Droloxifene | CAS#82413-20-5 | tamoxifen analog | SERM

MedKoo Cat#: 540113 | Name: Droloxifene

Description:

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

Droloxifene is a tamoxifen analog and SERM that acts as an ER agonist in bone and as an ER antagonist in breast tissue. It increases apoptosis in luteal cells, inhibits bone resorption and turnover, and decreases levels of E-selectin.

Chemical Structure

Droloxifene

CAS#82413-20-5 (free base)

Theoretical Analysis

MedKoo Cat#: 540113

Name: Droloxifene

CAS#: 82413-20-5 (free base)

Chemical Formula: C26H29NO2

Exact Mass: 387.2198

Molecular Weight: 387.52

Elemental Analysis: C, 80.59; H, 7.54; N, 3.61; O, 8.26

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Related CAS #

97752-20-0 (citrate) 82413-20-5 (free base)

Synonym

Droloxifene; K 060E; K-060E; K060E; K 21060E; K 21060E

IUPAC/Chemical Name

(E)-3-(1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenylbut-1-en-1-yl)phenol

InChi Key

ZQZFYGIXNQKOAV-OCEACIFDSA-N

InChi Code

InChI=1S/C26H29NO2/c1-4-25(20-9-6-5-7-10-20)26(22-11-8-12-23(28)19-22)21-13-15-24(16-14-21)29-18-17-27(2)3/h5-16,19,28H,4,17-18H2,1-3H3/b26-25+

SMILES Code

OC1=CC=CC(/C(C2=CC=C(OCCN(C)C)C=C2)=C(C3=CC=CC=C3)\CC)=C1

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

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Droloxifene, a Tamoxifen derivative, is an orally active and selective estrogen receptor modulator.

In vitro activity:

DROL (droloxifene) dose-dependently inhibited the E2-induced stimulation of growth of these cells in medium without phenol red, but TAM inhibited the growth only at high concentrations. Reference: Jpn J Pharmacol. 1993 Sep;63(1):27-34. https://pubmed.ncbi.nlm.nih.gov/8271528/

In vivo activity:

Pregnant rats were treated orally with droloxifene at 10:00 AM on d 2 at doses of 1.25-20 mg/kg to observe anti-implantation effects, and then doses of 14 mg/kg or 2.5 mg/kg were given at different time on d 2 to d 5 to determine the optimal administration time for anti-implantation effects. Pregnant rats were treated with a combination of droloxifene (2.5 mg/kg, ig) and E2 (0.5-8.0 microg/kg, sc) on the optimal administration time to observe the antagonistic effect of external estrogen on the anti-implantation effect of droloxifene. Droloxifene has anti-implantation effects in rats. Reference: Acta Pharmacol Sin. 2005 Oct;26(10):1243-7. https://pubmed.ncbi.nlm.nih.gov/16174441/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	77.41
	DMF:PBS (pH 7.2) (1:3)	0.3	0.65
	DMSO	32.5	83.87
	Ethanol	1.0	2.58

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 387.52 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. Kawamura I, Mizota T, Lacey E, Tanaka Y, Manda T, Shimomura K, Kohsaka M. The estrogenic and antiestrogenic activities of droloxifene in human breast cancers. Jpn J Pharmacol. 1993 Sep;63(1):27-34. doi: 10.1254/jjp.63.27. PMID: 8271528. 2. Löser R, Seibel K, Roos W, Eppenberger U. In vivo and in vitro antiestrogenic action of 3-hydroxytamoxifen, tamoxifen and 4-hydroxytamoxifen. Eur J Cancer Clin Oncol. 1985 Aug;21(8):985-90. doi: 10.1016/0277-5379(85)90119-1. PMID: 4043181. 3. Huang Y, Shen Y, Feng Y, Cao L, Leng Y. Anti-implantation effect of droloxifene in rats and its relationship with anti-estrogenic activity. Acta Pharmacol Sin. 2005 Oct;26(10):1243-7. doi: 10.1111/j.1745-7254.2005.00191.x. PMID: 16174441. 4. Grasser WA, Pan LC, Thompson DD, Paralkar VM. Common mechanism for the estrogen agonist and antagonist activities of droloxifene. J Cell Biochem. 1997 May;65(2):159-71. doi: 10.1002/(sici)1097-4644(199705)65:2<159::aid-jcb3>3.0.co;2-t. PMID: 9136075.

In vitro protocol:

In vivo protocol:

1. Huang Y, Shen Y, Feng Y, Cao L, Leng Y. Anti-implantation effect of droloxifene in rats and its relationship with anti-estrogenic activity. Acta Pharmacol Sin. 2005 Oct;26(10):1243-7. doi: 10.1111/j.1745-7254.2005.00191.x. PMID: 16174441. 2. Grasser WA, Pan LC, Thompson DD, Paralkar VM. Common mechanism for the estrogen agonist and antagonist activities of droloxifene. J Cell Biochem. 1997 May;65(2):159-71. doi: 10.1002/(sici)1097-4644(199705)65:2<159::aid-jcb3>3.0.co;2-t. PMID: 9136075.

1: Buzdar A, Hayes D, El-Khoudary A, Yan S, Lønning P, Lichinitser M, Gopal R, Falkson G, Pritchard K, Lipton A, Wolter K, Lee A, Fly K, Chew R, Alderdice M, Burke K, Eisenber P; Droloxifene 301 Study Group. Phase III randomized trial of droloxifene and tamoxifen as first-line endocrine treatment of ER/PgR-positive advanced breast cancer. Breast Cancer Res Treat. 2002 May;73(2):161-75. PubMed PMID: 12088118. 2: Grasser WA, Pan LC, Thompson DD, Paralkar VM. Common mechanism for the estrogen agonist and antagonist activities of droloxifene. J Cell Biochem. 1997 May;65(2):159-71. PubMed PMID: 9136075. 3: Rivera-Gonzalez R, Petersen DN, Tkalcevic G, Thompson DD, Brown TA. Estrogen-induced genes in the uterus of ovariectomized rats and their regulation by droloxifene and tamoxifen. J Steroid Biochem Mol Biol. 1998 Jan;64(1-2):13-24. PubMed PMID: 9569006. 4: Leng Y, Gu ZP, Cao L. Apoptosis induced by droloxifene and C-myc, Bax, Bcl-2 protein expression in corpus luteum of pregnant rats. Acta Pharmacol Sin. 2001 Apr;22(4):327-34. PubMed PMID: 11742585. 5: Seely EW, Brosnihan KB, Jeunemaitre X, Okamura K, Williams GH, Hollenberg NK, Herrington DM. Effects of conjugated oestrogen and droloxifene on the renin-angiotensin system, blood pressure and renal blood flow in postmenopausal women. Clin Endocrinol (Oxf). 2004 Mar;60(3):315-21. PubMed PMID: 15008996. 6: Su AL, Chen BA, Huang CY, Gao F, Cheng J, Xu WL, Shen HL, Sun XC, Cheng HY, Ding JH, Gao C, Sun YY, Wang J, Zhao G, Chen NN, Zhao HH. [Effect of tetrandrine in combination with droloxifen on the expression of NF-kappaB protein in K562 and K562/A02 cell lines]. Zhonghua Xue Ye Xue Za Zhi. 2008 May;29(5):321-4. Chinese. PubMed PMID: 18844070. 7: Chen BA, Qian XJ, Cheng J, Gao F. [Effect of tetrandrine combined with Droloxifen on the expression of bcr/abl of K562 at both mRNA and protein levels]. Zhongguo Shi Yan Xue Ye Xue Za Zhi. 2005 Feb;13(1):95-9. Chinese. PubMed PMID: 15748444. 8: Marqusee E, Braverman LE, Lawrence JE, Carroll JS, Seely EW. The effect of droloxifene and estrogen on thyroid function in postmenopausal women. J Clin Endocrinol Metab. 2000 Nov;85(11):4407-10. PubMed PMID: 11095487. 9: Huang Y, Shen Y, Feng Y, Cao L, Leng Y. Anti-implantation effect of droloxifene in rats and its relationship with anti-estrogenic activity. Acta Pharmacol Sin. 2005 Oct;26(10):1243-7. PubMed PMID: 16174441. 10: Hasmann M, Rattel B, Löser R. Preclinical data for Droloxifene. Cancer Lett. 1994 Sep 15;84(2):101-16. Review. PubMed PMID: 8076367. 11: Lien EA, Anker G, Lønning PE, Ueland PM. Determination of droloxifene and two metabolites in serum by high-pressure liquid chromatography. Ther Drug Monit. 1995 Jun;17(3):259-65. PubMed PMID: 7624922. 12: Leng Y, Feng Y, Cao L, Gu ZP. Effects of droloxifene on apoptosis and Bax, Bcl-2 protein expression of luteal cells in pseudopregnant rats. Acta Pharmacol Sin. 2001 Feb;22(2):155-62. PubMed PMID: 11741521. 13: Geisler J, Ekse D, Hösch S, Lønning PE. Influence of droloxifene (3-hydroxytamoxifen), 40 mg daily, on plasma gonadotrophins, sex hormone binding globulin and estrogen levels in postmenopausal breast cancer patients. J Steroid Biochem Mol Biol. 1995 Nov;55(2):193-5. PubMed PMID: 7495698. 14: John BA, Brodie RR, Baldock GA, McBurney A, Chasseaud LF, Jank P, Von Nieciecki A. Pharmacokinetics and metabolism of the anti-oestrogen droloxifene in female human subjects. Xenobiotica. 2002 Aug;32(8):699-713. PubMed PMID: 12296990. 15: Herrington DM, Pusser BE, Riley WA, Thuren TY, Brosnihan KB, Brinton EA, MacLean DB. Cardiovascular effects of droloxifene, a new selective estrogen receptor modulator, in healthy postmenopausal women. Arterioscler Thromb Vasc Biol. 2000 Jun;20(6):1606-12. PubMed PMID: 10845879. 16: Yao D, Zhang F, Yu L, Yang Y, van Breemen RB, Bolton JL. Synthesis and reactivity of potential toxic metabolites of tamoxifen analogues: droloxifene and toremifene o-quinones. Chem Res Toxicol. 2001 Dec;14(12):1643-53. PubMed PMID: 11743747. 17: Herrington DM, Brosnihan KB, Pusser BE, Seely EW, Ridker PM, Rifai N, MacLean DB. Differential effects of E and droloxifene on C-reactive protein and other markers of inflammation in healthy postmenopausal women. J Clin Endocrinol Metab. 2001 Sep;86(9):4216-22. PubMed PMID: 11549652. 18: Gao HD, Sun JZ, Bi DS, Ma R. [Status of estrogen receptor affects the drug sensitivity of drug-resistant MCF-7/Adr human breast cancer cells to droloxifene and Adriamycin]. Ai Zheng. 2003 Apr;22(4):376-9. Chinese. PubMed PMID: 12703992. 19: Tanaka Y, Sekiguchi M, Sawamoto T, Hata T, Esumi Y, Sugai S, Ninomiya S. Pharmacokinetics of droloxifene in mice, rats, monkeys, premenopausal and postmenopausal patients. Eur J Drug Metab Pharmacokinet. 1994 Jan-Mar;19(1):47-58. PubMed PMID: 7957452. 20: Eppenberger U, Wosikowski K, Küng W. Pharmacologic and biologic properties of droloxifene, a new antiestrogen. Am J Clin Oncol. 1991;14 Suppl 2:S5-14. Review. PubMed PMID: 1962598.