Oxamniquine

Identification

Generic Name
Oxamniquine
DrugBank Accession Number
DB01096
Background

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)

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 279.3348
Monoisotopic: 279.158291553
Chemical Formula
C14H21N3O3
Synonyms
Not Available
External IDs
  • UK-4261
  • UK-4271

Pharmacology

Indication

For treatment of Schistosomiasis caused by Schistosoma mansoni

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Oxamniquine 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 action

Oxamniquine 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.

TargetActionsOrganism
ADNA
other/unknown
Humans
Absorption

Well absorbed orally

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Probably hepatic

Route of elimination

Not Available

Half-life

1-2.5 hours

Clearance

Not Available

Adverse Effects
Adverseeffects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcebutololThe metabolism of Acebutolol can be decreased when combined with Oxamniquine.
AcetaminophenThe metabolism of Acetaminophen can be decreased when combined with Oxamniquine.
AlmotriptanThe metabolism of Almotriptan can be decreased when combined with Oxamniquine.
AlogliptinThe metabolism of Alogliptin can be decreased when combined with Oxamniquine.
AminophenazoneThe metabolism of Aminophenazone can be decreased when combined with Oxamniquine.
AmitriptylineThe metabolism of Amitriptyline can be decreased when combined with Oxamniquine.
AmoxapineThe metabolism of Amoxapine can be decreased when combined with Oxamniquine.
AmphetamineThe metabolism of Amphetamine can be decreased when combined with Oxamniquine.
AmprenavirThe metabolism of Amprenavir can be decreased when combined with Oxamniquine.
AntipyrineThe metabolism of Antipyrine can be decreased when combined with Oxamniquine.
Interactions
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Food Interactions
Not Available

Products

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International/Other Brands
Mansil / Vansil

Categories

ATC Codes
P02BA02 — Oxamniquine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as nitroquinolines and derivatives. These are compounds containing a nitro group attached to a quinoline moiety.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Quinolines and derivatives
Sub Class
Nitroquinolines and derivatives
Direct Parent
Nitroquinolines and derivatives
Alternative Parents
Hydroquinolines / Nitroaromatic compounds / Secondary alkylarylamines / Aralkylamines / Benzenoids / Propargyl-type 1,3-dipolar organic compounds / Organic oxoazanium compounds / Dialkylamines / Azacyclic compounds / Primary alcohols
show 5 more
Substituents
Alcohol / Allyl-type 1,3-dipolar organic compound / Amine / Aralkylamine / Aromatic alcohol / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / C-nitro compound / Hydrocarbon derivative
show 18 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
C-nitro compound, quinolines, secondary amino compound, aromatic primary alcohol (CHEBI:78416)
Affected organisms
  • Schistosoma mansoni

Chemical Identifiers

UNII
0O977R722D
CAS number
21738-42-1
InChI Key
XCGYUJZMCCFSRP-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

References

Synthesis Reference
US3821228
General References
  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. [Article]
Human Metabolome Database
HMDB0015228
KEGG Drug
D00460
KEGG Compound
C07341
PubChem Compound
4612
PubChem Substance
46508789
ChemSpider
4451
RxNav
7778
ChEBI
78416
ChEMBL
CHEMBL847
Therapeutic Targets Database
DAP000992
PharmGKB
PA164748782
Drugs.com
Drugs.com Drug Page
Wikipedia
Oxamniquine
MSDS
Download (50 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)147-149 °CPhysProp
water solubility820 mg/LNot Available
logP2.24SANGSTER (1993)
Predicted Properties
PropertyValueSource
Water Solubility0.124 mg/mLALOGPS
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 Area90.11 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity79.86 m3·mol-1ChemAxon
Polarizability30.19 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9156
Blood Brain Barrier-0.6502
Caco-2 permeable-0.5759
P-glycoprotein substrateSubstrate0.872
P-glycoprotein inhibitor INon-inhibitor0.6528
P-glycoprotein inhibitor IINon-inhibitor0.8828
Renal organic cation transporterNon-inhibitor0.7578
CYP450 2C9 substrateNon-substrate0.797
CYP450 2D6 substrateNon-substrate0.8735
CYP450 3A4 substrateNon-substrate0.583
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorNon-inhibitor0.6334
CYP450 3A4 inhibitorNon-inhibitor0.8603
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8783
Ames testAMES toxic0.9107
CarcinogenicityNon-carcinogens0.7461
BiodegradationNot ready biodegradable0.9958
Rat acute toxicity3.5281 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.5899
hERG inhibition (predictor II)Inhibitor0.6207
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-001i-0090000000-cbc05dcd3c76cb5e6dbc
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0090000000-13f1262c88faee196444
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0950000000-082ec38664b574d25a9c
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00dj-0900000000-781fed8c05ecf56fc5b6
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-006t-0900000000-9e5d872a8378b48f787f
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00dj-2910000000-90237e532f4d41c89192

Targets

Drugtargets2
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Kind
Nucleotide
Organism
Humans
Pharmacological action
Yes
Actions
Other/unknown
DNA is the molecule of heredity, as it is responsible for the genetic propagation of most inherited traits. It is a polynucleic acid that carries genetic information on cell growth, division, and function. DNA consists of two long strands of nucleotides twisted into a double helix and held together by hydrogen bonds. The sequence of nucleotides determines hereditary characteristics. Each strand serves as the template for subsequent DNA replication and as a template for mRNA production, leading to protein synthesis via ribosomes.
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. [Article]
  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. [Article]
  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. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Masimirembwa CM, Hasler JA, Johansson I: Inhibitory effects of antiparasitic drugs on cytochrome P450 2D6. Eur J Clin Pharmacol. 1995;48(1):35-8. [Article]

Drug created on June 13, 2005 13:24 / Updated on May 07, 2021 21:22