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

General Information of Drug (ID: DR5466)
Drug Name
Penicillin
Synonyms
Cillin; Pentids; 3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; 3,3-Dimethyl-7-oxo-6-[(phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (Phenylmethyl)penicillin; 7005-30-3; NSC131815; (Phenylmethyl)penicillinic acid; 3,3-dimethyl-7-oxo-6-((phenylacetyl)amino)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; AC1L1DHC; AC1Q5UVJ; Penicilline G sodium salt; Oprea1_713794; Oprea1_861345; CHEMBL300052; SCHEMBL2109546; CTK2H5530
Indication Bacterial infection [ICD11: 1A00-1C4Z] 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
2349
CAS Number
61-33-6
TTD Drug ID
D0R1BD
Formula
C16H18N2O4S
Canonical SMILES
CC1(C(N2C(S1)C(C2=O)NC(=O)CC3=CC=CC=C3)C(=O)O)C
InChI
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)
InChIKey
JGSARLDLIJGVTE-UHFFFAOYSA-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 - Unclear 1 [5] , [4]
Penicilloic acid DM001188
52921568
Unclear - Unclear 1 [5]
Phenyl acetic acid DM001228
999
Unclear - Unclear 1 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR008130 Penicillin 6-aminopenicillanic acid Unclear - Unclear pac [5], [4]
MR008131 Penicillin Penicilloic acid Unclear - Unclear Unclear [5]
MR008132 Penicillin Phenylacetic acid Unclear - Unclear pac [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
beta-lactamase TEM-1 (bla TEM-1) DMEN875 Bacteroides fragilis Not Available Not Available [2] , [3]
Penicillin G acylase (pac) DMEN749 Escherichia coli Not Available Not Available [4]
References
1 ClinicalTrials.gov (NCT00363688) Treating Patients With a History of Non-Life Threatening Allergic Reaction to Penicillin With Penicillin. U.S. National Institutes of Health.
2 Mass spectral kinetic study of acylation and deacylation during the hydrolysis of penicillins and cefotaxime by beta-lactamase TEM-1 and the G238S mutant
3 N-aryl 3-halogenated azetidin-2-ones and benzocarbacephems, inhibitors of beta-lactamases
4 Ligand-induced conformational change in penicillin acylase
5 Metabolism of penicillins to penicilloic acids and 6-aminopenicillanic acid in man and its significance in assessing penicillin absorption

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