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

General Information of Drug (ID: DR0352)
Drug Name
Clonidine
Synonyms
Catapressan; Catarpres; Catarpresan; Chlornidinum; Clonidin; Clonidina; Clonidina [INN-Spanish]; Clonidinhydrochlorid; Clonidinum; Clonidinum [INN-Latin]; Adesipress; CATAPRES-TTS-1; CATAPRES-TTS-2; CATAPRES-TTS-3; CLORPRES; Catapres; Catapres- TTS; Catapres-TTS; Catapresan; Dixarit; Duraclon; Hemiton; Isoglaucon; M-5041T; SKF 34427; ST 155BS; ST-155-BS; clonidine; clonidine (amino form); 2-(2,6-Dichloroanilino)-2-imidazoline; 4205-90-7; N-(2,6-Dichlorophenyl)-4,5-dihydro-1H-imidazol-2-amine
Indication Essential hypertension [ICD11: BA00] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 230.09 Topological Polar Surface Area 36.4
Heavy Atom Count 14 Rotatable Bond Count 2
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 1
Cross-matching ID
PubChem CID
2803
PubChem SID
840960 ; 841959 ; 4807400 ; 5991864 ; 7847347 ; 7978974 ; 8151812 ; 10522369 ; 10527768 ; 11110984 ; 11110985 ; 11113648 ; 11120350 ; 11120838 ; 11121326 ; 11121653 ; 11122133 ; 11335949 ; 11361188 ; 11362722 ; 11364235 ; 11365284 ; 11366797 ; 11367846 ; 11369359 ; 11370715 ; 11370716 ; 11371375 ; 11373447 ; 11374710 ; 11376008 ; 11377521 ; 11462160 ; 11466276 ; 11467396 ; 11484969 ; 11485991 ; 11489003 ; 11490174 ; 11492771 ; 11495155 ; 14822899 ; 15172366 ; 26697416 ; 26697467 ; 26751841 ; 26751842 ; 29221958 ; 46508119 ; 47216577
ChEBI ID
ChEBI:46632
CAS Number
4205-90-7
TTD Drug ID
D03SKR
Formula
C9H9Cl2N3
Canonical SMILES
C1CN=C(N1)NC2=C(C=CC=C2Cl)Cl
InChI
1S/C9H9Cl2N3/c10-6-2-1-3-7(11)8(6)14-9-12-4-5-13-9/h1-3H,4-5H2,(H2,12,13,14)
InChIKey
GJSURZIOUXUGAL-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
2,6-dichlorophenylguanidine DM006120
12253686
Unclear 1 [4]
4,5-dehydroclonidine DM006121 N. A. Unclear 1 [4]
4-Hydroxyclonidine DM006119
92660
Oxidation - 4-hydroxylation 1 [2]
4-oxoclonidine DM006122 N. A. Unclear 1 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006587 Clonidine 4-Hydroxyclonidine Oxidation - 4-hydroxylation CYP2D6 ... [2]
MR006588 Clonidine 2,6-dichlorophenylguanidine Unclear Unclear [4]
MR006589 Clonidine 4,5-dehydroclonidine Unclear Unclear [4]
MR006590 Clonidine 4-oxoclonidine Unclear Unclear [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A1 (CYP1A1) DME0006 Homo sapiens
CP1A1_HUMAN
1.14.14.1
[2]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[2]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1254 Bacteroides thetaiotaomicron Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1364 Bacteroides coprophilus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1376 Bacteroides ovatus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1379 Bacteroides stercoris Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [3]
⏷ Show the Full List of 13  DME(s)
References
1 Clonidine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 CYP2D6 mediates 4-hydroxylation of clonidine in vitro: implication for pregnancy-induced changes in clonidine clearance. Drug Metab Dispos. 2010 Sep;38(9):1393-6.
3 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
4 The metabolism of N,N'-dimethylclonidine by rat liver microsomes [proceedings]

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