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

General Information of Drug (ID: DR5155)
Drug Name
Hetacillin
Synonyms
Etacillina; Hetacilina; Hetacilline; Hetacillinum; Phenazacillin; Versapen; Etacillina [DCIT]; HETACILLIN POTASSIUM; BRL 804; BL-P 804; BRL-804; Hetacilina [INN-Spanish]; Hetacilline [INN-French]; Hetacillinum [INN-Latin]; Versapen (TN); Hetacillin (USAN/INN); Hetacillin [USAN:INN:BAN]; N,N'-Isopropylidene-A-amino-benzyl penicillin; (2S,%R,6R)-6-(2,2-Dimethyl-5-oxo-4-phenyl-1-imidazolidinyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptan-2-carbonsaeure; (2S,5R)-6-[(4R)-2,2-dimethyl-5-oxo-4-phenylimidazolidin-1-yl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,5R,6R)-6-(2,2-dimethyl-5-oxo-4-phenylimidazolidin-1-yl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,5R,6R)-6-[(4R)-2,2-dimethyl-5-oxo-4-phenylimidazolidin-1-yl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; 6-(2,2-Dimethyl-5-oxo-4-phenyl-1-imidazolidinyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid; 6-(2,2-Dimethyl-5-oxo-4-phenyl-1-imidazolidinyl)penicillansaeure; 6-(2,2-dimethyl-5-oxo-4-phenylimidazolidin-1-yl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; 6beta-[(4R)-2,2-dimethyl-5-oxo-4-phenylimidazolidin-1-yl]-2,2-dimethylpenam-3alpha-carboxylic acid; 6beta-[(4R)-2,2-dimethyl-5-oxo-4-phenylimidazolidin-1-yl]penicillanic acid
Indication Bacterial infection [ICD11: 1A00-1C4Z] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 389.5 Topological Polar Surface Area 115
Heavy Atom Count 27 Rotatable Bond Count 3
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
443387
ChEBI ID
CHEBI:5683
CAS Number
3511-16-8
TTD Drug ID
D0W7RJ
Formula
C19H23N3O4S
Canonical SMILES
CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)N3C(=O)[C@H](NC3(C)C)C4=CC=CC=C4)C(=O)O)C
InChI
InChI=1S/C19H23N3O4S/c1-18(2)13(17(25)26)21-15(24)12(16(21)27-18)22-14(23)11(20-19(22,3)4)10-8-6-5-7-9-10/h5-9,11-13,16,20H,1-4H3,(H,25,26)/t11-,12-,13+,16-/m1/s1
InChIKey
DXVUYOAEDJXBPY-NFFDBFGFSA-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
Acetone DM014806
180
Hydrolysis - Hydrolysis 1 [2]
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
MR008087 Hetacillin Ampicillin Hydrolysis - Hydrolysis LE [2]
MR008088 Hetacillin Acetone Hydrolysis - Hydrolysis LE [2]
References
1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 Biotransformation of hetacillin to ampicillin in man

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