SRX246

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 is ongoing.[5] It is also being studied for the treatment of post-traumatic stress disorder.[6]

SRX246
Clinical data
ATC code
  • None
Identifiers
IUPAC name
  • (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)
SMILES
  • 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
  • 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

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. 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): 2054–80. 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. Griebel G, Holmes A (September 2013). "50 years of hurdles and hope in anxiolytic drug discovery". Nature Reviews. Drug Discovery. 12 (9): 667–87. doi:10.1038/nrd4075. PMC 4176700. PMID 23989795.
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