SRX246

SRX246
Clinical data
ATC code
  • None
Identifiers
  • (R)-4-([1,4'-bipiperidin]-1'-yl)-4-oxo-2-((3S,4R)-2-oxo-3-((S)-2-oxo-4-phenyloxazolidin-3-yl)-4-((E)-styryl)azetidin-1-yl)-N-((R)-1-phenylethyl)butanamide
CAS Number
ChemSpider
UNII
Chemical and physical data
FormulaC42H49N5O5
Molar mass703.884 g·mol−1
3D model (JSmol)
  • O=C1[C@@H](N2C(OC[C@@H]2C3=CC=CC=C3)=O)[C@@H](/C=C/C4=CC=CC=C4)N1[C@@H](C(N[C@H](C)C5=CC=CC=C5)=O)CC(N6CCC(N7CCCCC7)CC6)=O
  • InChI=1S/C42H49N5O5/c1-30(32-16-8-3-9-17-32)43-40(49)36(28-38(48)45-26-22-34(23-27-45)44-24-12-5-13-25-44)46-35(21-20-31-14-6-2-7-15-31)39(41(46)50)47-37(29-52-42(47)51)33-18-10-4-11-19-33/h2-4,6-11,14-21,30,34-37,39H,5,12-13,22-29H2,1H3,(H,43,49)/b21-20+/t30-,35-,36-,37-,39+/m1/s1
  • Key:FJUKOXWSIGULLE-JVOQCOEYSA-N

SRX246, also known as API-246, is a small-molecule, centrally-active, highly-selective vasopressin V1A receptor antagonist which is under investigation by Azevan Pharmaceuticals for the treatment of affective and anger disorders.[1][2][3]

It is an azetidinone derivative, and was developed from LY-307174 as a lead compound.[4] A Phase II activity trial of the drug in the treatment of adults with intermittent explosive disorder showed a reduction in aggression not any higher than that of the placebo.[5] In another Phase II trial it decreased aggression in patients with Huntington's disease, especially those in the middle and late stages who had a history of violent behavior.[6] It was also being studied for the treatment of post-traumatic stress disorder,[7] but the study was terminated due to lack of funding.[8]

See also

References

  1. ↑ Fabio KM, Guillon CD, Lu SF, Heindel ND, Brownstein MJ, Lacey CJ, et al. (June 2013). "Pharmacokinetics and metabolism of SRX246: a potent and selective vasopressin 1a antagonist". Journal of Pharmaceutical Sciences. 102 (6): 2033–2043. Bibcode:2013JPhmS.102.2033F. doi:10.1002/jps.23495. PMID 23471831.
  2. ↑ Simon NG, Guillon C, Fabio K, Heindel ND, Lu SF, Miller M, et al. (June 2008). "Vasopressin antagonists as anxiolytics and antidepressants: recent developments". Recent Patents on CNS Drug Discovery. 3 (2): 77–93. doi:10.2174/157488908784534586. PMID 18537767.
  3. ↑ DeLisi M, Vaughn MG (5 December 2014). The Routledge International Handbook of Biosocial Criminology. Routledge. pp. 241–. ISBN 978-1-317-93674-9.
  4. ↑ Guillon CD, Koppel GA, Brownstein MJ, Chaney MO, Ferris CF, Lu SF, et al. (March 2007). "Azetidinones as vasopressin V1a antagonists". Bioorganic & Medicinal Chemistry. 15 (5): 2054–2080. doi:10.1016/j.bmc.2006.12.031. PMC 2067992. PMID 17234419.
  5. ↑ Clinical trial number NCT02055638 for "Safety, Tolerability and Activity of SRX246 in Adults With Intermittent Explosive Disorder (AVN009)" at ClinicalTrials.gov
  6. ↑ Maibach HT, Brownstein MJ, Hersch SM, Anderson KE, Itzkowitz DE, Damiano EM, et al. (September 2022). "The Vasopressin 1a Receptor Antagonist SRX246 Reduces Aggressive Behavior in Huntington's Disease". Journal of Personalized Medicine. 12 (10): 1561. doi:10.3390/jpm12101561. PMC 9605366. PMID 36294700.
  7. ↑ Griebel G, Holmes A (September 2013). "50 years of hurdles and hope in anxiolytic drug discovery". Nature Reviews. Drug Discovery. 12 (9): 667–687. doi:10.1038/nrd4075. PMC 4176700. PMID 23989795.
  8. ↑ "A Proof of Concept (POC) Clinical Trial for Post-Traumatic Stress Disorder (PTSD) With a First-In-Class Vasopressin 1a Receptor Antagonist (SRX246)". clinicaltrials.gov. 25 October 2021. Retrieved 30 August 2026.
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