H6278

4-Hydroxytamoxifen

≥98% (HPLC), powder, Tamoxifen metabolite

• 동의어(들): 4-(1-[4-(Dimethylaminoethoxy)phenyl]-2-phenyl-1-butenyl)phenol, 4-OHT, cis/trans-4-Hydroxytamoxifen
• 실험식(Hill 표기법): C₂₆H₂₉NO₂
• CAS Number: 68392-35-8
• Molecular Weight: 387.51
• UNSPSC 코드: 51111800
• PubChem Substance ID: 24895736
• NACRES: NA.77

속성

• 제품명: 4-Hydroxytamoxifen, ≥70% Z isomer (remainder primarily E-isomer)
• Quality Level: 300
• 분석: ≥98% (HPLC)
• 양식: powder
• 저장 조건: desiccated; protect from light
• solubility: methanol: 10 mg/mL; ethanol: 20 mg/mL (with heating)
• 항생제 활성 스펙트럼: neoplastics
• 동작 모드: enzyme | inhibits
• 주관자: AstraZeneca
• 저장 온도: 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
• 유전자 정보: human ... ESR1(2099) , ESR2(2100) , ESRRG(2104) , IL6(3569) ; rat ... Ar(24208) , Esr1(24890) , Esr2(25149)

설명

일반 설명

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]

애플리케이션

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]

생화학적/생리학적 작용

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.

특징 및 장점

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.

안전성 정보

• 픽토그램: GHS08,GHS07
• 신호어: Warning
• 유해 및 위험 성명서: H302 + H312 + H332,H315,H319,H361fd
• 예방조치 성명서: 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
• 개인 보호 장비: Eyeshields, Gloves, type P3 (EN 143) respirator cartridges