Ormeloxifene free base
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MedKoo CAT#: 584947

CAS#: 31477-60-8 (free base)

Description: Ormeloxifene, also known as centchroman, is one of the selective estrogen receptor modulators, or SERMs, a class of medication which acts on the estrogen receptor. 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). 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, ] but did not affect ovulation in the majority of women, while causing the lining of the uterus to build more slowly.


Chemical Structure

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Ormeloxifene free base
CAS# 31477-60-8 (free base)

Theoretical Analysis

MedKoo Cat#: 584947
Name: Ormeloxifene free base
CAS#: 31477-60-8 (free base)
Chemical Formula: C30H35NO3
Exact Mass: 457.2617
Molecular Weight: 457.614
Elemental Analysis: C, 78.74; H, 7.71; N, 3.06; O, 10.49

Price and Availability

Size Price Availability Quantity
5.0mg USD 270.0 2 Weeks
25.0mg USD 650.0 2 Weeks
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Related CAS #: 31477-60-8 (free base)   51023-56-4 (HCl)    

Synonym: Ormeloxifene; Centchroman; 67/20CDRI; CDRI 67/20; CDRI-67/20; CDRI6720; CDRI 6/20; CDRI-6720; CDRI67/20;

IUPAC/Chemical Name: Pyrrolidine, 1-(2-(4-(3,4-dihydro-7-methoxy-2,2-dimethyl-3-phenyl-2H-1-benzopyran-4-yl)phenoxy)ethyl)-, trans-

InChi Key: XZEUAXYWNKYKPL-URLMMPGGSA-N

InChi Code: 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

SMILES Code: CC1(C)[C@H](C2=CC=CC=C2)[C@@H](C3=CC=C(OCCN4CCCC4)C=C3)C5=CC=C(OC)C=C5O1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 457.614 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Sharma A, Jaiswal S, Shukla M, Ravindrachary K, Lal J. Coadministration of HMG-CoA reductase inhibitors, atorvastatin and rosuvastatin, does not affect contraceptive efficacy of centchroman. Eur J Contracept Reprod Health Care. 2015 Jun;20(3):231-5. doi: 10.3109/13625187.2015.1017756. Epub 2015 Mar 23. PubMed PMID: 25798535.

2: Kamboj VP, Ray S, Anand N. Centchroman: A safe reversible postcoital contraceptive with curative and prophylactic activity in many disorders. Front Biosci (Elite Ed). 2018 Jan 1;10:1-14. PubMed PMID: 28930603.

3: Rathi J, Chawla I, Singh K, Chawla A. Centchroman as First-line Treatment for Mastalgia: Results of an Open-label, Single-arm Trial. Breast J. 2016 Jul;22(4):407-12. doi: 10.1111/tbj.12593. Epub 2016 Apr 5. PubMed PMID: 27059808.

4: Jain BK, Bansal A, Choudhary D, Garg PK, Mohanty D. Centchroman vs tamoxifen for regression of mastalgia: a randomized controlled trial. Int J Surg. 2015 Mar;15:11-6. doi: 10.1016/j.ijsu.2014.12.033. Epub 2015 Jan 22. PubMed PMID: 25619124.

5: Dewangan J, Kaushik S, Rath SK, Balapure AK. Centchroman regulates breast cancer angiogenesis via inhibition of HIF-1α/VEGFR2 signalling axis. Life Sci. 2018 Jan 15;193:9-19. doi: 10.1016/j.lfs.2017.11.045. Epub 2017 Nov 28. PubMed PMID: 29196053.

6: Shyam H, Singh N, Kaushik S, Sharma R, Balapure AK. Centchroman induces redox-dependent apoptosis and cell-cycle arrest in human endometrial cancer cells. Apoptosis. 2017 Apr;22(4):570-584. doi: 10.1007/s10495-017-1346-6. PubMed PMID: 28176146.

7: Tejwani PL, Srivastava A, Nerkar H, Dhar A, Hari S, Thulkar S, Chumber S, Kumar S. Centchroman regresses mastalgia: a randomized comparison with danazol. Indian J Surg. 2011 Jun;73(3):199-205. doi: 10.1007/s12262-010-0216-z. Epub 2010 Nov 30. PubMed PMID: 22654331; PubMed Central PMCID: PMC3087062.

8: Khan S, Shukla S, Sinha S, Meeran SM. Centchroman altered the expressions of tumor-related genes through active chromatin modifications in mammary cancer. Mol Carcinog. 2016 Nov;55(11):1747-1760. doi: 10.1002/mc.22424. Epub 2015 Oct 14. PubMed PMID: 26465660.

9: Kumar V, Lal J, Singh MM, Gupta RC. Effect of concurrently coadministered drugs on the pharmacokinetic/pharmacodynamic profile of centchroman, a nonsteroidal oral contraceptive, in rats. Contraception. 2006 Aug;74(2):165-73. Epub 2006 Apr 27. PubMed PMID: 16860055.

10: Kaushik S, Shyam H, Sharma R, Balapure AK. Genistein synergizes centchroman action in human breast cancer cells. Indian J Pharmacol. 2016 Nov-Dec;48(6):637-642. doi: 10.4103/0253-7613.194852. PubMed PMID: 28066099; PubMed Central PMCID: PMC5155462.

11: Mukhopadhyay A, Ray S, Giri AK. Anticlastogenic effects of d- and l-centchroman in Swiss albino mice. 2. Subacute study in vivo and comparison with tamoxifen. Cytobios. 2001;106(412):77-86. PubMed PMID: 11503975.

12: Gupta V, Singh S, Srivarstava M, Ahmad H, Pachauri SD, Khandelwal K, Dwivedi P, Dwivedi AK. Effect of polydimethylsiloxane and ethylcellulose on in vitro permeation of centchroman from its transdermal patches. Drug Deliv. 2016;23(1):113-22. doi: 10.3109/10717544.2014.905882. Epub 2014 Apr 30. PubMed PMID: 24786481.

13: Tejwani PL, Nerkar H, Dhar A, Kataria K, Hari S, Thulkar S, Chumber S, Kumar S, Srivastava A. Regression of Fibroadenomas with Centchroman: a Randomized Controlled Trial. Indian J Surg. 2015 Dec;77(Suppl 2):484-9. doi: 10.1007/s12262-013-0886-4. Epub 2013 Feb 21. PubMed PMID: 26730050; PubMed Central PMCID: PMC4692841.

14: Ghassab-Abdollahi N, Mirghafourvand M, Osouli Tabrizi S. The effect of centchroman on mastalgia: a systematic review. Eur J Contracept Reprod Health Care. 2019 Feb;24(1):71-79. doi: 10.1080/13625187.2018.1564816. Epub 2019 Feb 7. PubMed PMID: 30730217.

15: Singh MM. Centchroman, a selective estrogen receptor modulator, as a contraceptive and for the management of hormone-related clinical disorders. Med Res Rev. 2001 Jul;21(4):302-47. Review. PubMed PMID: 11410933.

16: Paliwal JK, Grover PK, Asthana OP, Nityanand S, Gupta RC. Excretion of centchroman in breast milk. Br J Clin Pharmacol. 1994 Nov;38(5):485-6. PubMed PMID: 7893594; PubMed Central PMCID: PMC1364886.

17: Rama Raju KS, Taneja I, Singh SP, Tripathi A, Mishra DP, Hussain KM, Gayen JR, Singh SK, Wahajuddin M. Simultaneous determination of centchroman and tamoxifen along with their metabolites in rat plasma using LC-MS/MS. Bioanalysis. 2015;7(8):967-79. doi: 10.4155/bio.14.253. PubMed PMID: 25966009.

18: Hou J, Li P, Zeng J, Xu X, Xiong X, Mi M. [Effect of xy2004, a centchroman derivative, on proliferation of MCF-7 cells in vitro and the mechanism]. Nan Fang Yi Ke Da Xue Xue Bao. 2014 Oct;34(10):1511-4. Chinese. PubMed PMID: 25345952.

19: Singh MM, Sreenivasulu S, Kamboj VP. Duration of anti-implantation action of the triphenylethylene anti-oestrogen centchroman in adult female rats. J Reprod Fertil. 1994 Mar;100(2):367-74. PubMed PMID: 8021853.

20: Rajswaroob U, Kannan R, Kannan NS, Tirouaroul T. Effectiveness of Centchroman on Regression of Fibroadenosis and Mastalgia. J Clin Diagn Res. 2016 Oct;10(10):PC10-PC14. Epub 2016 Oct 1. PubMed PMID: 27891390; PubMed Central PMCID: PMC5121728.