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

General Information of Drug (ID: DR0123)
Drug Name
Apomorphine
Synonyms
Apokyn; Apomorfin; Apomorphin; Apomorphine (BAN); Apomorphine [BAN]; Apomorphine hydrochloride; Apomorphinium chloride hemihydrate; Apormorphine; Ixense; L-Apomorphine; R-(-)-Apomorphine; Uprima; Uprima (TN); VR-040; VR-400; apomorphine; (-)-10,11-Dihydroxyaporphine; 58-00-4; 6a-beta-Aporphine-10,11-diol; 6abeta-Aporphine-10,11-diol; Apomorphine hydrochloride hemihydrate; C17H17NO2; CHEBI:48538; CHEMBL53; DSSTox_CID_2614; EINECS 200-360-0; HSDB 3289; N21FAR7B4S; NCGC00025349-02; UNII-N21FAR7B4S; VR004
Indication Parkinsonism [ICD11: 8A00] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 267.32 Topological Polar Surface Area 43.7
Heavy Atom Count 20 Rotatable Bond Count 0
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
6005
PubChem SID
7978719 ; 8153735 ; 11114270 ; 11466129 ; 11467249 ; 11485757 ; 14823961 ; 14848260 ; 24262970 ; 26752261 ; 29225019 ; 46508653 ; 47216673 ; 47365074 ; 47365075 ; 47662161 ; 47662162 ; 47662163 ; 48110346 ; 48184887 ; 48259117 ; 48415574 ; 49658769 ; 49698343 ; 49871434 ; 50322702 ; 51091791 ; 57323108 ; 85788349 ; 85856298 ; 92308726 ; 92729815 ; 93622853 ; 103167211 ; 103916308 ; 104310845 ; 124887059 ; 124887060 ; 126522630 ; 129497604 ; 134337595 ; 134971357 ; 135304977 ; 135649950 ; 137001467 ; 142333205 ; 144204518 ; 160964058 ; 163667986 ; 164788060
ChEBI ID
CHEBI:48538
CAS Number
58-00-4
TTD Drug ID
D0H6QU
Formula
C17H17NO2
Canonical SMILES
CN1CCC2=C3C1CC4=C(C3=CC=C2)C(=C(C=C4)O)O
InChI
1S/C17H17NO2/c1-18-8-7-10-3-2-4-12-15(10)13(18)9-11-5-6-14(19)17(20)16(11)12/h2-6,13,19-20H,7-9H2,1H3/t13-/m1/s1
InChIKey
VMWNQDUVQKEIOC-CYBMUJFWSA-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
Apocodeine DM000617
12545
Conjugation - O-Methylation 1 [2]
Apocodeine sulfate DM000616 N. A. Conjugation - Conjugation 1 [4] , [2]
Apomorphine 10-glucuronide DM000620 N. A. Conjugation - O-Glucuronidation 1 [6]
Apomorphine 11-glucuronide DM000621 N. A. Conjugation - O-Glucuronidation 1 [6]
Isoapocodeine DM000618
217214
Conjugation - O-Methylation 1 [2]
Norapomorphine DM000622
30133
Oxidation - N-Demethylation 1 [3]
O-quinone DM000619
95198701
Oxidation - Oxidation 1 [7]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000250 Apomorphine Apocodeine sulfate Conjugation - Conjugation SULT1A1 [4], [2]
MR000251 Apomorphine Apocodeine Conjugation - O-Methylation COMT [2]
MR000252 Apomorphine Isoapocodeine Conjugation - O-Methylation Unclear [2]
MR000253 Apomorphine O-quinone Oxidation - Oxidation Unclear [7]
MR000254 Apomorphine Apomorphine 10-glucuronide Conjugation - O-Glucuronidation Unclear [6]
MR000255 Apomorphine Apomorphine 11-glucuronide Conjugation - O-Glucuronidation Unclear [6]
MR000256 Apomorphine Norapomorphine Oxidation - N-Demethylation CYP2B6 ... [3]
⏷ Show the Full List of 7 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Catechol O-methyltransferase (COMT) DME0043 Homo sapiens
COMT_HUMAN
2.1.1.6
[2]
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[3]
Sulfotransferase 1A1 (SULT1A1) DME0008 Homo sapiens
ST1A1_HUMAN
2.8.2.1
[4]
Unclear metabolic mechanism (DME-unclear) DME1362 Bacteroides caccae Not Available Not Available [5]
⏷ Show the Full List of 7  DME(s)
References
1 Apomorphine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Pharmacokinetics, enantiomer interconversion, and metabolism of R-apomorphine in patients with idiopathic Parkinson's disease Clin Neuropharmacol. 1998 May-Jun;21(3):159-68.
3 The pharmacology and clinical pharmacokinetics of apomorphine SL BJU Int. 2001 Oct;88 Suppl 3:18-21. doi: 10.1046/j.1464-4096.2001.00124.x.
4 Sulfation of apomorphine by human sulfotransferases: evidence of a major role for the polymorphic phenol sulfotransferase, SULT1A1. Xenobiotica. 2003 Nov;33(11):1139-48.
5 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
6 Glucuronidation of apomorphine Life Sci. 2000 Aug 25;67(14):1735-45. doi: 10.1016/s0024-3205(00)00764-5.
7 DrugBank(Pharmacology-Metabolism)Apomorphine

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