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

General Information of Drug (ID: DR0119)
Drug Name
Q-100648
Synonyms
654-II; SCHEMBL620576; ZINC2112569; anisodamine; (-)-Anisodamine; (6S)-6-Hydroxyhyoscyamine; (S)-((1S,3S,5S,6S)-6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl) 3-hydroxy-2-phenylpropanoate; 55869-99-3; 8053AH; 869A993; AC1L4C7W; AC1O6SQS; API0000388; [(1S,3S,5S,6S)-6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (2S)-3-hydroxy-2-phenylpropanoate
Indication Eclampsia [ICD11: JA25] Phase 3 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 305.4 Topological Polar Surface Area 70
Heavy Atom Count 22 Rotatable Bond Count 5
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
183088
PubChem SID
23921219 ; 33505583 ; 50427808 ; 104438665 ; 114606727 ; 136229770 ; 137237428 ; 162220214 ; 226921751
CAS Number
55869-99-3
TTD Drug ID
D06VFO
Formula
C17H23NO4
Canonical SMILES
CN1C2CC(CC1C(C2)O)OC(=O)C(CO)C3=CC=CC=C3
InChI
1S/C17H23NO4/c1-18-12-7-13(9-15(18)16(20)8-12)22-17(21)14(10-19)11-5-3-2-4-6-11/h2-6,12-16,19-20H,7-10H2,1H3/t12-,13+,14-,15+,16+/m1/s1
InChIKey
WTQYWNWRJNXDEG-LEOABGAYSA-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
6beta-hydroxytropine DM005954
13855897
Hydrolysis - Hydrolysis 1 [3]
Anisodamine N-oxide DM005959
101767608
Oxidation - N-oxidation 1 [3]
Glucuronide conjugated anisodamine DM005964 N. A. Conjugation - Conjugation 1 [3]
Hydroxyanisodamine DM005956 N. A. Oxidation - Hydrolyzationn 1 [3]
N-demethylanisodamine DM005960
101767609
Oxidation - N-demethylation 1 [3]
Sulfate conjugated anisodamine DM005962 N. A. Conjugation - Conjugation 1 [3]
Tropic acid DM005963
10726
Hydrolysis - Hydrolysis 1 [3]
Glucuronide conjugated N-demethylanisodamine DM005961 N. A. Conjugation - Conjugation 2 [3]
Hydroxyscopolamine N-oxide DM005958 N. A. Oxidation - Hydrolyzationn 2 [3]
Hydroxyscopolamine N-oxide DM005958 N. A. Oxidation - N-oxidation 2 [3]
N-dimethyl-6beta-hydroxytropine DM005955
101767607
Oxidation - N-demethylation 2 [3]
Sulfate conjugated hydroxyanisodamine DM005957 N. A. Conjugation - Conjugation 2 [3]
⏷ Show the Full List of 12  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006412 Q-100648 6beta-hydroxytropine Hydrolysis - Hydrolysis Unclear [3]
MR006414 Q-100648 Hydroxyanisodamine Oxidation - Hydrolyzationn Unclear [3]
MR006417 Q-100648 Anisodamine N-oxide Oxidation - N-oxidation Unclear [3]
MR006419 Q-100648 N-demethylanisodamine Oxidation - N-demethylation Unclear [3]
MR006421 Q-100648 Sulfate conjugated anisodamine Conjugation - Conjugation SULT [3]
MR006422 Q-100648 Tropic acid Hydrolysis - Hydrolysis Unclear [3]
MR006423 Q-100648 Glucuronide conjugated anisodamine Conjugation - Conjugation SLC35A2 [3]
MR006413 6beta-hydroxytropine N-dimethyl-6beta-hydroxytropine Oxidation - N-demethylation Unclear [3]
MR006418 Anisodamine N-oxide Hydroxyscopolamine N-oxide Oxidation - Hydrolyzationn Unclear [3]
MR006415 Hydroxyanisodamine Sulfate conjugated hydroxyanisodamine Conjugation - Conjugation SULT [3]
MR006416 Hydroxyanisodamine Hydroxyscopolamine N-oxide Oxidation - N-oxidation Unclear [3]
MR006420 N-demethylanisodamine Glucuronide conjugated N-demethylanisodamine Conjugation - Conjugation SLC35A2 [3]
⏷ Show the Full List of 12 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
UDP-galactose translocator (SLC35A2) DMEN301 Homo sapiens
S35A2_HUMAN
Not Available [3]
References
1 ClinicalTrials.gov (NCT01929044) Efficacy of Buscopan® in Comparison With 654-II (Anisodamine) in Acute Gastric or Intestinal Pain.
2 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.
3 Liquid chromatography-tandem mass spectrometry analysis of anisodamine and its phase I and II metabolites in rat urine

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