TC OT 39

TC OT 39
Clinical data
Other names"Compound 39"; SynOTA
Drug classOxytocin receptor agonist; Vasopressin receptor modulator
ATC code
  • None
Identifiers
  • (2S)-N-[[4-[(4,10-dihydro-1-methylpyrazolo[3,4-b][1,5]benzodiazepin-5(1H)-yl)carbonyl]-2-methylphenyl]methyl]-2-[(hexahydro-4-methyl-1H-1,4-diazepin-1-yl)thioxomethyl]-1-pyrrolidinecarboxamide
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC32H40N8O2S
Molar mass600.79 g·mol−1
3D model (JSmol)
  • Cc1cc(ccc1CNC(=O)N2CCC[C@H]2C(=S)N3CCCN(CC3)C)C(=O)N4Cc5cnn(c5Nc6c4cccc6)C
  • InChI=1S/C32H40N8O2S/c1-22-18-23(30(41)40-21-25-20-34-37(3)29(25)35-26-8-4-5-9-27(26)40)11-12-24(22)19-33-32(42)39-15-6-10-28(39)31(43)38-14-7-13-36(2)16-17-38/h4-5,8-9,11-12,18,20,28,35H,6-7,10,13-17,19,21H2,1-3H3,(H,33,42)/t28-/m0/s1
  • Key:KSNHHKZYKYNBEI-NDEPHWFRSA-N

TC OT 39, also known as "compound 39", is a non-peptide partial agonist of the oxytocin and vasopressin V2 receptors (Ki = 147 nM and >1,000 nM, respectively) and antagonist of the vasopressin V1A receptor (Ki = 330 nM). The EC50Tooltip half-maximal effective concentration values of the drug were 33 nM at the oxytocin receptor and 850 nM at the vasopressin V2 receptor. TC OT 39 was first described in the scientific literature by Gary R. W. Pitt and colleagues in 2004. The drug was the first small-molecule oxytocin receptor agonist to be described, though it was the lead optimized compound of a described series of compounds. Subsequently, improved analogues like WAY-267,464 (2010), LIT-001 (2018), and LIT-002 (2026) were described.

See also

References

  1. 1 2 3 4 5 Pitt GR, Batt AR, Haigh RM, Penson AM, Robson PA, Rooker DP, Tartar AL, Trim JE, Yea CM, Roe MB (September 2004). "Non-peptide oxytocin agonists". Bioorganic & Medicinal Chemistry Letters. 14 (17): 4585–4589. doi:10.1016/j.bmcl.2004.04.107. PMID 15357997.
  2. ↑ Pederson, Cort (30 November 2015). "Preclinical Testing of Novel Oxytocin Receptor Activators in Models of Autism Phenotypes". apps.dtic.mil. Retrieved 19 July 2026.
  3. 1 2 3 4 Nashar PE, Whitfield AA, Mikusek J, Reekie TA (2022). "The Current Status of Drug Discovery for the Oxytocin Receptor". Methods Mol Biol. 2384: 153–174. doi:10.1007/978-1-0716-1759-5_10. PMID 34550574.
  4. ↑ Ring RH, Schechter LE, Leonard SK, Dwyer JM, Platt BJ, Graf R, Grauer S, Pulicicchio C, Resnick L, Rahman Z, Sukoff Rizzo SJ, Luo B, Beyer CE, Logue SF, Marquis KL, Hughes ZA, Rosenzweig-Lipson S (January 2010). "Receptor and behavioral pharmacology of WAY-267464, a non-peptide oxytocin receptor agonist". Neuropharmacology. 58 (1): 69–77. doi:10.1016/j.neuropharm.2009.07.016. PMID 19615387.
  5. ↑ Frantz MC, Pellissier LP, Pflimlin E, Loison S, Gandía J, Marsol C, Durroux T, Mouillac B, Becker JA, Le Merrer J, Valencia C, Villa P, Bonnet D, Hibert M (October 2018). "LIT-001, the First Nonpeptide Oxytocin Receptor Agonist that Improves Social Interaction in a Mouse Model of Autism". J Med Chem. 61 (19): 8670–8692. doi:10.1021/acs.jmedchem.8b00697. PMID 30199637.
  6. ↑ Hibert M, Zhao Q, Noel-Duchesneau L, Peron F, Brugoux A, Bolot F, Marsol C, Bonnet D, Verner E, Kos I, Iminov R, Kondratov I, Orcel H, Couvineau P, Cong X, Ben Boubaker R, Mouillac B, Valencia C, Gizzi P, Daubeuf F, Garnier D, Villa P, Poirier R, Mery S, Laboute T, Le Merrer J, Becker J (April 2026). "LIT-002, a highly potent and selective nonpeptide oxytocin receptor agonist that improves social interaction in mouse models of autism". SSRN Electronic Journal. doi:10.2139/ssrn.6624262.