Oxamniquine

Base Information

• Chemical Name: Oxamniquine
• CAS No.: 21738-42-1
• Molecular Formula: C₁₄H₂₁N₃O₃
• Molecular Weight: 279.339
• Hs Code.: 2933499090
• European Community (EC) Number: 244-556-4
• NSC Number: 352888
• UNII: 0O977R722D,00BCY677OT,7GIJ138H3K
• DSSTox Substance ID: DTXSID3023398
• Nikkaji Number: J457.027H,J11.157K
• Wikipedia: Oxamniquine
• Wikidata: Q682497
• NCI Thesaurus Code: C66258
• Metabolomics Workbench ID: 43326
• ChEMBL ID: CHEMBL847
• Mol file: 21738-42-1.mol

Synonyms:Oxaminiquine;Oxamniquine;UK 4271;UK-4271;UK4271

Chemical Property of Oxamniquine

Chemical Property:

• Vapor Pressure: 1.19E-08mmHg at 25°C
• Melting Point: 147-149°
• Refractive Index: 1.5700 (estimate)
• Boiling Point: 443.6°Cat760mmHg
• PKA: pKa 3.28 ± 0.07;9.53(H2O,t =25) (Uncertain)
• Flash Point: 222.1°C
• PSA: 90.11000
• Density: 1.174g/cm³
• LogP: 2.86390
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 279.15829154
• Heavy Atom Count: 20
• Complexity: 332

Purity/Quality:

99%, ^*data from raw suppliers

Oxamniquine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)NCC1CCC2=CC(=C(C=C2N1)[N+](=O)[O-])CO
• Indications: Oxamniquine is used against S. mansoni infections, including advanced cases with hepatomegaly, ascites or with colonic polyposis. Oxamniquine (Vansil) is a tetrahydroquinoline that stimulates parasite muscular activity at low concentrations but causes paralysis at higher concentrations. The drug may act by esterification and binding of DNA, leading to the death of the schistosome by interruption of its nucleic acid and protein synthesis. The fluke may esterify oxamniquine to produce a reactive metabolite that alkylates parasite DNA. Resistance results from absent or defective esterifying activity of the drug. Oxamniquine has a restricted range of efficacy, being active only against S. mansoni infections. Oxamniquine is given orally and is readily absorbed from the intestinal tract. Peak concentrations in plasma are obtained in about 3 hours. The drug is excreted in urine mostly as a 6-carboxyl derivative. Side effects include CNS toxicity with unsteadiness and occasionally seizures, especially in patients with a history of seizures. It is contraindicated in pregnancy.
• Description: Oxamniquine 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.
• Uses: Antischistosomal.
• Clinical Use: 1,2,3,4-Tetrahydro-2-[(isopropylamino)methyl]-7-nitro-6-quinolinemethanol (Vansil) is an antischistosomal agent thatis indicated for the treatment of Schistosoma mansoni (intestinalschistosomiasis) infection. It has been shown to inhibitDNA, RNA, and protein synthesis in schistosomes. The6-hydroxymethyl group is critical for activity; metabolic activationof precursor 6-methyl derivatives is critical. Theoral bioavailability of oxamniquine is good; effectiveplasma levels are achieved in 1 to 1.5 hours. The plasmahalf-life is 1 to 2.5 hours. The drug is extensively metabolizedto inactive metabolites, of which the principal one isthe 6-carboxy derivative.The free base occurs as a yellow crystalline solid thatis slightly soluble in water but soluble in dilute aqueousmineral acids and soluble in most organic solvents. Itis available in capsules containing 250 mg of the drug.Oxamniquine is generally well tolerated. Dizziness anddrowsiness are common, but transitory, side effects. Seriousreactions, such as epileptiform convulsions, are rare. Infection with S. mansoni

Technology Process of Oxamniquine

There total 1 articles about Oxamniquine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

→ oxaminiquine (21738-42-1,40247-39-0,119678-90-9)

Guidance literature:

2-N-Isopropylaminomethyl-6-methyl-7-nitro-1,2,3,4-tetrahydrochinolin, enzym. Oxid. (Aspergillus sclero...);

DOI:10.1021/jm00293a004

Reference yield:

oxaminiquine (21738-42-1,40247-39-0,119678-90-9) → N2-<(2-nitrophenyl)thio>oxamniquine aldehyde (114719-26-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / MnO₂ / CH₂Cl₂

2: 90 percent / triethylamine / CH₂Cl₂ / 1 h / Ambient temperature

With manganese(IV) oxide; triethylamine; In dichloromethane;

DOI:10.1021/jm00403a024

Reference yield:

oxaminiquine (21738-42-1,40247-39-0,119678-90-9) → N2-<(2-nitrophenyl)thio>oxamniquine (114719-27-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / MnO₂ / CH₂Cl₂

2: 90 percent / triethylamine / CH₂Cl₂ / 1 h / Ambient temperature

3: 95 percent / NaBH₄ / CH₂Cl₂; methanol / 2 h / Ambient temperature

With manganese(IV) oxide; sodium tetrahydroborate; triethylamine; In methanol; dichloromethane;

DOI:10.1021/jm00403a024

Downstream raw materials:

N²-<(2-nitrophenyl)thio>oxamniquine aldehyde

N²-<(2-nitrophenyl)thio>oxamniquine

Acetic acid 2-{[isopropyl-(2-nitro-phenylsulfanyl)-amino]-methyl}-7-nitro-1,2,3,4-tetrahydro-quinolin-6-ylmethyl ester

N²-<(2-nitrophenyl)thio>oxamniquine N-methylcarbamate