trans-4-Hydroxytamoxifen | CAS#68047-06-3

trans-4-Hydroxytamoxifen
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 540203

CAS#: 68047-06-3

Description: trans-4-Hydroxytamoxifen is a SERM and active metabolite of tamoxifen. The Z isomer is more active than the E isomer. It induces autophagy, vacuole formation and KRAS degredation in cancer cells and decreases contractility in myocytes.

Chemical Structure

trans-4-Hydroxytamoxifen

CAS# 68047-06-3

Instruction

Theoretical Analysis

MedKoo Cat#: 540203
Name: trans-4-Hydroxytamoxifen
CAS#: 68047-06-3
Chemical Formula: C26H29NO2
Exact Mass: 387.22
Molecular Weight: 387.520
Elemental Analysis: C, 80.59; H, 7.54; N, 3.61; O, 8.26

Price and Availability

Size	Price	Availability
50mg	USD 450	2 Weeks
100mg	USD 750	2 Weeks
200mg	USD 1350	2 Weeks
500mg	USD 2150	2 Weeks
1g	USD 3150	2 Weeks
2g	USD 5450	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: (Z)-4-Hydroxytamoxifen; trans-4-Hydroxytamoxifen; ICI 79280; ICI79280; ICI-79280

IUPAC/Chemical Name: (Z)-4-(1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenylbut-1-en-1-yl)phenol

InChi Key: TXUZVZSFRXZGTL-QPLCGJKRSA-N

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

SMILES Code: OC1=CC=C(/C(C2=CC=C(OCCN(C)C)C=C2)=C(C3=CC=CC=C3)\CC)C=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:

Certificate of Analysis:

View CoA: current batch, Lot# CMC90130

Safety Data Sheet (SDS):

View Safety Data Sheet (SDS)

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

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:
In vitro protocol:
In vivo protocol:

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1: Williams ML, Lennard MS, Martin IJ, Tucker GT. Interindividual variation in the isomerization of 4-hydroxytamoxifen by human liver microsomes: involvement of cytochromes P450. Carcinogenesis. 1994 Dec;15(12):2733-8. PubMed PMID: 8001229.

2: Crewe HK, Notley LM, Wunsch RM, Lennard MS, Gillam EM. Metabolism of tamoxifen by recombinant human cytochrome P450 enzymes: formation of the 4-hydroxy, 4'-hydroxy and N-desmethyl metabolites and isomerization of trans-4-hydroxytamoxifen. Drug Metab Dispos. 2002 Aug;30(8):869-74. PubMed PMID: 12124303.

3: Ogura K, Ishikawa Y, Kaku T, Nishiyama T, Ohnuma T, Muro K, Hiratsuka A. Quaternary ammonium-linked glucuronidation of trans-4-hydroxytamoxifen, an active metabolite of tamoxifen, by human liver microsomes and UDP-glucuronosyltransferase 1A4. Biochem Pharmacol. 2006 Apr 28;71(9):1358-69. Epub 2006 Feb 14. PubMed PMID: 16480962.

4: Mauvais-Javis P, Baudot N, Castaigne D, Banzet P, Kuttenn F. trans-4-Hydroxytamoxifen concentration and metabolism after local percutaneous administration to human breast. Cancer Res. 1986 Mar;46(3):1521-5. PubMed PMID: 3943109.

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6: Osborne CK, Coronado E, Allred DC, Wiebe V, DeGregorio M. Acquired tamoxifen resistance: correlation with reduced breast tumor levels of tamoxifen and isomerization of trans-4-hydroxytamoxifen. J Natl Cancer Inst. 1991 Oct 16;83(20):1477-82. PubMed PMID: 1920493.

7: Poulin R, Merand Y, Poirier D, Levesque C, Dufour JM, Labrie F. Antiestrogenic properties of keoxifene, trans-4-hydroxytamoxifen, and ICI 164384, a new steroidal antiestrogen, in ZR-75-1 human breast cancer cells. Breast Cancer Res Treat. 1989 Oct;14(1):65-76. PubMed PMID: 2605344.

8: Anzai Y, Holinka CF, Kuramoto H, Gurpide E. Stimulatory effects of 4-hydroxytamoxifen on proliferation of human endometrial adenocarcinoma cells (Ishikawa line). Cancer Res. 1989 May 1;49(9):2362-5. PubMed PMID: 2706624.

9: Nishiyama T, Ogura K, Nakano H, Ohnuma T, Kaku T, Hiratsuka A, Muro K, Watabe T. Reverse geometrical selectivity in glucuronidation and sulfation of cis- and trans-4-hydroxytamoxifens by human liver UDP-glucuronosyltransferases and sulfotransferases. Biochem Pharmacol. 2002 May 15;63(10):1817-30. PubMed PMID: 12034366.

10: Malet C, Gompel A, Spritzer P, Bricout N, Yaneva H, Mowszowicz I, Kuttenn F, Mauvais-Jarvis P. Tamoxifen and hydroxytamoxifen isomers versus estradiol effects on normal human breast cells in culture. Cancer Res. 1988 Dec 15;48(24 Pt 1):7193-9. PubMed PMID: 3056610.

11: Pearce V, Nawaz Z, Xiao W, Wiedenfeld D, Boyle N, Smith D. 4-ethoxymethylphenol: a novel phytoestrogen that acts as an agonist for human estrogen receptors. J Steroid Biochem Mol Biol. 2003 Mar;84(4):431-9. PubMed PMID: 12732288.

12: Falany CN, Wheeler J, Oh TS, Falany JL. Steroid sulfation by expressed human cytosolic sulfotransferases. J Steroid Biochem Mol Biol. 1994 Mar;48(4):369-75. PubMed PMID: 8142314.

13: Murphy CS, Langan-Fahey SM, McCague R, Jordan VC. Structure-function relationships of hydroxylated metabolites of tamoxifen that control the proliferation of estrogen-responsive T47D breast cancer cells in vitro. Mol Pharmacol. 1990 Nov;38(5):737-43. PubMed PMID: 2233701.

14: Graumann K, Jungbauer A. Agonistic and synergistic activity of tamoxifen in a yeast model system. Biochem Pharmacol. 2000 Jan 15;59(2):177-85. PubMed PMID: 10810452.

15: Fanidi A, Courion-Guichardaz C, Fayard JM, Pageaux JF, Laugier C. Effects of tamoxifen, tamoxifen metabolites, and nafoxidine on adenosine 3',5'-monophosphate phosphodiesterase: correlations with growth inhibitory activities but not estrogen receptor affinities. Endocrinology. 1989 Sep;125(3):1187-93. PubMed PMID: 2547579.

16: Tamrazi A, Carlson KE, Katzenellenbogen JA. Molecular sensors of estrogen receptor conformations and dynamics. Mol Endocrinol. 2003 Dec;17(12):2593-602. Epub 2003 Aug 28. PubMed PMID: 12947047.

17: Osborne CK, Jarman M, McCague R, Coronado EB, Hilsenbeck SG, Wakeling AE. The importance of tamoxifen metabolism in tamoxifen-stimulated breast tumor growth. Cancer Chemother Pharmacol. 1994;34(2):89-95. PubMed PMID: 8194171.

18: Ohtake E, Kakihara F, Matsumoto N, Ozawa S, Ohno Y, Hasegawa S, Suzuki H, Kubota T. Frequency distribution of phenol sulfotransferase 1A1 activity in platelet cells from healthy Japanese subjects. Eur J Pharm Sci. 2006 Jul;28(4):272-7. Epub 2006 Apr 18. PubMed PMID: 16621480.

19: Smith CL, Conneely OM, O'Malley BW. Modulation of the ligand-independent activation of the human estrogen receptor by hormone and antihormone. Proc Natl Acad Sci U S A. 1993 Jul 1;90(13):6120-4. PubMed PMID: 8327492; PubMed Central PMCID: PMC46879.

20: Wiebe VJ, Osborne CK, McGuire WL, DeGregorio MW. Identification of estrogenic tamoxifen metabolite(s) in tamoxifen-resistant human breast tumors. J Clin Oncol. 1992 Jun;10(6):990-4. PubMed PMID: 1588380.

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