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
이름 더 보기
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
- 형식 전하
- 0
- 복잡도
- 726
실험 및 물리화학적 성질
Collision Cross Section
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
- 산도 계수 (pKa)
- 9.98 · 9.98±0.26(Predicted)
- 색상
- 노란색
- 생물학적 소스
- synthetic (organic)
- Merck
- 14 · 14,3998
- 안정성
- 감광성 - 빛 노출로부터 보호
- InChIKey
- AKJHMTWEGVYYSE-FXILSDISSA-N
- SMILES
- C(NC1=CC=C(O)C=C1)(=O)/C=C(/C=C/C=C(/C=C/C1C(C)(C)CCCC=1C)\C)\C
화학적 성질
4-HYDROXYPHENYLRETINAMIDE is Yellow Powder
안전 및 규제
GHS 분류
GHS Classification
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
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
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Repr. 1BSkin Irrit. 2STOT SE 3
- 스토리지 클래스
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
화학 및 산업
약리 정보
Mechanism of Action
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.
MeSH Pharmacological Classification
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
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
상류 원료
공급사100 곳
추가 설명
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.
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