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Tanaproget

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Chemical compound Pharmaceutical compound
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 Edit this at Wikidata
Chemical and physical data
FormulaC16H15N3OS
Molar mass297.38 g·mol
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

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

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

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 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.
Progestogens and antiprogestogens
Progestogens
(and progestins)
PRTooltip Progesterone receptor agonists
Antiprogestogens
SPRMsTooltip Selective progesterone receptor modulators
PRTooltip Progesterone receptor antagonists
See also
Progesterone receptor modulators
Androgens and antiandrogens
Estrogens and antiestrogens
List of progestogens
Progesterone receptor modulators
PRTooltip Progesterone receptor
Agonists
Mixed
(SPRMsTooltip Selective progesterone receptor modulators)
Antagonists
mPRTooltip Membrane progesterone receptor
(PAQRTooltip Progestin and adipoQ receptor)
Agonists
Antagonists
See also
Receptor/signaling modulators
Progestogens and antiprogestogens
Androgen receptor modulators
Estrogen receptor modulators
List of progestogens


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