Ferroquine

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]

Ferroquine
Identifiers
  • 7-chloro-N-(2-((dimethylamino)methyl)ferrocenyl)quinolin-4-amine
CAS Number
PubChem CID
CompTox Dashboard (EPA)
ECHA InfoCard100.208.008
Chemical and physical data
FormulaC23H24ClFeN3
Molar mass433.76 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

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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