Tanaproget

For research use only. Not for therapeutic Use.

  • CAT Number: I003069
  • CAS Number: 304853-42-7
  • Molecular Formula: C16H15N3OS
  • Molecular Weight: 297.37
  • Purity: ≥95%
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Tanaproget (NSP-989) is a novel nonsteroidal progesterone receptor agonist which can bind to the PR from various species with a higher relative affinity than reference steroidal progestins.
IC50 value: 0.1 nM (EC50, induce alkaline phosphatase activity) [1]
Target: progesterone receptor
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.
in vitro: In T47D cells, TNPR induces alkaline phosphatase activity with an EC(50) value of 0.1 nm, comparable with potent steroidal progestins such as medroxyprogesterone acetate (MPA) and trimegestone (TMG), albeit with a reduced efficacy ( approximately 60%). In a mammalian two-hybrid assay to measure PR agonist-induced interaction between steroid receptor co-activator-1 and PR, TNPR showed similar potency (EC(50) value of 0.02 nm) and efficacy to MPA and TMG [1].
in vivo: TNPR effectively down-regulated MMP expression in vitro and induced significant reduction of lesions in mice with disease established by tissues from endometriosis patients [2]. The maximum concentration (C(max)) of tanaproget occurred approximately 2 to 3 h after administration. 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 [3].
Toxicity: All doses of tanaproget decreased cervical mucus scores (using a modified Insler method), indicating poor production and poor quality of cervical mucus. The most frequent treatment-emergent adverse events were vaginal bleeding/spotting, abdominal cramping and vomiting; their incidence was not dose related and most events were mild [3].


Catalog Number I003069
CAS Number 304853-42-7
Synonyms

5-(4,4-dimethyl-2-sulfanylidene-1H-3,1-benzoxazin-6-yl)-1-methylpyrrole-2-carbonitrile

Molecular Formula C16H15N3OS
Purity ≥95%
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)
InChIKey PYVFWTPEBMRKSR-UHFFFAOYSA-N
SMILES CC1(C2=C(C=CC(=C2)C3=CC=C(N3C)C#N)NC(=S)O1)C
Reference

[1]. Bruner-Tran KL, et al. 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. J Clin Endocrin
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[2]. Zhang Z, et al. Molecular and pharmacological properties of a potent and selective novel nonsteroidal progesterone receptor agonist tanaproget. J Biol Chem. 2005 Aug 5;280(31):28468-75.
 [Content Brief]

[3]. Bapst JL, et al. Pharmacokinetics and safety of tanaproget, a nonsteroidal progesterone receptor agonist, in healthy women. Contraception. 2006 Nov;74(5):414-8.
 [Content Brief]

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