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Merck

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

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About This Item

Empirical Formula (Hill Notation):
C26H33NO2
CAS Number:
65646-68-6
Molecular Weight:
391.55
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD00792674

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Product Name

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

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

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

Quality Level

100

Related Categories

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

Disclaimer

Toxicity: Harmful & Carcinogenic / Teratogenic (E)

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.

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.

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.

Legal Information

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

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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