Crinecerfont | SSR125543 | CAS#752253-39-7 | CRF1 Antagonist

MedKoo Cat#: 522656 | Name: Crinecerfont

Description:

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

Crinecerfont, also known as SSR125543, is a potent, selective, and orally active corticotropin-releasing factor 1 receptor (CRF1) antagonist (pKi values of 8.73 and 9.08 for human cloned or native CRF1 receptors, respectively). SSR125543 attenuates long-term cognitive deficit induced by acute inescapable stress in mice, independently from the hypothalamic pituitary adrenal axis. SSR125543 prevents stress-induced cognitive deficit associated with hippocampal dysfunction.

Chemical Structure

Crinecerfont

CAS#752253-39-7 (free base)

Theoretical Analysis

MedKoo Cat#: 522656

Name: Crinecerfont

CAS#: 752253-39-7 (free base)

Chemical Formula: C27H28ClFN2OS

Exact Mass: 482.1595

Molecular Weight: 483.04

Elemental Analysis: C, 67.14; H, 5.84; Cl, 7.34; F, 3.93; N, 5.80; O, 3.31; S, 6.64

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 #

752253-39-7 (HCl) 752253-39-7 (free base)

Synonym

SSR125543; SSR-125543; SSR 125543; SSR125543A; SSR-125543A; SSR 125543A; Crinecerfont

IUPAC/Chemical Name

(S)-4-(2-chloro-4-methoxy-5-methylphenyl)-N-(2-cyclopropyl-1-(3-fluoro-4-methylphenyl)ethyl)-5-methyl-N-(prop-2-yn-1-yl)thiazol-2-amine

InChi Key

IEAKXXNRGSLYTQ-DEOSSOPVSA-N

InChi Code

InChI=1S/C27H28ClFN2OS/c1-6-11-31(24(13-19-8-9-19)20-10-7-16(2)23(29)14-20)27-30-26(18(4)33-27)21-12-17(3)25(32-5)15-22(21)28/h1,7,10,12,14-15,19,24H,8-9,11,13H2,2-5H3/t24-/m0/s1

SMILES Code

C#CCN([C@H](C1=CC=C(C)C(F)=C1)CC2CC2)C3=NC(C4=CC(C)=C(OC)C=C4Cl)=C(C)S3

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, not in water

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 483.04 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

1: Philbert J, Beeské S, Belzung C, Griebel G. The CRF₁ receptor antagonist SSR125543 prevents stress-induced long-lasting sleep disturbances in a mouse model of PTSD: comparison with paroxetine and d-cycloserine. Behav Brain Res. 2015 Feb 15;279:41-6. doi: 10.1016/j.bbr.2014.11.006. Epub 2014 Nov 12. PubMed PMID: 25446760. 2: Ramos Ade T, Homem KS, Suchecki D, Tufik S, Troncone LR. Drug-induced suppression of ACTH secretion does not promote anti-depressive or anxiolytic effects. Behav Brain Res. 2014 May 15;265:69-75. doi: 10.1016/j.bbr.2014.02.024. Epub 2014 Feb 22. PubMed PMID: 24569014. 3: Douma TN, Millan MJ, Boulay D, Griebel G, Verdouw PM, Westphal KG, Olivier B, Groenink L. CRF1 receptor antagonists do not reverse pharmacological disruption of prepulse inhibition in rodents. Psychopharmacology (Berl). 2014 Apr;231(7):1289-303. doi: 10.1007/s00213-013-3315-2. Epub 2013 Nov 2. PubMed PMID: 24186076. 4: Philbert J, Belzung C, Griebel G. The CRF₁ receptor antagonist SSR125543 prevents stress-induced cognitive deficit associated with hippocampal dysfunction: comparison with paroxetine and D-cycloserine. Psychopharmacology (Berl). 2013 Jul;228(1):97-107. doi: 10.1007/s00213-013-3020-1. Epub 2013 Feb 14. PubMed PMID: 23407783. 5: Dournes C, Beeské S, Belzung C, Griebel G. Deep brain stimulation in treatment-resistant depression in mice: comparison with the CRF1 antagonist, SSR125543. Prog Neuropsychopharmacol Biol Psychiatry. 2013 Jan 10;40:213-20. PubMed PMID: 23367508. 6: Philbert J, Pichat P, Palme R, Belzung C, Griebel G. The CRF₁ receptor antagonist SSR125543 attenuates long-term cognitive deficit induced by acute inescapable stress in mice, independently from the hypothalamic pituitary adrenal axis. Pharmacol Biochem Behav. 2012 Sep;102(3):415-22. doi: 10.1016/j.pbb.2012.05.013. Epub 2012 May 31. PubMed PMID: 22659580. 7: Murat B, Devost D, Andrés M, Mion J, Boulay V, Corbani M, Zingg HH, Guillon G. V1b and CRHR1 receptor heterodimerization mediates synergistic biological actions of vasopressin and CRH. Mol Endocrinol. 2012 Mar;26(3):502-20. doi: 10.1210/me.2011-1202. Epub 2012 Feb 2. PubMed PMID: 22301784. 8: Knapp DJ, Overstreet DH, Huang M, Wills TA, Whitman BA, Angel RA, Sinnett SE, Breese GR. Effects of a stressor and corticotrophin releasing factor on ethanol deprivation-induced ethanol intake and anxiety-like behavior in alcohol-preferring P rats. Psychopharmacology (Berl). 2011 Nov;218(1):179-89. doi: 10.1007/s00213-011-2366-5. Epub 2011 Jun 4. PubMed PMID: 21643675. 9: Surget A, Tanti A, Leonardo ED, Laugeray A, Rainer Q, Touma C, Palme R, Griebel G, Ibarguen-Vargas Y, Hen R, Belzung C. Antidepressants recruit new neurons to improve stress response regulation. Mol Psychiatry. 2011 Dec;16(12):1177-88. doi: 10.1038/mp.2011.48. Epub 2011 May 3. PubMed PMID: 21537331; PubMed Central PMCID: PMC3223314. 10: Knapp DJ, Whitman BA, Wills TA, Angel RA, Overstreet DH, Criswell HE, Ming Z, Breese GR. Cytokine involvement in stress may depend on corticotrophin releasing factor to sensitize ethanol withdrawal anxiety. Brain Behav Immun. 2011 Jun;25 Suppl 1:S146-54. doi: 10.1016/j.bbi.2011.02.018. Epub 2011 Mar 4. PubMed PMID: 21377524; PubMed Central PMCID: PMC3138123. 11: Urani A, Philbert J, Cohen C, Griebel G. The corticotropin-releasing factor 1 receptor antagonist, SSR125543, and the vasopressin 1b receptor antagonist, SSR149415, prevent stress-induced cognitive impairment in mice. Pharmacol Biochem Behav. 2011 May;98(3):425-31. doi: 10.1016/j.pbb.2011.02.019. Epub 2011 Feb 26. PubMed PMID: 21356230. 12: Surget A, Wang Y, Leman S, Ibarguen-Vargas Y, Edgar N, Griebel G, Belzung C, Sibille E. Corticolimbic transcriptome changes are state-dependent and region-specific in a rodent model of depression and of antidepressant reversal. Neuropsychopharmacology. 2009 May;34(6):1363-80. doi: 10.1038/npp.2008.76. Epub 2008 Jun 4. PubMed PMID: 18536703; PubMed Central PMCID: PMC2669699. 13: Surget A, Saxe M, Leman S, Ibarguen-Vargas Y, Chalon S, Griebel G, Hen R, Belzung C. Drug-dependent requirement of hippocampal neurogenesis in a model of depression and of antidepressant reversal. Biol Psychiatry. 2008 Aug 15;64(4):293-301. doi: 10.1016/j.biopsych.2008.02.022. Epub 2008 Apr 11. PubMed PMID: 18406399. 14: Doyon C, Samson P, Lalonde J, Richard D. Effects of the CRF1 receptor antagonist SSR125543 on energy balance and food deprivation-induced neuronal activation in obese Zucker rats. J Endocrinol. 2007 Apr;193(1):11-9. PubMed PMID: 17400798. 15: Claustre Y, Rouquier L, Desvignes C, Leonetti M, Montégut J, Aubin N, Allouard N, Bougault I, Oury-Donat F, Steinberg R. Effects of the vasopressin (V1b) receptor antagonist, SSR149415, and the corticotropin-releasing factor 1 receptor antagonist, SSR125543, on FG 7142-induced increase in acetylcholine and norepinephrine release in the rat. Neuroscience. 2006 Sep 1;141(3):1481-8. Epub 2006 Jun 15. PubMed PMID: 16781820. 16: Louis C, Cohen C, Depoortère R, Griebel G. Antidepressant-like effects of the corticotropin-releasing factor 1 receptor antagonist, SSR125543, and the vasopressin 1b receptor antagonist, SSR149415, in a DRL-72 s schedule in the rat. Neuropsychopharmacology. 2006 Oct;31(10):2180-7. Epub 2006 Feb 1. PubMed PMID: 16452986. 17: Overstreet DH, Griebel G. Antidepressant-like effects of CRF1 receptor antagonist SSR125543 in an animal model of depression. Eur J Pharmacol. 2004 Aug 16;497(1):49-53. PubMed PMID: 15321734.