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]

Contents

Ormeloxifene has also been licensed under the trade names Ormalin, Novex-DS, Centron, and Sevista.

Medical uses

Ormeloxifene is primarily used as a contraceptive but may also be effective for dysfunctional uterine bleeding and advanced breast cancer. [6]

Birth control

Ormeloxifene may be used as a weekly oral contraceptive. [6] 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.[ citation needed ]

For the first twelve weeks of use, it is advised to take the ormeloxifene pill twice per week. [6] From the thirteenth week on, it is taken once per week. [6] [7] 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%. [8]

It has a failure rate of about 1-2% with ideal use which is slightly less effective than found for combined oral contraceptive pills. [9]

Other indications

Side effects

There are concerns that ormeloxifene may cause delayed menstruation. [12]

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). [13] [14] [15] 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, [9] 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. [9] Presumably, this combination of effects creates an environment such that if fertilization occurs, implantation will not be possible. [9]

History

Ormeloxifene was first discovered by Central Drug Research Institute (CDRI) in Lucknow, India. [13] [16] Ormeloxifene was marketed in Delhi in July 1991 and in India in 1992, under the brand names Saheli and Choice-7. [9] [17]

Since 2018, Centchroman is provided free-of-cost to the women in India by the government under the brand name Chhaya. [4] [18] [19] [20]

Society and culture

Marketing

As of 2009, ormeloxifene was legally available only in India. [21]

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

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 colloquially as "the pill", is a type of birth control that is designed to be taken orally by women. It is the oral form of combined hormonal contraception. 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 names Plan B One-Step and Julie, 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 57–93%. 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">Selective estrogen receptor modulator</span> Drugs acting on the estrogen receptor

Selective estrogen receptor modulators (SERMs), also known as estrogen receptor agonists/antagonists (ERAAs), are a class of drugs that act on estrogen receptors (ERs). Compared to pure ER agonists–antagonists, SERMs are more tissue-specific, allowing them to selectively inhibit or stimulate estrogen-like action in various tissues.

Progestogen-only pills (POPs), colloquially known as "mini pills", are a type of oral contraceptive that contain synthetic progestogens (progestins) and do not contain estrogens. They are primarily used for the prevention of undesired pregnancy, although additional medical uses also exist.

<span class="mw-page-title-main">Ethinylestradiol</span> Estrogen medication

Ethinylestradiol (EE) is an estrogen medication which is used widely in birth control pills in combination with progestins. In the past, EE was widely used for various indications such as the treatment of menopausal symptoms, gynecological disorders, and certain hormone-sensitive cancers. It is usually taken by mouth but is also used as a patch and vaginal ring.

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

Desogestrel is a progestin medication which is used in birth control pills. 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">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">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.

Oral contraceptives, abbreviated OCPs, also known as birth control pills, are medications taken by mouth for the purpose of birth control. The introduction of the birth control pill in 1960 revolutionized the options for contraception, sparking vibrant discussion in the scientific and social science literature and in the media. Much attention focused on issues of women's rights, including ethics and personal choice. But these medications also introduced new questions about risk.

<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> Injectable 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, paraphilia, 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">Ulipristal acetate</span> Chemical compound

Ulipristal acetate, sold under the brand name Ella among others, is a medication used for emergency contraception and uterine fibroids. As emergency contraception it should be used within 120 hours of vaginally penetrating intercourse. For fibroids it may be taken for up to six months. It is taken by mouth.

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

An estrogen (E) is a type of medication which is used most commonly in hormonal birth control and menopausal hormone therapy, and as part of feminizing hormone therapy for transgender women. They can also be used in the treatment of hormone-sensitive cancers like breast cancer and prostate cancer and for various other indications. Estrogens are used alone or in combination with progestogens. They are available in a wide variety of formulations and for use by many different routes of administration. Examples of estrogens include bioidentical estradiol, natural conjugated estrogens, synthetic steroidal estrogens like ethinylestradiol, and synthetic nonsteroidal estrogens like diethylstilbestrol. Estrogens are one of three types of sex hormone agonists, the others being androgens/anabolic steroids like testosterone and progestogens like progesterone.

<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.

The pharmacology of progesterone, a progestogen medication and naturally occurring steroid hormone, concerns its pharmacodynamics, pharmacokinetics, and various routes of administration.

References

  1. ↑ Gupta RC, Paliwal JK, Nityanand S, Asthana OP, Lal J (November 1995). "Centchroman: a new non-steroidal oral contraceptive in human milk". Contraception. 52 (5): 301–305. doi:10.1016/0010-7824(95)00214-U. PMID   8585887.
  2. ↑ Makker A, Tandon I, Goel MM, Singh M, Singh MM (June 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): 2298–2307. 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 "Chhaya". Centre for Health Informatics (CHI) of the National Health Portal (NHP), by the Ministry of Health and Family Welfare (MoHFW). Government of India. Archived from the original on 11 May 2021. Retrieved 29 June 2020.
  5. ↑ "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.
  6. 1 2 3 4 Lal J (April 2010). "Clinical pharmacokinetics and interaction of centchroman--a mini review". Contraception. 81 (4): 275–280. doi:10.1016/j.contraception.2009.11.007. PMID   20227542.
  7. ↑ "Home | ReproLinePlus".
  8. ↑ 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.
  9. 1 2 3 4 5 Singh MM (July 2001). "Centchroman, a selective estrogen receptor modulator, as a contraceptive and for the management of hormone-related clinical disorders". Medicinal Research Reviews. 21 (4): 302–347. doi:10.1002/med.1011. PMID   11410933. S2CID   37474826.
  10. ↑ Kriplani A, Kulshrestha V, Agarwal N (August 2009). "Efficacy and safety of ormeloxifene in management of menorrhagia: a pilot study". The Journal of Obstetrics and Gynaecology Research. 35 (4): 746–752. doi:10.1111/j.1447-0756.2008.00987.x. PMID   19751337. S2CID   39172838.
  11. ↑ Dhar A, Srivastava A (June 2007). "Role of centchroman in regression of mastalgia and fibroadenoma". World Journal of Surgery. 31 (6): 1178–1184. doi:10.1007/s00268-007-9040-4. PMID   17431715. S2CID   22828570.
  12. ↑ 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): 163–181. doi:10.1097/OGX.0b013e31816400d7. PMID   18279543. S2CID   23585991.
  13. 1 2 "CSIR-CDRI | Home". cdri.res.in. Retrieved 29 June 2020.
  14. ↑ Kumar GR, Rituraj K, Hemant BK, Singh MM (November 2007). 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. Vol. 30. p. 35.
  15. ↑ Nigam M, Ranjan V, Srivastava S, Sharma R, Balapure AK (March 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): 577–590. doi:10.1016/j.lfs.2007.11.028. PMID   18279897.
  16. ↑ "Centchroman". CSIR-CDRI. Archived from the original on 14 February 2019. Retrieved 25 September 2018.
  17. ↑ Lal J (April 2010). "Clinical pharmacokinetics and interaction of centchroman--a mini review". Contraception. 81 (4): 275–280. doi:10.1016/j.contraception.2009.11.007. PMID   20227542.
  18. ↑ "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.
  19. ↑ Bhatia I (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.
  20. ↑ Shelar J (12 January 2018). "BMC rolls out new contraceptive pill". The Hindu. ISSN   0971-751X . Retrieved 29 June 2020.
  21. ↑ Tribhuwan RD, Patil BD (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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