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Substance Name: Oxamniquine [USAN:USP:INN:BAN]
RN: 21738-42-1
UNII: 0O977R722D
InChIKey: XCGYUJZMCCFSRP-UHFFFAOYSA-N

Note

  • 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 Martindale, The Extra Pharmacopoeia, 31st ed, p121)

Molecular Formula

  • C14-H21-N3-O3

Molecular Weight

  • 279.338
 

Classification Codes

  • Anthelmintics
  • Anti-Infective Agents
  • Antiparasitic Agents
  • Antiplatyhelmintic Agents
  • Antischistosomal
  • Drug / Therapeutic Agent
  • Mutation Data
  • Schistosomicides
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Names and Synonyms

Name of Substance

  • Oxamniquine
  • Oxamniquine [USAN:USP:INN:BAN]

MeSH Heading

  • Oxamniquine

Synonyms

  • 1,2,3,4-Tetrahydro-2-(((1-methylethyl)amino)methyl)-7-nitro-6-quinolinemethanol
  • 1,2,3,4-Tetrahydro-2-((isopropylamino)methyl)-7-nitro-6-quinolinemethanol
  • 2-((Isopropylamino)methyl)-7-nitro-1,2,3,4-tetrahydro-6-quinolinemethanol
  • 5-22-11-00475 (Beilstein Handbook Reference)
  • 6-Hydroxymethyl-2-isopropylaminomethyl-7-nitro-1,2,3,4-tetrahydroquinoline
  • 6-Quinolinemethanol, 1,2,3,4-tetrahydro-2-(((1-methylethyl)amino)methyl)-7-nitro-
  • BRN 0485597
  • CCRIS 4113
  • EINECS 244-556-4
  • HSDB 6510
  • Mansil
  • NSC 352888
  • Oxaminiquine
  • Oxamniquina
  • Oxamniquina [INN-Spanish]
  • Oxamniquine
  • Oxamniquinum
  • Oxamniquinum [INN-Latin]
  • UK 4271
  • UK-4271
  • UNII-0O977R722D
  • Vansil

Systematic Names

  • 6-Quinolinemethanol, 1,2,3,4-tetrahydro-2-(((1-methylethyl)amino)methyl)-7-nitro-
  • 6-Quinolinemethanol, 1,2,3,4-tetrahydro-2-((isopropylamino)methyl)-7-nitro-
  • Oxaminiquine
  • Oxamniquine

Registry Numbers

CAS Registry Number

  • 21738-42-1

FDA UNII

  • 0O977R722D

System Generated Number

  • 0021738421

Structure Descriptors

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

InChIKey

XCGYUJZMCCFSRP-UHFFFAOYSA-N

Smiles

c12c(cc(CO)c(c1)[N+](=O)[O-])CC[C@@H](N2)CNC(C)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
hamster LD50 oral 950mg/kg (950mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA
Drug Development Research. Vol. 4, Pg. 229, 1984.
mouse LD50 intramuscular 2gm/kg (2000mg/kg)   Acta Leidensia. Vol. 57, Pg. 201, 1989.
mouse LD50 intraperitoneal 650mg/kg (650mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Drug Development Research. Vol. 4, Pg. 229, 1984.
mouse LD50 oral 1300mg/kg (1300mg/kg)   Revista do Instituto de Medicina Tropical de Sao Paulo. Vol. 15(Suppl,
rabbit LD50 intramuscular > 1gm/kg (1000mg/kg)   Revista do Instituto de Medicina Tropical de Sao Paulo. Vol. 15(Suppl,
rabbit LD50 oral 500mg/kg (500mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Drug Development Research. Vol. 4, Pg. 229, 1984.
rat LD50 intramuscular 60mg/kg (60mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LIVER: FATTY LIVER DEGERATION

BEHAVIORAL: ATAXIA
Drug Development Research. Vol. 4, Pg. 229, 1984.
rat LD50 intraperitoneal 20mg/kg (20mg/kg) LIVER: FATTY LIVER DEGERATION

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA
Drug Development Research. Vol. 4, Pg. 229, 1984.
rat LD50 oral 30mg/kg (30mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA

LIVER: FATTY LIVER DEGERATION
Drug Development Research. Vol. 4, Pg. 229, 1984.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 147-149 deg C   EXP
log P (octanol-water) 2.24 (none)   EXP
Water Solubility 820 mg/L 25 EST
Vapor Pressure 7.80E-10 mm Hg 25 EST
Henry's Law Constant 2.27E-16 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.31E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.