Fenretinide

HCID 5288209
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Grundinformationen

CAS
65646-68-6
Standard-SMILES
CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)Nc2ccc(O)cc2)C(C)(C)CCC1
InChIKey
AKJHMTWEGVYYSE-FXILSDISSA-N
Summenformel
C26H33NO2
Durchschnittliche Molmasse
391,5 g/mol
Monoisotopische Masse
391,2511293

Überblick

4-hydroxyphenyl retinamide is a retinoid obtained by formal condensation of the carboxy group of all-trans retinoic acid and the anilino group of 4-hydroxyaniline. Synthetic retinoid agonist. Antiproliferative, antioxidant and anticancer agent with a long half-life in vivo. Apoptotic effects appear to be mediated by a mechanism distinct from that of 'classical' retinoids. It has a role as an antioxidant and an antineoplastic agent. It is a retinoid and a monocarboxylic acid amide. It is functionally related to an all-trans-retinoic acid.

Namen und Bezeichner

Bevorzugter Name
Fenretinide
IUPAC
(2E,4E,6E,8E)-N-(4-hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenamide
Englischer Name
4-HYDROXYPHENYLRETINAMIDE
Summenformel
C26H33NO2
Molmasse
391.55

Namen und Synonyme

FENRETINIDE65646-68-6N-(4-Hydroxyphenyl)retinamide4-HPR4-hydroxyphenylretinamide4-Hydroxyphenyl retinamideall-trans-4'-HydroxyretinanilideFenretinidaMcN-R-1967FenretinidumRetinamide, N-(4-hydroxyphenyl)-N-(4-Hydroxyphenyl)all-Trans Retinamide
Weitere Namen anzeigen
hprRETINAMIDE4HPRMK-4016CNTFRalphaFenretinide(4-HPR)Fenretinide, >=98%
4-hydroxy(phenyl)retinamideRii retinamideDTXSID2032005all-trans-n-(4-hydroxyphenyl)retinamide15-[(4-hydroxyphenyl)amino]retinal187EJ7QEXLNSC-760419Fenretinimide

Datenbank-Bezeichner

CAS
65646-68-6
PubChem CID
5288209
DTXSID
DTXSID2032005
ChEMBL
CHEMBL7301
ChEBI
CHEBI:42588
UNII
187EJ7QEXL
EC Number
636-255-5
Nikkaji
J2.845.877K、J23.263G

Eigenschaften

Berechnete Struktureigenschaften

XLogP
7,3
Polarare Oberfläche (TPSA)
49,3 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
6
Schwere Atome
29

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15
Collision Cross Section · 2 Einträge

197.14 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

200.5 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physikochemische Eigenschaften

Schmelzpunkt
162 · 162-163°C
Siedepunkt
597.6 · 597.6±42.0 °C(Predicted)
Dichte
1.081 · 1.081±0.06 g/cm3(Predicted)
storage temp.
-20 °C · -20°C
Löslichkeit
Chloroform (Slightly), Methanol (Slightly)
Aggregatzustand
Orange solid

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H302 (97.7%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 43 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 4 (97.7%)

Sicherheitsdaten

wgk
3
hs_code
2924297099
RTECS-Nr.
VH6420000
risk_code
60-61-20/21/22-36/37/38
hazard_code
T
safety_code
53-26-36/37/39-45-52

Chemie und Industrie

Pharmakologische Informationen

Mechanism of Action · 1 Eintrag

Fenretinide inhibits the growth of several human cancer cell lines, acting through both retinoid-receptor-dependent and retinoid-receptor-independent mechanisms.1In vivo, fenretinide selectively accumulates in breast tissue and is particularly active in inhibiting rat mammary carcinogenesis.1 An important feature of fenretinide is its ability to inhibit cell growth through the induction of apoptosis rather than through differentiation, an effect that is strikingly different from that of vitamin A.1 In contrast to tamoxifen, which inhibits only estrogen receptor (ER)-positive tumors, fenretinide induces apoptosis in both ER-positive and ER-negative breast cancer cell lines.2 All of these properties render fenretinide an attractive candidate for breast cancer chemoprevention.

Metabolism/MetabolitesFenretinide has known human metabolites that include (2S,3S,4S,5R)-6-[4-[[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoyl]amino]phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid.
MeSH Pharmacological Classification · 2 Einträge

Substances that inhibit or prevent the proliferation of NEOPLASMS.

Agents that reduce the frequency or rate of spontaneous or induced tumors independently of the mechanism involved.

Anwendungen · 1 Eintrag

Verwenden4-HYDROXYPHENYLRETINAMIDE is an effective agent for the chemoprevention and growth modulation of oncogene-induced prostate cancer in the mouse prostate reconstitution model system and may be effective for the chemoprevention of human prostate cancer

Vor- und nachgelagerte Produkte

Anbieter100 Anbieter

北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]
Hong Kong Tiansheng New Material Trading Co., Ltd+8617320695765 · [email protected]
Ergänzende Hinweise · 1 Eintrag

DefinitionChEBI: A retinoid obtained by formal condensation of the carboxy group of all-trans retinoic acid and the anilino group of 4-hydroxyaniline. Synthetic retinoid agonist. Antiproliferative, antioxidant and anticancer agent with a long half-life in ivo. Apoptotic effects appear to be mediated by a mechanism distinct from that of 'classical' retinoids.

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