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
• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 0:
  Molecular Weight (mw); 279.33
  Topological Polar Surface Area (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 [2]
  Half-life: The concentration or amount of drug in body reduced by one-half in 1 - 2.5 hours [3]
  Metabolism: The drug is metabolized via the hepatic [2]
• 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	[4]

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 2D6 (CYP2D6) Main DME	DECB0K3	CP2D6_HUMAN	Substrate	[5]

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]	[16]
Bupropion	DM5PCS7	Major	Increased risk of lowers seizure threshold by the combination of Oxamniquine and Bupropion.	Nicotine use disorder [6C4A]	[17]
ABIRATERONE	DM8V75C	Moderate	Decreased metabolism of Oxamniquine caused by ABIRATERONE mediated inhibition of CYP450 enzyme.	Prostate cancer [2C82]	[18]
Aripiprazole	DM3NUMH	Moderate	Decreased metabolism of Oxamniquine caused by Aripiprazole mediated inhibition of CYP450 enzyme.	Schizophrenia [6A20]	[19]
Pitolisant	DM8RFNJ	Moderate	Decreased metabolism of Oxamniquine caused by Pitolisant mediated inhibition of CYP450 enzyme.	Somnolence [MG42]	[20]

References

• [1] Opportunities and challenges in antiparasitic drug discovery. Nat Rev Drug Discov. 2005 Sep;4(9):727-40.
• [2] FDA approval: ado-trastuzumab emtansine for the treatment of patients with HER2-positive metastatic breast cancer. Clin Cancer Res. 2014 Sep 1;20(17):4436-41.
• [3] Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
• [4] Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
• [5] Inhibitory effects of antiparasitic drugs on cytochrome P450 2D6. Eur J Clin Pharmacol. 1995;48(1):35-8.
• [6] Inhibitory effects of anticancer drugs on dextromethorphan-O-demethylase activity in human liver microsomes. Cancer Chemother Pharmacol. 1993;32(6):491-5.
• [7] Effect of genetic polymorphism on the metabolism of endogenous neuroactive substances, progesterone and p-tyramine, catalyzed by CYP2D6. Brain Res Mol Brain Res. 2004 Oct 22;129(1-2):117-23.
• [8] CYP2D6 polymorphisms and tamoxifen metabolism: clinical relevance. Curr Oncol Rep. 2010 Jan;12(1):7-15.
• [9] Metabolic interactions between acetaminophen (paracetamol) and two flavonoids, luteolin and quercetin, through in-vitro inhibition studies. J Pharm Pharmacol. 2017 Dec;69(12):1762-1772.
• [10] Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
• [11] Inhibition of cytochrome P450 2D6: structure-activity studies using a series of quinidine and quinine analogues. Chem Res Toxicol. 2003 Apr;16(4):450-9.
• [12] Effects of propofol on human hepatic microsomal cytochrome P450 activities. Xenobiotica. 1998 Sep;28(9):845-53.
• [13] Pharmacogenetics of schizophrenia. Am J Med Genet. 2000 Spring;97(1):98-106.
• [14] Roles of CYP2A6 and CYP2B6 in nicotine C-oxidation by human liver microsomes. Arch Toxicol. 1999 Mar;73(2):65-70.
• [15] Structure-activity relationship for human cytochrome P450 substrates and inhibitors. Drug Metab Rev. 2002 Feb-May;34(1-2):69-82.
• [16] Product Information. Suprep Bowel Prep Kit (magnesium/potassium/sodium sulfates). Braintree Laboratories, Braintree, MA.
• [17] Product Information. Wellbutrin XL (buPROPion). GlaxoSmithKline, Philadelphia, PA.
• [18] Product Information. Zytiga (abiraterone). Centocor Inc, Malvern, PA.
• [19] Product Information. Abilify (aripiprazole). Bristol-Myers Squibb, Princeton, NJ.
• [20] Cerner Multum, Inc. "UK Summary of Product Characteristics.".