Isotibolone | CAS#1162-60-3 | progestational

MedKoo Cat#: 585358 | Name: Isotibolone

Description:

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

Isotibolone is a metabolite of tibolone and has progestational activity without estrogenic activity seen in tibolone.

Chemical Structure

Isotibolone

CAS#1162-60-3

Theoretical Analysis

MedKoo Cat#: 585358

Name: Isotibolone

CAS#: 1162-60-3

Chemical Formula: C21H28O2

Exact Mass: 312.2089

Molecular Weight: 312.45

Elemental Analysis: C, 80.73; H, 9.03; O, 10.24

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.

Bulk Inquiry

Related CAS #

No Data

Synonym

Isotibolone; U-13,851; U13,851; U 13,851

IUPAC/Chemical Name

17-ethynyl-17-hydroxy-7,13-dimethyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one

InChi Key

WAOKMNBZWBGYIK-UHFFFAOYSA-N

InChi Code

InChI=1S/C21H28O2/c1-4-21(23)10-8-18-19-13(2)11-14-12-15(22)5-6-16(14)17(19)7-9-20(18,21)3/h1,12-13,16-19,23H,5-11H2,2-3H3

SMILES Code

O=C1CCC2C3CCC4(C)C(O)(C#C)CCC4C3C(C)CC2=C1

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

>3 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 312.45 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: Guzel E, Buchwalder L, Basar M, Kayisli U, Ocak N, Bozkurt I, Lockwood CJ, Schatz F. Effects of tibolone and its metabolites on prolactin and insulin-like growth factor binding protein-1 expression in human endometrial stromal cells. Gynecol Endocrinol. 2015 May;31(5):414-8. doi: 10.3109/09513590.2015.1014788. Epub 2015 Apr 9. PubMed PMID: 25856298. 2: Penning TM, Chen M, Jin Y. Promiscuity and diversity in 3-ketosteroid reductases. J Steroid Biochem Mol Biol. 2015 Jul;151:93-101. doi: 10.1016/j.jsbmb.2014.12.003. Epub 2014 Dec 10. Review. PubMed PMID: 25500069; PubMed Central PMCID: PMC4458445. 3: Stark J, Varbiro S, Sipos M, Tulassay Z, Sara L, Adler I, Dinya E, Magyar Z, Szekacs B, Marczell I, Kloosterboer HJ, Racz K, Bekesi G. Antioxidant effect of the active metabolites of tibolone. Gynecol Endocrinol. 2015 Jan;31(1):31-5. doi: 10.3109/09513590.2014.943727. Epub 2014 Jul 23. PubMed PMID: 25054375. 4: Bianco-Miotto T, Trotta AP, Need EF, Lee AM, Ochnik AM, Giorgio L, Leach DA, Swinstead EE, O'Loughlin MA, Newman MR, Birrell SN, Butler LM, Harris JM, Buchanan G. Molecular and structural basis of androgen receptor responses to dihydrotestosterone, medroxyprogesterone acetate and Δ(4)-tibolone. Mol Cell Endocrinol. 2014 Feb 15;382(2):899-908. doi: 10.1016/j.mce.2013.11.002. Epub 2013 Nov 14. PubMed PMID: 24239616. 5: Jin Y, Duan L, Chen M, Penning TM, Kloosterboer HJ. Metabolism of the synthetic progestogen norethynodrel by human ketosteroid reductases of the aldo-keto reductase superfamily. J Steroid Biochem Mol Biol. 2012 Apr;129(3-5):139-44. doi: 10.1016/j.jsbmb.2011.12.002. Epub 2011 Dec 28. PubMed PMID: 22210085; PubMed Central PMCID: PMC3303946. 6: Escande A, Servant N, Rabenoelina F, Auzou G, Kloosterboer H, Cavaillès V, Balaguer P, Maudelonde T. Regulation of activities of steroid hormone receptors by tibolone and its primary metabolites. J Steroid Biochem Mol Biol. 2009 Aug;116(1-2):8-14. doi: 10.1016/j.jsbmb.2009.03.008. Epub 2009 Apr 2. PubMed PMID: 19464167. 7: Qiu J, Bosch MA, Rønnekleiv OK, Kloosterboer HJ, Kelly MJ. Tibolone rapidly attenuates the GABAB response in hypothalamic neurones. J Neuroendocrinol. 2008 Dec;20(12):1310-8. doi: 10.1111/j.1365-2826.2008.01789.x. PubMed PMID: 19094079; PubMed Central PMCID: PMC2613946. 8: Barbier C, Kloosterboer HJ, Kaufman DG. Effects of tibolone metabolites on human endometrial cell lines in co-culture. Reprod Sci. 2008 Jan;15(1):75-82. doi: 10.1177/19337191073097198. PubMed PMID: 18212357; PubMed Central PMCID: PMC2874819. 9: Verheul HA, Blok LJ, Burger CW, Hanifi-Moghaddam P, Kloosterboer HJ. Levels of tibolone and estradiol and their nonsulfated and sulfated metabolites in serum, myometrium, and vagina of postmenopausal women following treatment for 21 days with tibolone, estradiol, or estradiol plus medroxyprogestrone acetate. Reprod Sci. 2007 Feb;14(2):160-8. PubMed PMID: 17636227. 10: Kloosterboer HJ, Löfgren L, von Schoulz E, von Schoultz B, Verheul HA. Estrogen and tibolone metabolite levels in blood and breast tissue of postmenopausal women recently diagnosed with early-stage breast cancer and treated with tibolone or placebo for 14 days. Reprod Sci. 2007 Feb;14(2):151-9. PubMed PMID: 17636226. 11: Raobaikady B, Parsons MF, Reed MJ, Purohit A. Tibolone and its delta-4, 7alpha-methyl norethisterone metabolite are reversible inhibitors of human aromatase. J Steroid Biochem Mol Biol. 2007 May;104(3-5):154-60. Epub 2007 Mar 24. PubMed PMID: 17467267. 12: Verheul HA, van Iersel ML, Delbressine LP, Kloosterboer HJ. Selective tissue distribution of tibolone metabolites in mature ovariectomized female cynomolgus monkeys after multiple doses of tibolone. Drug Metab Dispos. 2007 Jul;35(7):1105-11. Epub 2007 Apr 9. PubMed PMID: 17420283. 13: Verheul HA, Timmer CJ, van Iersel ML, Delbressine LP, Kloosterboer HJ. Pharmacokinetic parameters of tibolone and metabolites in plasma, urine, feces, and bile from ovariectomized cynomolgus monkeys after a single dose or multiple doses of tibolone. Drug Metab Dispos. 2007 Jul;35(7):1112-8. Epub 2007 Apr 9. PubMed PMID: 17420282. 14: Verheul HA, Timmer CJ, Kloosterboer HJ. Pharmacokinetic parameters of sulfated tibolone metabolites in postmenopausal women after single and multiple doses of tibolone. Clin Pharmacol Ther. 2007 Apr;81(4):573-9. Epub 2007 Feb 14. PubMed PMID: 17301737. 15: Verheul HA, Kloosterboer HJ. Metabolism of exogenous sex steroids and effect on brain functions with a focus on tibolone. J Steroid Biochem Mol Biol. 2006 Dec;102(1-5):195-204. Review. PubMed PMID: 17113982. 16: Mirkin S, Wong BC, Archer DF. Effects of 17beta-estradiol, progesterone, synthetic progestins, tibolone, and raloxifene on vascular endothelial growth factor and Thrombospondin-1 messenger RNA in breast cancer cells. Int J Gynecol Cancer. 2006;16 Suppl 2:560-3. PubMed PMID: 17010073. 17: Genazzani AR, Pluchino N, Bernardi F, Centofanti M, Luisi M. Beneficial effect of tibolone on mood, cognition, well-being, and sexuality in menopausal women. Neuropsychiatr Dis Treat. 2006 Sep;2(3):299-307. PubMed PMID: 19412477; PubMed Central PMCID: PMC2671819. 18: Schatz F, Kuczynski E, Kloosterbooer L, Krikun G, Buchwalder LF, Rahman M, Lockwood CJ. Tibolone exerts progestational inhibition of matrix metalloproteinase expression in human endometrial stromal cells. Steroids. 2006 Sep;71(9):768-75. Epub 2006 Jun 27. PubMed PMID: 16806336. 19: Raobaikady B, Parsons MF, Reed MJ, Purohit A. Lack of aromatisation of the 3-keto-4-ene metabolite of tibolone to an estrogenic derivative. Steroids. 2006 Jul;71(7):639-46. Epub 2006 May 18. PubMed PMID: 16712888. 20: Schatz F, Kuczynski E, Kloosterboer HJ, Buchwalder L, Tang C, Krikun G, Lockwood CJ. Tibolone and its metabolites enhance tissue factor and PAI-1 expression in human endometrial stromal cells: Evidence of progestogenic effects. Steroids. 2005 Nov;70(12):840-5. PubMed PMID: 16011840.