4-히드록시페닐레틴아미드

Fenretinide

HCID 5288209

기본 정보

CAS
65646-68-6
표준 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
분자식
C26H33NO2
평균 분자량
391.5 g/mol
단동위원소 질량
391.2511293

개요

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.

이름 및 식별자

우선 이름
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
현지명
4-히드록시페닐레틴아미드
영어명
4-HYDROXYPHENYLRETINAMIDE
분자식
C26H33NO2
분자량
391.55

이름 및 동의어

FENRETINIDE65646-68-6N-(4-Hydroxyphenyl)retinamide4-HPR4-hydroxyphenylretinamide4-Hydroxyphenyl retinamideall-trans-4'-HydroxyretinanilideFenretinidaMcN-R-1967FenretinidumRetinamide, N-(4-hydroxyphenyl)-N-(4-Hydroxyphenyl)all-Trans Retinamide
이름 더 보기
4-히드록시페닐레틴아미드hprRETINAMIDE4HPRMK-4016CNTFRalphaFenretinide(4-HPR)Fenretinide, >=98%
4-hydroxy(phenyl)retinamideRii retinamideDTXSID2032005all-trans-n-(4-hydroxyphenyl)retinamide15-[(4-hydroxyphenyl)amino]retinal187EJ7QEXLNSC-760419Fenretinimide

데이터베이스 식별자

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

물성

구조 계산 물성

XLogP
7.3
극성 표면적
49.3 Ų
수소 결합 공여자 수
2
수소 결합 수용자 수
2
회전 가능 결합 수
6
무거운 원자 수
29

실험 및 물리화학적 성질

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

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]

물리화학적 성질

녹는점
162 · 162-163°C
끓는 점
597.6 · 597.6±42.0 °C(Predicted)
밀도
1.081 · 1.081±0.06 g/cm3(Predicted)
저장 조건
-20 °C · -20°C
용해도
클로로포름(약간 용해됨), 메탄올(약간 용해됨)
물리적 상태
주황색 고체

화학적 성질

4-HYDROXYPHENYLRETINAMIDE is Yellow Powder

안전 및 규제

GHS 분류

GHS Classification · 4건

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.

유해성 정보

Hazard Classes and CategoriesAcute Tox. 4 (97.7%)

안전 데이터

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

화학 및 산업

약리 정보

Mechanism of Action · 1건

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 · 2건

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.

응용 분야 · 2건

용도4-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

일반 설명Retinoic acid p-hydroxyanilide is a synthetic analog of retinoid.

상·하류 제품 정보

공급사100 곳

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]
추가 설명 · 1건

정의ChEBI: 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.

관련 반응

6건

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