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Ormeloxifene

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Ormeloxifene
Clinical data
Trade namesCentron, Novex-DS, Saheli, Sevista, Chhaya
Other namesCentchroman
Routes of
administration		By mouth
Drug classSelective estrogen receptor modulator
ATC code
Legal status
Legal status
  • US: Not FDA approved
  • Rx-only in India
Pharmacokinetic data
Elimination half-life7 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
FormulaC30H35NO3
Molar mass457.614 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 ☒N
  • Key:XZEUAXYWNKYKPL-URLMMPGGSA-N ☒N
 ☒NcheckY (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
RisksDelayed 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]

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

Medical uses

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

Birth control

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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.

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

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Side effects

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

Pharmacology

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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

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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

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Marketing

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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.

  • manufactured by Torrent Pharmaceuticals, and marketed as birth control under the trade name Centron. Centron was discontinued.
  • A new license for ormeloxifene was issued to Hindustan Latex Ltd., which now manufactures ormeloxifene as birth control under the trade names Saheli, Novex, and Novex-DS.
  • Torrent Pharmaceuticals has resumed manufacture of ormeloxifene under the trade name Sevista, as a treatment for dysfunctional uterine bleeding.

See also

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References

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  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. ^ a b "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. ^ a b c d 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. ^ a b c d e 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. ^ a b "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.

Further reading

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  • Ray S, Grover PK, Kamboj VP, Setty BS, Kar AB, Anand N (February 1976). "Antifertility agents. 12. Structure-activity relationship of 3,4-diphenylchromenes and -chromans". Journal of Medicinal Chemistry. 19 (2): 276–279. doi:10.1021/jm00224a014. PMID 1249807.
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