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

General Information of Drug (ID: DR5098)
Drug Name
Dipivefrin
Prodrug Info Dipivefrin is the prodrug of Epinephrine
Synonyms
AKPro; Dipivefrina; Dipivefrine; Dipivefrinum; Propine; Dipivalyl epinephrine; Dipivefrin HCL; Dipivefrin [USAN]; K 30081; Dipivefrin (USAN); Dipivefrina [INN-Spanish]; Dipivefrine (INN); Dipivefrinum [INN-Latin]; Ophtho-Dipivefrin; Propine C Cap B.I.D.; [2-(2,2-dimethylpropanoyloxy)-4-[1-hydroxy-2-(methylamino)ethyl]phenyl] 2,2-dimethylpropanoate; (+-)-3,4-Dihydroxy-alpha-((methylamino)methyl)benzyl alcohol 3,4-dipivalate; (+-)-4-[1-hydroxy-2-(methylamino)ethyl]-o-phenylene divavalate; (-)-2,2-Dimethylpropansaeure-4-(1-hydroxy-2-(methylamino)ethyl)-1,2-phenylenester; (-)-4-(1-Hydroxy-2-methylaminoethyl)-o-phenylendipivalat; (RS)-4-(1-Hydroxy-2-(methylamino)ethyl)-1,2-phenylen dipivalat; 1-(3',4'-dipivaloyloxyphenyl)-2-methylamino-1-ethanol; 2,2-Dimethylpropanoic acid 4-[1-hydroxy-2-(methylamino)ethyl]-1,2-phenylene ester; 4-(1-Hydroxy-2-(methylamino)ethyl)-1,2-phenylen dipivalat; 4-[1-hydroxy-2-(methylamino)ethyl]-o-phenylene divavalate; 4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diyl bis(2,2-dimethylpropanoate)
Indication Glaucoma [ICD11: 9C61] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 351.4 Topological Polar Surface Area 84.9
Heavy Atom Count 25 Rotatable Bond Count 9
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
3105
ChEBI ID
CHEBI:4646
CAS Number
52365-63-6
TTD Drug ID
D01JFT
Formula
C19H29NO5
Canonical SMILES
CC(C)(C)C(=O)OC1=C(C=C(C=C1)C(CNC)O)OC(=O)C(C)(C)C
InChI
InChI=1S/C19H29NO5/c1-18(2,3)16(22)24-14-9-8-12(13(21)11-20-7)10-15(14)25-17(23)19(4,5)6/h8-10,13,20-21H,11H2,1-7H3
InChIKey
OCUJLLGVOUDECM-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
Epinephrine DM000283
5816
Hydrolysis - Hydrolysis 1 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007738 Dipivefrin Epinephrine Hydrolysis - Hydrolysis CES [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Acetylcholinesterase (ACHE) DMEN853 Oryctolagus cuniculus
ACES_RABIT
3.1.1.7
[2]
Butyrylcholine esterase (BCHE) DME0069 Homo sapiens
CHLE_HUMAN
3.1.1.8
[3]
Butyrylcholine esterase (BCHE) DME0069 Homo sapiens
CHLE_HUMAN
3.1.1.8
[2]
References
1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 Characterization of esterases involved in the hydrolysis of dipivefrin hydrochloride
3 Dipivefrin and echothiophate: contraindications to combined use
4 Site of ocular hydrolysis of a prodrug, dipivefrin, and a comparison of its ocular metabolism with that of the parent compound, epinephrine

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