Ormeloxifene


Ormeloxifene
Ormeloxifene
Systematic (IUPAC) name
1-[2-[4-[(3S,4R)-7-methoxy-2,2- dimethyl-3-phenyl-chroman-4-yl] phenoxy] ethyl] pyrrolidine
Clinical data
Trade names Centron, Novex-DS, Saheli, Sevista
Pregnancy cat.  ?
Legal status  ?
Routes Oral
Pharmacokinetic data
Half-life 7 days
Identifiers
CAS number 78994-24-8 YesY
ATC code None
PubChem CID 154413
ChemSpider 32935 YesY
UNII 44AXY5VE90 N
KEGG D08301 YesY
ChEMBL CHEMBL301327 YesY
Synonyms Centchroman
Chemical data
Formula C30H35NO3 
Mol. mass 457.604 g/mol
SMILES eMolecules & PubChem
 N(what is this?)  (verify)
Ormeloxifene
Background
Birth control type Anti-estrogen
First use 1991
Failure rates (first year)
Perfect use 2%
Typical use 9%
Usage
Duration effect One week
Reversibility Immediate
User reminders Taken twice weekly for first 13 weeks
Clinic review Annually
Advantages and disadvantages
STD protection No
Periods May disrupt
Weight No proven effect
Medical notes
Only approved as a contraceptive in India

Ormeloxifene (also known as centchroman) is one of the selective estrogen receptor modulators,[1] or SERMs, a class of medication which acts on the estrogen receptor. It is best known as a non-hormonal, non-steroidal oral contraceptive which is taken once per week. In India, ormeloxifene has been available as birth control since the early 1990s, and it is currently marketed there under the trade name Saheli.[2] 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.[3]

As birth control

Ormeloxifene may be used as a weekly oral contraceptive.[3] Hormonal birth control pills should be taken at approximately the same time each day. In the case of progestogen only pills other than Cerazette that do not consistently inhibit ovulation, a delay of as little as three hours can increase the risk of pregnancy because of the limited duration of their effect on the cervical mucus. Ormeloxifene's weekly schedule is an advantage for women who prefer an oral contraceptive, but find it difficult or impractical to adhere to a daily schedule.

For the first twelve weeks of use, it is advised to take the ormeloxifene pill twice per week.[3] From the thirteenth week on, it is taken once per week.[3][4] The consensus is that backup protection in the first month is a cautious but sensible choice. A standard dose is 30mg weekly, but 60mg loading doses can reduce pregnancy rates by 38%.[5]

It has a failure rate of about 1-2% with ideal use which is slight less effective than found for combined oral contraceptive pills.[6]

Other

Ormeloxifene has also been proposed as a treatment for menorrhagia.[7]

Use in treatment of mastalgia and fibroadenoma has also been described.[8]

Adverse effects

There are concerns that ormeloxifene may cause urinary incontinence or uterine prolapse.[9]

Method of action

Ormeloxifene is a SERM, or selective estrogen receptor modulator. In some parts of the body, its action is estrogenic (e.g, bones), in other parts of the body, its action is anti-estrogenic (e.g., uterus, breasts.[10][11]) 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,[6] 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.[6] Presumably, this combination of effects creates an environment such that if fertilization occurs, implantation will not be possible.[6]

Marketing

Ormeloxifene is only legally available in India as of 2009.[12]

Ormeloxifene has been tested and licensed as a form of birth control, as well as a treatment for dysfunctional uterine bleeding. It was first 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 name Saheli. Torrent Pharmaceuticals has resumed manufacture of ormeloxifene under the trade name Sevista, as a treatment for dysfunctional uterine bleeding.

Synthesis

Centchroman synthesis.png

See also

References

  1. ^ 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. 
  2. ^ >">"<< HLL - Product Overview >>". http://www.hindlatex.com/TipsnGuidesdetails.aspx?valid=1&category=0&id=170&type=25. 
  3. ^ a b c d Lal, J (2010 Apr). "Clinical pharmacokinetics and interaction of centchroman--a mini review.". Contraception 81 (4): 275-80. PMID 20227542. 
  4. ^ http://www.reproline.jhu.edu/english/1fp/1advances/old/1centch/ceorvw.htm
  5. ^ 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. 
  6. ^ a b c d 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. 
  7. ^ 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. 
  8. ^ 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. 
  9. ^ Shelly, W; Draper, MW, Krishnan, V, Wong, M, Jaffe, RB (2008 Mar). "Selective estrogen receptor modulators: an update on recent clinical findings.". Obstetrical & gynecological survey 63 (3): 163-81. PMID 18279543. 
  10. ^ 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 p35.
  11. ^ 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. 
  12. ^ Patil, Robin D. Tribhuwan & Benazir D. (2009). Body image : human reproduction and birth control : a tribal perspective. New Delhi: Discovery Pub. House. pp. 20. ISBN 9788183563888. http://books.google.com/books?id=VYYoDoJTwIkC&pg=PA20. 

Further reading

  • Ray, Suprabhat; Grover, Payara K.; Kamboj, Ved P.; Setty, B. S.; Kar, Amiya B.; Anand, Nitya (1976). "Antifertility agents. 12. Structure-activity relation of 3,4-diphenylchromenes and -chromans". Journal of Medicinal Chemistry 19 (2): 276–9. doi:10.1021/jm00224a014. PMID 1249807. 

External links


Wikimedia Foundation. 2010.

Look at other dictionaries:

  • Hormonal contraception — Infobox Birth control name = Hormonal contraception width = caption = bc type = Hormonal date first use = 1960 rate type = Failure perfect failure% = Varies by method: 0.05 2 typical failure% = Varies by method: 0.05 9 duration effect = Various… …   Wikipedia

  • Selective estrogen receptor modulator — Selective Estrogen Receptor Modulators (SERMs) are a class of medication that acts on the estrogen receptor.cite journal |author=Riggs BL, Hartmann LC|title=Selective estrogen receptor modulators mechanisms of action and application to clinical… …   Wikipedia

  • Comparison of birth control methods — Different types of birth control methods have large differences in effectiveness, actions required of users, and side effects. Contents 1 Ease of use 2 User dependence 3 Side effects 4 Effectiveness …   Wikipedia

  • Oral contraceptive — Oral contraceptives are medications taken by mouth for the purpose of birth control.FemaleTwo types of female oral contraceptive pill are widely available: *The combined oral contraceptive pill contains oestrogen and a progestogen, and is taken… …   Wikipedia

  • Hindustan Latex Limited — Infobox Company company name = Hindustan Latex Limited company company type = Public company slogan = Innovating for Healthy Generations foundation = 1966, Thiruvananthapuram location = Thiruvananthapuram, Kerala, India key people = M. Ayyappan,… …   Wikipedia

  • Oral contraceptive pill — Oral contraceptives are medications taken by mouth for the purpose of birth control. Female Two types of female oral contraceptive pill are widely available: The combined oral contraceptive pill contains oestrogen and a progestogen, and is taken… …   Wikipedia

  • Abortion — Induced abortion Classification and external resources ICD 10 O04 …   Wikipedia

  • Coitus interruptus — Background Birth control type Behavioral First use Ancient Failure rates (first year) Perfect use 4% Typical use 15 28% …   Wikipedia

  • Condom — This article is about the transmission barrier and contraceptive device. For other uses, see Condom (disambiguation). Condom …   Wikipedia

  • Intrauterine device — Copper IUD (Paragard T 380A) Hormonal …   Wikipedia


Share the article and excerpts

Direct link
Do a right-click on the link above
and select “Copy Link”

We are using cookies for the best presentation of our site. Continuing to use this site, you agree with this.