Ferroquine

Ferroquine
Identifiers
	IUPAC name 7-chloro-N-(2-((dimethylamino)methyl)ferrocenyl)quinolin-4-amine;
CAS Number	185055-67-8;
PubChem CID	140118553;
CompTox Dashboard (EPA)	DTXSID00939922 ;
ECHA InfoCard	100.208.008
Chemical and physical data
Formula	C23H24ClFeN3
Molar mass	433.76 g·mol−1
	InChI 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

^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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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[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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Identifiers

IUPAC name 7-chloro-N-(2-((dimethylamino)methyl)ferrocenyl)quinolin-4-amine
CAS Number	185055-67-8
PubChem CID	140118553
CompTox Dashboard (EPA)	DTXSID00939922
ECHA InfoCard	100.208.008
Chemical and physical data
Formula	C₂₃H₂₄ClFeN₃
Molar mass	433.76 g·mol⁻¹
InChI 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