General Information of Drug (ID: DM2QDX1)

Drug Name
Oxamniquine
Synonyms
Mansil; Oxaminiquine; Oxamniquina; Oxamniquinum; Vansil; UK 4261; UK 4271; Mansil (TN); Oxamniquina [INN-Spanish]; Oxamniquinum [INN-Latin]; UK-4271; Vansil (TN); Oxamniquine (USAN/INN); Oxamniquine [USAN:BAN:INN]; {2-[(Isopropylamino)methyl]-7-nitro-1,2,3,4-tetrahydroquinolin-6-yl}methanol; [7-nitro-2-[(propan-2-ylamino)methyl]-1,2,3,4-tetrahydroquinolin-6-yl]methanol; (2-{[(1-methylethyl)amino]methyl}-7-nitro-1,2,3,4-tetrahydroquinolin-6-yl)methanol; 1,2,3,4-Tetrahydro-2-(((1-methylethyl)amino)methyl)-7-nitro-6-quinolinemethanol; 1,2,3,4-Tetrahydro-2-((isopropylamino)methyl)-7-nitro-6-quinolinemethanol; 1,2,3,4-Tetrahydro-2-[(isopropylamino)methyl]-7-nitro-6-quinolinemethanol; 2-((Isopropylamino)methyl)-7-nitro-1,2,3,4-tetrahydro-6-quinolinemethanol; 2-(Isopropylaminomethyl)-7-nitro-1,2,3,4-tetrahydroquinoline-6-methanol; 6-Hydroxymethyl-2-isopropylaminomethyl-7-nitro-1,2,3,4-tetrahydroquinoline
Indication
Disease Entry ICD 11 Status REF
Schistosomiasis 1F86 Approved [1]
Therapeutic Class
Schistosomicides
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 279.33
Logarithm of the Partition Coefficient (xlogp) 2.2
Rotatable Bond Count (rotbonds) 4
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 5
ADMET Property
Absorption
The drug is well absorbed orally []
Half-life
The concentration or amount of drug in body reduced by one-half in 1 - 2.5 hours [2]
Metabolism
The drug is metabolized via the hepatic []
Chemical Identifiers
Formula
C14H21N3O3
IUPAC Name
[7-nitro-2-[(propan-2-ylamino)methyl]-1,2,3,4-tetrahydroquinolin-6-yl]methanol
Canonical SMILES
CC(C)NCC1CCC2=CC(=C(C=C2N1)[N+](=O)[O-])CO
InChI
InChI=1S/C14H21N3O3/c1-9(2)15-7-12-4-3-10-5-11(8-18)14(17(19)20)6-13(10)16-12/h5-6,9,12,15-16,18H,3-4,7-8H2,1-2H3
InChIKey
XCGYUJZMCCFSRP-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
4612
ChEBI ID
CHEBI:78416
CAS Number
21738-42-1
DrugBank ID
DB01096
TTD ID
D0P4MT
INTEDE ID
DR1211

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Schistosoma Deoxyribonucleic acid (Schist DNA) TTB1TZG NOUNIPROTAC Modulator [3]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 2D6 (CYP2D6)
Main DME
DECB0K3 CP2D6_HUMAN Substrate [4]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Oxamniquine (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Polyethylene glycol DM4I1JP Moderate Increased risk of lowers seizure threshold by the combination of Oxamniquine and Polyethylene glycol. Irritable bowel syndrome [DD91] [5]
Bupropion DM5PCS7 Major Increased risk of lowers seizure threshold by the combination of Oxamniquine and Bupropion. Nicotine use disorder [6C4A] [6]
ABIRATERONE DM8V75C Moderate Decreased metabolism of Oxamniquine caused by ABIRATERONE mediated inhibition of CYP450 enzyme. Prostate cancer [2C82] [7]
Aripiprazole DM3NUMH Moderate Decreased metabolism of Oxamniquine caused by Aripiprazole mediated inhibition of CYP450 enzyme. Schizophrenia [6A20] [8]
Pitolisant DM8RFNJ Moderate Decreased metabolism of Oxamniquine caused by Pitolisant mediated inhibition of CYP450 enzyme. Somnolence [MG42] [9]

References

1 Opportunities and challenges in antiparasitic drug discovery. Nat Rev Drug Discov. 2005 Sep;4(9):727-40.
2 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
3 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
4 Inhibitory effects of antiparasitic drugs on cytochrome P450 2D6. Eur J Clin Pharmacol. 1995;48(1):35-8.
5 Product Information. Suprep Bowel Prep Kit (magnesium/potassium/sodium sulfates). Braintree Laboratories, Braintree, MA.
6 Product Information. Wellbutrin XL (buPROPion). GlaxoSmithKline, Philadelphia, PA.
7 Product Information. Zytiga (abiraterone). Centocor Inc, Malvern, PA.
8 Product Information. Abilify (aripiprazole). Bristol-Myers Squibb, Princeton, NJ.
9 Cerner Multum, Inc. "UK Summary of Product Characteristics.".