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{{expert-subject|Medicine}}
{{Drugbox
{{BirthControl infobox |
| Verifiedfields = changed
| image                =
| Watchedfields = changed
| width                =
| verifiedrevid = 461741567
| caption              =
| IUPAC_name = 1-[2-[4-[(3''S'',4''R'')-7-methoxy-2,2- dimethyl-3-phenyl-chroman-4-yl] phenoxy] ethyl] pyrrolidine
| bc_type              = Anti-estrogen
| image = Ormeloxifene structure.svg
| date_first_use      = 1988
 
| rate_type            = Failure
<!--Clinical data-->
| perfect_failure%    = 2
| tradename = Centron, Novex-DS, Saheli, Sevista
| typical_failure%    = 9
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| duration_effect      = One week
| pregnancy_US = <!-- A / B            / C / D / X -->
| reversibility        = Immediate
| pregnancy_category =
| user_reminders      = Taken twice weekly for first 13 weeks
| legal_AU = <!-- Unscheduled / S2 / S3 / S4  / S8 -->
| clinic_interval      = Annually
| legal_CA = <!--                            / Schedule I, II, III, IV, V, VI, VII, VIII -->
| STD_protection_YesNo = No
| legal_UK = <!-- GSL        / P      / POM / CD / Class A, B, C -->
| benefits            =
| legal_US = <!-- OTC                  / Rx-only  / Schedule I, II, III, IV, V -->
| periods              = May disrupt
| legal_status =
| weight_gain_loss    = No proven effect
| routes_of_administration = Oral
| risks                =  
 
| medical_notes        = Only approved as a contraceptive in India
<!--Pharmacokinetic data-->
}}
| bioavailability =
{{drugbox |
| protein_bound =
| IUPAC_name = 1-[2-[4-[(3''S'',4''R'')-7-methoxy-2,2- dimethyl-3-phenyl-chroman-4-yl] phenoxy] ethyl] pyrrolidine  
| metabolism =
| image = Ormeloxifene.svg
| elimination_half-life = 7 days
| CAS_number = 78994-24-8  
| excretion =
| ATC_prefix =  
 
| ATC_suffix =  
<!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 78994-24-8
| ATC_prefix = G03
| ATC_suffix = XC04
| PubChem = 154413
| PubChem = 154413
| DrugBank =  
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 32935
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 44AXY5VE90
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D08301
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 301327
| synonyms = Centchroman
 
<!--Chemical data-->
| C=30 | H=35 | N=1 | O=3
| C=30 | H=35 | N=1 | O=3
| molecular_weight = 457.604 g/mol
| molecular_weight = 457.604 g/mol
| bioavailability =  
| smiles = CC1([C@@H]([C@H](c2ccc(cc2O1)OC)c3ccc(cc3)OCCN4CCCC4)c5ccccc5)C
| protein_bound =  
| InChI = 1/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+/m1/s1
| metabolism =
| InChIKey = XZEUAXYWNKYKPL-WDYNHAJCBQ
| elimination_half-life = 7 days
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| excretion =
| StdInChI = 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
| pregnancy_AU =  <!-- A / B1 / B2 / B3 / C / D / X -->
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| pregnancy_US =  <!-- A / B            / C / D / X -->
| StdInChIKey = XZEUAXYWNKYKPL-URLMMPGGSA-N
| pregnancy_category =
}}
| legal_AU = <!-- Unscheduled / S2 / S3 / S4  / S8 -->
{{Infobox Birth control
| legal_CA =  <!--                             / Schedule I, II, III, IV, V, VI, VII, VIII -->
|image                =
| legal_UK = <!-- GSL        / P       / POM / CD / Class A, B, C -->
|width                =
| legal_US = <!-- OTC                  / Rx-only  / Schedule I, II, III, IV, V -->
|caption              =
| legal_status =  
|bc_type              = Anti-estrogen
| routes_of_administration = Oral
|date_first_use      = 1991
|rate_type            = Failure
|perfect_failure%    = 2
|typical_failure%    = 9
|duration_effect      = One week
|reversibility        = Immediate
|user_reminders       = Taken twice weekly for first 13 weeks
|clinic_interval      = Annually
|STD_protection_YesNo = No
|benefits            =
|periods              = May disrupt
|weight_gain_loss    = No proven effect
|risks                =
|medical_notes        = Only approved as a contraceptive in India
}}
}}
'''Ormeloxifene''' (also known as '''Centchroman''') is one of the [[selective estrogen receptor modulator|selective estrogen receptor modulators]], 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'''.  Ormeloxifene has also been licensed under the trade names '''Centron''' and '''Sevista'''.


==Method of action==
'''Ormeloxifene''' (also known as '''centchroman''') is one of the [[selective estrogen receptor modulator]]s,<ref name="pmid18675966">{{cite journal |doi=10.1016/j.fertnstert.2008.04.018 |title=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 |year=2009 |last1=Makker |first1=Annu |last2=Tandon |first2=Indu |last3=Goel |first3=Madhu Mati |last4=Singh |first4=Mastan |last5=Singh |first5=Man Mohan |journal=Fertility and Sterility |volume=91 |issue=6 |pages=2298–307 |pmid=18675966}}</ref> 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'''.<ref>{{cite web |url=http://www.hindlatex.com/TipsnGuidesdetails.aspx?valid=1&category=0&id=170&type=25 |title=HLL - Product Overview |format= |work= |accessdate=}}</ref>  Ormeloxifene has also been licensed under the trade names '''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]].<ref name=Review10>{{cite journal|last=Lal|first=J|title=Clinical pharmacokinetics and interaction of centchroman--a mini review.|journal=Contraception|date=April 2010|volume=81|issue=4|pages=275–80|pmid=20227542|doi=10.1016/j.contraception.2009.11.007}}</ref>
 
===Birth control===
Ormeloxifene may be used as a weekly oral contraceptive.<ref name=Review10/>  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.<ref name=Review10/>  From the thirteenth week on, it is taken once per week.<ref name=Review10/><ref>http://www.reproline.jhu.edu/english/1fp/1advances/old/1centch/ceorvw.htm</ref>
The consensus is that backup protection in the first month is a cautious but sensible choice.  A standard dose is 30&nbsp;mg weekly, but 60&nbsp;mg loading doses can reduce pregnancy rates by 38%.<ref name="pmid11257249">{{cite journal | author = Lal J, Nitynand S, Asthana OP, Nagaraja NV, Gupta RC | title = Optimization of contraceptive dosage regimen of Centchroman | journal = Contraception | volume = 63 | issue = 1 |pages = 47–51 |date=January 2001 | pmid = 11257249 | doi = 10.1016/S0010-7824(00)00189-X }}</ref>


Ormeloxifene is a [[Selective estrogen receptor modulator|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).{{Fact|date=August 2007}} 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 (Singh 2001), 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 tube]]s more quickly than is normal (Singh 2001).  Presumably, this combination of effects creates an environment such that if fertilization occurs, implantation will not be possible.<ref name="Singh 2001">{{cite journal | author = Singh M | title = Centchroman, a selective estrogen receptor modulator, as a contraceptive and for the management of hormone-related clinical disorders.| journal = Med Res Rev | volume = 21 | issue = 4 | pages = 302-47 | year = 2001 | id = PMID 11410933}}</ref>
It has a failure rate of about 1-2% with ideal use which is slightly less effective than found for [[combined oral contraceptive pill]]s.<ref name="Singh 2001"/>


==Usage==
===Other indications===
Ormeloxifene may be used as a contraceptive or as a treatment for dysfunctional uterine bleeding.
* Ormeloxifene has also been tested in experimental setting as a treatment for [[menorrhagia]].<ref name="pmid19751337">{{cite journal | author = Kriplani A, Kulshrestha V, Agarwal N | title = Efficacy and safety of ormeloxifene in management of menorrhagia: a pilot study | journal = J. Obstet. Gynaecol. Res. | volume = 35 | issue = 4 | pages = 746–52 |date=August 2009 | pmid = 19751337 | doi = 10.1111/j.1447-0756.2008.00987.x }}</ref>


===As birth control===
* use in treatment of [[mastalgia]] and [[fibroadenoma]] has also been described.<ref name="pmid17431715">{{cite journal | author = Dhar A, Srivastava A | title = Role of centchroman in regression of mastalgia and fibroadenoma | journal = World J Surg | volume = 31 | issue = 6 |pages = 1178–84 |date=June 2007 | pmid = 17431715 | doi = 10.1007/s00268-007-9040-4 }}</ref>
Ormeloxifene may be used as a weekly oral contraceptive.  This is touted as a major advantage by its developer and its manufacturer. Hormonal birth control pills should be taken at approximately the same time each day.  In the case of [[progestogen only pill]]s 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.  From the thirteenth week on, it is taken once per week. The consensus is that backup protection in the first month is a cautious but sensible choice.{{Fact|date=August 2007}}
==Adverse effects==
There are concerns that ormeloxifene may cause [[delayed mensturation]].<ref>{{cite journal|last=Shelly|first=W|coauthors=Draper, MW, Krishnan, V, Wong, M, Jaffe, RB|title=Selective estrogen receptor modulators: an update on recent clinical findings.|journal=Obstetrical & gynecological survey|date=March 2008|volume=63|issue=3|pages=163–81|pmid=18279543|doi=10.1097/OGX.0b013e31816400d7}}</ref>


==Effectiveness==
==Method of action==
One [[Clinical trial#Phase III|Phase III]] [[multicenter trial]] of ormeloxifene 30 mg weekly by 898 women for an average of 15 months found a ''method failure'' [[Pearl Index]] of 2.84.<!--
  --><ref name="Puri 1988">{{cite book |author=Puri V, et al. |year=1988 |chapter=Results of multicentric trial of Centchroman |editor=Dhwan B. N., et al. (eds.) |title=Pharmacology for Health in Asia : Proceedings of Asian Congress of Pharmacology, 15-19 January 1985, New Dehli, India |location=Ahmedabad |publisher=Allied Publishers}}</ref>


A second Phase III multicenter trial of ormeloxifene 30 mg twice-a-week for 3 months followed by 30 mg weekly by 376 women for an average of 10.5 months found a ''method failure'' Pearl Index of 1.83 and a 12-month [[decrement table|life-table]] ''method failure'' pregnancy rate of 1.63% ±0.74%.<!--
Ormeloxifene is a [[Selective estrogen receptor modulator|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.<ref>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.</ref><ref name="pmid18279897">{{cite journal |doi=10.1016/j.lfs.2007.11.028 |title=Centchroman induces G0/G1 arrest and Caspase-dependent Apoptosis involving Mitochondrial Membrane Depolarization in MCF-7 and MDA MB-231 Human Breast Cancer Cells |year=2008 |last1=Nigam |first1=Manisha |last2=Ranjan |first2=Vishal |last3=Srivastava |first3=Swasti |last4=Sharma |first4=Ramesh |last5=Balapure |first5=Anil K. |journal=Life Sciences |volume=82 |issue=11–12 |pages=577–90 |pmid=18279897}}</ref>) 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,<ref name="Singh 2001"/> 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 tube]]s more quickly than is normal.<ref name="Singh 2001"/>  Presumably, this combination of effects creates an environment such that if fertilization occurs, implantation will not be possible.<ref name="Singh 2001">{{cite journal |doi=10.1002/med.1011 |title=Centchroman, a selective estrogen receptor modulator, as a contraceptive and for the management of hormone-related clinical disorders |year=2001 |last1=Singh |first1=M.M. |journal=Medicinal Research Reviews |volume=21 |issue=4 |pages=302–47 |pmid=11410933}}</ref>
  --><ref name="Nityanand 1990">{{cite book |author=Nityanand S, et al. |year=1990 |chapter=Clinical evaluation of Centchroman: a new oral contraceptive |editor=Puri, Chander P.; Van Look, Paul F. A. (eds.) |title=Hormone Antagonists for Fertility Regulation |location=Bombay |publisher=Indian Society for the Study of Reproduction and Fertility}}</ref>


The overall ''actual use'' (''method failure'' plus ''user failure'') Pearl Index was 9 in both Phase III multicenter trials of ormeloxifene — an order of magnitude less effective than found in Phase III multicenter trials of [[combined oral contraceptive pill]]s.<ref name="Singh 2001"/>
==Marketing==
Ormeloxifene is only legally available in India as of 2009.<ref>{{cite book|last=Patil|first=Robin D. Tribhuwan & Benazir D.|title=Body image : human reproduction and birth control : a tribal perspective|year=2009|publisher=Discovery Pub. House|location=New Delhi|isbn=978-81-8356-388-8|pages=20|url=http://books.google.com/books?id=VYYoDoJTwIkC&pg=PA20}}</ref>


==Manufacture and marketing==
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''', '''Novex''' and '''Novex-DS'''.  Torrent Pharmaceuticals has resumed manufacture of ormeloxifene under the trade name '''Sevista''', as a treatment for dysfunctional uterine bleeding.
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==
[[File:Centchroman synthesis.png|600px]]


==See also==
==See also==
* [[Hormonal contraception]]
* [[Hormonal contraception]]
* [[Selective estrogen receptor modulator]]
* [[Levormeloxifene]], a related SERM
* [[Reproductive health]]


==References==
==References==
{{reflist|2}}
{{Reflist|2}}
 
==Further reading==
*{{cite journal |doi=10.1021/jm00224a014 |title=Antifertility agents. 12. Structure-activity relation of 3,4-diphenylchromenes and -chromans |year=1976 |last1=Ray |first1=Suprabhat |last2=Grover |first2=Payara K. |last3=Kamboj |first3=Ved P. |last4=Setty |first4=B. S. |last5=Kar |first5=Amiya B. |last6=Anand |first6=Nitya |journal=Journal of Medicinal Chemistry |volume=19 |issue=2 |pages=276–9 |pmid=1249807}}


==External links==
==External links==
* [http://www.nlm.nih.gov/cgi/mesh/2006/MB_cgi United States National Library of Medicine] ''Ormeloxifene'' entry in the [[Medical Subject Headings]] (MeSH) database
* [http://www.nlm.nih.gov/cgi/mesh/2006/MB_cgi?mode=&term=Centchroman&field=entry United States National Library of Medicine] ''Centchroman'' entry in the [[Medical Subject Headings]] (MeSH) database
* [http://www.nlm.nih.gov/cgi/mesh/2006/MB_cgi?mode=&term=Centchroman&field=entry United States National Library of Medicine] ''Centchroman'' entry in the [[Medical Subject Headings]] (MeSH) database
* [http://www.reproline.jhu.edu/english/1fp/1advances/old/1centch/ceorvw.htm Reproductive Health Online], a [[Johns Hopkins University]] affiliate providing information on Centchroman
* [http://www.reproline.jhu.edu/english/1fp/1advances/old/1centch/ceorvw.htm Reproductive Health Online], a [[Johns Hopkins University]] affiliate providing information on Centchroman
* [http://www.hindlatex.com/TipsnGuidesdetails.aspx?valid=1&category=0&id=170&type=25 Saheli manufacturer's website] - Product details
* [http://www.hindlatex.com/TipsnGuidesdetails.aspx?valid=1&category=0&id=170&type=25 Saheli manufacturer's website] - Product details
* [http://www.hindlatex.com/TipsnGuidesdetails.aspx?valid=1&category=0&id=166&type=17 Saheli manufacturer's website] - Clinical studies
* [http://www.cdriindia.org/Centchroman.htm Central Drug Research Institute], Lucknow, [[India]]: a government-funded laboratory, conducting [[R&D]] on Centchroman as birth control.
* [http://www.cdriindia.org/Centchroman.htm Central Drug Research Institute], Lucknow, [[India]]: a government-funded laboratory, conducting [[R&D]] on Centchroman as birth control.  
* [http://mohfw.nic.in/ Ministry of Health and Family Welfare] - Indian government site; information about availability of Saheli.
* [http://mohfw.nic.in/ Ministry of Health and Family Welfare] - Indian government site; information about availability of Saheli.  
 
*  [http://www.aphroditewomenshealth.com/forums/ubbthreads.php?ubb=postlist&Board=4 Aphrodite Women's Health] - user experiences of Centchroman
* [http://health.groups.yahoo.com/group/centchroman/ Centchroman Health Group] - user experiences of Centchroman


{{BirthControl}}
{{Estrogens}}
{{Birth control methods}}
{{Estrogenics}}
{{Use dmy dates|date=September 2011}}


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Revision as of 12:29, 8 April 2015

Ormeloxifene
File:Ormeloxifene structure.svg
Clinical data
Trade namesCentron, Novex-DS, Saheli, Sevista
SynonymsCentchroman
Routes of
administration		Oral
ATC code
Pharmacokinetic data
Elimination half-life7 days
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC30H35NO3
Molar mass457.604 g/mol
3D model (JSmol)
 ☒N☑Y (what is this?)  (verify)

Template:Infobox Birth control

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.

Medical uses

Ormeloxifene is primarily used as a contraceptive but may also be effective for dysfunctional uterine bleeding and advanced breast cancer.[3]

Birth control

Ormeloxifene may be used as a weekly oral contraceptive.[3] 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.[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 30 mg weekly, but 60 mg loading doses can reduce pregnancy rates by 38%.[5]

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

Other indications

  • Ormeloxifene has also been tested in experimental setting as a treatment for menorrhagia.[7]

Adverse effects

There are concerns that ormeloxifene may cause delayed mensturation.[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, Novex and Novex-DS. Torrent Pharmaceuticals has resumed manufacture of ormeloxifene under the trade name Sevista, as a treatment for dysfunctional uterine bleeding.

Synthesis

File: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".
  3. ↑ 3.0 3.1 3.2 3.3 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.
  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. ↑ 6.0 6.1 6.2 6.3 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 (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. Unknown parameter |coauthors= ignored (help)
  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. p. 20. ISBN 978-81-8356-388-8.

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


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