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

General Information of Drug (ID: DR0909)
Drug Name
Labetalol
Synonyms
Labetalol [INN:BAN]; Labetalolum; Labetalolum [INN-Latin]; Labetolol; Normodyne; SGUAFYQXFOLMHL-UHFFFAOYSA-N; ScH 15719W; Trandate; labetalol; AH 5158; Albetol; Ibidomide; 2-Hydroxy-5-(1-hydroxy-2-((4-phenylbutan-2-yl)amino)ethyl)benzamide; 2-hydroxy-5-[1-hydroxy-2-(4-phenylbutan-2-ylamino)ethyl]benzamide; 3-Carboxamido-4-hydroxy-alpha-((1-methyl-3-phenylpropylamino)methyl)benzyl alcohol; 36894-69-6; 5-(1-Hydroxy-2-(1-methyl-3-phenylpropylamino)ethyl)salicylamide; CHEBI:6343; EINECS 253-258-3; HSDB 6537; UNII-R5H8897N95
Indication Essential hypertension [ICD11: BA00] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 328.4 Topological Polar Surface Area 95.6
Heavy Atom Count 24 Rotatable Bond Count 8
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
3869
PubChem SID
9275 ; 5142009 ; 7979714 ; 8152441 ; 11335649 ; 11360888 ; 11364501 ; 11367063 ; 11369625 ; 11372741 ; 11373866 ; 11377787 ; 11461860 ; 11466305 ; 11467425 ; 11484641 ; 11486109 ; 11488679 ; 11491396 ; 11491999 ; 11495421 ; 14777379 ; 29222985 ; 46505511 ; 47216734 ; 47736423 ; 47885363 ; 48184950 ; 48259181 ; 48259182 ; 48259183 ; 48259184 ; 48416150 ; 49698939 ; 49832659 ; 49876891 ; 50105268 ; 53790399 ; 56413046 ; 56464163 ; 57322029 ; 77168696 ; 85209992 ; 85788805 ; 90341718 ; 92716935 ; 96024796 ; 103165317 ; 104304757 ; 118314781
ChEBI ID
ChEBI:6343
CAS Number
36894-69-6
TTD Drug ID
D0A8XN
Formula
C19H24N2O3
Canonical SMILES
CC(CCC1=CC=CC=C1)NCC(C2=CC(=C(C=C2)O)C(=O)N)O
InChI
1S/C19H24N2O3/c1-13(7-8-14-5-3-2-4-6-14)21-12-18(23)15-9-10-17(22)16(11-15)19(20)24/h2-6,9-11,13,18,21-23H,7-8,12H2,1H3,(H2,20,24)
InChIKey
SGUAFYQXFOLMHL-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
Labetalol 3-hydroxylated metabolite (VI) DM002837
137553862
Oxidation - 3-Hydroxylation 1 [5]
Labetalol Benzyl glucuronide metabolite (II) DM002832
137553860
Conjugation - O-Glucuronidation 1 [4] , [6]
Labetalol Hydroxylated metabolite (IV) DM002835
12814789
Oxidation - 4-Hydroxylation 1 [5]
Labetalol N-glucuronide metabolite DM002834 N. A. Conjugation - O-Glucuronidation 1 [4] , [6]
Labetalol Phenolic glucuronide metabolite (III) DM002833 N. A. Conjugation - O-Glucuronidation 1 [4] , [6]
Labetalol C1' Glucuronidated metabolite (VII) DM002841
137553863
Conjugation - O-Glucuronidation 2 [7]
Labetalol C3 Glucuronidated metabolite (VIII) DM002842
137553864
Conjugation - O-Glucuronidation 2 [7]
Labetalol Phenolic glucuronide metabolite (V) DM002836
137553861
Conjugation - O-Glucuronidation 2 [5]
Labetalol Theoretical metabolite (IX) DM002838 N. A. Unclear 2 [7]
Labetalol Theoretical metabolite (X) DM002839
137553867
Conjugation - O-Glucuronidation 3 [7]
Labetalol Theoretical metabolite (XI) DM002840
137553866
Conjugation - O-Glucuronidation 3 [7]
⏷ Show the Full List of 11  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001385 Labetalol Labetalol Benzyl glucuronide metabolite (II) Conjugation - O-Glucuronidation UGT1A1 ... [4], [6]
MR001386 Labetalol Labetalol Phenolic glucuronide metabolite (III) Conjugation - O-Glucuronidation UGT1A1 ... [4], [6]
MR001387 Labetalol Labetalol N-glucuronide metabolite Conjugation - O-Glucuronidation UGT1A1 ... [4], [6]
MR001388 Labetalol Labetalol Hydroxylated metabolite (IV) Oxidation - 4-Hydroxylation Unclear [5]
MR001389 Labetalol Labetalol 3-hydroxylated metabolite (VI) Oxidation - 3-Hydroxylation Unclear [5]
MR001380 Labetalol 3-hydroxylated metabolite (VI) Labetalol Theoretical metabolite (IX) Unclear Unclear [7]
MR001381 Labetalol 3-hydroxylated metabolite (VI) Labetalol C1' Glucuronidated metabolite (VII) Conjugation - O-Glucuronidation Unclear [7]
MR001382 Labetalol 3-hydroxylated metabolite (VI) Labetalol C3 Glucuronidated metabolite (VIII) Conjugation - O-Glucuronidation Unclear [7]
MR001379 Labetalol Hydroxylated metabolite (IV) Labetalol Phenolic glucuronide metabolite (V) Conjugation - O-Glucuronidation Unclear [5]
MR001383 Labetalol Theoretical metabolite (IX) Labetalol Theoretical metabolite (X) Conjugation - O-Glucuronidation Unclear [7]
MR001384 Labetalol Theoretical metabolite (IX) Labetalol Theoretical metabolite (XI) Conjugation - O-Glucuronidation Unclear [7]
⏷ Show the Full List of 11 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[3]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[4]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[4]
UDP-glucuronosyltransferase 2B4 (UGT2B4) DME0047 Homo sapiens
UD2B4_HUMAN
2.4.1.17
[4]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[4]
⏷ Show the Full List of 6  DME(s)
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
UDP-glucuronosyltransferase 2B4 (UGT2B4) DME0047 Km = 0.368 microM
UD2B4_HUMAN
[4]
References
1 Labetalol was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Comparison of verapamil, diltiazem, and labetalol on the bioavailability and metabolism of imipramine. J Clin Pharmacol. 1992 Feb;32(2):176-83.
3 Drug Interactions Flockhart Table
4 Regulation of UDP-glucuronosyltransferase (UGT) 1A1 by progesterone and its impact on labetalol elimination. Xenobiotica. 2008 Jan;38(1):62-75.
5 Urinary metabolites of (R),(R)-labetalol Drug Metab Dispos. 1994 Nov-Dec;22(6):866-72.
6 Pregnancy-Related Hormones Increase UGT1A1-Mediated Labetalol Metabolism in Human Hepatocytes Front Pharmacol. 2021 Apr 15;12:655320. doi: 10.3389/fphar.2021.655320.
7 DrugBank(Pharmacology-Metabolism)Labetalol

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