390900

4-Hydroxyphenylretinamide

A synthetic amide of all-trans retinoic acid (RA) that displays reduced toxicity relative to RA while maintaining significant biological activity.

• Synonym(s): 4-Hydroxyphenylretinamide, Fenretinide, 4HPR, N-(4-Hydroxyphenyl)-all- trans Retinamide
• Empirical Formula (Hill Notation): C₂₆H₃₃NO₂
• CAS Number: 65646-68-6
• Molecular Weight: 391.55
• UNSPSC Code: 12352200
• NACRES: NA.77
• MDL number: MFCD00792674
• Assay: ≥97% (TLC)
• Form: solid
• Quality level: 100
• Storage condition: OK to freeze, protect from light

Properties

• Quality Level: 100
• description: Merck USA index - 14, 3998
• assay: ≥97% (TLC)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze, protect from light
• color: orange
• solubility: DMSO: 25 mg/mL, acetone: soluble, ethanol: soluble
• shipped in: ambient
• storage temp.: −20°C
• SMILES string: N(c2ccc(cc2)O)C(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(CCCC1(C)C)C
• InChI: 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+
• InChI key: AKJHMTWEGVYYSE-FXILSDISSA-N

Description

General description

A synthetic amide of all-trans retinoic acid (RA) that displays reduced toxicity relative to RA while maintaining significant biological activity. Active in the prevention and treatment of a variety of neoplasms in animals. Inhibits proliferation in cell lines of human breast cancer, prostate adenocarcinoma, and ovarian carcinoma. Inhibits angiogenesis, as well as endothelial cell motility and tubule formation. Induces apoptosis in malignant hemopoietic cell lines.

Biochem/physiol Actions

Cell permeable: no

Primary Target
Active in the prevention and treatment of a variety of neoplasms in animals.

Product does not compete with ATP.

Reversible: no

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Formelli, F., et al. 1996. FASEB J. 10, 1014.
Naik, H.R., et al. 1995. Adv. Pharmacol. 33, 315.
Delia, D., et al. 1993. Cancer Res. 53, 6036.
Pienta, K.J., et al. 1993. Cancer Res. 53, 224.
Grubbs, C.J., et al. 1990. Anticancer Res. 10, 661.
McCarthy, D.J., et al. 1987. Cancer Res.47, 5014.
Moon, R.C., et al. 1979. Cancer Res.39, 1339.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Harmful & Carcinogenic / Teratogenic (E)

Safety Information

• pictograms: GHS08,GHS07
• signalword: Danger
• hcodes: H302 + H312 + H332,H315,H319,H335,H360
• pcodes: P280 - P301 + P312 - P302 + P352 + P312 - P304 + P340 + P312 - P305 + P351 + P338 - P308 + P313
• Hazard Classifications: Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Repr. 1B - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable