Fenretinide 全反式-N-(4-羟苯基)维甲酸

CAS 65646-68-6 MFCD00792674

化学结构图

65646-68-6
SMILES: CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)Nc2ccc(O)cc2)C(C)(C)CCC1

化学属性

Mol. FormulaC26H33NO2
Mol. Weight391.54572
Melting Point170.0 to 174.0 deg-C
Appearance Solid powder
SolubilitySoluble in DMSO, not in water

别名和识别编码

Chemical NameFenretinide
CAS Number65646-68-6
Synonym (2E,4E,6E,8E)-N-(4-Hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenamide 4-HPR 4-HPR Fenretinide N-(4-Hydroxyphenyl)retinamide 4-HPR, Fenretinide, N-(4-Hydroxyphenyl)retinamide 4-HPR; McNR-1967; McNR1967; McNR 1967; HPR; Fenretinide 4-HYDROXYPHENYLRETINAMIDE 4HPR FENRETINIDE Fenretinide Fenretinimide N-(4-HYDROXYPHENYL)-ALL-TRANS RETINAMIDE N-(4-HYDROXYPHENYL)RETINAMIDE N-(4-Hydroxyphenyl)retinamide RETINAMIDE RETINOIC ACID P-HYDROXYANILIDE Retinoic acid p-hydroxyanilide Retinoic acid p-hydroxyphenylamide hpr n-(4-hydroxyphenyl)-retinamid p-Hydroxyphenylretinamide
MDL NumberMFCD00792674
PubChem Substance ID253662215
Chemical Name Translation全反式-N-(4-羟苯基)维甲酸
Reaxys-RN5769490
Merck Number3998
Beilstein Registry Number5769490
FormulaC26H33NO2
IUPAC Name(2E,4E,6E,8E)-N-(4-hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenamide
InChIKeyAKJHMTWEGVYYSE-FXILSDISSA-N
InChIInChI=1S/C26H33NO2/c1-19(11-16-24-21(3)10-7-17-26(24,4)5)8-6-9-20(2)18-25(29)27-22-12-14-23(28)15-13-22/h6,8-9,11-16,18,28H,7,10,17H2,1-5H3,(H,27,29)/b9-6+,16-11+,19-8+,20-18+
Canonical SMILESO=C(NC1=CC=C(O)C=C1)/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)CCCC2(C)C
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分类

  • Drug Analogues
  • {SNA} Bioactive Small Molecule Alphabetical Index, Gene Regulation, Gene Regulation and Expression, PPAR and RXR Regulators, R, Vitamin A, Vitamins, 抗肿瘤药物, 生化试剂, 生物活性小分子, 癌症研究, 细胞信号转导和神经科学, 细胞生物学
  • Retinoids,
  • {SNA} Bioactive Small Molecule Alphabetical Index, Gene Regulation, Gene Regulation and Expression, PPAR and RXR Regulators, R, Vitamin A, Vitamins, 抗肿瘤药物, 生物活性小分子, 癌症研究, 细胞信号转导和神经科学, 细胞生物学, 营养研究
  • {SNA} Antitumor Agents,

产品应用

  • Fenretinide is an orally-active synthetic phenylretinamide analogue of retinol (vitamin A) with potential antineoplastic and chemopreventive activities. Fenretinide binds to and activates retinoic acid receptors (RARs), thereby inducing cell differentiation and apoptosis in some tumor cell types. This agent also inhibits tumor growth by modulating angiogenesis-associated growth factors and their receptors and exhibits retinoid receptor-independent apoptotic properties.

相关文献及参考

  • [2]. Bikman, Benjamin T., et al. Fenretinide Prevents Lipid-induced Insulin Resistance by Blocking Ceramide Biosynthesis. Journal of Biological Chemistry (2012), 287(21), 17426-17437.
  • [3]. Cooper JP, et al. Fenretinide metabolism in humans and mice: utilizing pharmacological modulation of its metabolic pathway to increase systemic exposure. Br J Pharmacol. 2011 Jul;163(6):1263-75.
  • [4]. Golubkov V, et al. Action of fenretinide (4-HPR) on ovarian cancer and endothelial cells. Anticancer Res. 2005 Jan-Feb;25(1A):249-53.
  • Costa., A., et al.: Cancer Res., 54, Suppl., 2032s (1994),
  • Delia, D., et al.: Cancer Res., 53, 6036 (1993),
  • Marth, C., et al.:J. Nat. Cancer Inst., 75, 871 (1985),
  • [1]. Apraiz, Aintzane., et al.
  • [1]. Apraiz, Aintzane., et al. Dihydroceramide accumulation and reactive oxygen species are distinct and nonessential events in 4-HPR-mediated leukemia cell death. Biochemistry and Cell Biology (2012), 90(2), 209-223.

安全信息

WGK Germany3
GHS Symbol
Precautionary statements
  • P271 Use only outdoors or in a well-ventilated area.? 只能在室外或通风良好的地方使用。
  • P308+P313
  • P332+P313
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
  • P301+P312+P330
  • P302+P350
  • P337+P313
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P305+P351+P338
  • P201 Obtain special instructions before use. 使用前获取专门指示。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西，喝水或吸烟。
  • P202 Do not handle until all safety precautions have been read and understood. 已阅读并理解所有的安全预防措施之前，切勿操作。
  • P304+P340+P312
  • P305+P351+P338+P337+P313
Hazard statements
  • H332 Harmful if inhaled 吸入有害
  • H315 Causes skin irritation 会刺激皮肤
  • H302 Harmful if swallowed 吞食有害
  • H312 Harmful in contact with skin 皮肤接触有害
  • H335 May cause respiratory irritation 可能导致呼吸道刺激
  • H319 Causes serious eye irritation 严重刺激眼睛
  • H360 May damage fertility or the unborn child 可能对生育能力或未出生婴儿造成伤害
  • H302+H312+H332
RTECSVH6420000
Signal word Danger
Personal Protective Equipment Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
Hazard Codes T
Safety Statements
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后，立即用大量水冲洗并征求医生意见；
  • S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护；
  • S45 In case of accident or if you feel unwell seek medical advice immediately (show the label where possible) 发生事故时或感觉不适时，立即求医（可能时出示标签）；
  • S53 Avoid exposure - obtain special instructions before use 避免接触，使用前获得特别指示说明；
Risk Statements
  • R60 May impair fertility 可能降低生殖能力
  • R61 May cause harm to the unborn child 可能对未出生的婴儿导致伤害
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
  • R20/21/22 Harmful by inhalation, in contact with skin and if swallowed 吸入、皮肤接触和不慎吞咽有害
Storage condition -20°C Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years). 
TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human - woman
DOSE/DURATION           : 210 mg/kg/2W-I
TOXIC EFFECTS :
   Sense Organs and Special Senses (Eye) - retinal changes (pigmentary
   depositions, retinitis, other)
REFERENCE :
   AROPAW Archives of Ophthalmology (Chicago).  (AMA, 535 N. Dearborn St.,
   Chicago, IL 60610)  New series: V.1-44(3), 1929-50; V.64-    1960-
   Volume(issue)/page/year: 104,69,1986

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human - man
DOSE/DURATION           : 180 mg/kg/18D-I
TOXIC EFFECTS :
   Sense Organs and Special Senses (Eye) - retinal changes (pigmentary
   depositions, retinitis, other)
REFERENCE :
   AROPAW Archives of Ophthalmology (Chicago).  (AMA, 535 N. Dearborn St.,
   Chicago, IL 60610)  New series: V.1-44(3), 1929-50; V.64-    1960-
   Volume(issue)/page/year: 104,69,1986

TYPE OF TEST            : Morphological transformation
TEST SYSTEM             : Rodent - mouse Mammary gland
DOSE/DURATION           : 10 umol/L
REFERENCE :
   NUCADQ Nutrition and Cancer.  (Franklin Institute Press, POB 2266,
   Phildelphia, PA 19103) V.1-    1978-  Volume(issue)/page/year: 7,105,1985

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE                    : 400 mg/kg
SEX/DURATION            : female 11 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
   TJADAB Teratology, The International Journal of Abnormal Development. (Alan
   R. Liss, Inc., 41 E. 11th St., New York, NY 10003)  V.1-    1968-
   Volume(issue)/page/year: 45,175,1992

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 600 mg/kg
SEX/DURATION            : female 10-11 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Fertility - post-implantation mortality (e.g. dead and/or
   resorbed implants per total number of implants)
REFERENCE :
   IJEPEI International Journal of Experimental Pathology.  (Blackwell
   Scientific Publications Ltd., POB 88, Oxford, OX2 0NE, United kingdom) V.71-
      1990-  Volume(issue)/page/year: 73,551,1992

系列性分类

  1. Life Science 生命科学
  2. Cell Biology 细胞生物学
  3. Cell Signaling and Neuroscience - Cell Biology
  4. Gene Regulation and Expression - Cell Signaling and Neuroscience
  5. PPAR and RXR Regulators - Gene Regulation and Expression
  1. Life Science 生命科学
  2. Cell Biology 细胞生物学
  3. Cell Signaling and Neuroscience - Cell Biology
  4. Gene Regulation and Expression - Cell Signaling and Neuroscience
  5. PPAR and RXR Regulators - Gene Regulation and Expression
  1. Medical Research Areas
  2. Metabolism
  3. Retinoid Receptor
  1. Medical Research Areas
  2. Metabolism
  3. RAR/RXR  (维甲酸受体)

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