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Oxamniquine

HCID 4612
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
119678-90-9
Standard SMILES
CC(C)NCC1CCc2cc(CO)c([N+](=O)[O-])cc2N1
InChIKey
XCGYUJZMCCFSRP-UHFFFAOYSA-N
Molecular formula
C14H21N3O3
Average molar mass
279.33 g/mol
Monoisotopic mass
279.15829154

Overview

{2-[(isopropylamino)methyl]-7-nitro-1,2,3,4-tetrahydroquinolin-6-yl}methanol is a member of the class of quinolines that is 1,2,3,4-tetrahydroquinoline which is substituted at positions 2, 6, and 7 by (isopropylamino)methyl, hydroxymethyl, and nitro groups, respectively. It is a member of quinolines, an aromatic primary alcohol, a C-nitro compound and a secondary amino compound.

Names & identifiers

Preferred name
Oxamniquine
IUPAC
[7-nitro-2-[(propan-2-ylamino)methyl]-1,2,3,4-tetrahydroquinolin-6-yl]methanol
English name
OXAMNIQUINE(200MG)DISCONTINUED
Molecular formula
C14H21N3O3
Molecular weight
279.33484

Names & synonyms

oxamniquine21738-42-1MansilVansilOxaminiquineUK-4271OxamniquinumOxamniquinaUK 4271DTXSID3023398Oxamniquinum [INN-Latin]Oxamniquina [INN-Spanish]
Show more names
uk4261uk4271NSC 352888UK 4271/Vansiloxamniquinum(inn-latin)oxamniquina(inn-spanish)OXAMNIQUINE(200MG)DISCONTINUED
NSC-3528880O977R722DUK-42611,2,3,4-Tetrahydro-2-((isopropylamino)methyl)-7-nitro-6-quinolinemethanol6-Hydroxymethyl-2-isopropylaminomethyl-7-nitro-1,2,3,4-tetrahydroquinoline(7-nitro-2-{[(propan-2-yl)amino]methyl}-1,2,3,4-tetrahydroquinolin-6-yl)methanol1,2,3,4-Tetrahydro-2-(((1-methylethyl)amino)methyl)-7-nitro-6-quinolinemethanol6-Quinolinemethanol, 1,2,3,4-tetrahydro-2-(((1-methylethyl)amino)methyl)-7-nitro-

Database identifiers

CAS
119678-90-9、21738-42-1、40247-39-0
PubChem CID
4612
DTXSID
DTXSID3023398
ChEMBL
CHEMBL847

Properties

Computed structural properties

XLogP
2.2
Topological polar surface area
90.1 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
5
Rotatable bonds
4
Heavy atoms
20
Formal charge
0
Complexity
332

Experimental & physicochemical properties

pH8-10 /Aqueous suspensions/
LogP · 2 items

1.5

2.24

Color/Form · 2 items

Pale yellow crystals from isopropanol

Yellow-orange, crystalline solid

Solubility · 2 items

1 part in about 3300 parts of water at 27 °C

1.24e-01 g/L

Human Drugs · 3 items

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Antischistosomals and other antitrematode medicines

Melting Point · 3 items

147-149 °C

147-149 °C

147 - 149 °C

Physical DescriptionSolid
Other Experimental Properties/Oxamniquine/ is structurally similar to hycanthone and lucanthone.

Physicochemical properties

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Warning

H302 (97.4%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P273, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

FDA Requirements · 2 items

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed drug products, incl oxamniquine, approved on the basis of safety and effectiveness by FDA under sections 505 and 507 of the Federal Food, Drug, and Cosmetic Act. /From the Prescription Drug Product List/

Hazard Classes and CategoriesAcute Tox. 4 (97.4%)

Safety & protection

Storage ConditionsOxamniquine should be stored in well closed containers. Commercially available oxamniquine capsules should be stored in tight containers at a temperature less than 30 °C.

Toxicology

Interactions · 2 items

Limited evidence from one study in mice indicates that the antischistosomal activity of oxamniquine and praziquantel may be synergistic against Schistosoma mansoni when the two drugs are administered concomitantly.

Chemistry & industry

Pharmacology

ATC Code · 3 items

P - Antiparasitic products, insecticides and repellents

QP - Antiparasitic products, insecticides and repellents

P02BA02

Pharmacodynamics · 1 item

Oxamniquine is an anthelmintic with schistosomicidal activity against <i>Schistosoma mansoni</i>, 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 · 3 items

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.

Causes the worms to be dislodged from their usual site of residence in the mesenteric veins to the liver where they are retained and subsequently killed by host tissue reactions (eg, phagocytosis). The dislodgment of worms appears to result principally from contraction and paralysis of their musculature and subsequent immobilization of their suckers, which causes the worms to detach from the blood vessel wall, thereby allowing passive dislodgement by normal blood flow.

Hycanthone-sensitive and hycanthone-resistant schistosomes (which are also sensitive and resistant to oxamniquine) were exposed in vitro to tritium-labelled oxamniquine. The initial uptake of the drug into the schistosomes was essentially the same for the 2 strains. The homogenate of worms incubated with tritiated oxamniquine was fractionated and a purified DNA fraction was obtained by ethanol precipitation, RNAase and protease digestion, repeated phenolchloroform extractions, cesium chloride gradient centrifugation and extensive dialysis. The DNA fraction from sensitive worms contained radioactive oxamniquine at a level corresponding to about 1 drug molecule per 50,000 base pairs, while the DNA from resistant worms contained essentially no drug. The results support the hypothesis that oxamniquine, like hycanthone, exerts its activity by alkylating macromolecules of sensitive schistosomes.

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
ChEBI
CHEBI:78416
UNII
00BCY677OT、0O977R722D、7GIJ138H3K
EC Number
244-556-4
Nikkaji
J11.157K、J457.027H
Melting point
147 · 147-149°
Boiling point
422.1 °C · 422.1°C (rough estimate)
Density
1.1119 · 1.1119 (rough estimate)
refractive index
1.57 · 1.5700 (estimate)
solubility
DMSO (Slightly), Methanol (Slightly)
form
Solid
pka
3.28 · pKa 3.28 ± 0.07;9.53(H2O,t =25) (Uncertain)
color
Light-orange powder
BCS Class
4 · 4/2
Stability
Hygroscopic
FDA UNII
0 O977R722D · 0O977R722D
ATC code
2 BA02 · P02BA02
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302-H413
Precautionary statements
264 · P264-P270-P301+P312-P330-P501
Hazardous Substances Data
21738 · 21738-42-1(Hazardous Substances Data)
Toxicity
50 in · LD50 in mice, rabbits (mg/kg): >2000, >1000 i.m., 1300, 800 orally (Foster)

The rate and extent of GI absorption of the drug are decreased by the presence of food.

Human Toxicity Excerpts · 5 items

Nervous system effects occur frequently with oxamniquine; however, most of these effects are mild and transient. The most frequent adverse effects of oxamniquine are dizziness, drowsiness, and headache, which occur in about 30-50% of patients receiving the drug. Other less frequent adverse nervous effects ... include behavioral changes, excitation, and hallucinations or distortion of reality. Insomnia, malaise, and reversible amnesia have been reported rarely. EEG abnormalities occur occasionally in patients. ... Generalized seizures, which usually occur within the first few hours ... and generally are associated with EEG changes, have been observed rarely in patients receiving the drug, particularly in those with a history of seizure disorders.

GI effects of oxamniquine, which occur less frequently than common nervous system effects, include nausea, vomiting, abdominal pain, anorexia and diarrhea.

Urticaria, rash, pruritus, and joint pain have been reported in some patients receiving oxamniquine. Fever, which occurs 1-5 days after administration of oxamniquine and persists for 2-5 days before defervescence, has been reported in patients receiving the drug for treatment of schistosomiasis principally in Egypt; fever reportedly has not occurred following im administration of the drug to healthy, uninfected adults. Minor, nonspecific ECG changes and pulmonary radiographic changes, principally characterized by pulmonary condensations have occurred in a few patients.

Minimal increases in eosinophil count appear to occur frequently following treatment with oxamniquine; however, eosinophilia is also associated with schistosomiasis and may also be a consequence of a host mediated immunologic response to antigen release during drug induced killing of the worms. Increased erythrocyte sedimentation rate, increased reticulocyte count, and increased or decreased leukocyte count also have been reported in a few patients receiving the drug.

For more Human Toxicity Excerpts (Complete) data for OXAMNIQUINE (6 total), please visit the HSDB record page.

Non-Human Toxicity Excerpts · 3 items

Although evidence of hepatic abnormalities has occurred in animals receiving relatively low doses of oxamniquine, no evidence of serious adverse hepatic effects has developed in humans, even in patients with schistosomal infection associated with severe hepatosplenic involvement. Mild to moderate, transient increases in serum alkaline phosphatase, AST (SGOT) and/or ALT (SGPT) concentrations have occurred in patients receiving the drug; however, these abnormalities generally were not considered drug related and were not clinically important.

Oxamniquine has generally been reported to lack mutagenic activity as determined by various assay methods including cytogenetic, dominant lethal, and host mediated assays; however, as high concentrations, evidence of weak mutagenic activity has been reported as determined by the Ames mutagenic assay with or without metabolic activation.

Oxamniquine has been shown to have embryocidal effects in mice and rabbits when given at dosages 10 times the usual human dosage.

Non-Human Toxicity Values · 4 items

LD50 Mouse im > 2000 mg/kg

LD50 Mouse oral 1300 mg/kg

LD50 Rabbit im > 1000 mg/kg

LD50 Rabbit oral 800 mg/kg

Regulatory information

FDA Requirements · 2 items

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed drug products, incl oxamniquine, approved on the basis of safety and effectiveness by FDA under sections 505 and 507 of the Federal Food, Drug, and Cosmetic Act. /From the Prescription Drug Product List/

Safety data

Toxicity
LD50 in mice, rabbits (mg/kg): >2000, >1000 i.m., 1300, 800 orally (Foster)
Signal word
Warning
Symbol(GHS)
GHS07
Hazard statements
H302-H413
Precautionary statements
P264-P270-P301+P312-P330-P501
Hazardous Substances Data
21738-42-1(Hazardous Substances Data)
Biological Half-Life · 2 items

1-2.5 hours

Oxamniquine has a plasma half-life of about 1-2.5 hours.

Metabolism/Metabolites · 2 items

Probably hepatic

The drug is extensively metabolized, principally in the GI mucosa and/or lumen via enzymatic oxidation of the 6-hydroxymethyl group to the 6-carboxylic acid metabolite. Trace amounts of the 2-carboxylic acid metabolite have also been observed in urine, which reflects oxidation of the side chain. These metabolites do not possess antichistosomal activity.

FDA Pharmacological Classification · 4 items

0O977R722D

OXAMNIQUINE

Established Pharmacologic Class [EPC] - Anthelmintic

Oxamniquine is an Anthelmintic.

MeSH Pharmacological ClassificationAgents that act systemically to kill adult schistosomes.
Absorption, Distribution and Excretion · 4 items

Well absorbed orally

Oxamniquine and its metabolites are excreted mainly in urine. Approximately 40-75% of an oral dose of the drug is excreted in urine within 24 hours of administration, principally as the 6-carboxylic acid metabolite. About 0.5-2% of an oral dose is excreted in urine unchanged; less than 1% of a dose is excreted in urine as the 2-carboxylic acid metabolite.

Oxamniquine is well absorbed following oral administration. The rate and extent of GI absorption of the drug are decreased by the presence of food. Peak plasma concentrations of oxamniquine occur approximately 1-3 hours after oral administration of usual doses of the drug. ... Interpatient variation in plasma oxamniquine concentrations may result from biodegradation of the drug in the GI mucosa during absorption. ... Oxamniquine undergoes extensive first pass metabolism in the GI lumen before absorption and/or in the GI mucosa during absorption in animals.

Following oral administration of a single 15 mg/kg dose of oxamniquine in adults and children with Schistosoma mansoni infection in one study, peak serum drug concentrations of 70-2595 and 89-1500 ng/ml, respectively, occurred at 1.5-3 hours. In another study, following oral administration of a single 1 g dose of oxamniquine in patients with advaced hepatosplenic schistosomiasis and in healthy adults, mean peak plasma drug concentrations of 1267 ng/ml at about 1.7 hours and 1983 ng/ml at about 1.4 hours occurred, respectively.

Cellular LocationsCytoplasm

Uses & manufacturing

UsesMEDICATION
Methods of ManufacturingCommercially available oxamniquine is prepared in the presence of Aspergillus sclerotiorum via microbial hydroxylation of the 6-methyl group of the drugs synthetic precursor 2-aminomethyltetrahydroquinoline.
Formulations/PreparationsOral capsules, 250 mg, Vansil (R), Pfizer
Applications · 2 items

DescriptionOxamniquine was originally investigated in the 1960s and was found to have limited antiprotozoal activity, with activity against Schi stosoma mansoni but no activity against the other two schistosomal organisms. In addition, the drug is stage specific, with activity against cercariae and very young schistosomula and adult worms. For reasons that remain unknown, the drug is more effective against adult male worms than against female worms. The drug has structural similarity to hycanthone, which is no longer used because of severe toxicity and teratogenic effects.

UsesAntischistosomal.

Upstream & downstream products

Upstream raw materials

6-Hydroxy-2(1H)-3,4-dihydroquinolinoneSOYBEAN MEALD-Glucose monohydrate

Suppliers17 total

杭州摩库生物医药科技有限公司+86-057181025280; +8617767106207 · [email protected]
BOC Sciences1-631-485-4226; 16314854226 · [email protected]
PT CHEM GROUP LIMITED+86-85511178; +86-85511178 · [email protected]
上海寰川实业有限公司021-61478794 · [email protected]
Chongqing jooe co., ltd+86-15223382610 · [email protected]
青岛海智微元生物科技有限公司18317699790 18317699790 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]
上海陶术生物科技股份有限公司13564774135 · [email protected]
杭州洁汉化工有限公司+86-571-86217390; +8618058761490 · [email protected]
江苏艾康生物医药研发有限公司025-58859352 19370895928 · [email protected]
上海瀚香生物科技有限公司17754423994 · [email protected]
安徽今昱生物化工产品技术研发有限公司055167162561 13295518198 · [email protected]
陕西缔都医药化工有限公司029-029-029-81148696 18161915376 · [email protected]
TargetMol中国(陶术生物)4008200310 15002144251 · [email protected]
南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]
Dideu Industries Group Limited+86-29-81148696 +86-15129568250 · [email protected]

Additional notes

DefinitionChEBI: A member of the class of quinolines that is 1,2,3,4-tetrahydroquinoline which is substituted at positions 2, 6, and 7 by (isopropylamino)methyl, hydroxymethyl, and nitro groups, respectively.