Mefloquine

  • CAT Number: I031872
  • CAS Number: 53230-10-7
  • Molecular Formula: C17H16F6N2O
  • Molecular Weight: 378.31
  • Purity: 98%
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Mefloquine (Cat.No:I031872) is a phospholipid-interacting antimalarial drug. It is very effective against Plasmodium Falciparium with very few side effects.

Catalog Number I031872
CAS Number 53230-10-7
Molecular Formula

C17H16F6N2O

Purity 98
Solubility Soluble in DMSO
Storage Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
IUPAC Name (S)-(2,8-bis(trifluoromethyl)quinolin-4-yl)((R)-piperidin-2-yl)methanol
InChI InChI=1S/C17H16F6N2O/c18-16(19,20)11-5-3-4-9-10(15(26)12-6-1-2-7-24-12)8-13(17(21,22)23)25-14(9)11/h3-5,8,12,15,24,26H,1-2,6-7H2/t12-,15+/m1/s1
InChIKey XEEQGYMUWCZPDN-DOMZBBRYSA-N
SMILES FC(F)(F)c1cccc2c1nc(C(F)(F)F)cc2[C@H](O)[C@H]3CCCCN3
Reference

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2: Janowsky A, Eshleman AJ, Johnson RA, Wolfrum KM, Hinrichs DJ, Yang J, Zabriskie TM, Smilkstein MJ, Riscoe MK. Mefloquine and psychotomimetics share neurotransmitter receptor and transporter interactions in vitro. Psychopharmacology (Berl). 2014 Jul;231(14):2771-83. doi: 10.1007/s00213-014-3446-0. Epub 2014 Feb 2. PubMed PMID: 24488404; PubMed Central PMCID: PMC4097020.
3: Tao Y, Xue J, Jiang B, Zhang HB, Xiao SH. Significance of higher drug concentration in erythrocytes of mice infected with Schistosoma japonicum and treated orally with mefloquine at single doses. Parasitol Res. 2015 Dec;114(12):4521-30. doi: 10.1007/s00436-015-4696-4. Epub 2015 Sep 4. PubMed PMID: 26341799.
4: Maaswinkel H, Zhu L, Weng W. A small-fish model for behavioral-toxicological screening of new antimalarial drugs: a comparison between erythro- and threo-mefloquine. BMC Res Notes. 2015 Apr 2;8:122. doi: 10.1186/s13104-015-1088-x. PubMed PMID: 25886204; PubMed Central PMCID: PMC4386100.
5: Jullien V, Valecha N, Srivastava B, Sharma B, Kiechel JR. Population pharmacokinetics of mefloquine, administered as a fixed-dose combination of artesunate-mefloquine in Indian patients for the treatment of acute uncomplicated Plasmodium falciparum malaria. Malar J. 2014 May 23;13:187. doi: 10.1186/1475-2875-13-187. PubMed PMID: 24886117; PubMed Central PMCID: PMC4046089.
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7: Rastelli EJ, Coltart DM. A Concise and Highly Enantioselective Total Synthesis of (+)-anti- and (-)-syn-Mefloquine Hydrochloride: Definitive Absolute Stereochemical Assignment of the Mefloquines. Angew Chem Int Ed Engl. 2015 Nov 16;54(47):14070-4. doi: 10.1002/anie.201507304. Epub 2015 Sep 30. PubMed PMID: 26422780.
8: Wernsdorfer WH, Noedl H, Rendi-Wagner P, Kollaritsch H, Wiedermann G, Mikolasek A, Karbwang J, Na-Bangchang K. Gender-specific distribution of mefloquine in the blood following the administration of therapeutic doses. Malar J. 2013 Dec 9;12:443. doi: 10.1186/1475-2875-12-443. PubMed PMID: 24321055; PubMed Central PMCID: PMC3901017.
9: Adamcova M, Schaerer MT, Bercaru I, Cockburn I, Rhein HG, Schlagenhauf P. Eye disorders reported with the use of mefloquine (Lariam(®)) chemoprophylaxis–A drug safety database analysis. Travel Med Infect Dis. 2015 Sep-Oct;13(5):400-8. doi: 10.1016/j.tmaid.2015.04.005. Epub 2015 Apr 30. PubMed PMID: 26119539.
10: Ritchie EC, Block J, Nevin RL. Psychiatric side effects of mefloquine: applications to forensic psychiatry. J Am Acad Psychiatry Law. 2013;41(2):224-35. PubMed PMID: 23771936.
11: Hamann AR, de Kock C, Smith PJ, van Otterlo WA, Blackie MA. Synthesis of novel triazole-linked mefloquine derivatives: biological evaluation against Plasmodium falciparum. Bioorg Med Chem Lett. 2014 Dec 1;24(23):5466-9. doi: 10.1016/j.bmcl.2014.10.015. Epub 2014 Oct 13. PubMed PMID: 25455485.
12: Dow GS, McCarthy WF, Reid M, Smith B, Tang D, Shanks GD. A retrospective analysis of the protective efficacy of tafenoquine and mefloquine as prophylactic anti-malarials in non-immune individuals during deployment to a malaria-endemic area. Malar J. 2014 Feb 6;13:49. doi: 10.1186/1475-2875-13-49. PubMed PMID: 24502679; PubMed Central PMCID: PMC3942710.
13: Piedade R, Traub S, Bitter A, Nüssler AK, Gil JP, Schwab M, Burk O. Carboxymefloquine, the major metabolite of the antimalarial drug mefloquine, induces drug-metabolizing enzyme and transporter expression by activation of pregnane X receptor. Antimicrob Agents Chemother. 2015 Jan;59(1):96-104. doi: 10.1128/AAC.04140-14. Epub 2014 Oct 13. PubMed PMID: 25313206; PubMed Central PMCID: PMC4291335.
14: Ingram K, Duthaler U, Vargas M, Ellis W, Keiser J. Disposition of mefloquine and enpiroline is highly influenced by a chronic Schistosoma mansoni infection. Antimicrob Agents Chemother. 2013 Sep;57(9):4506-11. doi: 10.1128/AAC.01129-13. Epub 2013 Jul 8. PubMed PMID: 23836173; PubMed Central PMCID: PMC3754359.
15: du Plessis LH, Helena C, van Huysteen E, Wiesner L, Kotzé AF. Formulation and evaluation of Pheroid vesicles containing mefloquine for the treatment of malaria. J Pharm Pharmacol. 2014 Jan;66(1):14-22. doi: 10.1111/jphp.12147. Epub 2013 Oct 13. PubMed PMID: 24117456.
16: Bermudez LE, Inderlied CB, Kolonoski P, Chee CB, Aralar P, Petrofsky M, Parman T, Green CE, Lewin AH, Ellis WY, Young LS. Identification of (+)-erythro-mefloquine as an active enantiomer with greater efficacy than mefloquine against Mycobacterium avium infection in mice. Antimicrob Agents Chemother. 2012 Aug;56(8):4202-6. doi: 10.1128/AAC.00320-12. Epub 2012 May 21. PubMed PMID: 22615290; PubMed Central PMCID: PMC3421598.
17: Nevin RL. Mefloquine gap junction blockade and risk of pregnancy loss. Biol Reprod. 2012 Sep 21;87(3):65. Print 2012 Sep. Review. PubMed PMID: 22837476.
18: Kamel RO. Interactions between mefloquine and the anti-fibrotic drug silymarin on Schistosoma mansoni infections in mice. J Helminthol. 2016 Nov;90(6):760-765. Epub 2016 Jan 29. PubMed PMID: 26824480.
19: Ingram K, Ellis W, Keiser J. Antischistosomal activities of mefloquine-related arylmethanols. Antimicrob Agents Chemother. 2012 Jun;56(6):3207-15. doi: 10.1128/AAC.06177-11. Epub 2012 Apr 2. PubMed PMID: 22470113; PubMed Central PMCID: PMC3370792.
20: Rueangweerayut R, Phyo AP, Uthaisin C, Poravuth Y, Binh TQ, Tinto H, Pénali LK, Valecha N, Tien NT, Abdulla S, Borghini-Fuhrer I, Duparc S, Shin CS, Fleckenstein L; Pyronaridine–Artesunate Study Team. Pyronaridine-artesunate versus mefloquine plus artesunate for malaria. N Engl J Med. 2012 Apr 5;366(14):1298-309. doi: 10.1056/NEJMoa1007125. PubMed PMID: 22475593.

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