Oxamniquine

Identification

Name

Oxamniquine

Accession Number

DB01096

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)

Type

Small Molecule

Groups

Approved

Structure

Similar Structures

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

Contraindications & Blackbox Warnings

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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.

Target	Actions	Organism
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

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Toxicity

Not Available

Affected organisms

Schistosoma mansoni

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.

Drug	Interaction
Unlock Additional Data
Acebutolol	The metabolism of Acebutolol can be decreased when combined with Oxamniquine.
Acetaminophen	The metabolism of Acetaminophen can be decreased when combined with Oxamniquine.
Almotriptan	The metabolism of Almotriptan can be decreased when combined with Oxamniquine.
Alogliptin	The metabolism of Alogliptin can be decreased when combined with Oxamniquine.
Aminophenazone	The metabolism of Aminophenazone can be decreased when combined with Oxamniquine.
Amitriptyline	The metabolism of Amitriptyline can be decreased when combined with Oxamniquine.
Amoxapine	The metabolism of Amoxapine can be decreased when combined with Oxamniquine.
Amphetamine	The metabolism of Amphetamine can be decreased when combined with Oxamniquine.
Amprenavir	The metabolism of Amprenavir can be decreased when combined with Oxamniquine.
Antipyrine	The metabolism of Antipyrine can be decreased when combined with Oxamniquine.

Additional Data Available

Extended Description

Available for Purchase

Extended description of the mechanism of action and particular properties of each drug interaction.

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Severity

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A severity rating for each drug interaction, from minor to major.

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Evidence Level

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A rating for the strength of the evidence supporting each drug interaction.

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Action

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An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions

Not Available

Products

International/Other Brands: Mansil / Vansil

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

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:17134907]

External Links

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

Phase	Status	Purpose	Conditions	Count

Pharmacoeconomics

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

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	147-149 °C	PhysProp
water solubility	820 mg/L	Not Available
logP	2.24	SANGSTER (1993)

Predicted Properties

Property	Value	Source
Water Solubility	0.124 mg/mL	ALOGPS
logP	1.54	ALOGPS
logP	1.57	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	14.55	ChemAxon
pKa (Strongest Basic)	9.9	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	90.11 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	79.86 m³·mol^-1	ChemAxon
Polarizability	30.19 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

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 inhibitor	Non-inhibitor	0.907
CYP450 2D6 inhibitor	Inhibitor	0.8932
CYP450 2C19 inhibitor	Non-inhibitor	0.6334
CYP450 3A4 inhibitor	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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-001i-0090000000-cbc05dcd3c76cb5e6dbc
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-00di-0090000000-13f1262c88faee196444
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-00di-0950000000-082ec38664b574d25a9c
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-00dj-0900000000-781fed8c05ecf56fc5b6
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-006t-0900000000-9e5d872a8378b48f787f
MS/MS Spectrum - , positive	LC-MS/MS	splash10-00dj-2910000000-90237e532f4d41c89192

Targets

Details1. DNA

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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
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:17016423]
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:17308787]

Enzymes

Details1. Cytochrome P450 2D6

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

Masimirembwa CM, Hasler JA, Johansson I: Inhibitory effects of antiparasitic drugs on cytochrome P450 2D6. Eur J Clin Pharmacol. 1995;48(1):35-8. [PubMed:7621845]