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MedKoo Cat#: 585198 | Name: Sitamaquine

Description:

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

Sitamaquine, also known as WR-6026, is an orally active 8-aminoquinoline analog with anti-leishmanial properties.

Chemical Structure

Sitamaquine
Sitamaquine
CAS#57695-04-2 (free base)

Theoretical Analysis

MedKoo Cat#: 585198

Name: Sitamaquine

CAS#: 57695-04-2 (free base)

Chemical Formula: C21H33N3O

Exact Mass: 343.2624

Molecular Weight: 343.52

Elemental Analysis: C, 73.43; H, 9.68; N, 12.23; O, 4.66

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.
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Related CAS #
57695-04-2 (free base) 1019640-33-5 (tosylate) 5330-29-0 (2HCl)
Synonym
Sitamaquine; WR-6026; WR6026; WR 6026
IUPAC/Chemical Name
1,6-Hexanediamine, N,N-diethyl-N'-(6-methoxy-4-methyl-8-quinolinyl)-
InChi Key
RVAKDGYPIVSYEU-UHFFFAOYSA-N
InChi Code
InChI=1S/C21H33N3O/c1-5-24(6-2)14-10-8-7-9-12-22-20-16-18(25-4)15-19-17(3)11-13-23-21(19)20/h11,13,15-16,22H,5-10,12,14H2,1-4H3
SMILES Code
CC1=CC=NC2=C(NCCCCCCN(CC)CC)C=C(OC)C=C12
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
Shelf Life
>3 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 343.52 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: Frampton JE. Tafenoquine: First Global Approval. Drugs. 2018 Sep;78(14):1517-1523. doi: 10.1007/s40265-018-0979-2. Review. PubMed PMID: 30229442. 2: Imbert L, Cojean S, Libong D, Chaminade P, Loiseau PM. Sitamaquine-resistance in Leishmania donovani affects drug accumulation and lipid metabolism. Biomed Pharmacother. 2014 Sep;68(7):893-7. doi: 10.1016/j.biopha.2014.08.009. Epub 2014 Aug 19. PubMed PMID: 25201056. 3: Sundar S, Sinha PK, Dixon SA, Buckley R, Miller AK, Mohamed K, Al-Banna M. Pharmacokinetics of oral sitamaquine taken with or without food and safety and efficacy for treatment of visceral leishmaniais: a randomized study in Bihar, India. Am J Trop Med Hyg. 2011 Jun;84(6):892-900. doi: 10.4269/ajtmh.2011.10-0409. PubMed PMID: 21633025; PubMed Central PMCID: PMC3110365. 4: Vercesi AE, Docampo R. Ca2+ transport by digitonin-permeabilized Leishmania donovani. Effects of Ca2+, pentamidine and WR-6026 on mitochondrial membrane potential in situ. Biochem J. 1992 Jun 1;284 ( Pt 2):463-7. PubMed PMID: 1376113; PubMed Central PMCID: PMC1132661. 5: Petty BG, Black JR, Hendrix CW, Lewis LD, Basiakos Y, Feinberg J, Pattison DG, Hafner R. Escalating multiple-dose safety and tolerance study of oral WR 6026 in HIV-infected subjects: AIDS clinical trials group 173. J Acquir Immune Defic Syndr. 1999 May 1;21(1):26-32. PubMed PMID: 10235511. 6: Ley B, Bancone G, von Seidlein L, Thriemer K, Richards JS, Domingo GJ, Price RN. Methods for the field evaluation of quantitative G6PD diagnostics: a review. Malar J. 2017 Sep 11;16(1):361. doi: 10.1186/s12936-017-2017-3. Review. PubMed PMID: 28893237; PubMed Central PMCID: PMC5594530. 7: López-Martín C, Pérez-Victoria JM, Carvalho L, Castanys S, Gamarro F. Sitamaquine sensitivity in Leishmania species is not mediated by drug accumulation in acidocalcisomes. Antimicrob Agents Chemother. 2008 Nov;52(11):4030-6. doi: 10.1128/AAC.00964-08. Epub 2008 Sep 15. PubMed PMID: 18794384; PubMed Central PMCID: PMC2573096. 8: Taylor T, Hawkins DR, Morris GR, Chung H. Pharmacokinetics of the anti-leishmanian agent WR 6026 in dogs. Eur J Drug Metab Pharmacokinet. 1991;Spec No 3:136-9. PubMed PMID: 1820868. 9: Nqoro X, Tobeka N, Aderibigbe BA. Quinoline-Based Hybrid Compounds with Antimalarial Activity. Molecules. 2017 Dec 19;22(12). pii: E2268. doi: 10.3390/molecules22122268. Review. PubMed PMID: 29257067; PubMed Central PMCID: PMC6149725. 10: Loiseau PM, Cojean S, Schrével J. Sitamaquine as a putative antileishmanial drug candidate: from the mechanism of action to the risk of drug resistance. Parasite. 2011 May;18(2):115-9. Review. PubMed PMID: 21678786; PubMed Central PMCID: PMC3671420. 11: Pérez-Victoria JM, Bavchvarov BI, Torrecillas IR, Martínez-García M, López-Martín C, Campillo M, Castanys S, Gamarro F. Sitamaquine overcomes ABC-mediated resistance to miltefosine and antimony in Leishmania. Antimicrob Agents Chemother. 2011 Aug;55(8):3838-44. doi: 10.1128/AAC.00065-11. Epub 2011 Jun 6. PubMed PMID: 21646479; PubMed Central PMCID: PMC3147638. 12: Baird JK. Tafenoquine for travelers' malaria: evidence, rationale and recommendations. J Travel Med. 2018 Jan 1;25(1). doi: 10.1093/jtm/tay110. PubMed PMID: 30380095; PubMed Central PMCID: PMC6243017. 13: Coimbra ES, Libong D, Cojean S, Saint-Pierre-Chazalet M, Solgadi A, Le Moyec L, Duenas-Romero AM, Chaminade P, Loiseau PM. Mechanism of interaction of sitamaquine with Leishmania donovani. J Antimicrob Chemother. 2010 Dec;65(12):2548-55. doi: 10.1093/jac/dkq371. Epub 2010 Oct 18. PubMed PMID: 20956354. 14: Garnier T, Brown MB, Lawrence MJ, Croft SL. In-vitro and in-vivo studies on a topical formulation of sitamaquine dihydrochloride for cutaneous leishmaniasis. J Pharm Pharmacol. 2006 Aug;58(8):1043-54. PubMed PMID: 16872550. 15: Mesquita JT, Tempone AG, Reimão JQ. Combination therapy with nitazoxanide and amphotericin B, Glucantime®, miltefosine and sitamaquine against Leishmania (Leishmania) infantum intracellular amastigotes. Acta Trop. 2014 Feb;130:112-6. doi: 10.1016/j.actatropica.2013.11.003. Epub 2013 Nov 13. PubMed PMID: 24239532. 16: Kulshrestha A, Singh R, Kumar D, Negi NS, Salotra P. Antimony-resistant clinical isolates of Leishmania donovani are susceptible to paromomycin and sitamaquine. Antimicrob Agents Chemother. 2011 Jun;55(6):2916-21. doi: 10.1128/AAC.00812-10. Epub 2011 Apr 4. PubMed PMID: 21464251; PubMed Central PMCID: PMC3101468. 17: Graves PM, Choi L, Gelband H, Garner P. Primaquine or other 8-aminoquinolines for reducing Plasmodium falciparum transmission. Cochrane Database Syst Rev. 2018 Feb 2;2:CD008152. doi: 10.1002/14651858.CD008152.pub5. Review. PubMed PMID: 29393511; PubMed Central PMCID: PMC5815493. 18: Chu CS, White NJ. Management of relapsing Plasmodium vivax malaria. Expert Rev Anti Infect Ther. 2016 Oct;14(10):885-900. doi: 10.1080/14787210.2016.1220304. Epub 2016 Aug 31. Review. PubMed PMID: 27530139; PubMed Central PMCID: PMC5039400. 19: Chu CS, Bancone G, Nosten F, White NJ, Luzzatto L. Primaquine-induced haemolysis in females heterozygous for G6PD deficiency. Malar J. 2018 Mar 2;17(1):101. doi: 10.1186/s12936-018-2248-y. Review. PubMed PMID: 29499733; PubMed Central PMCID: PMC5833093. 20: Wasunna MK, Rashid JR, Mbui J, Kirigi G, Kinoti D, Lodenyo H, Felton JM, Sabin AJ, Albert MJ, Horton J. A phase II dose-increasing study of sitamaquine for the treatment of visceral leishmaniasis in Kenya. Am J Trop Med Hyg. 2005 Nov;73(5):871-6. Erratum in: Am J Trop Med Hyg. 2006 Jan;74(1):185. Albert, M John [added]. PubMed PMID: 16282296.

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