Ferroquine

Last updated
Ferroquine
Ferroquine.png
Identifiers
  • 7-chloro-N-({2-[(dimethylamino)methyl]ferrocenyl}methyl)quinolin-4-amine
CAS Number
PubChem CID
UNII
CompTox Dashboard (EPA)
ECHA InfoCard 100.208.008 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C23H24ClFeN3
Molar mass 433.76 g·mol−1
  • InChI=1S/C18H19ClN3.C5H5.Fe/c1-22(2)12-14-5-3-4-13(14)11-21-17-8-9-20-18-10-15(19)6-7-16(17)18;1-2-4-5-3-1;/h3-10H,11-12H2,1-2H3,(H,20,21);1-5H;/q2*-1;+2
  • Key:DDENDDKMBDTHAX-UHFFFAOYSA-N

Ferroquine is a synthetic compound related to chloroquine which acts as an antimalarial, and shows good activity against chloroquine-resistant strains. [1] It contains an organometallic ferrocene ring which is unusual in pharmaceuticals, [2] [3] [4] and while it was first reported in 1997, [5] it has progressed slowly through clinical trials, with results from Phase II trials showing reasonable safety and efficacy, and further trials ongoing. [6] [7]

References

  1. ↑ Domarle O, Blampain G, Agnaniet H, Nzadiyabi T, Lebibi J, Brocard J, et al. (March 1998). "In vitro antimalarial activity of a new organometallic analog, ferrocene-chloroquine". Antimicrobial Agents and Chemotherapy. 42 (3): 540–544. doi:10.1128/AAC.42.3.540. PMC   105495 . PMID   9517929.
  2. ↑ Dive D, Biot C (March 2008). "Ferrocene conjugates of chloroquine and other antimalarials: the development of ferroquine, a new antimalarial". ChemMedChem. 3 (3): 383–391. doi:10.1002/cmdc.200700127. PMC   7162372 . PMID   17806092.
  3. ↑ Biot C, Nosten F, Fraisse L, Ter-Minassian D, Khalife J, Dive D (August 2011). "The antimalarial ferroquine: from bench to clinic". Parasite. 18 (3): 207–214. doi:10.1051/parasite/2011183207. PMC   3671469 . PMID   21894260.
  4. ↑ Wani WA, Jameel E, Baig U, Mumtazuddin S, Hun LT (August 2015). "Ferroquine and its derivatives: new generation of antimalarial agents". European Journal of Medicinal Chemistry. 101: 534–551. doi:10.1016/j.ejmech.2015.07.009. PMC   7115395 . PMID   26188909.
  5. ↑ Biot C, Glorian G, Maciejewski LA, Brocard JS (November 1997). "Synthesis and antimalarial activity in vitro and in vivo of a new ferrocene-chloroquine analogue". Journal of Medicinal Chemistry. 40 (23): 3715–3718. doi:10.1021/jm970401y. PMID   9371235.
  6. ↑ Held J, Supan C, Salazar CL, Tinto H, Bonkian LN, Nahum A, et al. (December 2015). "Ferroquine and artesunate in African adults and children with Plasmodium falciparum malaria: a phase 2, multicentre, randomised, double-blind, dose-ranging, non-inferiority study". The Lancet. Infectious Diseases. 15 (12): 1409–1419. doi:10.1016/S1473-3099(15)00079-1. PMID   26342427.
  7. ↑ Adoke Y, Zoleko-Manego R, Ouoba S, Tiono AB, Kaguthi G, Bonzela JE, et al. (May 2021). "A randomized, double-blind, phase 2b study to investigate the efficacy, safety, tolerability and pharmacokinetics of a single-dose regimen of ferroquine with artefenomel in adults and children with uncomplicated Plasmodium falciparum malaria". Malaria Journal. 20 (1): 222. doi: 10.1186/s12936-021-03749-4 . PMC   8135182 . PMID   34011358.
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