Ormeloxifene

Last updated

Ormeloxifene
Ormeloxifene structure.svg
Clinical data
Trade names Centron, Novex-DS, Saheli, Sevista, Chhaya
Other namesCentchroman
Routes of
administration 		By mouth
Drug class Selective estrogen receptor modulator
ATC code
Legal status
Legal status
  • US:Not FDA approved
  • Rx-only in India
Pharmacokinetic data
Elimination half-life 7 days
Identifiers
  • 1-[2-[4-[(3S,4S)-7-methoxy-2,2-dimethyl-3-phenyl-chroman-4-yl]phenoxy]ethyl]pyrrolidine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
Formula C30H35NO3
Molar mass 457.614 g·mol−1
3D model (JSmol)
  • CC1([C@@H]([C@H](c2ccc(cc2O1)OC)c3ccc(cc3)OCCN4CCCC4)c5ccccc5)C
  • InChI=1S/C30H35NO3/c1-30(2)29(23-9-5-4-6-10-23)28(26-16-15-25(32-3)21-27(26)34-30)22-11-13-24(14-12-22)33-20-19-31-17-7-8-18-31/h4-6,9-16,21,28-29H,7-8,17-20H2,1-3H3/t28-,29+/m0/s1 X mark.svgN
  • Key:XZEUAXYWNKYKPL-URLMMPGGSA-N X mark.svgN
 X mark.svgNYes check.svgY  (what is this?)    (verify)
Ormeloxifene
Background
TypeAntiestrogen
First use1991
Failure rates (first year)
Perfect use2%
Typical use9%
Usage
Duration effectOne week
ReversibilityImmediate
User remindersTaken twice weekly for first 13 weeks
Clinic reviewAnnually
Advantages and disadvantages
STI protectionNo
PeriodsMay disrupt
Safe while breastfeedingYes [1]
WeightNo proven effect
BenefitsNon hormonal
Risks Delayed menstruation
Medical notes
Only approved as a contraceptive in India

Ormeloxifene, also known as centchroman, is one of the selective estrogen receptor modulators, [2] or SERMs, a class of medication which acts on the estrogen receptor. It is best known as a nonsteroidal oral contraceptive which is taken once per week. In India, ormeloxifene has been available as birth control since the early 1990s, and it was marketed there under the trade name Saheli, [3] currently available free-of-cost for the women in India as Chhaya (Centchroman). [4] [5] [6] [7] [8] [9] Ormeloxifene has also been licensed under the trade names Novex-DS, Centron, and Sevista.

Contents

Medical uses

Ormeloxifene is primarily used as a contraceptive but may also be effective for dysfunctional uterine bleeding and advanced breast cancer. [10]

Birth control

Ormeloxifene may be used as a weekly oral contraceptive. [10] The weekly schedule is an advantage for women who prefer an oral contraceptive, but find it difficult or impractical to adhere to a daily schedule required by other oral contraceptives.

For the first twelve weeks of use, it is advised to take the ormeloxifene pill twice per week. [10] From the thirteenth week on, it is taken once per week. [10] [11] The consensus is that backup protection in the first month is a cautious but sensible choice. A standard dose is 30 mg weekly, but 60 mg loading doses can reduce pregnancy rates by 38%. [12]

It has a failure rate of about 1-2% with ideal use which is slightly less effective than found for combined oral contraceptive pills. [13]

Other indications

Side effects

There are concerns that ormeloxifene may cause delayed menstruation. [16]

Pharmacology

Ormeloxifene is a selective estrogen receptor modulator (SERM). In some parts of the body, its action is estrogenic (e.g., bones), in other parts of the body, its action is antiestrogenic (e.g., uterus, breasts). [17] [18] [19] It causes an asynchrony in the menstrual cycle between ovulation and the development of the uterine lining, although its exact mode of action is not well defined. In clinical trials, it caused ovulation to occur later than it normally would in some women, [13] but did not affect ovulation in the majority of women, while causing the lining of the uterus to build more slowly. It speeds the transport of any fertilized egg through the fallopian tubes more quickly than is normal. [13] Presumably, this combination of effects creates an environment such that if fertilization occurs, implantation will not be possible. [13]

History

Ormeloxifene was first discovered by Central Drug Research Institute (CDRI) in Lucknow, India. [17] [20] Ormeloxifene was marketed in Delhi in July 1991 and in India in 1992, under the brand names Saheli and Choice-7. [21] [22]

Since 2018, Centchroman is provided free-of-cost to the women in India by the government under the brand name Chhaya. [4] [5] [7] [8]

Society and culture

Marketing

As of 2009, ormeloxifene was legally available only in India. [23]

Ormeloxifene has been tested and licensed as a form of birth control, as well as a treatment for dysfunctional uterine bleeding.

See also

Related Research Articles

<span class="mw-page-title-main">Emergency contraception</span> Birth control measures taken after sexual intercourse

Emergency contraception (EC) is a birth control measure, used after sexual intercourse to prevent pregnancy.

<span class="mw-page-title-main">Combined oral contraceptive pill</span> Birth control method which is taken orally

The combined oral contraceptive pill (COCP), often referred to as the birth control pill, or simply as the pill, is a type of birth control that is designed to be taken orally by women. The pill contains two important hormones: a progestin and estrogen. When taken correctly, it alters the menstrual cycle to eliminate ovulation and prevent pregnancy.

<span class="mw-page-title-main">Progestogen (medication)</span> Medication producing effects similar to progesterone

A progestogen, also referred to as a progestagen, gestagen, or gestogen, is a type of medication which produces effects similar to those of the natural female sex hormone progesterone in the body. A progestin is a synthetic progestogen. Progestogens are used most commonly in hormonal birth control and menopausal hormone therapy. They can also be used in the treatment of gynecological conditions, to support fertility and pregnancy, to lower sex hormone levels for various purposes, and for other indications. Progestogens are used alone or in combination with estrogens. They are available in a wide variety of formulations and for use by many different routes of administration. Examples of progestogens include natural or bioidentical progesterone as well as progestins such as medroxyprogesterone acetate and norethisterone.

<span class="mw-page-title-main">Levonorgestrel</span> Hormonal medication used for birth control

Levonorgestrel is a hormonal medication which is used in a number of birth control methods. It is combined with an estrogen to make combination birth control pills. As an emergency birth control, sold under the brand name Plan B One-Step among others, it is useful within 72 hours of unprotected sex. The more time that has passed since sex, the less effective the medication becomes, and it does not work after pregnancy (implantation) has occurred. Levonorgestrel works by preventing ovulation or fertilization from occurring. It decreases the chances of pregnancy by 57 to 93%. In an intrauterine device (IUD), such as Mirena among others, it is effective for the long-term prevention of pregnancy. A levonorgestrel-releasing implant is also available in some countries.

<span class="mw-page-title-main">Desogestrel</span> Medication

Desogestrel is a progestin medication which is used in birth control pills for women. It is also used in the treatment of menopausal symptoms in women. The medication is available and used alone or in combination with an estrogen. It is taken by mouth.

<span class="mw-page-title-main">Drospirenone</span> Medication drug

Drospirenone is a progestin and antiandrogen medication which is used in birth control pills to prevent pregnancy and in menopausal hormone therapy, among other uses. It is available both alone under the brand name Slynd and in combination with an estrogen under the brand name Yasmin among others. The medication Is an analog of the drug spironolactone. Drospirenone is taken by mouth.

<span class="mw-page-title-main">Hormonal contraception</span> Birth control methods that act on the endocrine system

Hormonal contraception refers to birth control methods that act on the endocrine system. Almost all methods are composed of steroid hormones, although in India one selective estrogen receptor modulator is marketed as a contraceptive. The original hormonal method—the combined oral contraceptive pill—was first marketed as a contraceptive in 1960. In the ensuing decades many other delivery methods have been developed, although the oral and injectable methods are by far the most popular. Hormonal contraception is highly effective: when taken on the prescribed schedule, users of steroid hormone methods experience pregnancy rates of less than 1% per year. Perfect-use pregnancy rates for most hormonal contraceptives are usually around the 0.3% rate or less. Currently available methods can only be used by women; the development of a male hormonal contraceptive is an active research area.

<span class="mw-page-title-main">Levormeloxifene</span> Chemical compound

Levormeloxifene is a selective estrogen receptor modulator (SERM) which was being developed as an alternative to estrogen replacement therapy for the treatment and prevention of postmenopausal bone loss but did not complete development and hence was never marketed. The development was stopped because of a high incidence of gynecological side effects during clinical trials. Levormeloxifene is the levorotatory enantiomer of ormeloxifene, which, in contrast, has been marketed, though rather as a hormonal contraceptive.

<span class="mw-page-title-main">Norethisterone</span> Progestin medication

Norethisterone, also known as norethindrone and sold under many brand names, is a progestin medication used in birth control pills, menopausal hormone therapy, and for the treatment of gynecological disorders. The medication is available in both low-dose and high-dose formulations and both alone and in combination with an estrogen. It is used by mouth or, as norethisterone enanthate, by injection into muscle.

<span class="mw-page-title-main">Gestodene</span> Progestin medication

Gestodene, sold under the brand names Femodene and Minulet among others, is a progestin medication which is used in birth control pills for women. It is also used in menopausal hormone therapy. The medication is available almost exclusively in combination with an estrogen. It is taken by mouth.

<span class="mw-page-title-main">Mestranol</span> Chemical compound

Mestranol, sold under the brand names Enovid, Norinyl, and Ortho-Novum among others, is an estrogen medication which has been used in birth control pills, menopausal hormone therapy, and the treatment of menstrual disorders. It is formulated in combination with a progestin and is not available alone. It is taken by mouth.

Oral contraceptives, abbreviated OCPs, also known as birth control pills, are medications taken by mouth for the purpose of birth control.

<span class="mw-page-title-main">Estetrol</span> Chemical compound

Estetrol (E4), or oestetrol, is one of the four natural estrogenic steroid hormones found in humans, along with estrone (E1), estradiol (E2), and estriol (E3). Estetrol is a major estrogen in the body. In contrast to estrone and estradiol, estetrol is a native estrogen of fetal life. Estetrol is produced exclusively by the fetal liver and is found in detectable levels only during pregnancy, with relatively high levels in the fetus and lower levels in the maternal circulation.

<span class="mw-page-title-main">Medroxyprogesterone acetate</span> Injectible form of birth control

Medroxyprogesterone acetate (MPA), also known as depot medroxyprogesterone acetate (DMPA) in injectable form and sold under the brand name Depo-Provera among others, is a hormonal medication of the progestin type. It is used as a method of birth control and as a part of menopausal hormone therapy. It is also used to treat endometriosis, abnormal uterine bleeding, abnormal sexuality in males, and certain types of cancer. The medication is available both alone and in combination with an estrogen. It is taken by mouth, used under the tongue, or by injection into a muscle or fat.

<span class="mw-page-title-main">Anordrin</span> Chemical compound

Anordrin, also known as 2α,17α-diethynyl-A-nor-5α-androstane-2β,17β-diol dipropionate, is a synthetic, steroidal selective estrogen receptor modulator (SERM) which is used in China as an emergency contraceptive. It is the most commonly used emergency contraceptive in China. The drug is marketed in a combination formulation with mifepristone under the brand name Zi Yun. Anordrin has not been studied for use or marketed outside of China. It has been used in China since the 1970s.

<span class="mw-page-title-main">Estradiol (medication)</span> Steroidal hormone medication

Estradiol (E2) is a medication and naturally occurring steroid hormone. It is an estrogen and is used mainly in menopausal hormone therapy and to treat low sex hormone levels in women. It is also used in hormonal birth control for women, in hormone therapy for transgender women, and in the treatment of hormone-sensitive cancers like prostate cancer in men and breast cancer in women, among other uses. Estradiol can be taken by mouth, held and dissolved under the tongue, as a gel or patch that is applied to the skin, in through the vagina, by injection into muscle or fat, or through the use of an implant that is placed into fat, among other routes.

<span class="mw-page-title-main">Progesterone (medication)</span> Medication and naturally occurring steroid hormone

Progesterone (P4) is a medication and naturally occurring steroid hormone. It is a progestogen and is used in combination with estrogens mainly in hormone therapy for menopausal symptoms and low sex hormone levels in women. It is also used in women to support pregnancy and fertility and to treat gynecological disorders. Progesterone can be taken by mouth, in through the vagina, and by injection into muscle or fat, among other routes. A progesterone vaginal ring and progesterone intrauterine device used for birth control also exist in some areas of the world.

<span class="mw-page-title-main">Estetrol (medication)</span> Estrogen medication

Estetrol (E4) is an estrogen medication and naturally occurring steroid hormone which is used in combination with a progestin in combined birth control pills and is under development for various other indications. These investigational uses include menopausal hormone therapy to treat symptoms such as vaginal atrophy, hot flashes, and bone loss and the treatment of breast cancer and prostate cancer. It is taken by mouth.

References

  1. ↑ Gupta RC, Paliwal JK, Nityanand S, Asthana OP, Lal J (1995). "Centchroman: a new non-steroidal oral contraceptive in human milk". Contraception. 52 (5): 301–5. doi:10.1016/0010-7824(95)00214-U. PMID   8585887.
  2. ↑ Makker, Annu; Tandon, Indu; Goel, Madhu Mati; Singh, Mastan; Singh, Man Mohan (2009). "Effect of ormeloxifene, a selective estrogen receptor modulator, on biomarkers of endometrial receptivity and pinopode development and its relation to fertility and infertility in Indian subjects". Fertility and Sterility. 91 (6): 2298–307. doi: 10.1016/j.fertnstert.2008.04.018 . PMID   18675966.
  3. ↑ "HLL - Product Overview". Archived from the original on 1 November 2018.
  4. 1 2 humdo.nhp.gov.in https://humdo.nhp.gov.in/choice_for_planning/chhaya/ . Retrieved 29 June 2020.{{cite web}}: Missing or empty |title= (help)
  5. 1 2 "परिवार नियोजन विधियों में छाया से अधिक अंतरा में बढ़ी महिलाओं की दिलचस्पी, जानिये इनके बारे में". Patrika News (in Hindi). 22 May 2018. Retrieved 29 June 2020.
  6. ↑ "New Contraceptives". Hum Do | Family Planning. 28 July 2017. Retrieved 29 June 2020.
  7. 1 2 Bhatia, Ishita (7 April 2018). "antara chhaya: Two months after launch, Antara, Chhaya contraceptives get good response from locals". The Times of India. Retrieved 29 June 2020.
  8. 1 2 Shelar, Jyoti (12 January 2018). "BMC rolls out new contraceptive pill". The Hindu. ISSN   0971-751X . Retrieved 29 June 2020.
  9. ↑ "Contraception and women's empowerment: Here's how safe, reliable contraceptives are freeing women to earn". Hindustan Times. 10 July 2018. Retrieved 29 June 2020.
  10. 1 2 3 4 Lal, J (April 2010). "Clinical pharmacokinetics and interaction of centchroman--a mini review". Contraception. 81 (4): 275–80. doi:10.1016/j.contraception.2009.11.007. PMID   20227542.
  11. ↑ "Home | ReproLinePlus".
  12. ↑ Lal J, Nitynand S, Asthana OP, Nagaraja NV, Gupta RC (January 2001). "Optimization of contraceptive dosage regimen of Centchroman". Contraception. 63 (1): 47–51. doi:10.1016/S0010-7824(00)00189-X. PMID   11257249.
  13. 1 2 3 4 Singh, M.M. (2001). "Centchroman, a selective estrogen receptor modulator, as a contraceptive and for the management of hormone-related clinical disorders". Medicinal Research Reviews. 21 (4): 302–47. doi:10.1002/med.1011. PMID   11410933. S2CID   37474826.
  14. ↑ Kriplani A, Kulshrestha V, Agarwal N (August 2009). "Efficacy and safety of ormeloxifene in management of menorrhagia: a pilot study". J. Obstet. Gynaecol. Res. 35 (4): 746–52. doi:10.1111/j.1447-0756.2008.00987.x. PMID   19751337. S2CID   39172838.
  15. ↑ Dhar A, Srivastava A (June 2007). "Role of centchroman in regression of mastalgia and fibroadenoma". World J Surg. 31 (6): 1178–84. doi:10.1007/s00268-007-9040-4. PMID   17431715. S2CID   22828570.
  16. ↑ Shelly, W; Draper, MW; Krishnan, V; Wong, M; Jaffe, RB (March 2008). "Selective estrogen receptor modulators: an update on recent clinical findings". Obstetrical & Gynecological Survey. 63 (3): 163–81. doi:10.1097/OGX.0b013e31816400d7. PMID   18279543. S2CID   23585991.
  17. 1 2 "CSIR-CDRI | Home". cdri.res.in. Retrieved 29 June 2020.
  18. ↑ Gara Rishi Kumar, Konwar Rituraj, Bid Hemant K and MM Singh. In-vitro anti-cancer breast activity of ormeloxifene is mediated via induction of apoptosis and autophagy. 37th annual conference of the endocrine society of India. 30 Nov – 2 Dec 2007. Abstract p. 35.
  19. ↑ Nigam, Manisha; Ranjan, Vishal; Srivastava, Swasti; Sharma, Ramesh; Balapure, Anil K. (2008). "Centchroman induces G0/G1 arrest and Caspase-dependent Apoptosis involving Mitochondrial Membrane Depolarization in MCF-7 and MDA MB-231 Human Breast Cancer Cells". Life Sciences. 82 (11–12): 577–90. doi:10.1016/j.lfs.2007.11.028. PMID   18279897.
  20. ↑ "Centchroman". CSIR-CDRI. Archived from the original on 14 February 2019. Retrieved 25 September 2018.
  21. ↑ Singh MM (2001). "Centchroman, a selective estrogen receptor modulator, as a contraceptive and for the management of hormone-related clinical disorders". Med Res Rev. 21 (4): 302–47. doi:10.1002/med.1011. PMID   11410933. S2CID   37474826.
  22. ↑ Lal J (2010). "Clinical pharmacokinetics and interaction of centchroman--a mini review". Contraception. 81 (4): 275–80. doi:10.1016/j.contraception.2009.11.007. PMID   20227542.
  23. ↑ Patil, Robin D. Tribhuwan & Benazir D. (2009). Body image : human reproduction and birth control : a tribal perspective. New Delhi: Discovery Pub. House. p. 20. ISBN   978-81-8356-388-8.

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