Tanaproget | CAS#304853-42-7 | Non-Steroidal Progesterone Receptor Agonist

MedKoo Cat#: 529015 | Name: Tanaproget

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Tanaproget is a non-steroidal progesterone receptor agonist potentially for use as female contraception

Chemical Structure

Tanaproget

CAS#304853-42-7

Theoretical Analysis

MedKoo Cat#: 529015

Name: Tanaproget

CAS#: 304853-42-7

Chemical Formula: C16H15N3OS

Exact Mass: 297.0936

Molecular Weight: 297.37

Elemental Analysis: C, 64.62; H, 5.08; N, 14.13; O, 5.38; S, 10.78

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

Synonym

NSP-989, NSP989, NSP 989, Tanaproget

IUPAC/Chemical Name

5-(4,4-dimethyl-2-thioxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)-1-methyl-1H-pyrrole-2-carbonitrile

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)

SMILES Code

N#CC1=CC=C(C2=CC=C(NC(OC3(C)C)=S)C3=C2)N1C

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 297.37 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Haywood T, Kealey S, Sánchez-Cabezas S, Hall JJ, Allott L, Smith G, Plisson C, Miller PW. Carbon-11 radiolabelling of organosulfur compounds: (11) C synthesis of the progesterone receptor agonist tanaproget. Chemistry. 2015 Jun 15;21(25):9034-8. doi: 10.1002/chem.201501089. PubMed PMID: 25965348. 2: Bapst JL, Ermer JC, Ferron GM, Foss D, Orczyk GP. Pharmacokinetics and safety of tanaproget, a nonsteroidal progesterone receptor agonist, in healthy women. Contraception. 2006 Nov;74(5):414-8. PubMed PMID: 17046384. 3: Leung K. [(18)F]Fluoropropyl-Tanaproget. 2010 Oct 6 [updated 2010 Dec 11]. Molecular Imaging and Contrast Agent Database (MICAD) [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2004-2013. Available from http://www.ncbi.nlm.nih.gov/books/NBK50681/ PubMed PMID: 21204318. 4: Zhou HB, Lee JH, Mayne CG, Carlson KE, Katzenellenbogen JA. Imaging progesterone receptor in breast tumors: synthesis and receptor binding affinity of fluoroalkyl-substituted analogues of tanaproget. J Med Chem. 2010 Apr 22;53(8):3349-60. doi: 10.1021/jm100052k. PubMed PMID: 20355713; PubMed Central PMCID: PMC2884396. 5: Lee JH, Zhou HB, Dence CS, Carlson KE, Welch MJ, Katzenellenbogen JA. Development of [F-18]fluorine-substituted Tanaproget as a progesterone receptor imaging agent for positron emission tomography. Bioconjug Chem. 2010 Jun 16;21(6):1096-104. doi: 10.1021/bc1001054. PubMed PMID: 20496889. 6: Keating KA, McConnell O, Zhang Y, Shen L, Demaio W, Mallis L, Elmarakby S, Chandrasekaran A. NMR characterization of an S-linked glucuronide metabolite of the potent, novel, nonsteroidal progesterone agonist tanaproget. Drug Metab Dispos. 2006 Aug;34(8):1283-7. PubMed PMID: 16698893. 7: Fensome A, Bender R, Chopra R, Cohen J, Collins MA, Hudak V, Malakian K, Lockhead S, Olland A, Svenson K, Terefenko EA, Unwalla RJ, Wilhelm JM, Wolfrom S, Zhu Y, Zhang Z, Zhang P, Winneker RC, Wrobel J. 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. J Med Chem. 2005 Aug 11;48(16):5092-5. PubMed PMID: 16078826. 8: Bruner-Tran KL, Zhang Z, Eisenberg E, Winneker RC, Osteen KG. 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 Endocrinol Metab. 2006 Apr;91(4):1554-60. PubMed PMID: 16418212. 9: Zhang Z, Olland AM, Zhu Y, Cohen J, Berrodin T, Chippari S, Appavu C, Li S, Wilhem J, Chopra R, Fensome A, Zhang P, Wrobel J, Unwalla RJ, Lyttle CR, Winneker RC. 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. PubMed PMID: 15937332. 10: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2005 Sep;27(7):505-22. PubMed PMID: 16258596. 11: Crabtree JS, Zhang X, Peano BJ, Zhang Z, Winneker RC, Harris HA. Development of a mouse model of mammary gland versus uterus tissue selectivity using estrogen- and progesterone-regulated gene markers. J Steroid Biochem Mol Biol. 2006 Sep;101(1):11-21. PubMed PMID: 16920353. 12: Winneker RC, Fensome A, Zhang P, Yudt MR, McComas CC, Unwalla RJ. A new generation of progesterone receptor modulators. Steroids. 2008 Aug;73(7):689-701. doi: 10.1016/j.steroids.2008.03.005. Review. PubMed PMID: 18472121. 13: Söderholm AA, Lehtovuori PT, Nyrönen TH. Docking and three-dimensional quantitative structure-activity relationship (3D QSAR) analyses of nonsteroidal progesterone receptor ligands. J Med Chem. 2006 Jul 13;49(14):4261-8. PubMed PMID: 16821785.