Details of the Drug

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

Affected Organisms

Schistosoma mansoni

ATC Code

P02BA02: Oxamniquine

P02BA: Quinoline derivatives and related substances

P02B: ANTITREMATODALS

P02: ANTHELMINTICS

P: ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS

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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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: CHEMBL78416
CAS Number: 21738-42-1
UNII: 0O977R722D
DrugBank ID: DB01096
TTD ID: D0P4MT
INTEDE ID: DR1211

Drug ADMET Endpoint Profile (DAE)^NEW

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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)

MIA Detail

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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.".