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

General Information of Drug (ID: DR5102)
Drug Name
Brimonidine
Synonyms
brimonidine; 59803-98-4; Bromoxidine; UK 14,304; 5-Bromo-N-(4,5-dihydro-1H-imidazol-2-yl)-6-quinoxalinamine; 5-Bromo-6-(2-imidazolin-2-ylamino)quinoxaline; UK-14304; AGN 190342; UNII-E6GNX3HHTE; Brimonidine [INN:BAN]; UK 14304; C11H10BrN5; MLS000069370; 6-Quinoxalinamine, 5-bromo-N-(4,5-dihydro-1H-imidazol-2-yl)-; E6GNX3HHTE; CHEMBL844; AGN-190342; BRN 0751629; SMR000058355; CHEBI:3175; LK 14304-18; Brimonidine, 98%; NCGC00016069-09; EN300-50880; DSSTox_RID_80758; Brimonidine (bioerodible, extended release); [3H]brimonidine
Indication Glaucoma [ICD11: 9C61] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 292.13 Topological Polar Surface Area 62.2
Heavy Atom Count 17 Rotatable Bond Count 2
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
2435
ChEBI ID
CHEBI:3175
CAS Number
59803-98-4
TTD Drug ID
D0AE3X
Formula
C11H10BrN5
Canonical SMILES
C1CN=C(N1)NC2=C(C3=NC=CN=C3C=C2)Br
InChI
InChI=1S/C11H10BrN5/c12-9-7(17-11-15-5-6-16-11)1-2-8-10(9)14-4-3-13-8/h1-4H,5-6H2,(H2,15,16,17)
InChIKey
XYLJNLCSTIOKRM-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
Benzimidazole derivative DM018772 N. A. Unclear - Unclear 1 [2]
Brimonidine metabolite M1 DM018768 N. A. Unclear - Unclear 1 [3]
Brimonidine metabolite M2 DM016595
131770028
Oxidation - Oxidation 1 [3]
Brimonidine metabolite M3 DM016604
134687620
Oxidation - Oxidation 1 [3]
Brimonidine metabolite M4 DM018769 N. A. Unclear - Unclear 1 [3]
Brimonidine metabolite M5 DM018763 N. A. Unclear - Unclear 1 [3]
Dehydro-hydroxybrimonidine-M1 DM018770 N. A. Oxidation - Hydroxylation 1 [2]
Dehydro-hydroxybrimonidine-M2 DM018771 N. A. Oxidation - Hydroxylation 1 [2]
AGN 191858 DM018767 N. A. Oxidation - Oxidation 2 [3]
AGN 192076 DM015631
10214826
Unclear - Unclear 2 [3]
AGN 192119 DM018764 N. A. Unclear - Unclear 2 [3]
AGN 192614 DM018766 N. A. Unclear - Unclear 2 [3]
AGN 192597 DM018765 N. A. Unclear - Unclear 3 [3]
AGN 191383 DM015890
14928441
Oxidation - Oxidation 4 [3]
⏷ Show the Full List of 14  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR011077 Brimonidine Brimonidine metabolite M5 Unclear - Unclear Unclear [3]
MR011083 Brimonidine Brimonidine metabolite M2 Oxidation - Oxidation AOX1 [3]
MR011085 Brimonidine Brimonidine metabolite M3 Oxidation - Oxidation AOX1 [3]
MR011087 Brimonidine Brimonidine metabolite M1 Unclear - Unclear Unclear [3]
MR011088 Brimonidine Brimonidine metabolite M4 Unclear - Unclear Unclear [3]
MR011089 Brimonidine Dehydro-hydroxybrimonidine-M1 Oxidation - Hydroxylation Unclear [2]
MR011090 Brimonidine Dehydro-hydroxybrimonidine-M2 Oxidation - Hydroxylation Unclear [2]
MR011091 Brimonidine Benzimidazole derivative Unclear - Unclear Unclear [2]
MR011084 Brimonidine metabolite M2 AGN 191858 Oxidation - Oxidation AOX1 [3]
MR011086 Brimonidine metabolite M3 AGN 191858 Oxidation - Oxidation AOX1 [3]
MR011078 Brimonidine metabolite M5 AGN 192119 Unclear - Unclear Unclear [3]
MR011081 Brimonidine metabolite M5 AGN 192614 Unclear - Unclear Unclear [3]
MR011082 Brimonidine metabolite M5 AGN 192076 Unclear - Unclear Unclear [3]
MR011079 AGN 192119 AGN 192597 Unclear - Unclear Unclear [3]
MR011080 AGN 192597 AGN 191383 Oxidation - Oxidation Unclear [3]
⏷ Show the Full List of 15 MR(s)
References
1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 520).
2 Characterization of benzimidazole and other oxidative and conjugative metabolites of brimonidine in vitro and in rats in vivo using on-line HID exchange LC-MS/MS and stable-isotope tracer techniques
3 Characterization of brimonidine metabolism with rat, rabbit, dog, monkey and human liver fractions and rabbit liver aldehyde oxidase

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