Available from stock

4-Hydroxytamoxifen solution, 5 mg/ml in ethanol: isopropanol (95:5)

SKU: H0471

Category: Antibiotics

Synonyms: Afimoxifene, 4-OHT, cis/trans-4-Hydroxytamoxifen, (E/Z)-4-Hydroxytamoxifen, HTMX, 4-(1-[4-(Dimethylaminoethoxy)phenyl]-2-phenyl-1-butenyl)phenol; 68392-35-8 (comp.)
CAS-Number: C₂₆H₂₉NO₂
Molecular Formula: 387.51
Molecular Weight

For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.

Product Data
Handling
Safety Information
Details

Specifications

Purity: ≥98% (HPLC)
Appearance: Colourless liquid
Identity: 1H-NMR
Concentration: 5 mg/ml in ethanol: isopropanol (95:5)

Properties

Solvents: Soluble in ethanol.

Shipping: AMBIENT
Short Term Storage: +4°C
Long Term Storage: -20°C
Handling Advice: Protect from light and moisture.
Use / Stability: Stable for at least 2 years after receipt when stored at +4°C.

Hazard statements: H225,H319,H350,H360FD,H412
Precautionary statements: P202 - P210 - P233 - P273 - P305 + P351 + P338 - P308 + P313
GHS Symbol: GHS05+GHS07+GHS08
Signal word: Warning
Transportation: Not dangerous goods

Description: 4-Hydroxytamoxifen is an active metabolite of the chemotherapeutic drug tamoxifen, a selective estrogen receptor modulator (SERM) that acts as an agonist or antagonist in various tissues. 4-Hydroxytamoxifen acts as a tissue-selective agonist-antagonist of the estrogen receptors ERα and ERβ. 4-Hydroxytamoxifen is an isoform-specific inhibitor of orphan estrogen-receptor-related (ERR) nuclear receptors β and γ. 4-Hydroxytamoxifen exhibits anticancer chemotherapeutic activity, inducing autophagy and vacuole formation as well as KRAS degradation in various cancer cell lines. In cardiac myocytes, 4-hydroxytamoxifen decreases Ca2+ amplitude, slowing relaxation and decreasing contractility. 4-Hydroxytamoxifen has also shown to be a potent inhibitor of the mitochondrial permeability transition (MPT).
Smiles: CC/C(C1=CC=CC=C1)=C(C2=CC=C(O)C=C2)/C3=CC=C(OCCN(C)C)C=C3
InChi Key: TXUZVZSFRXZGTL-QPLCGJKRSA-N
References: [1] N. Terakawa, et al.; Cancer 61, 1312 (1988) , [2] H. Wiseman, et al.; FEBS Lett. 274, 107 (1990) , [3] G. Freiss, et al.; BBRC 173, 919 (1990) , [4] H. Wiseman, et al.; Biochem J. 292, 635 (1993) , [5] A.M. Davies, et al.; Biochem. Soc. Trans. 23, 439S (1995) , [6] S.T. Willard, et al.; Endocrine 14, 247 (2001) , [7] P. Coward, et al.; PNAS 98, 8880 (2001) , [8] G.B. Tremblay, et al.; Endocrinology 142, 4572 (2001) , [9] H.K. Crewe, et al.; Drug Metab. Dispos. 30, 869 (2002) , [10] C.M. Cardoso, et al.; Mitochondrion 1, 485 (2002) , [11] J.P. Monteiro, et al.; Toxicol. In Vitro 17, 629 (2003) , [12] Z. Desta, et al.; J. Pharmacol. Exp. Ther. 310, 1062 (2004) , [13] H. Seeger, et al.; Horm. Metab. Res. 36, 277 (2004) , [14] E.A. Ariazi & V.C. Jordan; Curr. Top. Med. Chem. 6, 203 (2006) (Review) , [15] M.L. Asp, et al.; PLoS One 8, e78768 (2013) , [16] L. Kohli, et al.; Cancer Res. 73, 4395 (2013) , [17] L. Duan, et al.; Cancer Lett. 353, 290 (2014)

4-Hydroxytamoxifen is an active metabolite of the chemotherapeutic drug tamoxifen, a selective estrogen receptor modulator (SERM) that acts as an agonist or antagonist in various tissues. 4-Hydroxytamoxifen acts as a tissue-selective agonist-antagonist of the estrogen receptors ERα and ERβ. 4-Hydroxytamoxifen is an isoform-specific inhibitor of orphan estrogen-receptor-related (ERR) nuclear receptors β and γ. 4-Hydroxytamoxifen exhibits anticancer chemotherapeutic activity, inducing autophagy and vacuole formation as well as KRAS degradation in various cancer cell lines. In cardiac myocytes, 4-hydroxytamoxifen decreases Ca2+ amplitude, slowing relaxation and decreasing contractility. 4-Hydroxytamoxifen has also shown to be a potent inhibitor of the mitochondrial permeability transition (MPT).

SKU: H0471 Category: Antibiotics

Additional information

Additional information

Synonyms	Afimoxifene, 4-OHT, cis/trans-4-Hydroxytamoxifen, (E/Z)-4-Hydroxytamoxifen, HTMX, 4-(1-[4-(Dimethylaminoethoxy)phenyl]-2-phenyl-1-butenyl)phenol
Purity	≥98% (HPLC)
Appearance	Colourless liquid
CAS-Number	68392-35-8 (comp.)
Molecular Formula	C26H29NO2
Molecular Weight	387.51
Identity	1H-NMR
Solvents	Soluble in ethanol.
Smiles	CC/C(C1=CC=CC=C1)=C(C2=CC=C(O)C=C2)/C3=CC=C(OCCN(C)C)C=C3
InChi Key	TXUZVZSFRXZGTL-QPLCGJKRSA-N
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	-20°C
Handling Advice	Protect from light and moisture.
Use / Stability	Stable for at least 2 years after receipt when stored at +4°C.
Hazard statements	H225,H319,H350,H360FD,H412
Precautionary statements	P202 – P210 – P233 – P273 – P305 + P351 + P338 – P308 + P313
GHS Symbol	GHS05+GHS07+GHS08
Signal word	Warning
Transportation	Not dangerous goods
References	[1] N. Terakawa, et al.; Cancer 61, 1312 (1988), [2] H. Wiseman, et al.; FEBS Lett. 274, 107 (1990), [3] G. Freiss, et al.; BBRC 173, 919 (1990), [4] H. Wiseman, et al.; Biochem J. 292, 635 (1993), [5] A.M. Davies, et al.; Biochem. Soc. Trans. 23, 439S (1995), [6] S.T. Willard, et al.; Endocrine 14, 247 (2001), [7] P. Coward, et al.; PNAS 98, 8880 (2001), [8] G.B. Tremblay, et al.; Endocrinology 142, 4572 (2001), [9] H.K. Crewe, et al.; Drug Metab. Dispos. 30, 869 (2002), [10] C.M. Cardoso, et al.; Mitochondrion 1, 485 (2002), [11] J.P. Monteiro, et al.; Toxicol. In Vitro 17, 629 (2003), [12] Z. Desta, et al.; J. Pharmacol. Exp. Ther. 310, 1062 (2004), [13] H. Seeger, et al.; Horm. Metab. Res. 36, 277 (2004), [14] E.A. Ariazi & V.C. Jordan; Curr. Top. Med. Chem. 6, 203 (2006) (Review), [15] M.L. Asp, et al.; PLoS One 8, e78768 (2013), [16] L. Kohli, et al.; Cancer Res. 73, 4395 (2013), [17] L. Duan, et al.; Cancer Lett. 353, 290 (2014)
Quantity	1 ml, Bulk
cdx-Concentration	5 mg/ml in ethanol: isopropanol (95:5)