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

General Information of Drug (ID: DR5938)
Drug Name
Bacampicillin
Prodrug Info Bacampicillin is the prodrug of Ampicillin
Synonyms
Bacampicilina; Bacampicilline; Bacampicillinum; Penglobe; Bacampicillin hydrochloride; Bacampicilina [INN-Spanish]; Bacampicillin (INN); Bacampicillin [INN:BAN]; Bacampicilline [INN-French]; Bacampicillinum [INN-Latin]; Penglobe (TN); Spectrobid (TN); (2S,5R,6R)-6((R)-(2-Amino-2-phenylacetamido))-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid ester with ethyl 1-hydroxyethylcarbonate; 1'-Ethoxycarbonyloxyethyl-(6-D-alpha-aminophenylacetamido)penicillanate; 1-Ethoxycarbonyloxyethyl (2S,5R,6R)-6((R)-(2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptan-2-carboxylat; 1-[(ethoxycarbonyl)oxy]ethyl (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; 1-[(ethoxycarbonyl)oxy]ethyl 6beta-[(2R)-2-amino-2-phenylacetamido]-2,2-dimethylpenam-3alpha-carboxylate; 1-ethoxycarbonyloxyethyl (2S,5R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate; 1-ethoxycarbonyloxyethyl (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; 1-ethoxycarbonyloxyethyl (2S,5R,6R)-6-[[(2S)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate; 6-((R)-2-Amino-2-phenylacetamido)penicillansaeure-(1-(ethoxycarbonyloxy)ethylester
Indication Bacterial infection [ICD11: 1A00-1C4Z] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 465.5 Topological Polar Surface Area 163
Heavy Atom Count 32 Rotatable Bond Count 10
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 9
Cross-matching ID
PubChem CID
441397
ChEBI ID
CHEBI:2968
CAS Number
50972-17-3
TTD Drug ID
D04CFW
Formula
C21H27N3O7S
Canonical SMILES
CCOC(=O)OC(C)OC(=O)[C@H]1C(S[C@H]2N1C(=O)[C@H]2NC(=O)[C@@H](C3=CC=CC=C3)N)(C)C
InChI
InChI=1S/C21H27N3O7S/c1-5-29-20(28)31-11(2)30-19(27)15-21(3,4)32-18-14(17(26)24(15)18)23-16(25)13(22)12-9-7-6-8-10-12/h6-11,13-15,18H,5,22H2,1-4H3,(H,23,25)/t11?,13-,14-,15+,18-/m1/s1
InChIKey
PFOLLRNADZZWEX-FFGRCDKISA-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 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR008908 Bacampicillin Ampicillin Hydrolysis - Hydrolysis ES [2]
References
1 FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (NDA) 050520.
2 Comparative study of bacampicillin and ampicillin in the treatment of uncomplicated gonorrhoea

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