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Tanaproget (NSP-989) is a novel, potent and non-steroidal progesterone receptor agonist that may be utilized as a method of contraception for women. Compared to reference steroidal progestins, it has a higher relative affinity to bind to the PR of different species.
Physicochemical Properties
| Molecular Formula | C16H15N3OS |
| Molecular Weight | 297.3748 |
| Exact Mass | 297.094 |
| Elemental Analysis | C, 64.62; H, 5.08; N, 14.13; O, 5.38; S, 10.78 |
| CAS # | 304853-42-7 |
| Related CAS # | 304853-42-7 |
| PubChem CID | 4369524 |
| Appearance | Light yellow to yellow solid powder |
| LogP | 3.181 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 1 |
| Heavy Atom Count | 21 |
| Complexity | 483 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | N#CC1=CC=C(C2=CC=C(NC(OC3(C)C)=S)C3=C2)N1C |
| InChi Key | PYVFWTPEBMRKSR-UHFFFAOYSA-N |
| InChi Code | 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) |
| Chemical Name | 5-(4,4-dimethyl-2-sulfanylidene-1H-3,1-benzoxazin-6-yl)-1-methylpyrrole-2-carbonitrile |
| Synonyms | Tanaproget; NSP 989; NSP-989; NSP989 |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| References |
[1]. 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. [2]. 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. [3]. Pharmacokinetics and safety of tanaproget, a nonsteroidal progesterone receptor agonist, in healthy women. Contraception. 2006 Nov;74(5):414-8. |
| Additional Infomation | Tanaproget (NSP-989) is an investigational non-steroidal progestin. It is a high affinity, high efficacy agonist of the progesterone receptor (PR) with a much more selective binding profile relative to most conventional progestins. Because of this tanaproget may prove to produce fewer side effects in comparison. It is currently in the process of being developed for clinical use as a contraceptive by Ligand Pharmaceuticals. An analog of tanaproget, 4-fluoropropyltanaproget (18F), has been developed as a radiotracer for imaging of the PR in positron emission tomography. |
Solubility Data
| Solubility (In Vitro) | DMSO: ≥ 50 mg/mL (~168.1 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.41 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.3628 mL | 16.8141 mL | 33.6281 mL | |
| 5 mM | 0.6726 mL | 3.3628 mL | 6.7256 mL | |
| 10 mM | 0.3363 mL | 1.6814 mL | 3.3628 mL |