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

General Information of Drug (ID: DR1359)
Drug Name
BCP-13498
Prodrug Info BCP-13498 is the prodrug of N-acetyl-4-Aminophenol
Synonyms
Propacetamol; Pro-Dafalgan; Propacetamol (INN); Propacetamol [INN:BAN]; Propacetamol [INN]; Propacetamolum; Propacetamolum [Latin]; Tox21_113811; ZINC55161176; (4-acetamidophenyl) 2-(diethylamino)acetate; 5CHW4JMR82; 66532-85-2; AC1L2ALY; AC1Q6199; AKOS015890722; BCP13498; CHEBI:135089; CHEMBL1851805; DB09288; DSSTox_CID_31589; DSSTox_GSID_57800; DSSTox_RID_97473; DTXSID3057800; EINECS 266-390-1; Glycine, N,N-diethyl-, 4-(acetylamino)phenyl ester; N,N-Diethylglycine, ester with 4'-hydroxyacetanilide; SCHEMBL26155; UNII-5CHW4JMR82
Indication Anaesthesia [ICD11: 8E22] Phase 2 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 264.32 Topological Polar Surface Area 58.6
Heavy Atom Count 19 Rotatable Bond Count 7
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
68865
ChEBI ID
CHEBI:135089
CAS Number
66532-85-2
Formula
C14H20N2O3
Canonical SMILES
CCN(CC)CC(=O)OC1=CC=C(C=C1)NC(=O)C
InChI
1S/C14H20N2O3/c1-4-16(5-2)10-14(18)19-13-8-6-12(7-9-13)15-11(3)17/h6-9H,4-5,10H2,1-3H3,(H,15,17)
InChIKey
QTGAJCQTLIRCFL-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
N, N-diethylglycine DM006756 N. A. Unclear 1 [4]
N-acetyl-4-Aminophenol DM004787
1983
Unclear 1 [4]
Glucuronidation of paracetamol DM006755 N. A. Conjugation - Glucuronidation 2 [6]
N-acetil-p-benzoquinone imine DM006754 N. A. Unclear 2 [3]
Unclear DM009999 N. A. Unclear 2 [9]
Unclear DM009999 N. A. Unclear 2 [8]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007295 BCP-13498 Paracetamol Unclear PE [4]
MR007299 BCP-13498 N, N-diethylglycine Unclear PE [4]
MR007296 Paracetamol N-acetil-p-benzoquinone imine Unclear CYP2E1 ... [3]
MR007297 Paracetamol Glucuronidation of paracetamol Conjugation - Glucuronidation UGT1A1 [6]
MR007298 Paracetamol Unclear Unclear UGT1A6 [8]
MR014085 Paracetamol Unclear Unclear UGT1A9 [9]
⏷ Show the Full List of 6 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[3]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[3]
Plasma esterase (PE) DMEN068 . Not Available Not Available [4]
Sulfotransferase 2A1 (SULT2A1) DME0074 Homo sapiens
ST2A1_HUMAN
2.8.2.14
[5]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[6]
UDP-glucuronosyltransferase 1A10 (UGT1A10) DME0075 Homo sapiens
UD110_HUMAN
2.4.1.17
[7]
UDP-glucuronosyltransferase 1A6 (UGT1A6) DME0072 Homo sapiens
UD16_HUMAN
2.4.1.17
[8]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[9]
⏷ Show the Full List of 9  DME(s)
References
1 ClinicalTrials.gov (NCT03878082) Propacetamol to Reduce Post Cesarean Section Uterine Contraction Pain.
2 Acetaminophen activation by human liver cytochromes P450IIE1 and P450IA2. Arch Biochem Biophys. 1989 Jun;271(2):270-83.
3 Involvement of human cytochrome P450 2D6 in the bioactivation of acetaminophen. Drug Metab Dispos. 2000 Dec;28(12):1397-400.
4 DrugBank(Pharmacology-Metabolism):BCP-13498
5 Interindividual variability in acetaminophen sulfation by human fetal liver: implications for pharmacogenetic investigations of drug-induced birth defects. Birth Defects Res A Clin Mol Teratol. 2008 Mar;82(3):155-65.
6 Paracetamol glucuronidation by recombinant rat and human phenol UDP-glucuronosyltransferases. Biochem Pharmacol. 1993 May 5;45(9):1809-14.
7 UDP-glucuronosyltransferases and clinical drug-drug interactions. Pharmacol Ther. 2005 Apr;106(1):97-132.
8 Human UGT1A6 pharmacogenetics: identification of a novel SNP, characterization of allele frequencies and functional analysis of recombinant allozymes in human liver tissue and in cultured cells. Pharmacogenetics. 2004 Aug;14(8):487-99.
9 Polymorphic expression of UGT1A9 is associated with variable acetaminophen glucuronidation in neonates: a population pharmacokinetic and pharmacogenetic study. Clin Pharmacokinet. 2018 Oct;57(10):1325-1336.

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