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Identification
NameOxamniquine
Accession NumberDB01096  (APRD01150)
Typesmall molecule
Groupsapproved
Description

An anthelmintic with schistosomicidal activity against Schistosoma mansoni, but not against other Schistosoma spp. Oxamniquine causes worms to shift from the mesenteric veins to the liver where the male worms are retained; the female worms return to the mesentery, but can no longer release eggs. (From Martidale, The Extra Pharmacopoeia, 31st ed, p121)

Structure
Thumb
SynonymsNot Available
SaltsNot Available
Brand names
NameCompany
MansilNot Available
VansilNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number21738-42-1
WeightAverage: 279.3348
Monoisotopic: 279.158291553
Chemical FormulaC14H21N3O3
InChI KeyXCGYUJZMCCFSRP-UHFFFAOYSA-N
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
IUPAC Name
(7-nitro-2-{[(propan-2-yl)amino]methyl}-1,2,3,4-tetrahydroquinolin-6-yl)methanol
SMILES
CC(C)NCC1CCC2=CC(CO)=C(C=C2N1)[N+]([O-])=O
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassQuinolines and Derivatives
SubclassNitroquinolines and Derivatives
Direct parentNitroquinolines and Derivatives
Alternative parentsHydroquinolines; Nitrobenzenes; Nitro Compounds; Nitronic Acids; Primary Alcohols; Organic Oxoazanium Compounds; Polyamines; Dialkylamines
Substituentstetrahydroquinoline; nitrobenzene; benzene; nitronic acid; nitro compound; secondary aliphatic amine; secondary amine; organic oxoazanium; polyamine; primary alcohol; organonitrogen compound; alcohol; amine
Classification descriptionThis compound belongs to the nitroquinolines and derivatives. These are compounds containing a nitro group attached to a quinoline moiety.
Pharmacology
IndicationFor treatment of Schistosomiasis caused by Schistosoma mansoni
PharmacodynamicsOxamniquine is an anthelmintic with schistosomicidal activity against Schistosoma mansoni, but not against other Schistosoma spp. Oxamniquine causes worms to shift from the mesenteric veins to the liver where the male worms are retained; the female worms return to the mesentery, but can no longer release egg.
Mechanism of actionOxamniquine may associate with an irreversible inhibition of the nucleic acid metabolism of the parasites. A hypothesis has been put forth that the drug is activated by a single step, in which a schistosome sulfotransferase enzyme converts oxamniquine into an ester (probably acetate, phosphate, or sulfate). Subsequently, the ester spontaneously dissociates, the resulting electrophilic reactant is capable of alkylation of schistosome DNA.
AbsorptionWell absorbed orally
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Probably hepatic

Route of eliminationNot Available
Half life1-2.5 hours
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Schistosoma mansoni
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9156
Blood Brain Barrier - 0.6502
Caco-2 permeable - 0.5759
P-glycoprotein substrate Substrate 0.872
P-glycoprotein inhibitor I Non-inhibitor 0.6528
P-glycoprotein inhibitor II Non-inhibitor 0.8828
Renal organic cation transporter Non-inhibitor 0.7578
CYP450 2C9 substrate Non-substrate 0.797
CYP450 2D6 substrate Non-substrate 0.8735
CYP450 3A4 substrate Non-substrate 0.583
CYP450 1A2 substrate Inhibitor 0.9107
CYP450 2C9 substrate Non-inhibitor 0.907
CYP450 2D6 substrate Inhibitor 0.8932
CYP450 2C19 substrate Non-inhibitor 0.6334
CYP450 3A4 substrate Non-inhibitor 0.8603
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8783
Ames test AMES toxic 0.9107
Carcinogenicity Non-carcinogens 0.7461
Biodegradation Not ready biodegradable 0.9958
Rat acute toxicity 3.5281 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.5899
hERG inhibition (predictor II) Inhibitor 0.6207
Pharmacoeconomics
Manufacturers
  • Pfizer laboratories div pfizer inc
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point147-149 °CPhysProp
water solubility820 mg/LNot Available
logP2.24SANGSTER (1993)
Predicted Properties
PropertyValueSource
water solubility1.24e-01 g/lALOGPS
logP1.54ALOGPS
logP1.57ChemAxon
logS-3.4ALOGPS
pKa (strongest acidic)14.55ChemAxon
pKa (strongest basic)9.9ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count5ChemAxon
hydrogen donor count3ChemAxon
polar surface area90.11ChemAxon
rotatable bond count5ChemAxon
refractivity79.87ChemAxon
polarizability30.19ChemAxon
number of rings2ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

DrugSyn.org

US3821228
General Reference
  1. Filho RP, de Souza Menezes CM, Pinto PL, Paula GA, Brandt CA, da Silveira MA: Design, synthesis, and in vivo evaluation of oxamniquine methacrylate and acrylamide prodrugs. Bioorg Med Chem. 2007 Feb 1;15(3):1229-36. Epub 2006 Nov 16. Pubmed
External Links
ResourceLink
KEGG DrugD00460
KEGG CompoundC07341
PubChem Compound4612
PubChem Substance46508789
ChemSpider4451
Therapeutic Targets DatabaseDAP000992
PharmGKBPA164748782
Drugs.comhttp://www.drugs.com/mtm/oxamniquine.html
WikipediaOxamniquine
ATC CodesP02BA02
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSshow(50 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. DNA

Kind: nucleotide

Organism: Human

Pharmacological action: yes

Actions: other/unknown

Components

Name UniProt ID Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Pica-Mattoccia L, Carlini D, Guidi A, Cimica V, Vigorosi F, Cioli D: The schistosome enzyme that activates oxamniquine has the characteristics of a sulfotransferase. Mem Inst Oswaldo Cruz. 2006 Sep;101 Suppl 1:307-12. Pubmed

Enzymes

1. Cytochrome P450 2D6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2D6 P10635 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on October 08, 2013 14:25