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

General Information of Drug (ID: DR2281)
Drug Name
Diphenylpyraline
Synonyms
Diafen; Difenilpiralina; Difenilpiralina [INN-Spanish]; Diphenylpyralamine; Diphenylpyraline (INN); Diphenylpyraline [INN:BAN]; Diphenylpyralinum; Diphenylpyrilene; Hispril; Histryl; Histyn; Hystryl; Lergobine; Lyssipoll; Mepiben; Allergen; Belfene; Dayfen; Neargal; 1-Methyl-4-piperidyl benzhydryl ether; 1-methyl-4-hydroxypiperidine benzhydryl ether; 4-(Benzhydryloxy)-1-methylpiperidine; 4-(Diphenylmethoxy)-1-methylpiperidine; 4-(benzhydryloxy)-N-methylpiperidine; 4-DIPHENYLMETHOXY-1-METHYLPIPERIDINE; 4-[(diphenylmethyl)oxy]-1-methylpiperidine; 4-benzhydryloxy-1-methylpiperidine; AN 1041; Dafen; Diphenylpyralinum [INN-Latin];Diphenylpyraline maleate (2:1); N-Methylpiperidyl-(4)-benzhydrylaether salzsauren salze; N-Methylpiperidyl-(4)-benzhydrylaether salzsauren salze [German]
Indication Allergy [ICD11: 4A80] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 281.4 Topological Polar Surface Area 12.5
Heavy Atom Count 21 Rotatable Bond Count 4
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
3103
PubChem SID
615228 ; 5046068 ; 8151975 ; 10508417 ; 11112289 ; 11336026 ; 11361265 ; 11363896 ; 11366458 ; 11369020 ; 11371242 ; 11374260 ; 11377182 ; 11455164 ; 11462237 ; 11466735 ; 11467855 ; 11484779 ; 11486550 ; 11488798 ; 11490217 ; 11492336 ; 11494816 ; 15442665 ; 29222246 ; 46504936 ; 47365245 ; 47365246 ; 47515368 ; 47736537 ; 47885465 ; 48185045 ; 48259283 ; 48334549 ; 48415912 ; 49698858 ; 50016255 ; 50123603 ; 50123604 ; 50938711 ; 57321610 ; 85171690 ; 85209863 ; 85788475 ; 92729772 ; 96024558 ; 99319623 ; 103555994 ; 103856536 ; 104098725
ChEBI ID
CHEBI:59788
CAS Number
147-20-6
TTD Drug ID
D0W6DY
Formula
C19H23NO
Canonical SMILES
CN1CCC(CC1)OC(C2=CC=CC=C2)C3=CC=CC=C3
InChI
1S/C19H23NO/c1-20-14-12-18(13-15-20)21-19(16-8-4-2-5-9-16)17-10-6-3-7-11-17/h2-11,18-19H,12-15H2,1H3
InChIKey
OWQUZNMMYNAXSL-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
Levomepromazine glucuronide DM000297 N. A. Conjugation - Glucuronidation 1 [2]
Levomepromazine sulfoxide DM000295
165566
Oxidation - Sulfoxidation 1 [7] , [8]
N-monodesmethyl Levomepromazine DM000296
10335813
Oxidation - N-Demethylation 1 [7] , [8]
O-monodesmethyl Levomepromazine DM000298 N. A. Oxidation - O-Demethylation 1 [8]
Unclear DM009999 N. A. Oxidation - Hydroxylation 1 [8]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003406 Diphenylpyraline Levomepromazine sulfoxide Oxidation - Sulfoxidation CYP3A4 [7], [8]
MR003407 Diphenylpyraline N-monodesmethyl Levomepromazine Oxidation - N-Demethylation CYP3A4 [7], [8]
MR003408 Diphenylpyraline Levomepromazine glucuronide Conjugation - Glucuronidation [2]
MR003409 Diphenylpyraline O-monodesmethyl Levomepromazine Oxidation - O-Demethylation [8]
MR003410 Diphenylpyraline . Oxidation - Hydroxylation [8]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Adenosine aminohydrolase (ADA) DME0060 Homo sapiens
ADA_HUMAN
3.5.4.4
[2]
Aldo-keto reductase 1B1 (AKR1B1) DME0087 Homo sapiens
ALDR_HUMAN
1.1.1.21
[3]
Aldo-keto reductase 1C1 (AKR1C1) DME0197 Homo sapiens
AK1C1_HUMAN
1.1.1.149
[3]
Aldo-keto reductase 1C2 (AKR1C2) DME0233 Homo sapiens
AK1C2_HUMAN
1.1.1.357
[3]
Aldo-keto reductase 1C3 (AKR1C3) DME0118 Homo sapiens
AK1C3_HUMAN
1.1.1.357
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[4]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[5]
NADPH-dependent carbonyl reductase 1 (CBR1) DME0067 Homo sapiens
CBR1_HUMAN
1.1.1.184
[3]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[3]
Unclear metabolic mechanism (DME-unclear) DME1391 Bifidobacterium ruminatum Not Available Not Available [6]
⏷ Show the Full List of 11  DME(s)
References
1 Diphenylpyraline was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 DrugBank(Pharmacology-Metabolism)Diphenylpyraline
3 In?vitro metabolism of fenofibric acid by carbonyl reducing enzymes Chem Biol Interact. 2016 Oct 25;258:153-8. doi: 10.1016/j.cbi.2016.09.001.
4 Pharmacogenomics as molecular autopsy for forensic toxicology: genotyping cytochrome P450 3A4*1B and 3A5*3 for 25 fentanyl cases J Anal Toxicol. 2005 Oct;29(7):590-8. doi: 10.1093/jat/29.7.590.
5 Drug Interactions Flockhart Table:Fentanyl citrate
6 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
7 Pharmacokinetics and first-pass metabolism of levomepromazine in the rat Acta Pharmacol Toxicol (Copenh). 1982 Feb;50(2):148-54. doi: 10.1111/j.1600-0773.1982.tb00956.x.
8 The influence of amitriptyline and carbamazepine on levomepromazine metabolism in human liver: an in vitro study Pharmacol Rep. 2014 Dec;66(6):1122-6. doi: 10.1016/j.pharep.2014.07.012.

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