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

General Information of Drug (ID: DR0796)
Drug Name
Guanfacine hydrochloride
Synonyms
Guanfacin hydrochloride; Guanfacine (hydrochloride); LON 798; guanfacine hydrochloride; 29110-48-3; 29520-14-7; BS 100-141; BS-100-141; MLS000069745; N-(Aminoiminomethyl)-2,6-dichlorobenzeneacetamide hydrochloride; N-(diaminomethylidene)-2-(2,6-dichlorophenyl)acetamide hydrochloride; N-Amidino-2-(2,6-dichlorophenyl)acetamide hydrochloride; N-Amidino-2-(2,6-dichlorophenyl)acetamide monohydrochloride; N-Carbamimidoyl-2-(2,6-dichlorophenyl)acetamide hydrochloride; UNII-PML56A160O; GUANFACINE HCL
Indication Attention deficit hyperactivity disorder [ICD11: 6A05] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 282.5 Topological Polar Surface Area 81.5
Heavy Atom Count 16 Rotatable Bond Count 2
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 1
Cross-matching ID
PubChem CID
71401
PubChem SID
7847672 ; 10321692 ; 11532959 ; 12013435 ; 14799743 ; 17405082 ; 43127732 ; 49878427 ; 50106306 ; 50125709 ; 53777625 ; 56422899 ; 57318182 ; 75139922 ; 85273773 ; 91011797 ; 92125343 ; 92304014 ; 103770477 ; 103840710 ; 103914179 ; 104350375 ; 117464967 ; 124891653 ; 126657731 ; 131315423 ; 134338574 ; 135030202 ; 137074791 ; 144075859 ; 144203710 ; 152106277 ; 160838238 ; 162174779 ; 162247844 ; 163098785 ; 163135011 ; 163403921 ; 163564473 ; 163621092 ; 163686415 ; 164814341 ; 170465381 ; 172908369 ; 175266064 ; 175611116 ; 175611812 ; 179149181 ; 185983130 ; 196106983
ChEBI ID
CHEBI:5559
CAS Number
29110-47-2
TTD Drug ID
D0WD8M
Formula
C9H10Cl3N3O
Canonical SMILES
C1=CC(=C(C(=C1)Cl)CC(=O)N=C(N)N)Cl.Cl
InChI
1S/C9H9Cl2N3O.ClH/c10-6-2-1-3-7(11)5(6)4-8(15)14-9(12)13;/h1-3H,4H2,(H4,12,13,14,15);1H
InChIKey
DGFYECXYGUIODH-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
3-hydroxyguanfacine DM004711
132831
Oxidation - Oxidationn 1 [3] , [4]
Guanfacine dihydro-diol DM004714 N. A. Multi-steps Reaction - Epoxidation; hydration 1 [5]
Guanfacine hydrochloride Metabolite M4 DM004715 N. A. Conjugation - Glucuronidation 1 [5]
Guanfacine hydrochloride Metabolite M5 DM004716 N. A. Conjugation - Glucuronidation 1 [5]
Guanfacine hydrochloride Metabolite M6 DM004719 N. A. Oxidation - Oxidationn 1 [5]
Guanfacine hydrochloride Metabolite M7 DM004717 N. A. Conjugation - Glucuronidation 1 [5]
Guanfacine hydrochloride Metabolite M8 DM004718 N. A. Conjugation - Glucuronidation 1 [5]
Guanfacine 3-glucuronide DM004713 N. A. Conjugation - O-glucuronidation 2 [6]
Guanfacine 3-sulfate DM004712 N. A. Conjugation - Sulfation 2 [6]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005062 Guanfacine hydrochloride 3-hydroxyguanfacine Oxidation - Oxidationn CYP3A4 [3], [4]
MR005065 Guanfacine hydrochloride Guanfacine dihydro-diol Multi-steps Reaction - Epoxidation; hydration Unclear [5]
MR005066 Guanfacine hydrochloride Guanfacine hydrochloride Metabolite M4 Conjugation - Glucuronidation Unclear [5]
MR005067 Guanfacine hydrochloride Guanfacine hydrochloride Metabolite M5 Conjugation - Glucuronidation Unclear [5]
MR005068 Guanfacine hydrochloride Guanfacine hydrochloride Metabolite M7 Conjugation - Glucuronidation Unclear [5]
MR005069 Guanfacine hydrochloride Guanfacine hydrochloride Metabolite M8 Conjugation - Glucuronidation Unclear [5]
MR005070 Guanfacine hydrochloride Guanfacine hydrochloride Metabolite M6 Oxidation - Oxidationn Unclear [5]
MR005063 3-hydroxyguanfacine Guanfacine 3-sulfate Conjugation - Sulfation Unclear [6]
MR005064 3-hydroxyguanfacine Guanfacine 3-glucuronide Conjugation - O-glucuronidation Unclear [6]
⏷ Show the Full List of 9 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
References
1 Guanfacine Hydrochloride was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Microsomal catalyzed N-hydroxylation of guanfacine and reduction of N-hydroxyguanfacine. Arch Pharm (Weinheim). 1997 Oct;330(9-10):303-6.
3 Determination of 3-hydroxy-guanfacine in biological fluids by electron-capture gas-liquid chromatography
4 Pharmacokinetics and metabolism of guanfacine in man: a review
5 Metabolite profiling of guanfacine in plasma and urine of healthy Japanese subjects after oral administration of guanfacine extended-release tablets
6 DrugBank(Pharmacology-Metabolism):Guanfacine hydrochloride

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