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MedKoo Cat#: 562980 | Name: FK3657

Description:

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

FK-3657 is a non-peptide bradykinin (BK)-B2 receptor antagonist. FK3657 given orally inhibited bradykinin-induced or dextran sulfate (an activator of kinin-kallikrein cascade)-induced bronchoconstriction and plasma extravasation in the lower airways (trachea and main bronchi) and nasal mucosa of guinea pigs with ED(50) of 0.04-0.23 mg/kg. In the antigen-induced dual asthmatic response model of guinea pigs, FK3657 significantly attenuated the late phase asthmatic response, but not the immediate asthmatic response. FK3657 also significantly inhibited the 2,4-tolylene diisocyanate (TDI)-induced plasma extravasation in nasal mucosa of TDI-sensitized guinea pigs. FK3657 may be useful for asthma or allergic rhinitis as a therapeutic drug.

Chemical Structure

FK3657
CAS#167838-64-4

Theoretical Analysis

MedKoo Cat#: 562980

Name: FK3657

CAS#: 167838-64-4

Chemical Formula: C30H27Cl2N5O4

Exact Mass: 591.1440

Molecular Weight: 592.47

Elemental Analysis: C, 60.82; H, 4.59; Cl, 11.97; N, 11.82; O, 10.80

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
FK-3657; FK 3657; FK3657; FR-173657; FR 173657; FR173657;
IUPAC/Chemical Name
(E)-3-(6-acetamidopyridin-3-yl)-N-(2-((2,4-dichloro-3-(((2-methylquinolin-8-yl)oxy)methyl)phenyl)(methyl)amino)-2-oxoethyl)acrylamide
InChi Key
XCKWRUGRUFVXGC-NTEUORMPSA-N
InChi Code
InChI=1S/C30H27Cl2N5O4/c1-18-7-10-21-5-4-6-25(30(21)35-18)41-17-22-23(31)11-12-24(29(22)32)37(3)28(40)16-34-27(39)14-9-20-8-13-26(33-15-20)36-19(2)38/h4-15H,16-17H2,1-3H3,(H,34,39)(H,33,36,38)/b14-9+
SMILES Code
CC1=NC2=C(C=CC=C2OCC3=C(Cl)C=CC(N(C)C(CNC(/C=C/C4=CN=C(NC(C)=O)C=C4)=O)=O)=C3Cl)C=C1
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

Preparing Stock Solutions

The following data is based on the product molecular weight 592.47 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.

Recalculate based on batch purity %
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
1: Muscella A, Cossa LG, Vetrugno C, Marsigliante S. Bradykinin stimulates prostaglandin E2 release in human skeletal muscular fibroblasts. Mol Cell Endocrinol. 2020 May 1;507:110771. doi: 10.1016/j.mce.2020.110771. Epub 2020 Feb 27. PMID: 32114020. 2: Fujimoto K, Yoshino T, Yoshioka K, Yuyama H, Masuda N, Takeda M. Intratesticular Bradykinin Involvement in Rat Testicular Pain Models. Low Urin Tract Symptoms. 2018 Jan;10(1):101-105. doi: 10.1111/luts.12133. Epub 2016 May 11. PMID: 27167873. 3: Fujimoto K, Yoshino T, Nakajima S, Yuyama H, Masuda N, Takeda M. Physiological Roles of Bradykinin and Involvement of Bradykinin B2 Receptor in Urethral Function in Humans and Animals. Low Urin Tract Symptoms. 2017 Sep;9(3):187-191. doi: 10.1111/luts.12131. Epub 2016 May 11. PMID: 27167682. 4: Lupala CS, Gomez-Gutierrez P, Perez JJ. New insights into the stereochemical requirements of the bradykinin B2 receptor antagonists binding. J Comput Aided Mol Des. 2016 Jan;30(1):85-101. doi: 10.1007/s10822-015-9890-z. Epub 2015 Dec 24. PMID: 26697880. 5: Pietrovski EF, Paludo KS, Mendes DA, Guimarães Fde S, Veiga SS, Buchi Dde F, Fonseca RG, Zampronio AR, Bader M, Pesquero JB, Ferreira J, Otuki MF, Cabrini DA. B1 and B2 kinin receptor participation in hyperproliferative and inflammatory skin processes in mice. J Dermatol Sci. 2011 Oct;64(1):23-30. doi: 10.1016/j.jdermsci.2011.06.016. Epub 2011 Jul 12. PMID: 21840178. 6: Costa R, Manjavachi MN, Motta EM, Marotta DM, Juliano L, Torres HA, Pesquero JB, Calixto JB. The role of kinin B1 and B2 receptors in the scratching behaviour induced by proteinase-activated receptor-2 agonists in mice. Br J Pharmacol. 2010 Feb;159(4):888-97. doi: 10.1111/j.1476-5381.2009.00571.x. Epub 2010 Jan 8. PMID: 20067469; PMCID: PMC2829214. 7: Kamata Y, Fujita T, Kato T, Hayashi I, Kurosaka M, Katori M, Fujita Y, Majima M. An ATP-sensitive potassium channel blocker suppresses sodium-induced hypertension through increased secretion of urinary kallikrein. Hypertens Res. 2009 Mar;32(3):220-6. doi: 10.1038/hr.2008.33. PMID: 19262486. 8: Pietrovski EF, Otuki MF, Regoli D, Bader M, Pesquero JB, Cabrini DA, Zampronio AR. The non-peptide kinin receptor antagonists FR 173657 and SSR 240612: preclinical evidence for the treatment of skin inflammation. Regul Pept. 2009 Jan 8;152(1-3):67-72. doi: 10.1016/j.regpep.2008.10.005. Epub 2008 Nov 1. PMID: 18977249. 9: Costa R, Marotta DM, Manjavachi MN, Fernandes ES, Lima-Garcia JF, Paszcuk AF, Quintão NL, Juliano L, Brain SD, Calixto JB. Evidence for the role of neurogenic inflammation components in trypsin-elicited scratching behaviour in mice. Br J Pharmacol. 2008 Jul;154(5):1094-103. doi: 10.1038/bjp.2008.172. Epub 2008 May 5. PMID: 18454165; PMCID: PMC2451046. 10: Hara DB, Fernandes ES, Campos MM, Calixto JB. Pharmacological and biochemical characterization of bradykinin B2 receptors in the mouse colon: influence of the TNBS-induced colitis. Regul Pept. 2007 Jun 7;141(1-3):25-34. doi: 10.1016/j.regpep.2006.12.013. Epub 2007 Jan 4. PMID: 17276525. 11: Chan SK, Rudd JA. Role of bradykinin B2 receptors in the modulation of the peristaltic reflex of the guinea pig isolated ileum. Eur J Pharmacol. 2006 Jun 6;539(1-2):108-15. doi: 10.1016/j.ejphar.2006.04.002. Epub 2006 Apr 6. PMID: 16650846. 12: Abraham WM, Scuri M, Farmer SG. Peptide and non-peptide bradykinin receptor antagonists: role in allergic airway disease. Eur J Pharmacol. 2006 Mar 8;533(1-3):215-21. doi: 10.1016/j.ejphar.2005.12.071. Epub 2006 Feb 7. PMID: 16455073. 13: Cucchi P, Meini S, Bressan A, Catalani C, Bellucci F, Santicioli P, Lecci A, Faiella A, Rotondaro L, Giuliani S, Giolitti A, Quartara L, Maggi CA. MEN16132, a novel potent and selective nonpeptide antagonist for the human bradykinin B2 receptor. In vitro pharmacology and molecular characterization. Eur J Pharmacol. 2005 Dec 28;528(1-3):7-16. doi: 10.1016/j.ejphar.2005.10.014. Epub 2005 Dec 1. PMID: 16324696. 14: Wang ZL. Research on airway inflammation: present status in Mainland China. Chin Med J (Engl). 2005 Jun 20;118(12):1007-14. PMID: 15978209. 15: Fujii M, Wada A, Ohnishi M, Tsutamoto T, Matsumoto T, Yamamoto T, Takayama T, Dohke T, Isono T, Eguchi Y, Horie M. Endogenous bradykinin suppresses myocardial fibrosis through the cardiac-generated endothelin system under chronic angiotensin-converting enzyme inhibition in heart failure. J Cardiovasc Pharmacol. 2004 Nov;44 Suppl 1:S346-9. doi: 10.1097/01.fjc.0000166265.09550.7c. PMID: 15838317. 16: Arakawa K, Takeyoshi I, Akao Y, Totsuka O, Matsumoto K, Morishita Y. Bradykinin B2 receptor antagonist FR173657 ameliorates small bowel ischemia- reperfusion injury in dogs. Dig Dis Sci. 2005 Jan;50(1):27-36. doi: 10.1007/s10620-005-1273-1. PMID: 15712633. 17: Yuhki K, Ueno A, Naraba H, Kojima F, Ushikubi F, Narumiya S, Oh-ishi S. Prostaglandin receptors EP2, EP3, and IP mediate exudate formation in carrageenin-induced mouse pleurisy. J Pharmacol Exp Ther. 2004 Dec;311(3):1218-24. doi: 10.1124/jpet.104.071548. Epub 2004 Aug 17. PMID: 15316088. 18: Ikeda Y, Hayashi I, Kamoshita E, Yamazaki A, Endo H, Ishihara K, Yamashina S, Tsutsumi Y, Matsubara H, Majima M. Host stromal bradykinin B2 receptor signaling facilitates tumor-associated angiogenesis and tumor growth. Cancer Res. 2004 Aug 1;64(15):5178-85. doi: 10.1158/0008-5472.CAN-03-3589. PMID: 15289322. 19: Kam YL, Rhee SJ, Choo HY. Solution-phase combinatorial synthesis of nonpeptide bradykinin antagonists. Bioorg Med Chem. 2004 Jul 1;12(13):3543-52. doi: 10.1016/j.bmc.2004.04.031. PMID: 15186838. 20: Hashimoto N, Takeyoshi I, Tsutsumi H, Sunose Y, Tokumine M, Totsuka O, Ohwada S, Matsumoto K, Morishita Y. Effects of a bradykinin B(2) receptor antagonist on ischemia-reperfusion injury in a canine lung transplantation model. J Heart Lung Transplant. 2004 May;23(5):606-13. doi: 10.1016/S1053-2498(03)00297-3. PMID: 15135378.

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MNI-135

MNI-135