164)
Drug Name
Penicillin G
Synonyms
Pharmacillin; Phenylacetamidopenicillanic acid; Pradupen; Specilline G; Ursopen; Bencilpenicilina; Benzopenicillin; Benzyl penicillin; Benzyl-6-aminopenicillinic acid; Benzylpenicillin G; Benzylpenicilline; Benzylpenicillinic acid; Benzylpenicillinum; Cilloral; Cilopen; Compocillin G; Cosmopen; Dropcillin; Free benzylpenicillin; Free penicillin G; Free penicillin II; Galofak; Gelacillin; Liquacillin; Pencillin G; Pfizerpen; penicillin g; 6-(2-Phenylacetamido)penicillanic acid; 61-33-6
Indication Diphtheria [ICD11: 1C17] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 334.4 Topological Polar Surface Area 112
Heavy Atom Count 23 Rotatable Bond Count 4
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
5904
PubChem SID
7885 ; 617709 ; 820202 ; 841337 ; 7849395 ; 7889969 ; 7980271 ; 8144852 ; 8153657 ; 11335491 ; 11360730 ; 11363827 ; 11366389 ; 11368951 ; 11371783 ; 11374081 ; 11377113 ; 11461702 ; 11467106 ; 11468226 ; 11484211 ; 11486734 ; 11488334 ; 11490358 ; 11492286 ; 11494747 ; 14875396 ; 15348041 ; 26711903 ; 29215263 ; 29224931 ; 46506778 ; 47291043 ; 47365102 ; 47588906 ; 47736376 ; 48035012 ; 48184904 ; 48184905 ; 49647119 ; 50050765 ; 53787815 ; 57323037 ; 57588014 ; 79379468 ; 81066337 ; 81093162 ; 85244562 ; 85788897 ; 85789209
ChEBI ID
ChEBI:18208
CAS Number
1110-47-0
TTD Drug ID
D00QAR
Formula
C16H18N2O4S
Canonical SMILES
CC1(C(N2C(S1)C(C2=O)NC(=O)CC3=CC=CC=C3)C(=O)O)C
InChI
1S/C16H18N2O4S/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)/t11-,12+,14-/m1/s1
InChIKey
JGSARLDLIJGVTE-MBNYWOFBSA-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
6-APA DM001190
11082
Unclear 1 [11]
Penicilloic acid DM001188
52921568
Unclear 1 [11]
8-hydroxypenillic acid DM001189
6451507
Oxidation - Hydroxylation 2 [11]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001970 Penicillin G Penicilloic acid Unclear Unclear [11]
MR001971 Penicillin G 6-aminopenicillanic acid Unclear Unclear [11]
MR001969 Penicilloic acid 8-hydroxypenillic acid Oxidation - Hydroxylation Unclear [11]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Beta-lactamase (blaB) DME1539 Prevotella pallens
F9DGI4_9BACT
3.5.2.6
[2]
Beta-lactamase (blaB) DME1224 Fusobacterium nucleatum
Q8RIK5_FUSNN
3.5.2.6
[3]
Beta-lactamase (blaB) DME1225 Fusobacterium varium
C6JIU1_FUSVA
3.5.2.6
[4]
Beta-lactamase (blaB) DME1230 Prevotella nigrescens
A0A246EJV2_9BACT
3.5.2.6
[2]
Beta-lactamase (blaB) DME1026 Bacteroides uniformis
BLAC_BACUN
3.5.2.6
[5]
Beta-lactamase (blaB) DME1095 Bacteroides fragilis
BLAB_BACFG
3.5.2.6
[4]
Beta-lactamase (blaB) DME1016 Prevotella melaninogenica
Q8KT52_9BACT
3.5.2.6
[4]
Beta-lactamase (blaB) DME1222 Empedobacter brevis
Q8GQK7_9FLAO
3.5.2.6
[6]
Beta-lactamase (blaB) DME2046 Chryseobacterium gleum
A0A4U8WDG3_9FLAO
3.5.2.6
[7]
Beta-lactamase (blaB) DME1332 Burkholderia cepacia
A0A2S8IKB0_BURCE
3.5.2.6
[8]
N-acylhomoserine lactone acylase (lacA) DME1021 Acidovorax ebreus
A0A0A1VBK6_9BURK
3.5.1.97
[9]
Pepsin A (PGA) DMEN077 . Not Available Not Available [10]
⏷ Show the Full List of 12  DME(s)
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
Beta-lactamase (blaB) DME1026 Km = 3.5 microM
BLAC_BACUN
[5]
References
1 Penicillin G was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Beta-lactamase production in Prevotella intermedia, Prevotella nigrescens, and Prevotella pallens genotypes and in vitro susceptibilities to selected antimicrobial agents. Antimicrob Agents Chemother. 1999 Oct;43(10):2383-8.
3 beta-lactamase production and antimicrobial susceptibility of oral heterogeneous Fusobacterium nucleatum populations in young children. Antimicrob Agents Chemother. 1999 May;43(5):1270-3.
4 Antimicrobial drugs used in the management of anaerobic infections in children. Drugs. 1983 Dec;26(6):520-9.
5 Purification and characterization of a new beta-lactamase from Bacteroides uniformis. Antimicrob Agents Chemother. 1995 Jul;39(7):1458-61.
6 EBR-1, a novel Ambler subclass B1 beta-lactamase from Empedobacter brevis. Antimicrob Agents Chemother. 2002 Oct;46(10):3223-7.
7 Genetic and biochemical characterization of CGB-1, an Ambler class B carbapenem-hydrolyzing beta-lactamase from Chryseobacterium gleum. Antimicrob Agents Chemother. 2002 Sep;46(9):2791-6.
8 Characterization of the penA and penR genes of Burkholderia cepacia 249 which encode the chromosomal class A penicillinase and its LysR-type transcriptional regulator. Antimicrob Agents Chemother. 1997 Nov;41(11):2399-405.
9 A novel quorum-quenching N-acylhomoserine lactone acylase from Acidovorax sp. strain MR-S7 mediates antibiotic resistance. Appl Environ Microbiol. 2017 Jun 16;83(13). pii: e00080-17.
10 Effect of fluconazole on the pharmacokinetics of a single dose of fedratinib in healthy adults. Cancer Chemother Pharmacol. 2022 Oct;90(4):325-334. doi: 10.1007/s00280-022-04464-w.
11 McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 1999. Bethesda, MD:American Society of Health-System Pharmacists, Inc. 1999 (Plus Supplements)., p. 1760

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