SSR-240612 HCl | CAS# 464930-42-5 | Bradykinin B1 receptor antagonist

MedKoo Cat#: 530125 | Name: SSR-240612 HCl

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Description:

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

SSR-240612 HCl is a bradykinin B1 receptor antagonist potentially for the treatment of chronic pain.

Chemical Structure

SSR-240612 HCl

CAS#464930-42-5 (HCl)

Theoretical Analysis

MedKoo Cat#: 530125

Name: SSR-240612 HCl

CAS#: 464930-42-5 (HCl)

Chemical Formula: C42H53ClN4O7S

Exact Mass: 0.0000

Molecular Weight: 793.42

Elemental Analysis: C, 63.58; H, 6.73; Cl, 4.47; N, 7.06; O, 14.12; S, 4.04

Price and Availability

Size	Price	Availability
1mg	USD 265.00	2 Weeks
5mg	USD 610.00	2 Weeks
10mg	USD 920.00	2 Weeks
25mg	USD 1,560.00	2 Weeks

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Related CAS #

465539-70-2 (free base)

Synonym

SSR-240612; SSR240612; SSR 240612

IUPAC/Chemical Name

D-Phenylalaninamide, (3S)-3-(1,3-benzodioxol-5-yl)-N-((6-methoxy-2-naphthalenyl)sulfonyl)-beta-alanyl-4-(((2R,6S)-2,6-dimethyl-1-piperidinyl)methyl)-N-methyl-N-(1-methylethyl)-, hydrochloride (1:1)

InChi Key

COPYTLTXSAQYFR-GDYXXZBVSA-N

InChi Code

InChI=1S/C42H52N4O7S.ClH/c1-27(2)45(5)38(20-30-10-12-31(13-11-30)25-46-28(3)8-7-9-29(46)4)42(48)44-41(47)37(34-16-19-39-40(23-34)53-26-52-39)24-43-54(49,50)36-18-15-32-21-35(51-6)17-14-33(32)22-36;/h10-19,21-23,27-29,37-38,43H,7-9,20,24-26H2,1-6H3,(H,44,47,48);1H/t28-,29+,37-,38-;/m1./s1

SMILES Code

O=C(NC([C@@H](C1=CC=C(OCO2)C2=C1)CNS(=O)(C3=CC=C4C=C(OC)C=CC4=C3)=O)=O)[C@@H](CC5=CC=C(CN6[C@H](C)CCC[C@@H]6C)C=C5)N(C)C(C)C.[H]Cl

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

SSR-240612 HCl is a bradykinin B1 receptor antagonist, with Kis of 0.48 nM and 0.73 nM for B1 kinin receptors of human fibroblast MRC5 and HEK cells expressing human B1 receptors, 481 nM and 358 nM for B2 receptors of guinea pig ileum membranes and CHO cells expressing human B1 receptor, respectively.

In vitro activity:

Treatment of bladder cancer cells with B1 and B2 receptor antagonists (SSR-240612 and HOE140) markedly inhibited the proliferation of T24 cells. Reference: Invest New Drugs. 2013 Aug;31(4):812-22. https://pubmed.ncbi.nlm.nih.gov/23224295/

In vivo activity:

SSR-240612 has potential as a treatment option for the treatment of tuberculosis. M. tuberculosis-infected macrophages incubated with SSR-240612, alone or in combination with des-Arg9-BK, displayed a marked inhibitory effect on CFU counts. However, the pre-incubation of the selective B1R and B2R agonists and antagonists, respectively, did not significantly affect the bacterial loads. There was a significant reduction in the CFU of M. tuberculosis in lungs and spleens of animals treated with SSR-240612. Reference: Tuberculosis (Edinb). 2018 Mar;109:1-7. https://pubmed.ncbi.nlm.nih.gov/29559112/

	Solvent	mg/mL	mM	comments
Solubility
	DMSO	50.0	63.02

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 793.42 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. Sgnaolin V, Pereira TC, Bogo MR, Zanin R, Battastini AM, Morrone FB, Campos MM. Functional and molecular characterization of kinin B1 and B 2 receptors in human bladder cancer: implication of the PI3Kγ pathway. Invest New Drugs. 2013 Aug;31(4):812-22. doi: 10.1007/s10637-012-9907-6. Epub 2012 Dec 7. PMID: 23224295. 2. Rodrigues-Junior VS, Pail PB, Villela AD, Falcão VCA, Dadda AS, Abbadi BL, Pesquero JB, Santos DS, Basso LA, Campos MM. Effect of the bradykinin 1 receptor antagonist SSR240612 after oral administration in Mycobacterium tuberculosis-infected mice. Tuberculosis (Edinb). 2018 Mar;109:1-7. doi: 10.1016/j.tube.2018.01.003. Epub 2018 Feb 2. PMID: 29559112. 3. Gougat J, Ferrari B, Sarran L, Planchenault C, Poncelet M, Maruani J, Alonso R, Cudennec A, Croci T, Guagnini F, Urban-Szabo K, Martinolle JP, Soubrié P, Finance O, Le Fur G. SSR240612 [(2R)-2-[((3R)-3-(1,3-benzodioxol-5-yl)-3-[[(6-methoxy-2-naphthyl)sulfonyl]amino]propanoyl)amino]-3-(4-[[2R,6S)-2,6-dimethylpiperidinyl]methyl]phenyl)-N-isopropyl-N-methylpropanamide hydrochloride], a new nonpeptide antagonist of the bradykinin B1 receptor: biochemical and pharmacological characterization. J Pharmacol Exp Ther. 2004 May;309(2):661-9. doi: 10.1124/jpet.103.059527. Epub 2004 Jan 27. PMID: 14747609.

In vitro protocol:

In vivo protocol:

1. Rodrigues-Junior VS, Pail PB, Villela AD, Falcão VCA, Dadda AS, Abbadi BL, Pesquero JB, Santos DS, Basso LA, Campos MM. Effect of the bradykinin 1 receptor antagonist SSR240612 after oral administration in Mycobacterium tuberculosis-infected mice. Tuberculosis (Edinb). 2018 Mar;109:1-7. doi: 10.1016/j.tube.2018.01.003. Epub 2018 Feb 2. PMID: 29559112. 2. Gougat J, Ferrari B, Sarran L, Planchenault C, Poncelet M, Maruani J, Alonso R, Cudennec A, Croci T, Guagnini F, Urban-Szabo K, Martinolle JP, Soubrié P, Finance O, Le Fur G. SSR240612 [(2R)-2-[((3R)-3-(1,3-benzodioxol-5-yl)-3-[[(6-methoxy-2-naphthyl)sulfonyl]amino]propanoyl)amino]-3-(4-[[2R,6S)-2,6-dimethylpiperidinyl]methyl]phenyl)-N-isopropyl-N-methylpropanamide hydrochloride], a new nonpeptide antagonist of the bradykinin B1 receptor: biochemical and pharmacological characterization. J Pharmacol Exp Ther. 2004 May;309(2):661-9. doi: 10.1124/jpet.103.059527. Epub 2004 Jan 27. PMID: 14747609.

1: Tidjane N, Gaboury L, Couture R. Cellular localisation of the kinin B1R in the pancreas of streptozotocin-treated rat and the anti-diabetic effect of the antagonist SSR240612. Biol Chem. 2016 Apr;397(4):323-36. doi: 10.1515/hsz-2015-0230. PubMed PMID: 26841446. 2: Dias JP, Gariépy Hde B, Ongali B, Couture R. Brain kinin B1 receptor is upregulated by the oxidative stress and its activation leads to stereotypic nociceptive behavior in insulin-resistant rats. Peptides. 2015 Jul;69:118-26. doi: 10.1016/j.peptides.2015.04.022. PubMed PMID: 25959537. 3: Silva CR, Oliveira SM, Hoffmeister C, Funck V, Guerra GP, Trevisan G, Tonello R, Rossato MF, Pesquero JB, Bader M, Oliveira MS, McDougall JJ, Ferreira J. The role of kinin B1 receptor and the effect of angiotensin I-converting enzyme inhibition on acute gout attacks in rodents. Ann Rheum Dis. 2016 Jan;75(1):260-8. doi: 10.1136/annrheumdis-2014-205739. PubMed PMID: 25344431. 4: More AS, Kim HM, Khang G, Hildebrandt T, Bernlöhr C, Doods H, Vanhoutte PM, Wu D. Des-Arg9-bradykinin causes kinin B1 receptor mediated endothelium-independent contractions in endotoxin-treated porcine coronary arteries. Pharmacol Res. 2014 Dec;90:18-24. doi: 10.1016/j.phrs.2014.09.001. PubMed PMID: 25258294. 5: Nicoletti NF, Erig TC, Zanin RF, Pereira TC, Bogo MR, Campos MM, Morrone FB. Mechanisms involved in kinin-induced glioma cells proliferation: the role of ERK1/2 and PI3K/Akt pathways. J Neurooncol. 2014 Nov;120(2):235-44. doi: 10.1007/s11060-014-1549-4. PubMed PMID: 25056222. 6: Lacoste B, Tong XK, Lahjouji K, Couture R, Hamel E. Cognitive and cerebrovascular improvements following kinin B1 receptor blockade in Alzheimer's disease mice. J Neuroinflammation. 2013 May 4;10:57. doi: 10.1186/1742-2094-10-57. PubMed PMID: 23642031; PubMed Central PMCID: PMC3710240. 7: De Brito Gariepy H, Talbot S, Sénécal J, Couture R. Brain kinin B₁ receptor contributes to the onset of stereotypic nocifensive behavior in rat. Behav Brain Res. 2013 Mar 15;241:17-26. doi: 10.1016/j.bbr.2012.11.032. PubMed PMID: 23219968. 8: Marcon R, Claudino RF, Dutra RC, Bento AF, Schmidt EC, Bouzon ZL, Sordi R, Morais RL, Pesquero JB, Calixto JB. Exacerbation of DSS-induced colitis in mice lacking kinin B(1) receptors through compensatory up-regulation of kinin B(2) receptors: the role of tight junctions and intestinal homeostasis. Br J Pharmacol. 2013 Jan;168(2):389-402. doi: 10.1111/j.1476-5381.2012.02136.x. PubMed PMID: 22889120; PubMed Central PMCID: PMC3572565. 9: Dias JP, Couture R. Suppression of vascular inflammation by kinin B1 receptor antagonism in a rat model of insulin resistance. J Cardiovasc Pharmacol. 2012 Jul;60(1):61-9. doi: 10.1097/FJC.0b013e3182576277. PubMed PMID: 22494994. 10: Dias JP, Couture R. Blockade of kinin B(1) receptor reverses plasma fatty acids composition changes and body and tissue fat gain in a rat model of insulin resistance. Diabetes Obes Metab. 2012 Mar;14(3):244-53. doi: 10.1111/j.1463-1326.2011.01521.x. PubMed PMID: 22023455. 11: 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. PubMed PMID: 21840178. 12: Pouliot M, Hétu S, Lahjouji K, Couture R, Vaucher E. Modulation of retinal blood flow by kinin B₁ receptor in Streptozotocin-diabetic rats. Exp Eye Res. 2011 Jun;92(6):482-9. doi: 10.1016/j.exer.2011.03.007. PubMed PMID: 21420952. 13: Dias JP, Talbot S, Sénécal J, Carayon P, Couture R. Kinin B1 receptor enhances the oxidative stress in a rat model of insulin resistance: outcome in hypertension, allodynia and metabolic complications. PLoS One. 2010 Sep 7;5(9):e12622. doi: 10.1371/journal.pone.0012622. PubMed PMID: 20830306; PubMed Central PMCID: PMC2935380. 14: Klein J, Gonzalez J, Decramer S, Bandin F, Neau E, Salant DJ, Heeringa P, Pesquero JB, Schanstra JP, Bascands JL. Blockade of the kinin B1 receptor ameloriates glomerulonephritis. J Am Soc Nephrol. 2010 Jul;21(7):1157-64. doi: 10.1681/ASN.2009090887. PubMed PMID: 20448019; PubMed Central PMCID: PMC3152233. 15: 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. PubMed PMID: 20067469; PubMed Central PMCID: PMC2829214. 16: 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. PubMed PMID: 18977249. 17: Klein J, Gonzalez J, Duchene J, Esposito L, Pradère JP, Neau E, Delage C, Calise D, Ahluwalia A, Carayon P, Pesquero JB, Bader M, Schanstra JP, Bascands JL. Delayed blockade of the kinin B1 receptor reduces renal inflammation and fibrosis in obstructive nephropathy. FASEB J. 2009 Jan;23(1):134-42. doi: 10.1096/fj.08-115600. PubMed PMID: 18809736. 18: Marceau F, Regoli D. Therapeutic options in inflammatory bowel disease: experimental evidence of a beneficial effect of kinin B1 receptor blockade. Br J Pharmacol. 2008 Jul;154(6):1163-5. doi: 10.1038/bjp.2008.233. PubMed PMID: 18536746; PubMed Central PMCID: PMC2483401. 19: 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. PubMed PMID: 18454165; PubMed Central PMCID: PMC2451046. 20: Dias JP, Ismael MA, Pilon M, de Champlain J, Ferrari B, Carayon P, Couture R. The kinin B1 receptor antagonist SSR240612 reverses tactile and cold allodynia in an experimental rat model of insulin resistance. Br J Pharmacol. 2007 Sep;152(2):280-7. PubMed PMID: 17618300; PubMed Central PMCID: PMC1978253.