Quinfamide | CAS#62265-68-3 | chronic amebiasis treatment

MedKoo Cat#: 592793 | Name: Quinfamide

Description:

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

Quinfamide is used in the treatment of chronic amebiasis in pediatric patients.

Chemical Structure

Quinfamide

CAS#62265-68-3

Theoretical Analysis

MedKoo Cat#: 592793

Name: Quinfamide

CAS#: 62265-68-3

Chemical Formula: C16H13Cl2NO4

Exact Mass: 353.0222

Molecular Weight: 354.18

Elemental Analysis: C, 54.26; H, 3.70; Cl, 20.02; N, 3.95; O, 18.07

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Synonym

Quinfamide; Quinfamido

IUPAC/Chemical Name

2-Furancarboxylic acid, 1-(dichloroacetyl)-1,2,3,4-tetrahydro-6-quinolinyl ester

InChi Key

SBJGFIXQRZOVTO-UHFFFAOYSA-N

InChi Code

InChI=1S/C16H13Cl2NO4/c17-14(18)15(20)19-7-1-3-10-9-11(5-6-12(10)19)23-16(21)13-4-2-8-22-13/h2,4-6,8-9,14H,1,3,7H2

SMILES Code

O=C(C1=CC=CO1)OC2=CC3=C(N(C(C(Cl)Cl)=O)CCC3)C=C2

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

>3 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

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Quinafimide is an investigational compound that has been used in trials for the treatment of Amoebiasis and Helminthiasis. The details of the mechanism of action are not known, but the overall effect is intraluminal immobilization of the Entamoeba.

In vitro activity:

The susceptibility of a strain of Giardia lamblia to benzimidazole carbamates, 5-nitroimidazoles, nitrofurans and other drugs was studied in vitro. Quinfamide did not inhibit the growth of the parasite at a concentration of 200 mg/L. Reference: Clin Drug Investig. 2000;20(2):89-93. https://pubmed.ncbi.nlm.nih.gov/1518040/

In vivo activity:

In this study, 3 groups underwent quinfamide treatment. Group 1 had patients that had three CPS analyses after 12 months; Group 2 had CPS analyses at months 3, 6, 9, and 12; and Group 3 had three CPS analyses at months 6 and 12. Group 1 had 37.6% of subjects still testing positive for Entamoeba histolytica cysts in stool samples; of Group 2, 12.5%; and Group 3, 23.5%. This study showed that antiamoebic chemoprophylaxis can be used for amoebic infection treatment when personal hygiene and diet are not improved. Reference: ScientificWorldJournal. 2002 Apr 20;2:1070-8. https://pubmed.ncbi.nlm.nih.gov/12805964/

	Solvent	mg/mL	mM
Solubility
	DMSO	3.5	10.00

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 354.18 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:

1. Naguib IA, Hassan ES, Emam AA, Abdelaleem EA. Development and Validation of HPTLC and Green HPLC Methods for Determination of a New Combination of Quinfamide and Mebendazole. J Chromatogr Sci. 2019 Dec 19;58(1):16-21. doi: 10.1093/chromsci/bmz100. PMID: 31879753. 2. Cedillo-Rivera R, Muñoz O. In-vitro susceptibility of Giardia lamblia to albendazole, mebendazole and other chemotherapeutic agents. J Med Microbiol. 1992 Sep;37(3):221-4. doi: 10.1099/00222615-37-3-221. PMID: 1518040. 3. Padilla N, Diaz R, Alarcon A, Barreda R. Antiamoebic chemoprophylaxis using quinfamide in children: a comparative study. ScientificWorldJournal. 2002 Apr 20;2:1070-8. doi: 10.1100/tsw.2002.174. PMID: 12805964; PMCID: PMC6009339. 4. Padilla N, Díaz R, Muñoz M. Efficacy and Safety of Quinfamide versus Secnidazole in the Management of Amoebic Non-Dysenteric Colitis in Children. Clin Drug Investig. 2000;20(2):89-93. doi: 10.2165/00044011-200020020-00003. PMID: 23315350.

In vitro protocol:

In vivo protocol:

1. Padilla N, Diaz R, Alarcon A, Barreda R. Antiamoebic chemoprophylaxis using quinfamide in children: a comparative study. ScientificWorldJournal. 2002 Apr 20;2:1070-8. doi: 10.1100/tsw.2002.174. PMID: 12805964; PMCID: PMC6009339. 2. Padilla N, Díaz R, Muñoz M. Efficacy and Safety of Quinfamide versus Secnidazole in the Management of Amoebic Non-Dysenteric Colitis in Children. Clin Drug Investig. 2000;20(2):89-93. doi: 10.2165/00044011-200020020-00003. PMID: 23315350.

1: Naguib IA, Abdelaleem EA, Hassan ES, Emam AA. Comparative study of eco- friendly spectrophotometric methods for accurate quantification of Mebendazole and Quinfamide combination; Content uniformity evaluation. Spectrochim Acta A Mol Biomol Spectrosc. 2020 Jul 5;235:118271. doi: 10.1016/j.saa.2020.118271. Epub 2020 Mar 17. PMID: 32220764. 2: Naguib IA, Hassan ES, Emam AA, Abdelaleem EA. Development and Validation of HPTLC and Green HPLC Methods for Determination of a New Combination of Quinfamide and Mebendazole. J Chromatogr Sci. 2019 Dec 19;58(1):16-21. doi: 10.1093/chromsci/bmz100. PMID: 31879753. 3: Zamudio-Tiburcio Á, Bermúdez-Ruiz H, Lezama-Guzmán HR, Guevara-Ortigoza MDP, Islas-Solares E, Sosa-López FA. Rompiendo paradigmas. Trasplante de microbiota intestinal: reporte preliminar [Breaking paradigms. Intestinal microbiota transplantation: Preliminar report]. Cir Cir. 2017 Dec;85 Suppl 1:6-12. Spanish. doi: 10.1016/j.circir.2016.11.017. Epub 2017 Jan 23. PMID: 28126184. 4: Padilla N, Diaz R, Alarcon A, Barreda R. Antiamoebic chemoprophylaxis using quinfamide in children: a comparative study. ScientificWorldJournal. 2002 Apr 20;2:1070-8. doi: 10.1100/tsw.2002.174. PMID: 12805964; PMCID: PMC6009339. 5: Davila-Gutierrez CE, Vasquez C, Trujillo-Hernandez B, Huerta M. Nitazoxanide compared with quinfamide and mebendazole in the treatment of helminthic infections and intestinal protozoa in children. Am J Trop Med Hyg. 2002 Mar;66(3):251-4. doi: 10.4269/ajtmh.2002.66.251. PMID: 12139216. 6: Morales JM, Jung CH, Alarcón A, Barreda A. Solid-phase extraction and liquid chromatographic quantitation of quinfamide in biological samples. J Chromatogr B Biomed Sci Appl. 2000 Sep 15;746(2):133-9. doi: 10.1016/s0378-4347(00)00307-8. PMID: 11076065. 7: Anaya-Velázquez F, Morales-Fuentes L. Phagocytosis of quinfamide particles by Entamoeba histolytica. Arch Med Res. 2000 Jul-Aug;31(4 Suppl):S10-1. doi: 10.1016/s0188-4409(00)00105-3. PMID: 11070204. 8: Padilla N, Díaz R, Muñoz M. Efficacy and Safety of Quinfamide versus Secnidazole in the Management of Amoebic Non-Dysenteric Colitis in Children. Clin Drug Investig. 2000;20(2):89-93. doi: 10.2165/00044011-200020020-00003. PMID: 23315350. 9: Cedillo-Rivera R, Tapia-Contreras A, Torres J, Muñoz O. In vitro susceptibility of Entamoeba histolytica to fluoroquinolones, nitrofurans and other antiamebic agents. Arch Med Res. 1997;28 Spec No:295-7. PMID: 9033107. 10: Olaeta Elizalde R, Pérez Huacuja R, Nájera Ruano S. Comparación quinfamida vs etofamida en población mexicana con amibiasis intestinal [Comparison of quinfamide vs etofamide in the Mexican population with intestinal amebiasis]. Acta Gastroenterol Latinoam. 1996;26(5):277-80. Spanish. PMID: 9363264. 11: Cedillo-Rivera R, Muñoz O. In-vitro susceptibility of Giardia lamblia to albendazole, mebendazole and other chemotherapeutic agents. J Med Microbiol. 1992 Sep;37(3):221-4. doi: 10.1099/00222615-37-3-221. PMID: 1518040. 12: Araujo Rojas F, Benavides Ledezma M, Vega Martinez C, Gomez Garza R. Treatment of chronic amebiasis in pediatric patients with a suspension of quinfamide. Clin Ther. 1983;6(1):47-51. PMID: 6673831. 13: Guevara L, Garcia Tsao G, Uscanga LF. A study with quinfamide in the treatment of chronic amebiasis in adults. Clin Ther. 1983;6(1):43-6. PMID: 6673830. 14: Baker JF, O'Melia PE, Benziger DP, Clemans SD, Edelson J. The disposition of quinfamide in the rat. Arch Int Pharmacodyn Ther. 1982 Jul;258(1):29-38. PMID: 7138144. 15: Slighter RG, Yarinsky A, Drobeck HP, Bailey DM. Activity of quinfamide against natural infections of Entamoeba criceti in hamsters: a new potent agent for intestinal amoebiasis. Parasitology. 1980 Aug;81(1):157-68. doi: 10.1017/s0031182000055128. PMID: 6252530. 16: Guevara L. Evaluación de la tolerancia y eficacia en humanos de quinfamide un nuevo amebicida intraluminal (tratamiento de un día). Estudio doble ciego [Evaluation of the tolerance and efficiency of quinfamide, a new intraluminal amebicide, in man (one day treatment). Double blind study]. Rev Gastroenterol Mex. 1980 Apr-Jun;45(2):93-7. Spanish. PMID: 7403767.