Ferroquine | CAS#185055-67-8 | hemozoin inhibitor

MedKoo Cat#: 529601 | Name: Ferroquine

Description:

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

Ferroquine is a ferrocene-based antimalarial with low-nanomolar IC₅₀ (~10 nM) against chloroquine-resistant Plasmodium falciparum. It accumulates in the parasite’s digestive vacuole, disrupting heme detoxification and inducing oxidative stress. Its redox-active ferrocene moiety enhances parasite killing by generating reactive oxygen species (ROS).

Chemical Structure

Ferroquine

CAS#185055-67-8

Theoretical Analysis

MedKoo Cat#: 529601

Name: Ferroquine

CAS#: 185055-67-8

Chemical Formula: C23H24ClFeN3

Exact Mass: 433.1008

Molecular Weight: 433.76

Elemental Analysis: C, 63.69; H, 5.58; Cl, 8.17; Fe, 12.87; N, 9.69

Price and Availability

Size	Price	Availability
5mg	USD 150.00	Ready to ship
10mg	USD 250.00	Ready to ship
25mg	USD 550.00	Ready to ship
50mg	USD 950.00	2 Weeks

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Related CAS #

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Synonym

SR-97193; SR 97193; SR97193; SSR97193; SSR 97193; SSR-97193; Ferrochloroquine; Ferroquine

IUPAC/Chemical Name

1-[[(7-Chloro-4-quinolinyl)amino]methyl]-2-[(dimethylamino)methyl]ferrocene

InChi Key

DDENDDKMBDTHAX-UHFFFAOYSA-N

InChi Code

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

SMILES Code

C(NC=1C2=C(C=C(Cl)C=C2)N=CC1)[C-]34[Fe+2]56789%10%11(C3(CN(C)C)=[CH]5[CH]6=[CH]74)[CH-]%12[CH]8=[CH]9[CH]%10=[CH]%11%12

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

>2 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

Certificate of Analysis

View CoA: current batch, Lot#C24S11C28

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Plasmodium

In vitro activity:

our more informative in vitro combination assay provided additional insights into the pharmacodynamic drug interactions compared to the in vivo systems, e.g., a concentration-dependent change in the maximum killing effect (Emax) and the concentration producing 50% of the killing maximum effect (EC50) of piperaquine or artefenomel or a directional reduction of the EC50 of ferroquine by artefenomel and a directional reduction of Emax of ferroquine by artefenomel. Reference: Wicha SG, Walz A, Cherkaoui-Rbati MH, Bundgaard N, Kuritz K, Gumpp C, Gobeau N, Möhrle J, Rottmann M, Demarta-Gatsi C. New In Vitro Interaction-Parasite Reduction Ratio Assay for Early Derisk in Clinical Development of Antimalarial Combinations. Antimicrob Agents Chemother. 2022 Nov 15;66(11):e0055622. doi: 10.1128/aac.00556-22. Epub 2022 Oct 5. PMID: 36197116; PMCID: PMC9664866.

In vivo activity:

Overall, the analysis of parasite killing in the PfalcHuMouse model is a unique and robust experimental in vivo tool to inform the selection of optimal combinations by pharmacometric pharmacokinetic and pharmacodynamic (PK/PD) modeling. Reference: Demarta-Gatsi C, Andenmatten N, Jiménez-Díaz MB, Gobeau N, Cherkaoui-Rabti MH, Fuchs A, Díaz P, Berja S, Sánchez R, Gómez H, Ruiz E, Sainz P, Salazar E, Gil-Merino R, Mendoza LM, Eguizabal C, Leroy D, Moehrle JJ, Tornesi B, Angulo-Barturen I. Predicting Optimal Antimalarial Drug Combinations from a Standardized Plasmodium falciparum Humanized Mouse Model. Antimicrob Agents Chemother. 2023 Jun 15;67(6):e0157422. doi: 10.1128/aac.01574-22. Epub 2023 May 3. PMID: 37133382; PMCID: PMC10269072.

	Solvent	mg/mL	mM
Solubility
	DMSO	4.4	10.03

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 433.76 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.

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

Formulation protocol:

In vitro protocol:

1: Wicha SG, Walz A, Cherkaoui-Rbati MH, Bundgaard N, Kuritz K, Gumpp C, Gobeau N, Möhrle J, Rottmann M, Demarta-Gatsi C. New In Vitro Interaction-Parasite Reduction Ratio Assay for Early Derisk in Clinical Development of Antimalarial Combinations. Antimicrob Agents Chemother. 2022 Nov 15;66(11):e0055622. doi: 10.1128/aac.00556-22. Epub 2022 Oct 5. PMID: 36197116; PMCID: PMC9664866. 2: Gendrot M, Jardot P, Delandre O, Boxberger M, Andreani J, Duflot I, Le Bideau M, Mosnier J, Fonta I, Hutter S, La Scola B, Pradines B. In Vitro Evaluation of the Antiviral Activity of Methylene Blue Alone or in Combination against SARS-CoV-2. J Clin Med. 2021 Jul 6;10(14):3007. doi: 10.3390/jcm10143007. PMID: 34300178; PMCID: PMC8307868.

In vivo protocol:

1: Demarta-Gatsi C, Andenmatten N, Jiménez-Díaz MB, Gobeau N, Cherkaoui-Rabti MH, Fuchs A, Díaz P, Berja S, Sánchez R, Gómez H, Ruiz E, Sainz P, Salazar E, Gil-Merino R, Mendoza LM, Eguizabal C, Leroy D, Moehrle JJ, Tornesi B, Angulo-Barturen I. Predicting Optimal Antimalarial Drug Combinations from a Standardized Plasmodium falciparum Humanized Mouse Model. Antimicrob Agents Chemother. 2023 Jun 15;67(6):e0157422. doi: 10.1128/aac.01574-22. Epub 2023 May 3. PMID: 37133382; PMCID: PMC10269072. 2: Pomel S, Dubar F, Forge D, Loiseau PM, Biot C. New heterocyclic compounds: Synthesis and antitrypanosomal properties. Bioorg Med Chem. 2015 Aug 15;23(16):5168-74. doi: 10.1016/j.bmc.2015.03.029. Epub 2015 Mar 20. PMID: 25835356.

1: Wani WA, Jameel E, Baig U, Mumtazuddin S, Hun LT. Ferroquine and its derivatives: new generation of antimalarial agents. Eur J Med Chem. 2015 Aug 28;101:534-51. doi: 10.1016/j.ejmech.2015.07.009. Review. PubMed PMID: 26188909. 2: Held J, Supan C, Salazar CL, Tinto H, Bonkian LN, Nahum A, Moulero B, Sié A, Coulibaly B, Sirima SB, Siribie M, Otsyula N, Otieno L, Abdallah AM, Kimutai R, Bouyou-Akotet M, Kombila M, Koiwai K, Cantalloube C, Din-Bell C, Djeriou E, Waitumbi J, Mordmüller B, Ter-Minassian D, Lell B, Kremsner PG. Ferroquine and artesunate in African adults and children with Plasmodium falciparum malaria: a phase 2, multicentre, randomised, double-blind, dose-ranging, non-inferiority study. Lancet Infect Dis. 2015 Dec;15(12):1409-19. doi: 10.1016/S1473-3099(15)00079-1. PubMed PMID: 26342427. 3: McCarthy JS, Rückle T, Djeriou E, Cantalloube C, Ter-Minassian D, Baker M, O'Rourke P, Griffin P, Marquart L, Hooft van Huijsduijnen R, Möhrle JJ. A Phase II pilot trial to evaluate safety and efficacy of ferroquine against early Plasmodium falciparum in an induced blood-stage malaria infection study. Malar J. 2016 Sep 13;15:469. doi: 10.1186/s12936-016-1511-3. PubMed PMID: 27624471; PubMed Central PMCID: PMC5022189. 4: Keiser J, Vargas M, Rubbiani R, Gasser G, Biot C. In vitro and in vivo antischistosomal activity of ferroquine derivatives. Parasit Vectors. 2014 Sep 4;7:424. doi: 10.1186/1756-3305-7-424. PubMed PMID: 25190030; PubMed Central PMCID: PMC4164798. 5: Supan C, Mombo-Ngoma G, Dal-Bianco MP, Ospina Salazar CL, Issifou S, Mazuir F, Filali-Ansary A, Biot C, Ter-Minassian D, Ramharter M, Kremsner PG, Lell B. Pharmacokinetics of ferroquine, a novel 4-aminoquinoline, in asymptomatic carriers of Plasmodium falciparum infections. Antimicrob Agents Chemother. 2012 Jun;56(6):3165-73. doi: 10.1128/AAC.05359-11. PubMed PMID: 22430976; PubMed Central PMCID: PMC3370764. 6: Jacobs L, de Kock C, de Villiers KA, Smith PJ, Smith VJ, van Otterlo WA, Blackie MA. Design, Synthesis, and Evaluation of Novel Ferroquine and Phenylequine Analogues as Potential Antiplasmodial Agents. ChemMedChem. 2015 Dec;10(12):2099-110. doi: 10.1002/cmdc.201500349. PubMed PMID: 26447782. 7: Dubar F, Slomianny C, Khalife J, Dive D, Kalamou H, Guérardel Y, Grellier P, Biot C. The ferroquine antimalarial conundrum: redox activation and reinvasion inhibition. Angew Chem Int Ed Engl. 2013 Jul 22;52(30):7690-3. doi: 10.1002/anie.201303690. PubMed PMID: 23765846. 8: Dive D, Biot C. Ferroquine as an oxidative shock antimalarial. Curr Top Med Chem. 2014;14(14):1684-92. PubMed PMID: 25116581. 9: Mombo-Ngoma G, Supan C, Dal-Bianco MP, Missinou MA, Matsiegui PB, Ospina Salazar CL, Issifou S, Ter-Minassian D, Ramharter M, Kombila M, Kremsner PG, Lell B. Phase I randomized dose-ascending placebo-controlled trials of ferroquine--a candidate anti-malarial drug--in adults with asymptomatic Plasmodium falciparum infection. Malar J. 2011 Mar 1;10:53. doi: 10.1186/1475-2875-10-53. PubMed PMID: 21362162; PubMed Central PMCID: PMC3056844. 10: Barends M, Jaidee A, Khaohirun N, Singhasivanon P, Nosten F. In vitro activity of ferroquine (SSR 97193) against Plasmodium falciparum isolates from the Thai-Burmese border. Malar J. 2007 Jun 27;6:81. PubMed PMID: 17597537; PubMed Central PMCID: PMC1934364. 11: Leimanis ML, Jaidee A, Sriprawat K, Kaewpongsri S, Suwanarusk R, Barends M, Phyo AP, Russell B, Renia L, Nosten F. Plasmodium vivax susceptibility to ferroquine. Antimicrob Agents Chemother. 2010 May;54(5):2228-30. doi: 10.1128/AAC.01572-09. PubMed PMID: 20308387; PubMed Central PMCID: PMC2863649. 12: Kreidenweiss A, Kremsner PG, Dietz K, Mordmüller B. In vitro activity of ferroquine (SAR97193) is independent of chloroquine resistance in Plasmodium falciparum. Am J Trop Med Hyg. 2006 Dec;75(6):1178-81. PubMed PMID: 17172389. 13: Daher W, Pelinski L, Klieber S, Sadoun F, Meunier V, Bourrié M, Biot C, Guillou F, Fabre G, Brocard J, Fraisse L, Maffrand JP, Khalife J, Dive D. In vitro metabolism of ferroquine (SSR97193) in animal and human hepatic models and antimalarial activity of major metabolites on Plasmodium falciparum. Drug Metab Dispos. 2006 Apr;34(4):667-82. PubMed PMID: 16415117. 14: Vausselin T, Calland N, Belouzard S, Descamps V, Douam F, Helle F, François C, Lavillette D, Duverlie G, Wahid A, Fénéant L, Cocquerel L, Guérardel Y, Wychowski C, Biot C, Dubuisson J. The antimalarial ferroquine is an inhibitor of hepatitis C virus. Hepatology. 2013 Jul;58(1):86-97. doi: 10.1002/hep.26273. PubMed PMID: 23348596. 15: Mustfa K, Landau I, Chabaud AG, Chavatte JM, Chandenier J, Duong TH, Richard-Lenoble D. Effects of the antimalarial drugs ferroquine and artesunate on Plasmodium yoelii yoelii gametocytegenesis and vectorial transmission. Sante. 2011 Jul-Sep;21(3):133-42. doi: 10.1684/san.2011.0261. PubMed PMID: 22294247. 16: Pomel S, Biot C, Bories C, Loiseau PM. Antiprotozoal activity of ferroquine. Parasitol Res. 2013 Feb;112(2):665-9. doi: 10.1007/s00436-012-3183-4. PubMed PMID: 23229318. 17: Biot C, Dubar F, Khalife J, Slomianny C. Opening up the advantages of the ruthenocenic bioprobes of ferroquine: distribution and localization in Plasmodium falciparum-infected erythrocytes. Metallomics. 2012 Aug;4(8):780-3. doi: 10.1039/c2mt20063e. PubMed PMID: 22700030. 18: Eyase FL, Akala HM, Johnson JD, Walsh DS. Inhibitory activity of ferroquine, versus chloroquine, against western Kenya Plasmodium falciparum field isolates determined by a SYBR Green I in vitro assay. Am J Trop Med Hyg. 2011 Dec;85(6):984-8. doi: 10.4269/ajtmh.2011.11-0260. PubMed PMID: 22144431; PubMed Central PMCID: PMC3225175. 19: Marfurt J, Chalfein F, Prayoga P, Wabiser F, Kenangalem E, Piera KA, Machunter B, Tjitra E, Anstey NM, Price RN. Ex vivo drug susceptibility of ferroquine against chloroquine-resistant isolates of Plasmodium falciparum and P. vivax. Antimicrob Agents Chemother. 2011 Sep;55(9):4461-4. doi: 10.1128/AAC.01375-10. PubMed PMID: 21730116; PubMed Central PMCID: PMC3165341. 20: Biot C, Nosten F, Fraisse L, Ter-Minassian D, Khalife J, Dive D. The antimalarial ferroquine: from bench to clinic. Parasite. 2011 Aug;18(3):207-14. Review. PubMed PMID: 21894260; PubMed Central PMCID: PMC3671469.