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

General Information of Drug (ID: DR1852)
Drug Name
SQ-109
Synonyms
SQ 109; SQ-109; JFIBVDBTCDTBRH-REZTVBANSA-N; SCHEMBL1780846; SCHEMBL1780848; ZINC39959796; 502487-67-4; 9AU7XUV31A; AC1NRWTN; BCP22030; BDBM50388398; CHEMBL561057; CS-1188; DB05186; DTXSID30964540; EX-A764; GTPL7997; HY-14989; N'-(2-adamantyl)-N-[(2E)-3,7-dimethylocta-2,6-dienyl]ethane-1,2-diamine; N-Geranyl-N'-(2-adamantyl)ethane-1,2-diamine; N-[(2e)-3,7-Dimethylocta-2,6-Dien-1-Yl]-N'-[(1r,3s,5r,7r)-Tricyclo[3.3.1.1~3,7~]dec-2-Yl]ethane-1,2-Diamine; NSC 722041; NSC722041; SCHEMBL10050752; SCHEMBL19630696; SQ109; UNII-9AU7XUV31A
Indication Pulmonary tuberculosis [ICD11: 1B10] Phase 2 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 330.5 Topological Polar Surface Area 24.1
Heavy Atom Count 24 Rotatable Bond Count 9
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
5274428
PubChem SID
8614182 ; 10584935 ; 24739760 ; 39284188 ; 75093607 ; 92309401 ; 99437063 ; 103681130 ; 113899654 ; 135263750 ; 137131345 ; 142872067 ; 144111190 ; 160867481 ; 163620820 ; 163686148 ; 172919583 ; 175426955 ; 179605483 ; 180438526 ; 184811979 ; 198949024 ; 227958686 ; 227958688 ; 235390810 ; 243768307 ; 249565677
CAS Number
502487-67-4
TTD Drug ID
D0K8DI
Formula
C22H38N2
Canonical SMILES
CC(=CCCC(=CCNCCNC1C2CC3CC(C2)CC1C3)C)C
InChI
1S/C22H38N2/c1-16(2)5-4-6-17(3)7-8-23-9-10-24-22-20-12-18-11-19(14-20)15-21(22)13-18/h5,7,18-24H,4,6,8-15H2,1-3H3/b17-7+
InChIKey
JFIBVDBTCDTBRH-REZTVBANSA-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
M/Z 347 DM003600 N. A. Oxidation - Epoxidation 1 [2]
SQ-109 Metabolite M1 DM003602 N. A. Oxidation - N-Nitrosylation 1 [2]
SQ-109 Metabolite M2-1 DM003605 N. A. Oxidation - Ring oxidation 1 [2]
SQ-109 Metabolite M3 DM003603 N. A. Oxidation - N-Nitrosylation 1 [2]
SQ-109 Metabolite M4 DM003604 N. A. Oxidation - N-Dealkylation 1 [2]
SQ-109 Metabolite M4-1 DM003607 N. A. Oxidation - Ring oxidation; N-hydroxylation 1 [2]
SQ-109 Metabolite M4-2 DM003606 N. A. Multi-steps Reaction - Ring oxidation; Epoxidation; rearrangement 1 [2]
SQ-109 Metabolite M2-2 DM003601 N. A. Other reaction - Rearrangement reaction 2 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004038 SQ-109 M/Z 347 Oxidation - Epoxidation CYP2C19 [2]
MR004040 SQ-109 SQ-109 Metabolite M1 Oxidation - N-Nitrosylation CYP2D6 ... [2]
MR004041 SQ-109 SQ-109 Metabolite M3 Oxidation - N-Nitrosylation CYP2C19 [2]
MR004042 SQ-109 SQ-109 Metabolite M4 Oxidation - N-Dealkylation CYP2C19 [2]
MR004043 SQ-109 SQ-109 Metabolite M2-1 Oxidation - Ring oxidation CYP2C19 [2]
MR004044 SQ-109 SQ-109 Metabolite M4-2 Multi-steps Reaction - Ring oxidation; Epoxidation; rearrangement CYP2D6 ... [2]
MR004045 SQ-109 SQ-109 Metabolite M4-1 Oxidation - Ring oxidation; N-hydroxylation CYP2D6 ... [2]
MR004039 M/Z 347 SQ-109 Metabolite M2-2 Other reaction - Rearrangement reaction Unclear [2]
⏷ Show the Full List of 8 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]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
References
1 ClinicalTrials.gov (NCT01218217) Early Bactericidal Activity (EBA) of SQ109 in Adult Subjects With Pulmonary TB.
2 Interspecies pharmacokinetics and in vitro metabolism of SQ109. Br J Pharmacol. 2006 Mar;147(5):476-85.

If you find any error in data or bug in web service, please kindly report it to Dr. Yin and Dr. Li.