フェンレチニド

Fenretinide

HCID 5288209
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基本情報

CAS
65646-68-6
標準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
分子式
C26H33NO2
平均分子量
391.5 g/mol
単同位体質量
391.2511293

概要

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.

名称と識別子

優先名称
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
現地名
フェンレチニド
英語名
4-HYDROXYPHENYLRETINAMIDE
分子式
C26H33NO2
分子量
391.55

名称と別名

FENRETINIDE65646-68-6N-(4-Hydroxyphenyl)retinamide4-HPR4-hydroxyphenylretinamide4-Hydroxyphenyl retinamideall-trans-4'-HydroxyretinanilideFenretinidaMcN-R-1967FenretinidumRetinamide, N-(4-hydroxyphenyl)-N-(4-Hydroxyphenyl)all-Trans Retinamide
名称をさらに表示
フェンレチニミドN-(4-ヒドロキシフェニル)-レチンアミドN-(4-ヒドロキシフェニル)レチンアミド4-ヒドロキシフェニルレチンアミド(2E,4E,6E,8E)-N-(4-ヒドロキシフェニル)-3,7-ジメチル-9-(2,6,6-トリメチル-1-シクロヘキセン-1-イル)-2,4,6,8-ノナテトラエナミドフェンレチニドall-trans-N-(4-ヒドロキシフェニル)レチンアミドレチノイン酸 p-ヒドロキシアニリド(2E,4E,6E,8E)-N-(4-ヒドロキシフェニル)-3,7-ジメチル-9-(2,6,6-トリメチルシクロヘキサ-1-エン-1-イル)ノナ-2,4,6,8-テトラエンアミドhprRETINAMIDE4HPRMK-4016CNTFRalphaFenretinide(4-HPR)Fenretinide, >=98%
4-hydroxy(phenyl)retinamideRii retinamideDTXSID2032005all-trans-n-(4-hydroxyphenyl)retinamide15-[(4-hydroxyphenyl)amino]retinal187EJ7QEXLNSC-760419Fenretinimide

データベース識別子

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

物性

構造計算による物性

XLogP
7.3
極性表面積
49.3 Ų
水素結合供与体数
2
水素結合受容体数
2
回転可能結合数
6
重原子数
29

実験および物理化学的性質

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

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]

物理化学的性質

融点
162 · 162-163°C
沸点
597.6 · 597.6±42.0 °C(Predicted)
比重(密度)
1.081 · 1.081±0.06 g/cm3(Predicted)
貯蔵温度
-20 °C · -20°C
溶解性
クロロホルム（微量）、メタノール（微量）
外見
オレンジ色の固体

化学的性質

化学的特性4-HYDROXYPHENYLRETINAMIDE is Yellow Powder

安全と法規制

GHS分類

GHS Classification · 4 件

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.

危険有害性情報

Hazard Classes and CategoriesAcute Tox. 4 (97.7%)

安全データ

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

化学と産業

薬理情報

Mechanism of Action · 1 件

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 件

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.

応用分野 · 2 件

使用4-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

一般的な説明Retinoic acid p-hydroxyanilide is a synthetic analog of retinoid.

上流・下流製品情報

サプライヤー100 社

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]
補足説明 · 1 件

定義ChEBI: 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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