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

General Information of Drug (ID: DR1367)
Drug Name	Propranolol hydrochloride
Synonyms	Panolol; Prandol; Pronovan; Propabloc; Propadex; Propalong; Propayerst; Proprahexal; Propral; Propranolol Hcl; Propranolol chloride; Propranolol hydrochloride; Propranovitan; Pylapron; Rapynogen; Scandrug; Sloprolol; Sudenol; Tiperal; (+)-1-Isopropylamino-3-(1-naphthyloxy)-2-propanol; (+)-Propranolol; (2R)-1-naphthalen-1-yloxy-3-(propan-2-ylamino)propan-2-ol; (R)-(+)-propranolol; (R)-Propranolol; 2-Propanol, 1-(isopropylamino)-3-(1-naphthyloxy)-, (+)-; 2R-Propranolol; 5051-22-9; CHEBI:8736; D-Propranolol; DEXPROPRANOLOL; Despropranolo [DCIT]; Dexpropranolol [INN:BAN]; Dexpropranololum; Dexpropranololum [INN-Latin]; Dextropropranolol; EINECS 225-749-2; NCGC00016429-05; PG6KY07UD7; R (+)-Propanolol; R-(+)-Propranolol; UNII-PG6KY07UD7; 318-98-9; Anaprilin; Apsolol; Arcablock; Artensol; Beprane; Berkolol; Beta Neg; Cardinol; Caridolol; Corbeta; Detensol; Dibudinate; Duranol; Efectolol; Emforal; Frekven; Hemipralon; Herzbase; Ikopal; Inderal; Inderalici; Inderex; Indermigran; Indobloc; InnoPran XL; Kemi; Kidoral; Naprilin; Nelderal; Noloten; Novopranol
Indication	Migraine [ICD11: 8A80]			Approved	[1]
Structure
Structure	3D MOL is unavailable		2D MOL
Pharmaceutical Properties	Molecular Weight	295.8	Topological Polar Surface Area		41.5
	Heavy Atom Count	20	Rotatable Bond Count		6
	Hydrogen Bond Donor Count	3	Hydrogen Bond Acceptor Count		3
Cross-matching ID	PubChem CID 62882 ChEBI ID CHEBI:8500 CAS Number 318-98-9 TTD Drug ID D04JEE Formula C16H22ClNO2 Canonical SMILES CC(C)NCC(COC1=CC=CC2=CC=CC=C21)O.Cl InChI 1S/C16H21NO2.ClH/c1-12(2)17-10-14(18)11-19-16-9-5-7-13-6-3-4-8-15(13)16;/h3-9,12,14,17-18H,10-11H2,1-2H3;1H InChIKey ZMRUPTIKESYGQW-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
1-Naphthol	DM003016	7005	Unclear	1	[9]
4'-hydroxypropanolol	DM003017	91565	Oxidation - 4-Hydroxylation	1	[10] , [11]
Alpha-Naphthoxylactic Acid	DM003020	115274	Oxidation - Oxidation	1	[12]
N-desisopropylpropranolol	DM003014	159899	Oxidation - N-Desisopropylation	1	[11]
Propranolol glucuronide	DM003015	119515	Conjugation - O-Glucuronidation	1	[12]
4-hydroxyalprenolol glucuronide	DM003018	129823	Conjugation - Glucuronidation	2	[10] , [11]
metaboliteVI	DM003021	76313	Unclear	2	[9]
Naphthalene-1,4-diol	DM003019	11305	Unclear	2	[9]

The Full List of Metabolic Reaction (MR) of This Drug

MR ID	Reactant	Product	MR Type	DME	REF
MR002192	Propranolol hydrochloride	N-desisopropylpropranolol	Oxidation - N-Desisopropylation	CYP1A2	[11]
MR002193	Propranolol hydrochloride	Propranolol glucuronide	Conjugation - O-Glucuronidation	Unclear	[12]
MR002194	Propranolol hydrochloride	1-Naphthol	Unclear	Unclear	[9]
MR002195	Propranolol hydrochloride	4'-hydroxypropanolol	Oxidation - 4-Hydroxylation	CYP2D6	[10], [11]
MR002196	Propranolol hydrochloride	Alpha-Naphthoxylactic Acid	Oxidation - Oxidation	Unclear	[12]
MR002189	4'-hydroxypropanolol	4-hydroxyalprenolol glucuronide	Conjugation - Glucuronidation	Unclear	[10], [11]
MR002190	4'-hydroxypropanolol	Naphthalene-1,4-diol	Unclear	Unclear	[9]
MR002191	Alpha-Naphthoxylactic Acid	metaboliteVI	Unclear	Unclear	[9]


⏷ Show the Full List of 8 MR(s)

Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug

DME Name	DME Info	Species	Uniprot ID	EC Number	REF
Cytochrome P450 102A1 (cyp102)	DME1075	Bacillus megaterium	CPXB_BACMB	1.14.14.1	[2]
Cytochrome P450 1A2 (CYP1A2)	DME0003	Homo sapiens	CP1A2_HUMAN	1.14.14.1	[3]
Cytochrome P450 2D6 (CYP2D6)	DME0009	Homo sapiens	CP2D6_HUMAN	1.14.14.1	[4]
Cytochrome P450 3A4 (CYP3A4)	DME0001	Homo sapiens	CP3A4_HUMAN	1.14.14.55	[5]
Cytochrome P450 3A5 (CYP3A5)	DME0012	Homo sapiens	CP3A5_HUMAN	1.14.14.1	[6]
Cytochrome P450 3A7 (CYP3A7)	DME0015	Homo sapiens	CP3A7_HUMAN	1.14.14.1	[6]
Dimethylaniline oxidase 2 (FMO2)	DME0283	Homo sapiens	FMO2_HUMAN	1.14.13.8	[7]
Mephenytoin 4-hydroxylase (CYP2C19)	DME0021	Homo sapiens	CP2CJ_HUMAN	1.14.14.1	[8]


⏷ Show the Full List of 8 DME(s)

References
1	Propranolol Hydrochloride was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2	acillus megaterium SF185 spores exert protective effects against oxidative stress in vivo and in vitro. Sci Rep. 2019 Aug 19;9(1):12082.
3	Synthetic and natural compounds that interact with human cytochrome P450 1A2 and implications in drug development. Curr Med Chem. 2009;16(31):4066-218.
4	Structure-activity relationship for human cytochrome P450 substrates and inhibitors. Drug Metab Rev. 2002 Feb-May;34(1-2):69-82.
5	Cytochrome P450 isozymes involved in propranolol metabolism in human liver microsomes. The role of CYP2D6 as ring-hydroxylase and CYP1A2 as N-desisopropylase. Drug Metab Dispos. 1994 Nov-Dec;22(6):909-15.
6	The influence of diltiazem versus cimetidine on propranolol metabolism. J Clin Pharmacol. 1992 Dec;32(12):1099-104.
7	Human FMO2-based microbial whole-cell catalysts for drug metabolite synthesis. Microb Cell Fact. 2015 Jun 12;14:82.
8	Clinical relevance of genetic polymorphisms in the human CYP2C subfamily. Br J Clin Pharmacol. 2001 Oct;52(4):349-55.
9	Propranolol metabolism in man and dog: mass spectrometric identification of six new metabolites J Pharmacol Exp Ther. 1972 Jul;182(1):83-92.
10	Isolation, purification, and structure identification of glucuronic acid conjugates of propranolol and alprenolol and their ring-hydroxylated metabolites Drug Metab Dispos. 1984 Nov-Dec;12(6):749-54.
11	Rapid and simultaneous extraction of propranolol, its neutral and basic metabolites from plasma and assay by high-performance liquid chromatography J Chromatogr. 1985 Oct 11;343(2):349-58. doi: 10.1016/s0378-4347(00)84603-4.
12	Propranolol metabolism in normal subjects: association with sex steroid hormones Clin Pharmacol Ther. 1994 Aug;56(2):127-32. doi: 10.1038/clpt.1994.115.

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