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

General Information of Drug (ID: DR5602)
Drug Name
Chloroprocaine
Synonyms
Chloroprocain; Chloroprocainum; Chlorprocaine; Chlorprocainum; Cloroprocaina; Halestyn; Nesacaine; Piocaine; Chloroprocaine [INN]; Chloroprocaine hydrochloride; Nesacaine MPF; Chlor-procaine; Chloroprocaine (INN); Chloroprocainum [INN-Latin]; Cloroprocaina [INN-Spanish]; Nesacaine (TN); Nesacaine-Ce; Nesacaine-MPF (TN); Benzoic acid, 4-amino-2-chloro-, 2-(diethylamino)ethyl ester; 2-(Diethylamino)ethyl 4-amino-2-chlorobenzoate; 2-(Diethylaminoethyl)-4-amino-2-chlorobenzoate; 2-Chloroprocaine; 2-diethylaminoethyl 4-amino-2-chlorobenzoate; 4-amino-2-chlorobenzoic acid 2-(diethylamino)ethyl ester
Indication Anaesthesia [ICD11: 9A76-9A78] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 270.75 Topological Polar Surface Area 55.6
Heavy Atom Count 18 Rotatable Bond Count 7
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
8612
ChEBI ID
CHEBI:3636
CAS Number
133-16-4
TTD Drug ID
D07NAJ
Formula
C13H19ClN2O2
Canonical SMILES
CCN(CC)CCOC(=O)C1=C(C=C(C=C1)N)Cl
InChI
InChI=1S/C13H19ClN2O2/c1-3-16(4-2)7-8-18-13(17)11-6-5-10(15)9-12(11)14/h5-6,9H,3-4,7-8,15H2,1-2H3
InChIKey
VDANGULDQQJODZ-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
2-chloro-p-aminobenzoic acid DM014975
17154
Hydrolysis - Hydrolysis 1 [2]
Diethylaminoethanol DM014907
7497
Hydrolysis - Hydrolysis 1 [3]
Diethylaminoethanol DM014907
7497
Hydrolysis - Hydrolysis 1 [4]
N-acetyl-2-chloro-p-aminobenzoic acid DM015239
181587
Conjugation - Acetylation 2 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR008653 Chloroprocaine 2-chloro-p-aminobenzoic acid Hydrolysis - Hydrolysis Unclear [2]
MR008655 Chloroprocaine Diethylaminoethanol Hydrolysis - Hydrolysis Unclear [4]
MR008654 2-chloro-p-aminobenzoic acid N-acetyl-2-chloro-p-aminobenzoic acid Conjugation - Acetylation Unclear [4]
References
1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7145).
2 High-performance liquid chromatographic analysis of the 2-chloroprocaine metabolite, diethylaminoethanol, in blood and serum
3 Metabolism and measurement of chloroprocaine, an ester-type local anesthetic
4 DrugBank(Pharmacology-Metabolism):Chloroprocaine

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