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MedKoo Cat#: 540203 | Name: trans-4-Hydroxytamoxifen
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Description:

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

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

Theoretical Analysis

MedKoo Cat#: 540203

Name: trans-4-Hydroxytamoxifen

CAS#: 68047-06-3

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

Price and Availability

Size Price Availability Quantity
50mg USD 450.00 2 Weeks
100mg USD 750.00 2 Weeks
200mg USD 1,350.00 2 Weeks
500mg USD 2,150.00 2 Weeks
1g USD 3,150.00 2 Weeks
2g USD 5,450.00 2 Weeks
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Related CAS #
No Data
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

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.

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
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. 5: McCague R, Leclercq G, Jordan VC. Nonisomerizable analogues of (Z)- and (E)-4-hydroxytamoxifen. Synthesis and endocrinological properties of substituted diphenylbenzocycloheptenes. J Med Chem. 1988 Jul;31(7):1285-90. PubMed PMID: 3385723. 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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