Toremifene
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MedKoo CAT#: 571455

CAS#: 89778-26-7 (free base)

Description: Toremifene is an oral selective estrogen receptor modulator (SERM) which helps oppose the actions of estrogen in the body. It is antagonistic on mammary and uterine tissue. Licensed in the United States under the brand name Fareston, toremifene is FDA-approved for use in advanced (metastatic) breast cancer. It is also being evaluated for prevention of prostate cancer under the brand name Acapodene.


Chemical Structure

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Toremifene
CAS# 89778-26-7 (free base)

Theoretical Analysis

MedKoo Cat#: 571455
Name: Toremifene
CAS#: 89778-26-7 (free base)
Chemical Formula: C26H28ClNO
Exact Mass: 405.1859
Molecular Weight: 405.97
Elemental Analysis: C, 76.92; H, 6.95; Cl, 8.73; N, 3.45; O, 3.94

Price and Availability

Size Price Availability Quantity
500.0mg USD 235.0 2 Weeks
1.0g USD 380.0 2 Weeks
5.0g USD 950.0 2 Weeks
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Related CAS #: 89778-27-8 (citrate)   89778-26-7 (free base)  

Synonym: Toremifene; Acapodene; Farestone

IUPAC/Chemical Name: Ethanamine, 2-(4-((1Z)-4-chloro-1,2-diphenyl-1-butenyl)phenoxy)-N,N-dimethyl-

InChi Key: XFCLJVABOIYOMF-QPLCGJKRSA-N

InChi Code: InChI=1S/C26H28ClNO/c1-28(2)19-20-29-24-15-13-23(14-16-24)26(22-11-7-4-8-12-22)25(17-18-27)21-9-5-3-6-10-21/h3-16H,17-20H2,1-2H3/b26-25-

SMILES Code: ClCC/C(C1=CC=CC=C1)=C(C2=CC=C(OCCN(C)C)C=C2)\C3=CC=CC=C3

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: >2 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 405.97 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: Vogel CL, Johnston MA, Capers C, Braccia D. Toremifene for breast cancer: a review of 20 years of data. Clin Breast Cancer. 2014 Feb;14(1):1-9. doi: 10.1016/j.clbc.2013.10.014. Epub 2013 Oct 31. Review. PubMed PMID: 24439786.

2: Hariri W, Sudha T, Bharali DJ, Cui H, Mousa SA. Nano-Targeted Delivery of Toremifene, an Estrogen Receptor-α Blocker in Prostate Cancer. Pharm Res. 2015 Aug;32(8):2764-74. doi: 10.1007/s11095-015-1662-x. Epub 2015 Mar 12. PubMed PMID: 25762087.

3: Fiore M, Colombo C, Radaelli S, Callegaro D, Palassini E, Barisella M, Morosi C, Baldi GG, Stacchiotti S, Casali PG, Gronchi A. Hormonal manipulation with toremifene in sporadic desmoid-type fibromatosis. Eur J Cancer. 2015 Dec;51(18):2800-7. doi: 10.1016/j.ejca.2015.08.026. Epub 2015 Nov 18. PubMed PMID: 26602014.

4: Kimura M, Tominaga T, Kimijima I, Takatsuka Y, Takashima S, Nomura Y, Kasumi F, Yamaguchi A, Masuda N, Noguchi S, Eshima N. Phase III randomized trial of toremifene versus tamoxifen for Japanese postmenopausal patients with early breast cancer. Breast Cancer. 2014 May;21(3):275-83. doi: 10.1007/s12282-012-0394-6. Epub 2012 Sep 12. PubMed PMID: 22968626.

5: Smith MR, Morton RA, Barnette KG, Sieber PR, Malkowicz SB, Rodriguez D, Hancock ML, Steiner MS. Toremifene to reduce fracture risk in men receiving androgen deprivation therapy for prostate cancer. J Urol. 2013 Jan;189(1 Suppl):S45-50. doi: 10.1016/j.juro.2012.11.016. PubMed PMID: 23234631.

6: Fujimura T, Takahashi S, Kume H, Urano T, Takayama K, Yamada Y, Suzuki M, Fukuhara H, Nakagawa T, Inoue S, Homma Y. Toremifene, a selective estrogen receptor modulator, significantly improved biochemical recurrence in bone metastatic prostate cancer: a randomized controlled phase II a trial. BMC Cancer. 2015 Nov 2;15:836. doi: 10.1186/s12885-015-1871-z. PubMed PMID: 26526623; PubMed Central PMCID: PMC4630884.

7: Chi F, Wu R, Zeng Y, Xing R, Liu Y, Xu Z. Effects of toremifene versus tamoxifen on breast cancer patients: a meta-analysis. Breast Cancer. 2013 Apr;20(2):111-22. doi: 10.1007/s12282-012-0430-6. Epub 2012 Dec 25. PubMed PMID: 23266963.

8: Mazzarino M, de la Torre X, Fiacco I, Palermo A, Botrè F. Drug-drug interaction and doping, part 1: an in vitro study on the effect of non-prohibited drugs on the phase I metabolic profile of toremifene. Drug Test Anal. 2014 May;6(5):482-91. doi: 10.1002/dta.1592. Epub 2014 Jan 15. PubMed PMID: 24431005.

9: Ye QL, Zhai ZM. Toremifene and tamoxifen have similar efficacy in the treatment of patients with breast cancer: a meta-analysis of randomized trials. Mol Biol Rep. 2014 Feb;41(2):751-6. doi: 10.1007/s11033-013-2914-7. Epub 2014 Jan 4. PubMed PMID: 24390230.

10: Ishizuna K, Ninomiya J, Ogawa T, Tsuji E, Kojima M, Kawashima M, Nozaki M, Yamagishi H, Ueda Y, Oya M. Efficacy of high-dose toremifene therapy in postmenopausal patients with metastatic breast cancer resistant to aromatase inhibitors:a retrospective, single-institution study. Gan To Kagaku Ryoho. 2014 Aug;41(8):965-70. PubMed PMID: 25132027.

11: De Cremer K, Delattin N, De Brucker K, Peeters A, Kucharíková S, Gerits E, Verstraeten N, Michiels J, Van Dijck P, Cammue BP, Thevissen K. Oral administration of the broad-spectrum antibiofilm compound toremifene inhibits Candida albicans and Staphylococcus aureus biofilm formation in vivo. Antimicrob Agents Chemother. 2014 Dec;58(12):7606-10. doi: 10.1128/AAC.03869-14. Epub 2014 Oct 6. PubMed PMID: 25288093; PubMed Central PMCID: PMC4249581.

12: Watanabe M, Watanabe N, Maruyama S, Kawashiro T. Comparative metabolic study between two selective estrogen receptor modulators, toremifene and tamoxifen, in human liver microsomes. Drug Metab Pharmacokinet. 2015 Oct;30(5):325-33. doi: 10.1016/j.dmpk.2015.05.004. Epub 2015 May 29. PubMed PMID: 26423799.

13: Zhao Y, Ren J, Harlos K, Jones DM, Zeltina A, Bowden TA, Padilla-Parra S, Fry EE, Stuart DI. Toremifene interacts with and destabilizes the Ebola virus glycoprotein. Nature. 2016 Jul 7;535(7610):169-172. doi: 10.1038/nature18615. Epub 2016 Jun 29. PubMed PMID: 27362232; PubMed Central PMCID: PMC4947387.

14: Gennari L, Merlotti D, Stolakis K, Nuti R. Pharmacokinetic evaluation of toremifene and its clinical implications for the treatment of osteoporosis. Expert Opin Drug Metab Toxicol. 2012 Apr;8(4):505-13. doi: 10.1517/17425255.2012.665873. Epub 2012 Feb 23. Review. PubMed PMID: 22356442.

15: Mazzarino M, Biava M, de la Torre X, Fiacco I, Botrè F. Characterization of the biotransformation pathways of clomiphene, tamoxifen and toremifene as assessed by LC-MS/(MS) following in vitro and excretion studies. Anal Bioanal Chem. 2013 Jun;405(16):5467-87. doi: 10.1007/s00216-013-6961-7. Epub 2013 Apr 23. PubMed PMID: 23604525.

16: Koike K, Edo M, Higaki M, Kitahara K, Satou S, Noshiro H. The clinical benefit of high-dose toremifene for metastatic breast cancer. Gan To Kagaku Ryoho. 2013 Jul;40(7):877-80. PubMed PMID: 23863727.

17: Ogata H, Okamoto Y, Arima Y, Fukushima H, Takeyama H, Yamashita A, Kinoshita M, Suzuki N, Sawada T, Koshida Y, Matsui A, Tachibana A, Nakayama H, Oishi Y, Nogi H, Uchida K. Phase II clinical trial of high-dose toremifene as primary hormone therapy in aromatase inhibitor-resistant breast cancer. Gan To Kagaku Ryoho. 2013 Jun;40(6):749-53. PubMed PMID: 23863651.

18: Kim J, Peraire C, Solà J, Johanning KM, Dalton JT, Veverka KA. Drug interaction potential of toremifene and N-desmethyltoremifene with multiple cytochrome P450 isoforms. Xenobiotica. 2011 Oct;41(10):851-62. doi: 10.3109/00498254.2011.590546. Epub 2011 Jul 5. PubMed PMID: 21726172.

19: Sakurai K, Fujisaki S, Nagashima S, Maeda T, Tomita R, Suzuki S, Hara Y, Hirano T, Enomoto K, Amano S. [Indoleamine 2,3-dioxygenase activity during toremifene therapy for aromatase inhibitor-resistant metastatic breast cancer]. Gan To Kagaku Ryoho. 2014 Oct;41(10):1286-8. Japanese. PubMed PMID: 25335719.

20: Mao C, Yang ZY, He BF, Liu S, Zhou JH, Luo RC, Chen Q, Tang JL. Toremifene versus tamoxifen for advanced breast cancer. Cochrane Database Syst Rev. 2012 Jul 11;(7):CD008926. doi: 10.1002/14651858.CD008926.pub2. Review. PubMed PMID: 22786516.

Toremifene

500.0mg / USD 235.0