tanaproget

{{Short description|Chemical compound}}

{{Drugbox

| IUPAC_name = 5-(4,4-Dimethyl-2-thioxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-1-methyl-1H-pyrrole-2-carbonitrile

| image = Tanaproget.svg

| CAS_number = 304853-42-7

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = W9F9H8GXWR

| ATC_prefix = none

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| PubChem = 4369524

| DrugBank = DB04787

| ChemSpiderID = 3572060

| C=16 | H=15 | N=3 | O=1 | S=1

| smiles = CC1(C2=C(C=CC(=C2)C3=CC=C(N3C)C#N)NC(=S)O1)C

| StdInChI = 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)

| StdInChIKey = PYVFWTPEBMRKSR-UHFFFAOYSA-N

| bioavailability =

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| pregnancy_AU =

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| legal_status = Investigational

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Tanaproget (INN; developmental code names NSP-989, WAY-166989) is an investigational nonsteroidal progestin.{{cite journal |vauthors=Zhang Z, Olland AM, Zhu Y, etal | title = Molecular and pharmacological properties of a potent and selective novel nonsteroidal progesterone receptor agonist tanaproget | journal = J. Biol. Chem. | volume = 280 | issue = 31 | pages = 28468–75 |date=August 2005 | pmid = 15937332 | doi = 10.1074/jbc.M504144200 | doi-access = free }} 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,[http://adisinsight.springer.com/drugs/800017577 Tanaproget] it is in phase II clinical trials in the process of being developed for clinical use as a contraceptive by Ligand Pharmaceuticals.{{cite journal |vauthors=Bapst JL, Ermer JC, Ferron GM, Foss D, Orczyk GP | title = Pharmacokinetics and safety of tanaproget, a nonsteroidal progesterone receptor agonist, in healthy women | journal = Contraception | volume = 74 | issue = 5 | pages = 414–8 |date=November 2006 | pmid = 17046384 | doi = 10.1016/j.contraception.2006.06.004 }}{{cite journal |vauthors=Bayés M, Rabasseda X, Prous JR | title = Gateways to clinical trials | journal = Methods Find Exp Clin Pharmacol | volume = 27 | issue = 7 | pages = 505–22 |date=September 2005 | pmid = 16258596 }}

An analog of tanaproget, 4-fluoropropyltanaproget (¹⁸F), has been developed as a radiotracer for imaging of the PR in positron emission tomography.{{cite journal |vauthors=Lee JH, Zhou HB, Dence CS, Carlson KE, Welch MJ, Katzenellenbogen JA | title = Development of [F-18]fluorine-substituted Tanaproget as a progesterone receptor imaging agent for positron emission tomography | journal = Bioconjug. Chem. | volume = 21 | issue = 6 | pages = 1096–104 |date=June 2010 | pmid = 20496889 | doi = 10.1021/bc1001054 }}