4-Hydroxytamoxifen

HCID 449459

Substructure search Find similar structures

Basic information

CAS: 68047-06-3
Standard SMILES: CC/C(=C(\c1ccc(O)cc1)c1ccc(OCCN(C)C)cc1)c1ccccc1
InChIKey: TXUZVZSFRXZGTL-QPLCGJKRSA-N
Molecular formula: C26H29NO2
Average molar mass: 387.5 g/mol
Monoisotopic mass: 387.21982917

Overview

Afimoxifene is a tertiary amino compound that is tamoxifen in which the phenyl group which is in a Z- relationship to the ethyl substituent is hydroxylated at the para- position. It is the active metabolite of tamoxifen. It has a role as a metabolite, an antineoplastic agent and an estrogen receptor antagonist. It is a member of phenols and a tertiary amino compound. It is functionally related to a tamoxifen.

Names & identifiers

Preferred name: 4-Hydroxytamoxifen
IUPAC: 4-[(Z)-1-[4-[2-(dimethylamino)ethoxy]phenyl]-2-phenylbut-1-enyl]phenol
English name: 4-HYDROXYTAMOXIFEN
Molecular formula: C26H29NO2
Molecular weight: 387.51

Names & synonyms

4-Hydroxytamoxifen(Z)-4-Hydroxytamoxifen68047-06-3HydroxytamoxifenDTXSID70223844-OHT hydrotamoxifen95K54647BZ4-[(Z)-1-[4-[2-(dimethylamino)ethoxy]phenyl]-2-phenylbut-1-enyl]phenol4-[(1Z)-1-{4-[2-(dimethylamino)ethoxy]phenyl}-2-phenylbut-1-en-1-yl]phenolDTXCID802384ICI-79280DTXCID0028161

Show more names

4-OHTtrans-4-Hydroxytamoxifen, (Z)-4-(1-[4-(Dimethylaminoethoxy)phenyl]-2-phenyl-1-butenyl)phenolC05011(Z)-4-OHTici79,280(E)-4’4-Benzyloxy β4-HYDROXYTAMOXIFENTAMOXIFEN, 4-HYDROXY-

DTXSID30370944-((Z)-1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenylbut-1-enyl)phenol4OH-tamoxifen4-((1Z)-1-(4-(2-(dimethylamino)ethoxy)phenyl)-2-phenylbut-1-en-1-yl)phenolRefChem:912611635-210-74-((Z)-1-(4-(2-dimethylaminoethyloxy)phenyl)-1-phenylbut-1-en-2-yl) phenolAfimoxifene

Database identifiers

CAS: 68047-06-3、68392-35-8
PubChem CID: 449459
DTXSID: DTXSID7022384
ChEMBL: CHEMBL489
ChEBI: CHEBI:44616
UNII: 95K54647BZ
EC Number: 635-210-7
Nikkaji: J354.277G

Properties

Computed structural properties

XLogP: 6.8
Topological polar surface area: 32.7 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 3
Rotatable bonds: 8
Heavy atoms: 29
Formal charge: 0
Complexity: 493

Experimental & physicochemical properties

Drugs · 2 items

Pharmaceuticals -> Antibiotics

Pharmaceuticals -> Listed in ZINC15

Endocrine DisruptorsPotential endocrine disrupting compound

Physicochemical properties

Melting point: 105 · 105-107°C
Boiling point: 513.45 °C · 513.45°C (rough estimate)
Density: 1.1005 · 1.1005 (rough estimate)
refractive index: 1.6 · 1.6000 (estimate)
storage temp.: 2 · 2-8°C
solubility: 95 % · 95% ethanol: 20 mg/mL
form: powder
pka: 10.35 · 10.35±0.15(Predicted)
color: white
Stability: Stable. Store cool. Incompatible with strong oxidizing agents.
InChI: 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-
InChIKey: TXUZVZSFRXZGTL-OCEACIFDSA-N
SMILES: C1(O)=CC=C(/C(/C2=CC=C(OCCN(C)C)C=C2)=C(/C2=CC=CC=C2)\CC)C=C1
CAS DataBase Reference: 68047 · 68047-06-3
NCI Dictionary of Cancer Terms: 4 · 4-hydroxytamoxifen
FDA UNII: 95 K54647BZ · 95K54647BZ
UNSPSC Code: 51111800 · 51111800
NACRES: 77 · NA.77
Symbol(GHS): 7 · GHS07,GHS08,GHS09
Signal word: Danger
Hazard statements: 302 · H302-H350-H360FD-H410
Precautionary statements: 201 · P201-P202-P264-P273-P301+P312-P308+P313
PPE: 3 · Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
Hazard Codes: Xn
Risk Statements: 20 · 20/21/22-63
Safety Statements: 22 · 22-23-36
WGK Germany: 3 · 3
RTECS: 1210000 · SL1210000
Storage Class: 6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications: 4 OralAquatic · Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Carc. 1BRepr. 1B

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P318, P321, P330, P362+P364, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Toxicology

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Safety data

PPE: Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
wgk: 3
rtecs: SL1210000
risk_code: 20/21/22-63
Signal word: Danger
Symbol(GHS): GHS07,GHS08,GHS09
hazard_code: Xn
safety_code: 22-23-36
Storage Class: 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard statements: H302-H350-H360FD-H410
Hazard Classifications: Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Carc. 1BRepr. 1B
Precautionary statements: P201-P202-P264-P273-P301+P312-P308+P313

Chemistry & industry

Pharmacology

Mechanism of ActionAfimoxifene binds to estrogen receptors (ER), inducing a conformational change in the receptor. This results in a blockage or change in the expression of estrogen dependent genes.

Metabolism/Metabolites4-Hydroxytamoxifen has known human metabolites that include Tamoxifen 4-O-glucuronide, Endoxifen, Tamoxifen 4-O-sulfate, and 3,4-Dihydroxy-Tamoxifen.

MeSH Pharmacological Classification · 3 items

Substances that inhibit or prevent the proliferation of NEOPLASMS.

Compounds which inhibit or antagonize the action or biosynthesis of estrogenic compounds.

A structurally diverse group of compounds distinguished from ESTROGENS by their ability to bind and activate ESTROGEN RECEPTORS but act as either an agonist or antagonist depending on the tissue type and hormonal milieu. They are classified as either first generation because they demonstrate estrogen agonist properties in the ENDOMETRIUM or second generation based on their patterns of tissue specificity. (Horm Res 1997;48:155-63)

Absorption, Distribution and ExcretionAbsorbed following topical application.

Tissue LocationsKidney

Cellular LocationsCytoplasm

Applications · 5 items

UsesA metabolite of Tamoxifen (T006000). A hydroxylated analogue of Tamoxifen with anti-estrogenic properties.

Uses(Z)-4-Hydroxy Tamoxifen is a metabolite of Tamoxifen (T006000). (Z)-4-Hydroxy Tamoxifen is a hydroxylated analogue of Tamoxifen. (Z)-4-Hydroxy Tamoxifen is a metabolite of Tamoxifen with anti-estrogenic properties.

Usestamoxifen metabolite, anti-estrogen, see Tamoxifen 1,01038

UsesA hydroxylated analogue of tamoxifen with anti-estrogenic properties. A metabolite of Tamoxifen.

General DescriptionA cell-permeable, active metabolite of Tamoxifen (Cat. No. 579000) that acts as a potent inhibitor of PKC. It is more potent than the parent compound and inhibits PKC by modifying its catalytic domain. Also available as a 10 mM solution in EtOH (Cat. No. 508225).

Upstream & downstream products

Upstream raw materials

185223-78-3 (E)-4-Hydroxytamoxifen 4-(1-(4-(2-bromoethoxy)phenyl)-2-phenylbut-1-en-1-yl)phenol(WXC07440)2-(4-BROMOPHENOXY)TETRAHYDRO-2H-PYRAN 1,1-bis(4-hydroxyphenyl)-2-phenylbut-1-ene Tamoxifen 4,4'-Dihydroxybenzophenone Dimethylamine Propiophenone 2-Dimethylaminoethyl chloride hydrochloride

Suppliers106 total

阿诺西（上海）生物技术有限公司400-1107768 15058188853 · [email protected]

湖北永阔科技有限公司027-59223108 15972152991 · [email protected]

湖南韵邦生物科技股份有限公司0731-88532326 13319508186 · [email protected]

湖北万得化工有限公司15377098680 15377098680 · [email protected]

武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]

Additional notes · 1 item

DefinitionChEBI: Afimoxifene is a tertiary amino compound that is tamoxifen in which the phenyl group which is in a Z- relationship to the ethyl substituent is hydroxylated at the para- position. It is the active metabolite of tamoxifen. It has a role as an antineoplastic agent, an estrogen receptor antagonist and a metabolite. It is a tertiary amino compound and a member of phenols. It is functionally related to a tamoxifen.

Related reactions

3 records

New reaction record

HRID 1074308As reactantuspto-grants-1990_11

HRID 1074309As reactantuspto-grants-1990_11

HRID 2296911As reactantuspto-grants-2002_12

Compound notes

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