General Information of Drug (ID: DR0514)
Drug Name
Diphenhydramine
Synonyms
Dabylen; Debendrin; Dermistina; Dermodrin; Desentol; Diabenyl; Diabylen; Dibondrin; Difedryl; Difenhydramin; Dihidral; Diphantine; Drylistan; Dylamon; Etanautine; Histaxin; Hyadrine; Ibiodral; Medidryl; Mephadryl; Nausen; Novamina; Probedryl; Alledryl; Allergical; Amidryl; Antistominum; Antomin; Bagodryl; Baramine; Benachlor; Benadrin; Benadryl; Benapon; Benodin; Benodine; Benylan; Benylin; Benzantine; Benzhydramine; Benzhydraminum; Benzhydril; Benzhydroamina; Betramin; Syntedril; diphenhydramine; 2-(Benzhydryloxy)-N,N-dimethylethanamine; 58-73-1
Indication Meniere disease [ICD11: AB31] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 255.35 Topological Polar Surface Area 12.5
Heavy Atom Count 19 Rotatable Bond Count 6
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
3100
PubChem SID
9174 ; 511392 ; 608048 ; 3154507 ; 5021578 ; 7847366 ; 7849634 ; 7885212 ; 7979103 ; 8151972 ; 10508422 ; 10528411 ; 10544720 ; 11111059 ; 11111060 ; 11335543 ; 11360782 ; 11363874 ; 11366436 ; 11368998 ; 11371539 ; 11374238 ; 11377160 ; 11407308 ; 11427137 ; 11461754 ; 11466093 ; 11467213 ; 11484697 ; 11485906 ; 11488777 ; 11490216 ; 11492335 ; 11494794 ; 14749996 ; 25768169 ; 26713829 ; 26751623 ; 29222243 ; 46505484 ; 47440177 ; 47588927 ; 47810670 ; 47810671 ; 48035032 ; 48110379 ; 48110380 ; 48184925 ; 48184926 ; 48415909
ChEBI ID
CHEBI:4636
CAS Number
58-73-1
TTD Drug ID
D01FGR
Formula
C17H21NO
Canonical SMILES
CN(C)CCOC(C1=CC=CC=C1)C2=CC=CC=C2
InChI
1S/C17H21NO/c1-18(2)13-14-19-17(15-9-5-3-6-10-15)16-11-7-4-8-12-16/h3-12,17H,13-14H2,1-2H3
InChIKey
ZZVUWRFHKOJYTH-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
Diphenhydramine N-glucuronide DM000109
178420
Conjugation - Glucuronidation 1 [5] , [6]
N-acetyldidesmethyldiphenhydramine DM000110 N. A. Unclear 1 [7]
N-desmethyldiphenhydramine DM000105
40791
Oxidation - N-Demethylation 1 [4] , [5] , [8] , [6]
N,N-didesmethyldiphenhydramine DM000106
36060
Oxidation - N-Demethylation 2 [4] , [5] , [8]
Diphenylmethoxyacetic acid DM000107
597513
Oxidation - Oxidation 3 [5] , [8]
N-acetyl-N-desmethyldiphenhydramine DM000108 N. A. Conjugation - Acetylation 3 [5] , [8]
Unclear DM009999 N. A. Conjugation - Conjugation 4 [9]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000876 Diphenhydramine N-desmethyldiphenhydramine Oxidation - N-Demethylation CYP2D6 ... [4], [5], [8], [6]
MR000877 Diphenhydramine Diphenhydramine N-glucuronide Conjugation - Glucuronidation UGT [5], [6]
MR000878 Diphenhydramine N-acetyldidesmethyldiphenhydramine Unclear Unclear [7]
MR000872 N-desmethyldiphenhydramine N,N-didesmethyldiphenhydramine Oxidation - N-Demethylation CYP2D6 ... [4], [5], [8]
MR000873 N,N-didesmethyldiphenhydramine Diphenylmethoxyacetic acid Oxidation - Oxidation Unclear [5], [8]
MR000874 N,N-didesmethyldiphenhydramine N-acetyl-N-desmethyldiphenhydramine Conjugation - Acetylation Unclear [5], [8]
MR000875 Diphenylmethoxyacetic acid . Conjugation - Conjugation Unclear [9]
⏷ Show the Full List of 7 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 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[3]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[4]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[5]
Prostaglandin G/H synthase 1 (COX-1) DME0091 Homo sapiens
PGH1_HUMAN
1.14.99.1
[5]
References
1 Diphenhydramine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Identification of human cytochrome p450 isozymes involved in diphenhydramine N-demethylation Drug Metab Dispos. 2007 Jan;35(1):72-8. doi: 10.1124/dmd.106.012088.
3 Pharmacogenomics in psychiatry: implications for practice. Recent Pat Biotechnol. 2014;8(2):152-9.
4 Identification of human cytochrome p450 isozymes involved in diphenhydramine N-demethylation. Drug Metab Dispos. 2007 Jan;35(1):72-8.
5 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
6 Non-invasive skin sampling detects systemically administered drugs in humans. PLoS One. 2022 Jul 26;17(7):e0271794. doi: 10.1371/journal.pone.0271794.
7 Metabolism of the ethanolamine-type antihistamine diphenhydramine (Benadryl) by the fungus Cunninghamella elegans Appl Microbiol Biotechnol. 2000 Mar;53(3):310-5. doi: 10.1007/s002530050026.
8 Bioconcentration, metabolism and effects of diphenhydramine on behavioral and biochemical markers in crucian carp (Carassius auratus) Sci Total Environ. 2016 Feb 15;544:400-9. doi: 10.1016/j.scitotenv.2015.11.132.
9 American Society of Health System Pharmacists; AHFS Drug Information 2010. Bethesda, MD. (2010), p. 2511

If you find any error in data or bug in web service, please kindly report it to Dr. Yin and Dr. Li.