MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 318394 | Name: Oxamniquine

Description:

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

Oxamniquine is a DNA synthesis inhibitor for treatment of Schistosoma mansoni infections. It causes irreversible paralysis and tegumental damage in the parasite, which leads to detachment and death. In clinical studies, oxamniquine has shown cure rates of about 70–90% against S. mansoni when administered at doses of 15–20 mg/kg as a single oral dose. Pharmacokinetically, it is well absorbed, reaching peak plasma concentrations within 1–3 hours and has a half-life of about 1–2.5 hours. Oxamniquine is generally effective against both immature and mature worms but is inactive against other Schistosoma species like S. haematobium or S. japonicum.

Chemical Structure

Oxamniquine
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

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
Bulk Inquiry
Related CAS #
No Data
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
More Info

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
1: González Cabrera D, Keiser J, Spangenberg T. Analysis of the Physicochemical Properties of Anti-Schistosomal Compounds to Identify Next-Generation Leads. ACS Med Chem Lett. 2024 Apr 25;15(5):626-630. doi: 10.1021/acsmedchemlett.4c00026. PMID: 38746890; PMCID: PMC11089657. 2: Anyubaga SB, Shallangwa GA, Uzairu A, Abechi SE. Chemo-informatics applications in the design of novel 7-keto-sempervirol derivatives as SmCB1 inhibitors with potential for treatment of Schistosomiasis. Heliyon. 2023 Dec 3;10(1):e23115. doi: 10.1016/j.heliyon.2023.e23115. PMID: 38173516; PMCID: PMC10761359. 3: Pfarr KM, Krome AK, Al-Obaidi I, Batchelor H, Vaillant M, Hoerauf A, Opoku NO, Kuesel AC. The pipeline for drugs for control and elimination of neglected tropical diseases: 2. Oral anti-infective drugs and drug combinations for off- label use. Parasit Vectors. 2023 Oct 31;16(1):394. doi: 10.1186/s13071-023-05909-8. PMID: 37907954; PMCID: PMC10619278. 4: Alwan SN, Taylor AB, Rhodes J, Tidwell M, McHardy SF, LoVerde PT. Oxamniquine derivatives overcome Praziquantel treatment limitations for Schistosomiasis. PLoS Pathog. 2023 Jul 10;19(7):e1011018. doi: 10.1371/journal.ppat.1011018. PMID: 37428793; PMCID: PMC10359000. 5: Toth K, Alwan S, Khan S, McHardy SF, LoVerde PT, Cameron MD. Addressing the oxamniquine in vitro-in vivo paradox to facilitate a new generation of anti- schistosome treatments. Int J Parasitol Drugs Drug Resist. 2023 Apr;21:65-73. doi: 10.1016/j.ijpddr.2023.01.003. Epub 2023 Jan 30. PMID: 36758271; PMCID: PMC9929523. 6: Rennar GA, Gallinger TL, Mäder P, Lange-Grünweller K, Haeberlein S, Grünweller A, Grevelding CG, Schlitzer M. Disulfiram and dithiocarbamate analogues demonstrate promising antischistosomal effects. Eur J Med Chem. 2022 Nov 15;242:114641. doi: 10.1016/j.ejmech.2022.114641. Epub 2022 Aug 18. PMID: 36027862. 7: Naidoo P, Mkhize-Kwitshana ZL. Clustered Regularly Interspaced Short Palindromic Repeats/ CRISPR associated protein 9-mediated editing of Schistosoma mansoni genes: Identifying genes for immunologically potent drug and vaccine development. Rev Soc Bras Med Trop. 2022 Aug 12;55:e0131. doi: 10.1590/0037-8682-0131-2022. PMID: 35976333; PMCID: PMC9405935. 8: Guzman MA, Rugel A, Alwan SN, Tarpley R, Taylor AB, Chevalier FD, Wendt GR, Collins JJ 3rd, Anderson TJC, McHardy SF, LoVerde PT. Schistosome Sulfotransferases: Mode of Action, Expression and Localization. Pharmaceutics. 2022 Jul 6;14(7):1416. doi: 10.3390/pharmaceutics14071416. PMID: 35890311; PMCID: PMC9323829. 9: Cheuka PM. Drug Discovery and Target Identification against Schistosomiasis: A Reality Check on Progress and Future Prospects. Curr Top Med Chem. 2022;22(19):1595-1610. doi: 10.2174/1568026621666210924101805. PMID: 34565320. 10: LoVerde PT, Alwan SN, Taylor AB, Rhodes J, Chevalier FD, Anderson TJ, McHardy SF. Rational approach to drug discovery for human schistosomiasis. Int J Parasitol Drugs Drug Resist. 2021 Aug;16:140-147. doi: 10.1016/j.ijpddr.2021.05.002. Epub 2021 Jun 4. Erratum in: Int J Parasitol Drugs Drug Resist. 2022 Apr;18:103. doi: 10.1016/j.ijpddr.2022.01.003. PMID: 34111649; PMCID: PMC8193065. 11: Sankaranarayanan G, Coghlan A, Driguez P, Lotkowska ME, Sanders M, Holroyd N, Tracey A, Berriman M, Rinaldi G. Large CRISPR-Cas-induced deletions in the oxamniquine resistance locus of the human parasite Schistosoma mansoni. Wellcome Open Res. 2021 Jan 20;5:178. doi: 10.12688/wellcomeopenres.16031.2. PMID: 32789192; PMCID: PMC7405262. 12: Ezebuo FC, Uzochukwu IC. Drug repurposing for schistosomiasis: molecular docking and dynamics investigations. J Biomol Struct Dyn. 2022 Feb;40(3):995-1009. doi: 10.1080/07391102.2020.1820382. Epub 2020 Sep 14. PMID: 32924851. 13: Buchter V, Ong YC, Mouvet F, Ladaycia A, Lepeltier E, Rothlisberger U, Keiser J, Gasser G. Multidisciplinary Preclinical Investigations on Three Oxamniquine Analogues as New Drug Candidates for Schistosomiasis*. Chemistry. 2020 Nov 26;26(66):15232-15241. doi: 10.1002/chem.202002856. Epub 2020 Oct 22. PMID: 32852116. 14: Guzman MA, Rugel AR, Tarpley RS, Alwan SN, Chevalier FD, Kovalskyy DP, Cao X, Holloway SP, Anderson TJC, Taylor AB, McHardy SF, LoVerde PT. An iterative process produces oxamniquine derivatives that kill the major species of schistosomes infecting humans. PLoS Negl Trop Dis. 2020 Aug 18;14(8):e0008517. doi: 10.1371/journal.pntd.0008517. PMID: 32810153; PMCID: PMC7454593. 15: Rugel AR, Guzman MA, Taylor AB, Chevalier FD, Tarpley RS, McHardy SF, Cao X, Holloway SP, Anderson TJC, Hart PJ, LoVerde PT. Why does oxamniquine kill Schistosoma mansoni and not S. haematobium and S. japonicum? Int J Parasitol Drugs Drug Resist. 2020 Aug;13:8-15. doi: 10.1016/j.ijpddr.2020.04.001. Epub 2020 Apr 10. PMID: 32315953; PMCID: PMC7167500. 16: Guzman M, Rugel A, Tarpley RS, Cao X, McHardy SF, LoVerde PT, Taylor AB. Molecular basis for hycanthone drug action in schistosome parasites. Mol Biochem Parasitol. 2020 Mar;236:111257. doi: 10.1016/j.molbiopara.2020.111257. Epub 2020 Feb 3. PMID: 32027942. 17: Chevalier FD, Le Clec'h W, McDew-White M, Menon V, Guzman MA, Holloway SP, Cao X, Taylor AB, Kinung'hi S, Gouvras AN, Webster BL, Webster JP, Emery AM, Rollinson D, Garba Djirmay A, Al Mashikhi KM, Al Yafae S, Idris MA, Moné H, Mouahid G, Hart PJ, LoVerde PT, Anderson TJC. Oxamniquine resistance alleles are widespread in Old World Schistosoma mansoni and predate drug deployment. PLoS Pathog. 2019 Oct 25;15(10):e1007881. doi: 10.1371/journal.ppat.1007881. PMID: 31652296; PMCID: PMC6834289. 18: Zhou Z, Du G, Kang Z. [Production and application of 3-phosphoadenosine-5- phosphosulfate]. Sheng Wu Gong Cheng Xue Bao. 2019 Jul 25;35(7):1222-1233. Chinese. doi: 10.13345/j.cjb.180527. PMID: 31328479. 19: Ezebuo FC, Uzochukwu IC. Schistosomal Sulfotransferase Interaction with Oxamniquine Involves Hybrid Mechanism of Induced-fit and Conformational Selection. Curr Comput Aided Drug Des. 2020;16(4):451-459. doi: 10.2174/1573409915666190708103132. PMID: 31284869. 20: Gregorio AW, Vasconcellos MRA, Enokihara MMSS, Guerra JM, Nonogaki S, Tomimori J. Cutaneous schistosomiasis and leishmaniasis coinfection: a case report. J Eur Acad Dermatol Venereol. 2019 Sep;33(9):1781-1783. doi: 10.1111/jdv.15521. Epub 2019 Mar 27. PMID: 30801816.

View History

Lucitanib HCl

Lucitanib HCl

Featured