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    Chemistry

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    Also known as: 128607-22-7, Fc-1271a, Osphena, Senshio, Deamino-hydroxytoremifene, Fc-1271
    Molecular Formula
    C24H23ClO2
    Molecular Weight
    378.9  g/mol
    InChI Key
    LUMKNAVTFCDUIE-VHXPQNKSSA-N
    FDA UNII
    B0P231ILBK
    Ospemifene
    Ospemifene is a new selective non-hormonal estrogen receptor modulator (SERM) that is used for the treatment of moderate to severe dyspareunia, a symptom of vulvar and vaginal atrophy, due to menopause. FDA approved on February 26, 2013.
    Ospemifene is an Estrogen Agonist/Antagonist. The mechanism of action of ospemifene is as a Selective Estrogen Receptor Modulator.
    1 2D Structure

    Ospemifene

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-[4-[(Z)-4-chloro-1,2-diphenylbut-1-enyl]phenoxy]ethanol
    2.1.2 InChI
    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-
    2.1.3 InChI Key
    LUMKNAVTFCDUIE-VHXPQNKSSA-N
    2.1.4 Canonical SMILES
    C1=CC=C(C=C1)C(=C(C2=CC=CC=C2)C3=CC=C(C=C3)OCCO)CCCl
    2.1.5 Isomeric SMILES
    C1=CC=C(C=C1)/C(=C(/C2=CC=CC=C2)\C3=CC=C(C=C3)OCCO)/CCCl
    2.2 Other Identifiers
    2.2.1 UNII
    B0P231ILBK
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Fc-1271a

    2. Osphena

    3. Senshio

    4. Z-2-(4-(4-chloro-1,2-diphenyl-but-1-enyl)phenoxy)ethanol

    2.3.2 Depositor-Supplied Synonyms

    1. 128607-22-7

    2. Fc-1271a

    3. Osphena

    4. Senshio

    5. Deamino-hydroxytoremifene

    6. Fc-1271

    7. 2-(4-(4-chloro-1,2-diphenyl-but-1-enyl)phenoxy)ethanol

    8. Tore Iii

    9. 2-(p-((z)-4-chloro-1,2-diphenyl-1-butenyl)phenoxy)ethanol

    10. Ccris 9205

    11. (deaminohydroxy) Toremifene

    12. B0p231ilbk

    13. Chebi:73275

    14. Ethanol, 2-[4-[(1z)-4-chloro-1,2-diphenyl-1-buten-1-yl]phenoxy]-

    15. Ethanol, 2-[4-[(1z)-4-chloro-1,2-diphenyl-1-butenyl]phenoxy]-

    16. 2-[4-[(z)-4-chloro-1,2-diphenylbut-1-enyl]phenoxy]ethanol

    17. (z)-2-(4-(4-chloro-1,2-diphenylbut-1-en-1-yl)phenoxy)ethan-1-ol

    18. 2-{4-[(1z)-4-chloro-1,2-diphenylbut-1-en-1-yl]phenoxy}ethanol

    19. Ospemifene [inn]

    20. Unii-b0p231ilbk

    21. Ophena

    22. Ospemifene [usan:inn:ban]

    23. Deaminotoremifene

    24. Ethanol, 2-(4-((1z)-4-chloro-1,2-diphenyl-1-butenyl)phenoxy)-

    25. Osphena (tn)

    26. Deaminohydroxytoremifene

    27. Ospemifene [mi]

    28. Ospemifene [usan]

    29. Ospemifene, Fc-1271a

    30. Ospemifene [vandf]

    31. Ospemifene [mart.]

    32. Ospemifene [who-dd]

    33. Ospemifene (inn/usan/ban)

    34. Schembl948118

    35. Gtpl7349

    36. Chembl2105395

    37. Ospemifene [orange Book]

    38. Hsdb 8281

    39. Dtxsid101025426

    40. Z-2-(4-(4-chloro-1,2-diphenyl-but-1-enyl)phenoxy)ethanol

    41. Bcp20981

    42. Hy-b0723

    43. Zinc1550766

    44. Mfcd00871890

    45. S4285

    46. Akos025401964

    47. Ccg-268392

    48. Cs-5961

    49. Db04938

    50. Ncgc00386347-01

    51. Ac-27645

    52. O0441

    53. Sw219657-1

    54. A14261

    55. D08958

    56. J-005613

    57. Q7107372

    58. Z-2-[4-(4-chloro-1,2-diphenyl-but-1-enyl)-phenoxy]-ethanol

    59. 2-[4-[(z)-4-chloro-1,2-di(phenyl)but-1-enyl]phenoxy]ethanol

    2.4 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 378.9 g/mol
    Molecular Formula C24H23ClO2
    XLogP36.5
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count8
    Exact Mass378.1386577 g/mol
    Monoisotopic Mass378.1386577 g/mol
    Topological Polar Surface Area29.5 Ų
    Heavy Atom Count27
    Formal Charge0
    Complexity441
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameOsphena
    PubMed HealthOspemifene (By mouth)
    Drug ClassesEndocrine-Metabolic Agent
    Drug LabelOSPHENA is anestrogen agonist/antagonist.The chemical structure of ospemifene is shown in Figure 1.Figure 1: Chemical structureThe chemical designation is Z-2-[4-(4-chloro-1,2-diphenylbut-1-enyl)phenoxy]ethanol, and has the empirical formula C24H...
    Active IngredientOspemifene
    Dosage FormTablet
    RouteOral
    Strength60mg
    Market StatusPrescription
    CompanyShionogi

    2 of 2  
    Drug NameOsphena
    PubMed HealthOspemifene (By mouth)
    Drug ClassesEndocrine-Metabolic Agent
    Drug LabelOSPHENA is anestrogen agonist/antagonist.The chemical structure of ospemifene is shown in Figure 1.Figure 1: Chemical structureThe chemical designation is Z-2-[4-(4-chloro-1,2-diphenylbut-1-enyl)phenoxy]ethanol, and has the empirical formula C24H...
    Active IngredientOspemifene
    Dosage FormTablet
    RouteOral
    Strength60mg
    Market StatusPrescription
    CompanyShionogi

    4.2 Therapeutic Uses

    /CLINICAL TRIALS/ ClinicalTrials.gov is a registry and results database of publicly and privately supported clinical studies of human participants conducted around the world. The Web site is maintained by the National Library of Medicine (NLM) and the National Institutes of Health (NIH). Each ClinicalTrials.gov record presents summary information about a study protocol and includes the following: Disease or condition; Intervention (for example, the medical product, behavior, or procedure being studied); Title, description, and design of the study; Requirements for participation (eligibility criteria); Locations where the study is being conducted; Contact information for the study locations; and Links to relevant information on other health Web sites, such as NLM's MedlinePlus for patient health information and PubMed for citations and abstracts for scholarly articles in the field of medicine. Ospemifene is included in the database.

    NIH/NLM; ClinicalTrials.Gov. Available from, as of September 30, 2015: https://clinicaltrials.gov/search/intervention=ospemifene%20OR%20Fc-1271

    Osphena is indicated for the treatment of moderate to severe dyspareunia, a symptom of vulvar and vaginal atrophy, due to menopause. /Included in US product label/

    NIH; DailyMed. Current Medication Information for Osphena (Ospemifene) Tablet, Film Coated (Updated: August 2015). Available from, as of November 20, 2015: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=8462d6ab-e3cd-4efa-a360-75bf8f917287

    4.3 Drug Warning

    /BOX WARNING/ There is a reported increased risk of stroke and deep vein thrombosis (DVT) in postmenopausal women (50 to 79 years of age) who received daily oral conjugated estrogens (CE) (0.625 mg)-alone therapy over 7.1 years as part of the Women's Health Initiative (WHI). In the clinical trials for Osphena (duration of treatment up to 15 months), the incidence rates of thromboembolic and hemorrhagic stroke were 0.72 and 1.45 per thousand women, respectively in Osphena 60 mg treatment group and 1.04 and 0 in placebo. The incidence of DVT was 1.45 per thousand women in Osphena 60 mg treatment group and 1.04 per thousand women in placebo. Osphena should be prescribed for the shortest duration consistent with treatment goals and risks for the individual woman.

    NIH; DailyMed. Current Medication Information for Osphena (Ospemifene) Tablet, Film Coated (Updated: August 2015). Available from, as of November 20, 2015: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=8462d6ab-e3cd-4efa-a360-75bf8f917287

    /BOX WARNING/ Osphena is an estrogen agonist/antagonist with tissue selective effects. In the endometrium, Osphena has estrogen agonistic effects. There is an increased risk of endometrial cancer in a woman with a uterus who uses unopposed estrogens. Adding a progestin to estrogen therapy reduces the risk of endometrial hyperplasia, which may be a precursor to endometrial cancer. Adequate diagnostic measures, including directed and random endometrial sampling when indicated, should be undertaken to rule out malignancy in postmenopausal women with undiagnosed persistent or recurring abnormal genital bleeding.

    NIH; DailyMed. Current Medication Information for Osphena (Ospemifene) Tablet, Film Coated (Updated: August 2015). Available from, as of November 20, 2015: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=8462d6ab-e3cd-4efa-a360-75bf8f917287

    /BOX WARNING/ What is the most important information I should know about Osphena? Osphena is a medicine that works like estrogen in the lining of the uterus (womb), but can work differently in other parts of the body. Taking estrogen-alone or Osphena may increase your chance of getting cancer of the lining of the uterus (womb). Vaginal bleeding after menopause may be a warning sign of cancer of the lining of the uterus (womb). Your healthcare provider should check any unusual vaginal bleeding to find out the cause. Tell your healthcare provider right away if you have any unusual vaginal bleeding while you are taking Osphena. Osphena may increase your chance of getting strokes and blood clots. You and your healthcare provider should talk regularly about whether you still need treatment with Osphena.

    NIH; DailyMed. Current Medication Information for Osphena (Ospemifene) Tablet, Film Coated (Updated: August 2015). Available from, as of November 20, 2015: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=8462d6ab-e3cd-4efa-a360-75bf8f917287

    The pharmacokinetics of ospemifene has not been studied in women with severe hepatic impairment (Child-Pugh Class C); therefore, Osphena should not be used in women with severe hepatic impairment.

    NIH; DailyMed. Current Medication Information for Osphena (Ospemifene) Tablet, Film Coated (Updated: August 2015). Available from, as of November 20, 2015: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=8462d6ab-e3cd-4efa-a360-75bf8f917287

    For more Drug Warnings (Complete) data for Ospemifene (16 total), please visit the HSDB record page.

    4.4 Drug Indication

    Ospemifene is used for the treatment of moderate to dyspareunia, a symptom of vulvar and vaginal atrophy, due to menopause.

    FDA Label

    Senshio is indicated for the treatment of moderate to severe symptomatic vulvar and vaginal atrophy (VVA) in post-menopausal women.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    The half maximal inhibitory concentration (IC50) for estrogen receptor (ER) alpha and beta are 0.8 M and 1.7 M, respectively. Ospemifene has potential uses in the management of osteoporosis in postmenopausal women. It interacts with osteoblasts and osteoclasts in such a way that it reduces bone turnover. It also has potential uses in the prevention of breast cancer. Studies suggest that ospemifene, in a dose-dependent manner, reduces the incidence of tumours.

    5.2 FDA Pharmacological Classification
    5.2.1 Active Moiety
    OSPEMIFENE
    5.2.2 FDA UNII
    B0P231ILBK
    5.2.3 Pharmacological Classes
    Selective Estrogen Receptor Modulators [MoA]; Estrogen Agonist/Antagonist [EPC]
    5.3 ATC Code

    G03XC05

    G - Genito urinary system and sex hormones

    G03 - Sex hormones and modulators of the genital system

    G03X - Other sex hormones and modulators of the genital system

    G03XC - Selective estrogen receptor modulators

    G03XC05 - Ospemifene

    5.4 Absorption, Distribution and Excretion

    Absorption

    When a single oral dose of ospemifene 60 mg is given to postmenopausal women under fasted conditions, the pharmacokinetic parameters are as follows: Tmax = 2 hours (range of 1 - 8 hours); Cmax = 533 ng/mL; AUC (0-inf) = 4165 nghr/mL. When the same aforementioned dose is given to postmenopausal women under fed conditions, the pharmacokinetic parameters are as follows: Tmax = 2.5 hours (1 - 6 hours); Cmax = 1198 ng/mL; AUC (0-inf) = 7521 nghr/mL. Accumulation occurs following repeated doses. Time to steady state = 9 days. Although the bioavailability of ospemifene has not been formally evaluated, it is expected to have a low bioavailability because of its lipophilic nature.

    Route of Elimination

    Following an oral administration of ospemifene, approximately 75% and 7% of the dose was excreted in feces and urine, respectively. Less than 0.2% of the ospemifene dose was excreted unchanged in urine.

    Volume of Distribution

    448 L

    Clearance

    Total body clearance = 9.16 L/hr.

    /MILK/ Human lacatation data is not available, however, the prodrug is rapidly metabolized upon absorption, and this agent is concentrated in the breast milk.

    Briggs, G.G., Freeman, R.K., Yaffee, S.J.; Drugs in Pregancy and Lactation Nineth Edition. Wolters Kluwer/Lippincott Williams & Wilkins, Philadelphia, PA. 2011, p. 839

    /MILK/ It is not known whether Osphena is excreted in human breast milk. In a nonclinical study, ospemifene was excreted in rat milk and detected at concentrations higher than that in maternal plasma.

    NIH; DailyMed. Current Medication Information for Osphena (Ospemifene) Tablet, Film Coated (Updated: August 2015). Available from, as of November 20, 2015: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=8462d6ab-e3cd-4efa-a360-75bf8f917287

    Following a single oral administration of Osphena 60 mg tablet in postmenopausal women under fasted condition, peak median serum concentrations was reached at approximately 2 hours (range: 1 to 8 hours) post-dose. Mean ospemifene C max and AUC 0-inf were 533 ng/mL and 4165 ng/hr/mL, respectively. After a single oral administration of Osphena 60 mg tablet in postmenopausal women with a high fat/high calorie (860 kcal) meal, C max was reached at approximately 2.5 hours (range: 1 to 6 hours) post-dose. Mean ospemifene C max and AUC 0-inf were 1198 ng/mL and 7521 ng/hr/mL, respectively. The absolute bioavailability of ospemifene was not evaluated. Ospemifene exhibits less than dose-proportional pharmacokinetics from 25 to 200 mg with ospemifene capsule formulation. Accumulation of ospemifene with respect to AUC 0-inf was approximately 2 after twelve weeks of daily administration. Steady-state was reached after nine days of ospemifene administration. Osphena is highly (>99 percent) bound to serum proteins. The apparent volume of distribution is 448 L. The apparent terminal half-life of ospemifene in postmenopausal women is approximately 26 hours. Following an oral administration of ospemifene, approximately 75% and 7% of the dose was excreted in feces and urine, respectively. Less than 0.2% of the ospemifene dose was excreted unchanged in urine.

    NIH; DailyMed. Current Medication Information for Osphena (Ospemifene) Tablet, Film Coated (Updated: August 2015). Available from, as of November 20, 2015: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=8462d6ab-e3cd-4efa-a360-75bf8f917287

    5.5 Metabolism/Metabolites

    Ospemifene is hepatically metabolized via CYP3A4, CYP2C9, CYP2C19, and CYP2B6. The major metabolite was 4-hydroxyospemifene, 25% of the parent compound will undergo this biotransformation. Other metabolites include 4'-hydroxy-ospemifene, <7% of the parent compound will undergo this biotransformation. In order of decreasing potency, ospemifene was suggested to be a weak inhibitor for CYP2B6, CYP2C9, CYP2C19, CYP2C8, CYP2D6 and CYP3A4.

    The objective of these investigations was to determine the possible effects of the novel selective estrogen receptor modulator, ospemifene, on cytochrome P450 (CYP)-mediated drug metabolism. Ospemifene underwent testing for possible effects on CYP enzyme activity in human liver microsomes and in isolated human hepatocytes. Based on the results obtained in vitro, three Phase 1 crossover pharmacokinetic studies were conducted in healthy postmenopausal women to assess the in vivo effects of ospemifene on CYP-mediated drug metabolism. Ospemifene and its main metabolites 4-hydroxyospemifene and 4'-hydroxyospemifene weakly inhibited a number of CYPs (CYP2B6, CYP2C9, CYP2C19, CYP2C8, and CYP2D6) in vitro. However, only CYP2C9 activity was inhibited by 4-hydroxyospemifene at clinically relevant concentrations. Induction of CYPs by ospemifene in cultured human hepatocytes was 2.4-fold or less. The in vivo studies showed that ospemifene did not have significant effects on the areas under the plasma concentration-time curves of the tested CYP substrates warfarin (CYP2C9), bupropion (CYP2B6) and omeprazole (CYP2C19), demonstrating that pretreatment with ospemifene did not alter their metabolism. Therefore, the risk that ospemifene will affect the pharmacokinetics of drugs that are substrates for CYP enzymes is low.

    PMID:23880855 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3742231 Turpeinen M et al; Int J Mol Sci 14(7): 14064-75 (2013).

    Ospemifene and its main metabolites 4-hydroxyospemifene and 4'-hydroxyospemifene weakly inhibited a number of CYPs (CYP2B6, CYP2C9, CYP2C19, CYP2C8, and CYP2D6) in vitro.

    PMID:23880855 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3742231 Turpeinen M et al; Int J Mol Sci 14(7): 14064-75 (2013).

    In vitro experiments with human liver microsomes indicated that ospemifene primarily undergoes metabolism via CYP3A4, CYP2C9 and CYP2C19. The major metabolite was 4-hydroxyospemifene. The apparent total body clearance is 9.16 L/hr using a population approach.

    NIH; DailyMed. Current Medication Information for Osphena (Ospemifene) Tablet, Film Coated (Updated: August 2015). Available from, as of November 20, 2015: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=8462d6ab-e3cd-4efa-a360-75bf8f917287

    5.6 Biological Half-Life

    Terminal half-life = 26 hours .

    The apparent terminal half-life of ospemifene in postmenopausal women is approximately 26 hours.

    NIH; DailyMed. Current Medication Information for Osphena (Ospemifene) Tablet, Film Coated (Updated: August 2015). Available from, as of November 20, 2015: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=8462d6ab-e3cd-4efa-a360-75bf8f917287

    5.7 Mechanism of Action

    Ospemifene is a next generation SERM (selective estrogen receptor modulator) that selectively binds to estrogen receptors and either stimulates or blocks estrogen's activity in different tissue types. It has an agonistic effect on the endometrium.

    OSPHENA is an estrogen agonist/antagonist with tissue selective effects. Its biological actions are mediated through binding to estrogen receptors. This binding results in activation of estrogenic pathways in some tissues (agonism) and blockade of estrogenic pathways in others (antagonism).

    NIH; DailyMed. Current Medication Information for Osphena (Ospemifene) Tablet, Film Coated (Updated: August 2015). Available from, as of November 20, 2015: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=8462d6ab-e3cd-4efa-a360-75bf8f917287

    API Reference Price

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    14-Sep-2021
    17-Sep-2024
    KGS
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