H6278

4-Hydroxytamoxifen

≥98% (HPLC), powder, Tamoxifen metabolite

• Synonym(s): 4-(1-[4-(Dimethylaminoethoxy)phenyl]-2-phenyl-1-butenyl)phenol, 4-OHT, cis/trans-4-Hydroxytamoxifen
• Empirical Formula (Hill Notation): C₂₆H₂₉NO₂
• CAS Number: 68392-35-8
• Molecular Weight: 387.51
• UNSPSC Code: 51111800
• PubChem Substance ID: 24895736
• NACRES: NA.77

Properties

• Product Name: 4-Hydroxytamoxifen, ≥70% Z isomer (remainder primarily E-isomer)
• Quality Level: 300
• Assay: ≥98% (HPLC)
• form: powder
• storage condition: desiccated; protect from light
• solubility: methanol: 10 mg/mL; ethanol: 20 mg/mL (with heating)
• antibiotic activity spectrum: neoplastics
• Mode of action: enzyme | inhibits
• originator: AstraZeneca
• storage temp.: 2-8°C
• SMILES string: CC\C(c1ccccc1)=C(/c2ccc(O)cc2)c3ccc(OCCN(C)C)cc3.CC\C(c4ccccc4)=C(\c5ccc(O)cc5)c6ccc(OCCN(C)C)cc6
• InChI: 1S/2C26H29NO2/c2*1-4-25(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/h2*5-17,28H,4,18-19H2,1-3H3/b26-25+;26-25-
• InChI key: ZJLDABGSDWXVGE-BDSXMVAQSA-N
• Gene Information: human ... ESR1(2099) , ESR2(2100) , ESRRG(2104) , IL6(3569) ; rat ... Ar(24208) , Esr1(24890) , Esr2(25149)

Description

General description

4-Hydroxytamoxifen (4-OHT), a first-generation selective estrogen receptor modulator (SERM), acts as an antagonist in breast cancer cells but exhibits estrogen-like effects in the uterus and bone.[1] It is an active metabolite of the pro-drug tamoxifen (TAM), functioning as an estrogen receptor antagonist. 4-OHT binds to estrogen receptors to inhibit estradiol-induced cell proliferation without inducing cytotoxicity. It is a metabolite of the antiestrogen, tamoxifen and exhibits a higher affinity than tamoxifen and its other metabolites for binding to estrogen receptors, making it 50 to 100 times more potent in inhibiting cell proliferation in normal human breast cells and breast cancer cell lines in culture.[2]

4-OHT effectively inhibited cell growth in the absence of estrogen when cell proliferation was stimulated by insulin or epidermal growth factor. 4-OHT inhibits lipid peroxidation within cell membranes and shows peroxyl radical scavenging activity.[3]

Application

4-Hydroxytamoxifen has been used:

• to induce the recombination of small intestinal organoids.[4]
• to study its impact on the ability of human peripheral blood mononuclear cells (PMNCs) to form hematopoietic colonies.[5]
• to induce overexpression of MYCN in the neuroblastoma cell line to determine how the elevated MYCN expression influences the sensitivity of neuroblastoma cells to BIRC5/survivin inhibitor, YM155-induced apoptosis.[6]

Biochem/physiol Actions

Metabolite of the chemotherapeutic drug tamoxifen, exhibiting more potent estrogen agonist/antagonist activity than the parent drug. Also active as intra-membranous inhibitor of lipid peroxidation.

Features and Benefits

This compound is featured on the Nuclear Receptors (Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

This compound was developed by AstraZeneca. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Safety Information

• Pictograms: GHS08,GHS07
• Signal Word: Warning
• Hazard Statements: H302 + H312 + H332,H315,H319,H361fd
• Precautionary Statements: P280 - P301 + P312 - P302 + P352 + P312 - P304 + P340 + P312 - P305 + P351 + P338 - P308 + P313
• Hazard Classifications: Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves