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Chemical Compound Review:

Tanaproget 5-(10,10-dimethyl-8- sulfanylidene-9-oxa-7...

Synonyms: NSP-989, CHEMBL539163, NSP 989, DCL000976, DPR000116, ...

Keating, K.A. et al., Bruner-Tran, K.L. et al., Fensome, A. et al., Bapst, J.L. et al., Zhang, Z. et al.

Fensome, Bender, Chopra, Cohen, Collins, Hudak, Malakian, Lockhead, Olland, Svenson, Terefenko, Unwalla, Wilhelm, Wolfrom, Zhu, Zhang, Zhang, Winneker, Wrobel, Bapst, Ermer, Ferron, Foss, Orczyk, Keating, McConnell, Zhang, Shen, Demaio, Mallis, Elmarakby, Chandrasekaran, Zhang, Olland, Zhu, Cohen, Berrodin, Chippari, Appavu, Li, Wilhem, Chopra, Fensome, Zhang, Wrobel, Unwalla, Lyttle, Winneker,

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Disease relevance of Tanaproget

In the current study we examined the ability of a newly developed progesterone receptor (PR) agonist, tanaproget (TNPR), to down-regulate endometrial MMP expression in vitro and regress experimental endometriosis in vivo [1].

High impact information on Tanaproget

Molecular and pharmacological properties of a potent and selective novel nonsteroidal progesterone receptor agonist tanaproget [2].
Down-regulation of endometrial matrix metalloproteinase-3 and -7 expression in vitro and therapeutic regression of experimental endometriosis in vivo by a novel nonsteroidal progesterone receptor agonist, tanaproget [1].
Tanaproget represents a potential first-in-class nonsteroidal PR agonist for contraception with improved safety and side effect profiles versus currently available steroidal oral contraceptives [3].
Synthesis and structure-activity relationship of novel 6-aryl-1,4-dihydrobenzo[d][1,3]oxazine-2-thiones as progesterone receptor modulators leading to the potent and selective nonsteroidal progesterone receptor agonist tanaproget [3].
A major in vitro and in vivo metabolite of tanaproget formed in humans was initially characterized as a glucuronide of tanaproget [4].

Biological context of Tanaproget

The elimination half-life (t(1/2)) ranged from 12 to 30 h, and the oral clearance was approximately 70 L/h. The pharmacokinetics of tanaproget was not noticeably altered with a high-fat meal [5].

Anatomical context of Tanaproget

CONCLUSIONS: Tanaproget was safe and well tolerated, decreased cervical mucus scores and had a pharmacokinetic profile acceptable for use as a once-daily oral contraceptive [5].

Analytical, diagnostic and therapeutic context of Tanaproget

Subsequent synthesis of the S- and N-glucuronides of tanaproget from tanaproget facilitated the unambiguous regio- and stereochemical assignment of the metabolite by comparison of 1D NMR chemical shifts and scalar coupling constants, 2D NMR correlations, and HPLC and LC/MS characteristics between the synthetic compounds and the metabolite [4].
However, whether the glucuronide was linked to the nitrogen or sulfur of the benzoxazine-2-thione group in tanaproget could not be determined by liquid chromatography/mass spectrometry (LC/MS) and LC-tandem mass spectrometry analysis [4].

References

Down-regulation of endometrial matrix metalloproteinase-3 and -7 expression in vitro and therapeutic regression of experimental endometriosis in vivo by a novel nonsteroidal progesterone receptor agonist, tanaproget. Bruner-Tran, K.L., Zhang, Z., Eisenberg, E., Winneker, R.C., Osteen, K.G. J. Clin. Endocrinol. Metab. (2006) [Pubmed]
Molecular and pharmacological properties of a potent and selective novel nonsteroidal progesterone receptor agonist tanaproget. Zhang, Z., Olland, A.M., Zhu, Y., Cohen, J., Berrodin, T., Chippari, S., Appavu, C., Li, S., Wilhem, J., Chopra, R., Fensome, A., Zhang, P., Wrobel, J., Unwalla, R.J., Lyttle, C.R., Winneker, R.C. J. Biol. Chem. (2005) [Pubmed]
Synthesis and structure-activity relationship of novel 6-aryl-1,4-dihydrobenzo[d][1,3]oxazine-2-thiones as progesterone receptor modulators leading to the potent and selective nonsteroidal progesterone receptor agonist tanaproget. Fensome, A., Bender, R., Chopra, R., Cohen, J., Collins, M.A., Hudak, V., Malakian, K., Lockhead, S., Olland, A., Svenson, K., Terefenko, E.A., Unwalla, R.J., Wilhelm, J.M., Wolfrom, S., Zhu, Y., Zhang, Z., Zhang, P., Winneker, R.C., Wrobel, J. J. Med. Chem. (2005) [Pubmed]
NMR characterization of an S-linked glucuronide metabolite of the potent, novel, nonsteroidal progesterone agonist tanaproget. Keating, K.A., McConnell, O., Zhang, Y., Shen, L., Demaio, W., Mallis, L., Elmarakby, S., Chandrasekaran, A. Drug Metab. Dispos. (2006) [Pubmed]
Pharmacokinetics and safety of tanaproget, a nonsteroidal progesterone receptor agonist, in healthy women. Bapst, J.L., Ermer, J.C., Ferron, G.M., Foss, D., Orczyk, G.P. Contraception. (2006) [Pubmed]

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