Oxamniquine
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 318394

CAS#: 21738-42-1

Description: Oxamniquine is used for treatment of schistosomiasis. It is an anthelmintic with schistosomicidal activity against Schistosoma mansoni, but not against other Schistosoma spp. Oxamniquine is a potent single-dose agent for treatment of S. mansoni infection in man, and it 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.


Chemical Structure

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Oxamniquine
CAS# 21738-42-1

Theoretical Analysis

MedKoo Cat#: 318394
Name: Oxamniquine
CAS#: 21738-42-1
Chemical Formula: C14H21N3O3
Exact Mass: 279.1583
Molecular Weight: 279.34
Elemental Analysis: C, 60.20; H, 7.58; N, 15.04; O, 17.18

Price and Availability

Size Price Availability Quantity
5.0mg USD 265.0 2 Weeks
25.0mg USD 800.0 2 Weeks
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Synonym: Oxamniquine, Oxamniquine, UK-4271, Mansil, Vansil

IUPAC/Chemical Name: [7-nitro-2-[(propan-2-ylamino)methyl]-1,2,3,4-tetrahydroquinolin-6-yl]methanol

InChi Key: XCGYUJZMCCFSRP-UHFFFAOYSA-N

InChi Code: 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

SMILES Code: OCC1=CC2=C(NC(CNC(C)C)CC2)C=C1[N+]([O-])=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 279.34 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Chevalier FD, Le Clec'h W, Eng N, Rugel AR, Assis RR, Oliveira G, Holloway SP, Cao X, Hart PJ, LoVerde PT, Anderson TJ. Independent origins of loss-of-function mutations conferring oxamniquine resistance in a Brazilian schistosome population. Int J Parasitol. 2016 Apr 9. pii: S0020-7519(16)30022-4. doi: 10.1016/j.ijpara.2016.03.006. [Epub ahead of print] PubMed PMID: 27073078.

2: Taylor AB, Pica-Mattoccia L, Polcaro CM, Donati E, Cao X, Basso A, Guidi A, Rugel AR, Holloway SP, Anderson TJ, Hart PJ, Cioli D, LoVerde PT. Structural and Functional Characterization of the Enantiomers of the Antischistosomal Drug Oxamniquine. PLoS Negl Trop Dis. 2015 Oct 20;9(10):e0004132. doi: 10.1371/journal.pntd.0004132. eCollection 2015. PubMed PMID: 26485649; PubMed Central PMCID: PMC4618941.

3: Mduluza T, Mutapi F, Ruwona T, Kaluka D, Midzi N, Ndhlovu PD. Similar cellular responses after treatment with either praziquantel or oxamniquine in Schistosoma mansoni infection. Malawi Med J. 2009 Dec;21(4):176-82. PubMed PMID: 21174933; PubMed Central PMCID: PMC3345748.

4: Mattos AC, Pereira GC, Jannotti-Passos LK, Kusel JR, Coelho PM. Evaluation of the effect of oxamniquine, praziquantel and a combination of both drugs on the intramolluscan phase of Schistosoma mansoni. Acta Trop. 2007 May;102(2):84-91. Epub 2007 Apr 6. PubMed PMID: 17498638.

5: de Souza JR, Morais CN, Aroucha ML, Miranda PJ, Barbosa CS, Domingues AL, Carvalho Júnior LB, Abath FG, Montenegro SM. Treatment of human acute schistosomiasis with oxamniquine induces an increase in interferon-gamma response to Schistosoma mansoni antigens. Mem Inst Oswaldo Cruz. 2007 May;102(2):225-8. PubMed PMID: 17426890.

6: 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 PMID: 17308787.

7: Costa G, Aguiar BG, Coelho PM, Cunha-Melo JR. On the increase of portal pressure during the acute and chronic phases of murine schistosomiasis mansoni and its reversibility after treatment with oxamniquine. Acta Trop. 2003 Dec;89(1):13-6. PubMed PMID: 14636977.

8: Thiong'o FW, Mbugua GG, Ouma JH, Sturrock RK. Efficacy of oxamniquine and praziquantel in school children from two Schistosoma mansoni endemic areas. East Afr Med J. 2002 Jan;79(1):29-33. PubMed PMID: 12380867.

9: Bonesso-Sabadini PI, de Souza Dias LC. Altered response of strain of Schistosoma mansoni to oxamniquine and praziquantel. Mem Inst Oswaldo Cruz. 2002 Apr;97(3):381-5. PubMed PMID: 12048569.

10: Filho SB, Gargioni C, Silva Pinto PL, Chiodelli SG, Gurgel Vellosa SA, da Silva RM, da Silveira MA. Synthesis and evaluation of new oxamniquine derivatives. Int J Pharm. 2002 Feb 21;233(1-2):35-41. PubMed PMID: 11897408.

11: Conceição MJ, Argento CA, Corrêa A. Study of Schistosoma mansoni isolates from patients with failure of treatment with oxamniquine. Mem Inst Oswaldo Cruz. 2000 May-Jun;95(3):375-80. PubMed PMID: 10800196.

12: Webster M, Fallon PG, Fulford AJ, Butterworth AE, Ouma JH, Kimani G, Dunne DW. Effect of praziquantel and oxamniquine treatment on human isotype responses to Schistosoma mansoni: elevated IgE to adult worm. Parasite Immunol. 1997 Jul;19(7):333-5. PubMed PMID: 9278946.

13: García Goyco C, Nazario-López H, Ruiz-Tiben E, Vázquez G, Borges T, Nash TE. The efficacy of oxamniquine in acute schistosomiasis: a clinical analysis of 28 treated patients. Bol Asoc Med P R. 1997 Apr-Jun;89(4-6):63-9. PubMed PMID: 9432187.

14: Coelho PM, Lima e Silva FC, Nogueira-Machado JA. Resistance to oxamniquine of a Schistosoma mansoni strain isolated from patient submitted to repeated treatments. Rev Inst Med Trop Sao Paulo. 1997 Mar-Apr;39(2):101-6. PubMed PMID: 9394523.

15: Kokwaro GO, Indalo AA. Effect of route of administration on systematic availability of oxamniquine in the rabbit. Afr J Health Sci. 1996 Aug;3(3):101-4. PubMed PMID: 17451310.

16: Kokwaro GO, Indalo AA, Taylor G. Pharmacokinetics of oxamniquine in rabbit and rat. Eur J Drug Metab Pharmacokinet. 1996 Jan-Mar;21(1):13-6. PubMed PMID: 8839672.

17: Fallon PG, Fookes RE, Wharton GA. Temporal differences in praziquantel- and oxamniquine-induced tegumental damage to adult Schistosoma mansoni: implications for drug-antibody synergy. Parasitology. 1996 Jan;112 ( Pt 1):47-58. PubMed PMID: 8587801.

18: Fallon PG, Hamilton JV, Doenhoff MJ. Efficacy of treatment of murine Schistosoma mansoni infections with praziquantel and oxamniquine correlates with infection intensity: role of host antibody. Parasitology. 1995 Jul;111 ( Pt 1):59-66. PubMed PMID: 7609991.

19: Abushoffa AM, Clark BJ. Resolution of the enantiomers of oxamniquine by capillary electrophoresis and high-performance liquid chromatography with cyclodextrins and heparin as chiral selectors. J Chromatogr A. 1995 May 12;700(1-2):51-8. PubMed PMID: 7767464.

20: Pica-Mattoccia L, Dias LC, Moroni R, Cioli D. Schistosoma mansoni: genetic complementation analysis shows that two independent hycanthone/oxamniquine-resistant strains are mutated in the same gene. Exp Parasitol. 1993 Dec;77(4):445-9. PubMed PMID: 8253157.