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

General Information of Drug (ID: DR5089)
Drug Name
Penicillin V
Synonyms
Apocillin; Apopen; Beromycin; Calcipen; Fenacilin; Fenospen; Fenossimetilpenicillina; Fenoximetilpenicilina; Fenoxymethylpenicillin; Fenoxypen; Meropenin; Oracillin; Oratren; Ospen; PNV; PVA; Phenocillin; Phenomycilline; Phenopenicillin; Phenoximethylpenicillinum; Phenoxomethylpenicillanyl; Phenoxomethylpenicillin; Phenoxymethylpenicillanyl; Phenoxymethylpenicillin; Phenoxymethylpenicilline; Phenoxymethylpenicillinum; Robicillin; Rocilin; Stabicillin; Vebecillin; Vegacillin; Acipen V; Compocillin V; Crystapen V; Distaquaine V; Eskacillian V; Eskacillin V; Fenossimetilpenicillina [DCIT]; Penicillin V [USAN]; Penicillin phenoxymethyl; Phenoxymethyl penicillin; Phenoxymethylenepenicillinic acid; Phenoxymethylpenicillinic acid; Phenoxymethylpenicillinic acid potassium salt; Acipen-v; Beromycin, Penicillin; Berromycin, Penicillin; Fenoximetilpenicilina [INN-Spanish]; Pen-Oral; Pen-V; Pen-vee; Penicillin V (USP); Penicillin, Phenoxymethyl; Phenoxymethylpenicillin (INN); Phenoxymethylpenicilline [INN-French]; Phenoxymethylpenicillinum [INN-Latin]; V-Cil; V-Cillin; V-Cylina; V-Cyline; V-Tablopen; P-Mega-Tablinen; V-Cillin (TN); (2S,5R,6R)-3,3-DIMETHYL-7-OXO-6-(2-PHENOXYACETAMIDO)-4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID; (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(2-phenoxyacetamido)-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid; (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[(phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,5R,6R)-3,3-dimethyl-7-oxo-6-{[(phenyloxy)acetyl]amino}-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; 2,2-dimethyl-6beta-[(phenoxyacetyl)amino]penam-3alpha-carbonyl; 2,2-dimethyl-6beta-[(phenoxyacetyl)amino]penam-3alpha-carboxylic acid; 3,3-Dimethyl-7-oxo-6-((phenyloxyacetyl)amino)-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid; 3,3-dimethyl-6beta-[(phenoxyacetyl)amino]penam-2alpha-carboxylic acid (PIN); 6-Phenoxyacetamidopenicillanic acid
Indication Bacterial infection [ICD11: 1A00-1C4Z] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 350.4 Topological Polar Surface Area 121
Heavy Atom Count 24 Rotatable Bond Count 5
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
6869
ChEBI ID
CHEBI:27446
CAS Number
87-08-1
TTD Drug ID
D09CPR
Formula
C16H18N2O5S
Canonical SMILES
CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)COC3=CC=CC=C3)C(=O)O)C
InChI
InChI=1S/C16H18N2O5S/c1-16(2)12(15(21)22)18-13(20)11(14(18)24-16)17-10(19)8-23-9-6-4-3-5-7-9/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22)/t11-,12+,14-/m1/s1
InChIKey
BPLBGHOLXOTWMN-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 - Unclear 1 [4]
Penicilloic acid DM001188
52921568
Hydrolysis - Hydrolysis 1 [2] , [3]
Penicillin V Potassium metabolite 1 DM015808
12548074
Unclear - Unclear 2 [3]
Penicillin V Potassium3 DM014982
19188
Unclear - Unclear 2 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR008109 Penicillin V Penicilloic acid Hydrolysis - Hydrolysis OtLac [2], [3]
MR008112 Penicillin V 6-aminopenicillanic acid Unclear - Unclear Unclear [4]
MR008110 Penicilloic acid Penicillin V metabolite 1 Unclear - Unclear Unclear [3]
MR008111 Penicilloic acid Penicillin V metabolite 3 Unclear - Unclear Unclear [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
#NAME? DMEN748 . Not Available Not Available [2]
penicillin V acylase (pva) DMEN874 . Not Available Not Available [3]
References
1 How many modes of action should an antibiotic have Curr Opin Pharmacol. 2008 Oct;8(5):564-73.
2 Enzyme-catalyzed biodegradation of penicillin fermentation residues by -lactamase OtLac from Ochrobactrum tritici
3 Isolation and Characterization of Ochrobactrum tritici for Penicillin V Potassium Degradation
4 Specificity of penicillin acylase of Fusarium and of Penicillium chrysogenum

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