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
• MDL number: MFCD00792674
• UNSPSC Code: 12352200
• NACRES: NA.77

Properties

• Quality Level: 100
• 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
• 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 human breast cancer, prostate adenocarcinoma, and ovarian carcinoma cell proliferation. Inhibits angiogenesis as well as endothelial cell motility and tubule formation. Induces apoptosis in malignant hemopoietic cell lines.

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

Warning

Toxicity: Harmful & Carcinogenic / Teratogenic (E)

Reconstitution

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

Safety Information

• Pictograms: GHS08,GHS07
• Signal Word: Danger
• Hazard Statements: H302 + H312 + H332,H315,H319,H335,H360
• Precautionary Statements: 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 Code: 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