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

General Information of Drug (ID: DR5261)
Drug Name
Pivampicillin
Prodrug Info Pivampicillin is the prodrug of Ampicillin
Synonyms
Pivaloylampicillin; Pivampicilina; Pivampicilline; Pivampicillinum; Pondocillin; Ampicillin Pivaloyl Ester; Ampicillin pivaloyloxymethyl ester; Pivaloyloxymethyl ampicillinate; Pivampicillin Monohydrochloride; MK 191; Pivampicilina [INN-Spanish]; Pivampicillin (INN); Pivampicillin [INN:BAN]; Pivampicilline [INN-French]; Pivampicillinum [INN-Latin]; Pondocillin (TN); [(2,2-dimethylpropanoyl)oxy]methyl 6beta-[(2R)-2-amino-2-phenylacetamido]-2,2-dimethylpenam-3alpha-carboxylate; 2,2-dimethylpropanoyloxymethyl (2S,5R,6R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
Indication Bacterial infection [ICD11: 1A00-1C4Z] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 463.5 Topological Polar Surface Area 153
Heavy Atom Count 32 Rotatable Bond Count 9
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 8
Cross-matching ID
PubChem CID
33478
ChEBI ID
CHEBI:8255
CAS Number
33817-20-8
TTD Drug ID
D04KAQ
Formula
C22H29N3O6S
Canonical SMILES
CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)N)C(=O)OCOC(=O)C(C)(C)C)C
InChI
InChI=1S/C22H29N3O6S/c1-21(2,3)20(29)31-11-30-19(28)15-22(4,5)32-18-14(17(27)25(15)18)24-16(26)13(23)12-9-7-6-8-10-12/h6-10,13-15,18H,11,23H2,1-5H3,(H,24,26)/t13-,14-,15+,18-/m1/s1
InChIKey
ZEMIJUDPLILVNQ-ZXFNITATSA-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
Ampicillin DM014898
6249
Hydrolysis - Hydrolysis 1 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR008089 Pivampicillin Ampicillin Hydrolysis - Hydrolysis ES [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Penicillinase (penP) DMEN869 Bacillus subtilis
BLAC_BACSU
3.5.2.6
[2]
References
1 Drug information of Pivampicillin, 2008. eduDrugs.
2 Kinetics and mechanism of enzymatic hydrolysis of pivampicillin monolayers
3 Absorption of ester prodrugs in Caco-2 and rat intestine models

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