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

General Information of Drug (ID: DR0933)
Drug Name
Levobunolol
Synonyms
Levobunolol (INN); Levobunolol HCl; Levobunolol [INN:BAN]; Levobunololum; Levobunololum [INN-Latin]; W-7000A; l-Bunolol; Akbeta; Betagan; LEVOBUNOLOL; (-)-Bunolol; (S)-5-(3-(tert-Butylamino)-2-hydroxypropoxy)-3,4-dihydronaphthalen-1(2H)-one; 1(2H)-Naphthalenone, 5-(3-((1,1-dimethylethyl)amino)-2-hydroxypropoxy)-3,4-dihydro-, (S)-; 47141-42-4; 5-[(2S)-3-(tert-butylamino)-2-hydroxypropoxy]-3,4-dihydro-2H-naphthalen-1-one; CCRIS 4375; CHEBI:6438; G6317AOI7K; UNII-G6317AOI7K
Indication Glaucoma [ICD11: 9C61] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 291.4 Topological Polar Surface Area 58.6
Heavy Atom Count 21 Rotatable Bond Count 6
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
39468
PubChem SID
10116 ; 7979771 ; 8147013 ; 8176045 ; 11112712 ; 11112713 ; 11466875 ; 11467995 ; 11486490 ; 14800093 ; 34705356 ; 46507518 ; 47216948 ; 47440435 ; 47810938 ; 47810939 ; 49698660 ; 50064797 ; 50100511 ; 57312300 ; 75377008 ; 85787332 ; 96024805 ; 104331810 ; 117598030 ; 123099352 ; 128233843 ; 134223509 ; 134337615 ; 135002286 ; 135650031 ; 137004994 ; 141191903 ; 160964543 ; 162172878 ; 163418962 ; 163851154 ; 164789572 ; 172860923 ; 175268158 ; 179150487 ; 184531333 ; 198967741 ; 223554927 ; 224987628 ; 226412538 ; 252351251
ChEBI ID
ChEBI:6438
CAS Number
47141-42-4
TTD Drug ID
D00IUG
Formula
C17H25NO3
Canonical SMILES
CC(C)(C)NCC(COC1=CC=CC2=C1CCCC2=O)O
InChI
1S/C17H25NO3/c1-17(2,3)18-10-12(19)11-21-16-9-5-6-13-14(16)7-4-8-15(13)20/h5-6,9,12,18-19H,4,7-8,10-11H2,1-3H3/t12-/m0/s1
InChIKey
IXHBTMCLRNMKHZ-LBPRGKRZSA-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
Hydroxy-LB DM000253 N. A. Oxidation - Hydroxylation 1 [2]
Levobunolol metabolite M10 DM000251
156613786
Oxidation - Oxidation 1 [2]
Levobunolol metabolite M11 DM000248
5460507
Reduction - Reduction 1 [2]
Levobunolol metabolite M12 DM000260 N. A. Oxidation - Dihydroxylation 1 [2]
Levobunolol metabolite M13 DM000259 N. A. Oxidation - Monohydroxylation 1 [2]
Levobunolol metabolite M9 DM000258 N. A. Oxidation - Monohydroxylation 1 [2]
Levobunolol metabolite M1 DM000252 N. A. Conjugation - Glucuronidation 2 [2]
Levobunolol metabolite M14 DM000256 N. A. Conjugation - Acetylation 2 [2]
Levobunolol metabolite M15 DM000257 N. A. Conjugation - Acetylation 2 [2]
Levobunolol metabolite M2 DM000254 N. A. Conjugation - Glucuronidation 2 [2]
Levobunolol metabolite M4 DM000249 N. A. Oxidation - Hydroxylation 2 [2]
Levobunolol metabolite M5 DM000255 N. A. Conjugation - Glucuronidation 2 [2]
Levobunolol metabolite M8 DM000250 N. A. Oxidation - Hydroxylation 2 [2]
⏷ Show the Full List of 13  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001461 Levobunolol Levobunolol metabolite M11 Reduction - Reduction CBR1 ... [2]
MR001462 Levobunolol Levobunolol metabolite M10 Oxidation - Oxidation Unclear [2]
MR001463 Levobunolol Hydroxy-LB Oxidation - Hydroxylation Unclear [2]
MR001464 Levobunolol Levobunolol metabolite M9 Oxidation - Monohydroxylation Unclear [2]
MR001465 Levobunolol Levobunolol metabolite M13 Oxidation - Monohydroxylation Unclear [2]
MR001466 Levobunolol Levobunolol metabolite M12 Oxidation - Dihydroxylation Unclear [2]
MR001457 Hydroxy-LB Levobunolol metabolite M2 Conjugation - Glucuronidation Unclear [2]
MR001458 Hydroxy-LB Levobunolol metabolite M5 Conjugation - Glucuronidation Unclear [2]
MR001459 Hydroxy-LB Levobunolol metabolite M14 Conjugation - Acetylation Unclear [2]
MR001460 Hydroxy-LB Levobunolol metabolite M15 Conjugation - Acetylation Unclear [2]
MR001456 Levobunolol metabolite M10 Levobunolol metabolite M1 Conjugation - Glucuronidation Unclear [2]
MR001454 Levobunolol metabolite M11 Levobunolol metabolite M4 Oxidation - Hydroxylation Unclear [2]
MR001455 Levobunolol metabolite M11 Levobunolol metabolite M8 Oxidation - Hydroxylation Unclear [2]
⏷ Show the Full List of 13 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Aldo-keto reductase 1B1 (AKR1B1) DME0087 Homo sapiens
ALDR_HUMAN
1.1.1.21
[2]
Corticosteroid 11-beta-dehydrogenase 2 (HSD11B2) DME0419 Homo sapiens
DHI2_HUMAN
1.1.1.B40
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[3]
NADPH-dependent carbonyl reductase 1 (CBR1) DME0067 Homo sapiens
CBR1_HUMAN
1.1.1.184
[2]
NADPH-dependent carbonyl reductase 3 (CBR3) DME0068 Homo sapiens
CBR3_HUMAN
1.1.1.184
[2]
Small intestine reductase (AKR1B10) DME0398 Homo sapiens
AK1BA_HUMAN
1.1.1.21
[2]
⏷ Show the Full List of 6  DME(s)
References
1 Levobunolol was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Ocular Metabolism of Levobunolol: Historic and Emerging Metabolic Pathways Drug Metab Dispos. 2016 Aug;44(8):1304-12. doi: 10.1124/dmd.116.070458.
3 Application of substrate depletion assay to evaluation of CYP isoforms responsible for stereoselective metabolism of carvedilol. Drug Metab Pharmacokinet. 2016 Dec;31(6):425-432.

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