Tanaproget

Tanaproget (INN; developmental code names NSP-989, WAY-166989) is an investigational nonsteroidal progestin.[1] It is a high affinity, high efficacy, and very selective agonist of the progesterone receptor (PR).[1] Due to its much more selective binding profile relative to most conventional, steroidal progestins, tanaproget may prove to produce fewer side effects in comparison.[1] As of December 2010,[2] it is in phase II clinical trials in the process of being developed for clinical use as a contraceptive by Ligand Pharmaceuticals.[3][4]

Tanaproget
Clinical data
ATC code
  • none
Legal status
Legal status
  • Investigational
Identifiers
IUPAC name
  • 5-(4,4-Dimethyl-2-thioxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-1-methyl-1H-pyrrole-2-carbonitrile
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.217.016
Chemical and physical data
FormulaC16H15N3OS
Molar mass297.38 g·mol−1
3D model (JSmol)
SMILES
  • CC1(C2=C(C=CC(=C2)C3=CC=C(N3C)C#N)NC(=S)O1)C
InChI
  • InChI=1S/C16H15N3OS/c1-16(2)12-8-10(4-6-13(12)18-15(21)20-16)14-7-5-11(9-17)19(14)3/h4-8H,1-3H3,(H,18,21)
  • Key:PYVFWTPEBMRKSR-UHFFFAOYSA-N

An analog of tanaproget, 4-fluoropropyltanaproget (18F), has been developed as a radiotracer for imaging of the PR in positron emission tomography.[5]

See also

References
  1. Zhang Z, Olland AM, Zhu Y, et al. (August 2005). "Molecular and pharmacological properties of a potent and selective novel nonsteroidal progesterone receptor agonist tanaproget". J. Biol. Chem. 280 (31): 28468–75. doi:10.1074/jbc.M504144200. PMID 15937332.
  2. Tanaproget
  3. Bapst JL, Ermer JC, Ferron GM, Foss D, Orczyk GP (November 2006). "Pharmacokinetics and safety of tanaproget, a nonsteroidal progesterone receptor agonist, in healthy women". Contraception. 74 (5): 414–8. doi:10.1016/j.contraception.2006.06.004. PMID 17046384.
  4. Bayés M, Rabasseda X, Prous JR (September 2005). "Gateways to clinical trials". Methods Find Exp Clin Pharmacol. 27 (7): 505–22. PMID 16258596.
  5. Lee JH, Zhou HB, Dence CS, Carlson KE, Welch MJ, Katzenellenbogen JA (June 2010). "Development of [F-18]fluorine-substituted Tanaproget as a progesterone receptor imaging agent for positron emission tomography". Bioconjug. Chem. 21 (6): 1096–104. doi:10.1021/bc1001054. PMID 20496889.


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