Ormeloxifene free base| CAS#31477-60-8 | anti-fertility

MedKoo Cat#: 584947 | Name: Ormeloxifene free base

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

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: 457.61

Elemental Analysis: C, 78.74; H, 7.71; N, 3.06; O, 10.49

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 350.00	2 Weeks
25mg	USD 1,150.00	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

Oil

Purity

>95% (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

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Ormeloxifene, also known as centchroman, is one of the selective estrogen receptor modulators, or SERMs.

In vitro activity:

Here, this study shows that ORM (ormeloxifene) can induce megakaryocyte and myeloid (granulocytic) but not erythroid differentiation in multipotent human myeloid leukemia cell line K562. This study shows that ORM at an IC50 of 7.5 µM can induce morphological changes similar to megakaryocytes in K562 cells. ORM led to increase in levels of megakaryocytic differentiation markers (CD41 and CD61) as well as key transcription factors GATA1 and AML1. ORM induces megakaryocytic differentiation in K562 cells through ERK activation and induction of autophagy in a fashion similar to other known inducers of megakaryocytic differentiation such as phorbol esters. Reference: Cell Biol Int. 2023 Mar 23. https://pubmed.ncbi.nlm.nih.gov/36950830/

In vivo activity:

Female (ovary-intact or ovariectomized) and male Sprague-Dawley rats received monocrotaline (60 mg/kg, once, subcutaneously), with or without ormeloxifene treatment (2.5 mg/kg, orally) for four weeks. Ormeloxifene was less uterotrophic; however, it attenuated both hypoxia and monocrotaline effects by improving pulmonary 17β-estradiol synthesis. Furthermore, ormeloxifene decreased cardiac hypertrophy and right ventricular remodeling induced by hypoxia and monocrotaline. Reference: Eur J Pharmacol. 2023 Mar 15;943:175558. https://pubmed.ncbi.nlm.nih.gov/36731722/

Preparing Stock Solutions

The following data is based on the product molecular weight 457.61 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.

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

Formulation protocol:

1. Mishra M, Singh AK, Thacker G, Upadhyay V, Sanyal S, Trivedi AK. Ormeloxifene, a nonsteroidal antifertility drug promotes megakaryocyte differentiation in leukemia cell line K562. Cell Biol Int. 2023 Mar 23. doi: 10.1002/cbin.12017. Epub ahead of print. PMID: 36950830. 2. Khan S, Shukla S, Farhan M, Sinha S, Lakra AD, Penta D, Kannan A, Meeran SM. Centchroman prevents metastatic colonization of breast cancer cells and disrupts angiogenesis via inhibition of RAC1/PAK1/β-catenin signaling axis. Life Sci. 2020 Sep 1;256:117976. doi: 10.1016/j.lfs.2020.117976. Epub 2020 Jun 16. PMID: 32561397. 3. Abdulkareem AO, Tiwari P, Lone ZR, Iqbal H, Gupta S, Jha RK, Chanda D, Jagavelu K, Hanif K. Ormeloxifene, a selective estrogen receptor modulator, protects against pulmonary hypertension. Eur J Pharmacol. 2023 Mar 15;943:175558. doi: 10.1016/j.ejphar.2023.175558. Epub 2023 Jan 30. PMID: 36731722. 4. Sirohi VK, Gupta K, Kumar R, Shukla V, Dwivedi A. Selective estrogen receptor modulator ormeloxifene suppresses embryo implantation via inducing miR-140 and targeting insulin-like growth factor 1 receptor in rat uterus. J Steroid Biochem Mol Biol. 2018 Apr;178:272-282. doi: 10.1016/j.jsbmb.2018.01.006. Epub 2018 Jan 10. PMID: 29330027.

In vitro protocol:

In vivo protocol:

1. Abdulkareem AO, Tiwari P, Lone ZR, Iqbal H, Gupta S, Jha RK, Chanda D, Jagavelu K, Hanif K. Ormeloxifene, a selective estrogen receptor modulator, protects against pulmonary hypertension. Eur J Pharmacol. 2023 Mar 15;943:175558. doi: 10.1016/j.ejphar.2023.175558. Epub 2023 Jan 30. PMID: 36731722. 2. Sirohi VK, Gupta K, Kumar R, Shukla V, Dwivedi A. Selective estrogen receptor modulator ormeloxifene suppresses embryo implantation via inducing miR-140 and targeting insulin-like growth factor 1 receptor in rat uterus. J Steroid Biochem Mol Biol. 2018 Apr;178:272-282. doi: 10.1016/j.jsbmb.2018.01.006. Epub 2018 Jan 10. PMID: 29330027.

1: Setua S, Shabir S, Shaji P, Bulnes AM, Dhasmana A, Holla S, Mittal NK, Sahoo N, Saini T, Giorgianni F, Sikander M, Massey AE, Hafeez BB, Tripathi MK, Diego VP, Jaggi M, Yue J, Zafar N, Yallapu MM, Behrman SW, Khan S, Chauhan SC. Exosomes derived from tumor adjacent fibroblasts efficiently target pancreatic tumors. Acta Pharm Sin B. 2024 Jul;14(7):3009-3026. doi: 10.1016/j.apsb.2024.04.003. Epub 2024 Apr 9. PMID: 39027237; PMCID: PMC11252470. 2: Sharaf S, S S, Regidi S, Santhosh Aprem A, Gopimohan R, S L. Evaluation of molecular effects associated with apoptosis, tumour progression, angiogenesis and metastasis by a novel combination of drugs with ormeloxifene in triple negative breast cancer cells. Explor Target Antitumor Ther. 2024;5(3):551-567. doi: 10.37349/etat.2024.00235. Epub 2024 Jun 11. PMID: 38966180; PMCID: PMC11220290. 3: Sinha N, Tajdar Y, Pankaj D, Kumar N, Muni S, Bhushan V. A Study Comparing Centchroman and Evening Primrose Oil in the Treatment of Benign Breast Disease. J Pharm Bioallied Sci. 2024 Apr;16(Suppl 2):S1544-S1548. doi: 10.4103/jpbs.jpbs_399_23. Epub 2024 Apr 16. PMID: 38882830; PMCID: PMC11174335. 4: Agrawal K, Silodia A, Yadav SK, Sharma DB, Sharma D. Double blind randomized controlled trial of efficacy of ormeloxifene for the treatment of fibroadenoma (The FIBROCENT study). World J Surg. 2024 May;48(5):1177-1182. doi: 10.1002/wjs.12150. Epub 2024 Mar 18. PMID: 38498009. 5: Patil M, Devarbhavi H, Mishra A, Pavan Kumar YM, Dhali GK, Chowdhury A. Clinical Features, Laboratory Characteristics and Outcome from Oral Contraceptives-induced Liver Injury in 43 Consecutive Patients and a Brief Review of Published Reports. J Clin Exp Hepatol. 2024 May-Jun;14(3):101322. doi: 10.1016/j.jceh.2023.101322. Epub 2023 Dec 16. PMID: 38283703; PMCID: PMC10818198. 6: Sharma AA, Kumar A, Pasi DK, Dhamija P, Garry GK, Saini A, Jakhar R. Mastalgia - The Burden Beneath. Eur J Breast Health. 2023 Dec 27;20(1):15-18. doi: 10.4274/ejbh.galenos.2023.2023-3-10. PMID: 38187109; PMCID: PMC10765463. 7: Roy S, Singh GN, Verma N, Parasher G, Suryavanshi P. Psychological Assessment and Treatment Effectiveness in Mastalgia: Developing a Treatment Algorithm. Cureus. 2023 Oct 11;15(10):e46838. doi: 10.7759/cureus.46838. PMID: 38021953; PMCID: PMC10643197. 8: Sikander M, Malik S, Apraku J, Kumari S, Khan P, Mandil H, Ganju A, Chauhan B, Bell MC, Singh MM, Khan S, Yallapu MM, Halaweish FT, Jaggi M, Chauhan SC. Synthesis and Antitumor Activity of Brominated-Ormeloxifene (Br-ORM) against Cervical Cancer. ACS Omega. 2023 Oct 12;8(42):38839-38848. doi: 10.1021/acsomega.3c02277. PMID: 37901538; PMCID: PMC10601051. 9: Porwal K, Sharma S, Kumar S, Tomar MS, Sadhukhan S, Rajput S, Kulkarni C, Shrivastava A, Kumar N, Chattopadhyay N. Hormonal and non-hormonal oral contraceptives given long-term to pubertal rats differently affect bone mass, quality and metabolism. Front Endocrinol (Lausanne). 2023 Aug 17;14:1233613. doi: 10.3389/fendo.2023.1233613. PMID: 37664835; PMCID: PMC10470083. 10: Abdulkareem AO, Tiwari P, Lone ZR, Iqbal H, Gupta S, Jha RK, Chanda D, Jagavelu K, Hanif K. Corrigendum to "Ormeloxifene, a selective estrogen receptor modulator, protects against pulmonary hypertension" [Eur. J. Pharmacol. 943 (2023) 175558]. Eur J Pharmacol. 2023 Jul 5;950:175750. doi: 10.1016/j.ejphar.2023.175750. Epub 2023 May 3. Erratum for: Eur J Pharmacol. 2023 Mar 15;943:175558. doi: 10.1016/j.ejphar.2023.175558. PMID: 37147146. 11: Mishra M, Singh AK, Thacker G, Upadhyay V, Sanyal S, Trivedi AK. Ormeloxifene, a nonsteroidal antifertility drug promotes megakaryocyte differentiation in leukemia cell line K562. Cell Biol Int. 2023 Jul;47(7):1247-1258. doi: 10.1002/cbin.12017. Epub 2023 Mar 23. PMID: 36950830. 12: Agarwal K, Dewan R. Evaluation of acceptability, safety, and continuation rates of centchroman as postabortion nonsteroidal contraceptive pill. Contraception. 2023 May;121:109961. doi: 10.1016/j.contraception.2023.109961. Epub 2023 Feb 1. PMID: 36736648. 13: Abdulkareem AO, Tiwari P, Lone ZR, Iqbal H, Gupta S, Jha RK, Chanda D, Jagavelu K, Hanif K. Ormeloxifene, a selective estrogen receptor modulator, protects against pulmonary hypertension. Eur J Pharmacol. 2023 Mar 15;943:175558. doi: 10.1016/j.ejphar.2023.175558. Epub 2023 Jan 30. Erratum in: Eur J Pharmacol. 2023 Jul 5;950:175750. doi: 10.1016/j.ejphar.2023.175750. PMID: 36731722. 14: Penta D, Tripathi P, Rajarajan D, Natesh J, Mondal P, Meeran SM. Diindolylmethane Promotes Metabolic Crisis and Enhances the Efficacy of Centchroman in Breast Cancer: A 1H NMR-Based Approach. ACS Omega. 2022 Nov 16;7(47):43147-43160. doi: 10.1021/acsomega.2c05832. PMID: 36467932; PMCID: PMC9713897. 15: Penta D, Natesh J, Mondal P, Meeran SM. Dietary Diindolylmethane Enhances the Therapeutic Effect of Centchroman in Breast Cancer by Inhibiting Neoangiogenesis. Nutr Cancer. 2023;75(2):734-749. doi: 10.1080/01635581.2022.2143825. Epub 2022 Nov 12. PMID: 36370104. 16: Mir SA, Ara R, Amin F, Malik A, Hamid L, Ali T, Bader GN, Wani SUD, Almuqbil M, Alshehri S, Alshehri AM, Shakeel F. Evaluation of the Safety and Efficacy of Ormeloxifene, a Selective Estrogen Receptor Modulator and Medroxyprogesterone Acetate in Women with Non-Structural Abnormal Uterine Bleeding: A Randomized Clinical Trial. Medicina (Kaunas). 2022 Oct 22;58(11):1503. doi: 10.3390/medicina58111503. PMID: 36363460; PMCID: PMC9692901. 17: Sarkar A, Wadhawan I, Raj A, Nagabhushana P, Singh P. Improving the Acceptance Rate of Centchroman As a Postpartum Contraceptive Through a Quality Improvement Initiative. Cureus. 2022 Sep 17;14(9):e29277. doi: 10.7759/cureus.29277. PMID: 36277560; PMCID: PMC9580608. 18: Verma A, Sharma DB, Yadav SK, Sharma D. Open-Label Three Arm Trial Comparing Ormeloxifene, Gamma Linolenic Acid With Methylcobalamine + Vitamin C and Placebo in Mastalgia. Eur J Breast Health. 2022 Jul 1;18(3):248-251. doi: 10.4274/ejbh.galenos.2022.2022-2-6. PMID: 35855192; PMCID: PMC9255657. 19: Ponkarpagam S, Vennila KN, Elango KP. Molecular spectroscopic and molecular simulation studies on the interaction of oral contraceptive drug Ormeloxifene with CT-DNA. Spectrochim Acta A Mol Biomol Spectrosc. 2022 Oct 5;278:121351. doi: 10.1016/j.saa.2022.121351. Epub 2022 May 6. PMID: 35567820. 20: S L, A S, Dv S, Bs R, R S, Sharaf S, Sa A, G R. Comparative differential cytotoxicity of clinically used SERMs in human cancer lines of different origin and its predictive molecular docking studies of key target genes involved in cancer progression and treatment responses. Curr Res Pharmacol Drug Discov. 2021 Dec 31;3:100080. doi: 10.1016/j.crphar.2021.100080. PMID: 35059624; PMCID: PMC8760488.

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GSK3182571

MedKoo CAT#: 533041

CAS#: N/A