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MedKoo Cat#: 558253 | Name: Ospemifene
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Description:

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

Ospemifene is an oral medication indicated for the treatment of dyspareunia – pain during sexual intercourse – encountered by some women, more often in those who are post-menopausal. Ospemifene is a selective estrogen receptor modulator (SERM) acting similarly to an estrogen on the vaginal epithelium, building vaginal wall thickness which in turn reduces the pain associated with dyspareunia. Dyspareunia is most commonly caused by "vulval and vaginal atrophy." The medication was approved by the FDA in February 2013. (Source: http://en.wikipedia.org/wiki/Ospemifene)

Chemical Structure

Ospemifene
Ospemifene
CAS#128607-22-7

Theoretical Analysis

MedKoo Cat#: 558253

Name: Ospemifene

CAS#: 128607-22-7

Chemical Formula: C24H23ClO2

Exact Mass: 378.1387

Molecular Weight: 378.90

Elemental Analysis: C, 76.08; H, 6.12; Cl, 9.36; O, 8.45

Price and Availability

Size Price Availability Quantity
100mg USD 450.00 2 Weeks
500mg USD 1,450.00 2 Weeks
1g USD 2,450.00 2 Weeks
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Related CAS #
No Data
Synonym
Osphena
IUPAC/Chemical Name
2-(p-((Z)-4-Chloro-1,2-diphenyl-1-butenyl)phenoxy)ethanol
InChi Key
LUMKNAVTFCDUIE-VHXPQNKSSA-N
InChi Code
InChI=1S/C24H23ClO2/c25-16-15-23(19-7-3-1-4-8-19)24(20-9-5-2-6-10-20)21-11-13-22(14-12-21)27-18-17-26/h1-14,26H,15-18H2/b24-23-
SMILES Code
ClCC/C(C1=CC=CC=C1)=C(C2=CC=C(OCCO)C=C2)\C3=CC=CC=C3
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
>5 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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Ospemifene is a non-estrogen selective estrogen receptor modulator (SERM), with Kis of 380 and 410 nM for estrogen receptor α (ERα) and Erβ.
In vitro activity:
Osp (ospemifene), similar to Ral and Tam, decreased the number of proliferating cells in a concentration-dependent manner (at 100 nM, P < 0.01) and strongly opposed 10 nM E2-stimulated proliferation (P < 0.001). Corresponding effects were observed in the proportions of cells expressing ERα and TFF1 (P < 0.001). At 14 days apoptosis was increased by 100 nM SERMs (P < 0.01), but, notably, decreased by 1 nM Osp and Ral at day 7 (P < 0.05). Reference: Menopause. 2016 Jul;23(7):719-30. https://pubmed.ncbi.nlm.nih.gov/27163517/
In vivo activity:
Ospemifene treatment reduced the loss of bone mineral content and density observed in untreated OVX rats, significantly increased distal femur bone mineral content at 51 weeks at 25 mg/kg dose compared with untreated OVX rats (p<0.01), and significantly increased trabecular bone mineral density of the distal femur and proximal tibia with 1, 5, or 25 mg/kg doses after 52 weeks. Ospemifene 5 and 25 mg/kg preserved distal femur trabecular structure; trabecular number was significantly increased, whereas trabecular separation and eroded surface values were significantly decreased (all p<0.01). Reference: Horm Metab Res. 2014 Jan;46(1):27-35. https://pubmed.ncbi.nlm.nih.gov/24108389/
Solvent mg/mL mM
Solubility
DMSO 65.0 171.55
DMSO:PBS (pH 7.2) (1:1) 0.5 1.32
Ethanol 1.5 3.96
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 378.90 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.

Recalculate based on batch purity %
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
Formulation protocol:
1. Eigeliene N, Kangas L, Hellmer C, Kauko T, Erkkola R, Härkönen P. Effects of ospemifene, a novel selective estrogen-receptor modulator, on human breast tissue ex vivo. Menopause. 2016 Jul;23(7):719-30. doi: 10.1097/GME.0000000000000624. PMID: 27163517. 2. Turpeinen M, Uusitalo J, Lehtinen T, Kailajärvi M, Pelkonen O, Vuorinen J, Tapanainen P, Stjernschantz C, Lammintausta R, Scheinin M. Effects of ospemifene on drug metabolism mediated by cytochrome P450 enzymes in humans in vitro and in vivo. Int J Mol Sci. 2013 Jul 5;14(7):14064-75. doi: 10.3390/ijms140714064. PMID: 23880855; PMCID: PMC3742231. 3. Kangas L, Härkönen P, Väänänen K, Peng Z. Effects of the selective estrogen receptor modulator ospemifene on bone in rats. Horm Metab Res. 2014 Jan;46(1):27-35. doi: 10.1055/s-0033-1355356. Epub 2013 Oct 9. PMID: 24108389. 4. Wurz GT, Read KC, Marchisano-Karpman C, Gregg JP, Beckett LA, Yu Q, Degregorio MW. Ospemifene inhibits the growth of dimethylbenzanthracene-induced mammary tumors in Sencar mice. J Steroid Biochem Mol Biol. 2005 Nov;97(3):230-40. doi: 10.1016/j.jsbmb.2005.06.027. Epub 2005 Sep 8. PMID: 16153821.
In vitro protocol:
1. Eigeliene N, Kangas L, Hellmer C, Kauko T, Erkkola R, Härkönen P. Effects of ospemifene, a novel selective estrogen-receptor modulator, on human breast tissue ex vivo. Menopause. 2016 Jul;23(7):719-30. doi: 10.1097/GME.0000000000000624. PMID: 27163517. 2. Turpeinen M, Uusitalo J, Lehtinen T, Kailajärvi M, Pelkonen O, Vuorinen J, Tapanainen P, Stjernschantz C, Lammintausta R, Scheinin M. Effects of ospemifene on drug metabolism mediated by cytochrome P450 enzymes in humans in vitro and in vivo. Int J Mol Sci. 2013 Jul 5;14(7):14064-75. doi: 10.3390/ijms140714064. PMID: 23880855; PMCID: PMC3742231.
In vivo protocol:
1. Kangas L, Härkönen P, Väänänen K, Peng Z. Effects of the selective estrogen receptor modulator ospemifene on bone in rats. Horm Metab Res. 2014 Jan;46(1):27-35. doi: 10.1055/s-0033-1355356. Epub 2013 Oct 9. PMID: 24108389. 2. Wurz GT, Read KC, Marchisano-Karpman C, Gregg JP, Beckett LA, Yu Q, Degregorio MW. Ospemifene inhibits the growth of dimethylbenzanthracene-induced mammary tumors in Sencar mice. J Steroid Biochem Mol Biol. 2005 Nov;97(3):230-40. doi: 10.1016/j.jsbmb.2005.06.027. Epub 2005 Sep 8. PMID: 16153821.
1: Di Carlo C, Cagnacci A, Murina F, Maffei S, Becorpi A, Lello S. Ospemifene and vulvovaginal atrophy: an update of the clinical profile for post-menopausal women. Expert Opin Pharmacother. 2024 Aug 12. doi: 10.1080/14656566.2024.2391009. Epub ahead of print. PMID: 39129457. 2: Marchetti G, Taithongchai A, Robinson D. Ospemifene for Genitourinary Syndrome of Menopause: Patient Selection. Int J Womens Health. 2024 Jun 5;16:1049-1053. doi: 10.2147/IJWH.S431520. PMID: 38855356; PMCID: PMC11162622. 3: Meriggiola MC, Villa P, Maffei S, Becorpi A, Di Paolantonio T, Nicolucci A, Salvatore S, Nappi RE; PEONY Study Group. Vulvovaginal atrophy in women with and without a history of breast cancer: Baseline data from the PatiEnt satisfactiON studY (PEONY) in Italy. Maturitas. 2024 May;183:107950. doi: 10.1016/j.maturitas.2024.107950. Epub 2024 Mar 5. PMID: 38462385. 4: Drugs for menopausal symptoms. Med Lett Drugs Ther. 2024 Mar 4;66(1697):33-38. doi: 10.58347/tml.2024.1697a. PMID: 38412276. 5: Motlani G, Motlani V, Acharya N, Dave A, Pamnani S, Somyani D, Agrawal S. Novel Advances in the Role of Selective Estrogen Receptor Modulators in Hormonal Replacement Therapy: A Paradigm Shift. Cureus. 2023 Nov 19;15(11):e49079. doi: 10.7759/cureus.49079. PMID: 38125238; PMCID: PMC10730982. 6: Pinkerton JV, Vaughan MH, Kaunitz AM. Hormonal Medications for Genitourinary Syndrome of Menopause. Clin Obstet Gynecol. 2024 Mar 1;67(1):68-78. doi: 10.1097/GRF.0000000000000835. Epub 2023 Nov 21. PMID: 38032827. 7: Gu R, Feng X, Bao M, Zhang X. Modular access to alkylgermanes via reductive germylative alkylation of activated olefins under nickel catalysis. Nat Commun. 2023 Nov 23;14(1):7669. doi: 10.1038/s41467-023-43561-z. PMID: 37996494; PMCID: PMC10667229. 8: Cancelo MJ, Sánchez Borrego R, Palacios S, Baquedano L, Corbacho Garza T, Fernández Aller N, García Ferreiro C, Quijano Martín JJ, González Calvo AJ. Vulvovaginal atrophy in the CRETA study: the healthcare professionals' perception. Gynecol Endocrinol. 2023 Dec;39(1):2264405. doi: 10.1080/09513590.2023.2264405. Epub 2023 Oct 9. PMID: 37811796. 9: Comini ACM, Carvalho BM, Moreira MJB, Reis PCA, Colapietro L, Northern J, Batalini F. Safety and Serum Estradiol Levels in Hormonal Treatments for Vulvovaginal Atrophy in Breast Cancer Survivors: A Systematic Review and Meta- Analysis. Clin Breast Cancer. 2023 Dec;23(8):835-846. doi: 10.1016/j.clbc.2023.08.003. Epub 2023 Aug 22. PMID: 37806915. 10: Wen H, Lu C, Zhang M, Qi X. A real-world disproportionality analysis of ospemifene: data mining of the public version of FDA adverse event reporting system. Expert Opin Drug Saf. 2023 Jul-Dec;22(11):1133-1142. doi: 10.1080/14740338.2023.2247971. Epub 2023 Aug 24. PMID: 37578751. 11: Casiano Evans EA, Hobson DTG, Aschkenazi SO, Alas AN, Balgobin S, Balk EM, Dieter AA, Kanter G, Orejuela FJ, Sanses TVD, Rahn DD. Nonestrogen Therapies for Treatment of Genitourinary Syndrome of Menopause: A Systematic Review. Obstet Gynecol. 2023 Sep 1;142(3):555-570. doi: 10.1097/AOG.0000000000005288. Epub 2023 Aug 4. PMID: 37543737. 12: Goldstein SR. Endometrial safety and efficacy of ospemifene. Menopause. 2023 Aug 1;30(8):788-790. doi: 10.1097/GME.0000000000002225. Epub 2023 Jul 18. PMID: 37467145. 13: Chang JG, Lewis MN, Wertz MC. Managing Menopausal Symptoms: Common Questions and Answers. Am Fam Physician. 2023 Jul;108(1):28-39. PMID: 37440735. 14: Simon JA, Ferenczy A, Black D, Castonguay A, Royer C, Marouf R, Beauchemin C. Efficacy, tolerability, and endometrial safety of ospemifene compared with current therapies for the treatment of vulvovaginal atrophy: a systematic literature review and network meta-analysis. Menopause. 2023 Aug 1;30(8):855-866. doi: 10.1097/GME.0000000000002211. Epub 2023 Jun 27. PMID: 37369079; PMCID: PMC10389189. 15: Mohamed-Ahmed R, Taithongchai A, da Silva AS, Robinson D, Cardozo L. Treating and Managing Urinary Incontinence: Evolving and Potential Multicomponent Medical and Lifestyle Interventions. Res Rep Urol. 2023 Jun 17;15:193-203. doi: 10.2147/RRU.S387205. PMID: 37351339; PMCID: PMC10284157. 16: Cox P, Panay N. Non-hormonal treatments for managing vulvovaginal atrophy/genitourinary syndrome of menopause. Climacteric. 2023 Aug;26(4):367-372. doi: 10.1080/13697137.2023.2210283. Epub 2023 May 18. PMID: 37199295. 17: Pietrzak BA, Wnuk A, Przepiórska K, Łach A, Kajta M. Posttreatment with Ospemifene Attenuates Hypoxia- and Ischemia-Induced Apoptosis in Primary Neuronal Cells via Selective Modulation of Estrogen Receptors. Neurotox Res. 2023 Aug;41(4):362-379. doi: 10.1007/s12640-023-00644-5. Epub 2023 May 2. PMID: 37129835; PMCID: PMC10354152. 18: Merlino L, D'Ovidio G, Matys V, Piccioni MG, Porpora MG, Senatori R, Viscardi MF, Vitale A, Della Rocca C, On Behalf Of Policlinico Umberto I Collaborators. Therapeutic Choices for Genitourinary Syndrome of Menopause (GSM) in Breast Cancer Survivors: A Systematic Review and Update. Pharmaceuticals (Basel). 2023 Apr 6;16(4):550. doi: 10.3390/ph16040550. PMID: 37111307; PMCID: PMC10142093. 19: Palacios S. Sequential treatment in vulvovaginal atrophy. Climacteric. 2023 Aug;26(4):292-295. doi: 10.1080/13697137.2023.2197588. Epub 2023 Apr 27. PMID: 37105219. 20: Palacios S, Sánchez-Borrego R, Suárez Álvarez B, Lugo Salcedo F, González Calvo AJ, Quijano Martín JJ, Cancelo MJ, Fasero M. Impact of vulvovaginal atrophy therapies on postmenopausal women's quality of life in the CRETA study measured by the Cervantes scale. Maturitas. 2023 Jun;172:46-51. doi: 10.1016/j.maturitas.2023.03.007. Epub 2023 Mar 30. PMID: 37099983.