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SRX246

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Chemical compound

Pharmaceutical compound

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	512784-93-9
ChemSpider	23290398
UNII	372X2P22UY
Chemical and physical data
Formula	C₄₂H₄₉N₅O₅
Molar mass	703.884 g·mol⁻¹
3D model (JSmol)	Interactive image
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

SRX246, also known asAPI-246, is asmall-molecule,centrally-active, highly-selectivevasopressin V_1A receptor antagonist which is under investigation by Azevan Pharmaceuticals for the treatment ofaffective andanger disorders.^[1]^[2]^[3] It is anazetidinone derivative, and was developed from LY-307174 as a lead compound.^[4] Aphase II activity trial of the drug in the treatment of adults withintermittent explosive disorder is ongoing.^[5] It is also being studied for the treatment ofpost-traumatic stress disorder.^[6]

^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.
^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.
^DeLisi M, Vaughn MG (5 December 2014).The Routledge International Handbook of Biosocial Criminology. Routledge. pp. 241–.ISBN 978-1-317-93674-9.
^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.
^Clinical trial numberNCT02055638 for "Safety, Tolerability and Activity of SRX246 in Adults With Intermittent Explosive Disorder (AVN009)" atClinicalTrials.gov
^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.

V_1A	Agonists:Felypressin Lypressin Ornipressin Selepressin Terlipressin Vasopressin (argipressin) Vasotocin (argiprestocin) Antagonists:Atosiban Balovaptan Conivaptan FR-218944 JNJ-17079166 JNJ-17308616 LIT-001 LY-307174 PF-184563 Relcovaptan RG7713 SRX246 SRX251 TC OT 39 WAY-267464 YM-218 YM-471 YM-35471
V_1B	Agonists:Desmopressin Felypressin Lypressin Ornipressin Terlipressin Vasopressin (argipressin) Vasotocin (argiprestocin) Antagonists:ABT-436 ABT-558 Brezivaptan Nelivaptan ORG-52186 (SCH-740935) TASP-0233278 TASP-0390325 Ligands:TASP-699
V₂	Agonists:Desmopressin Felypressin LIT-001 Lypressin Ornipressin TC OT 39 Terlipressin Vasopressin (argipressin) Vasotocin (argiprestocin) Antagonists:Conivaptan JNJ-17079166 Lixivaptan Mozavaptan RWJ-351647 Satavaptan Tolvaptan YM-471 YM-35471
Unsorted	Antagonists:Balovaptan Ribuvaptan RWJ-339489 VMAX-367 VMAX-372 VMAX-382 YM-222546 Other inhibitors:Demeclocycline Lithium (lithium carbonate)