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Fenretinide

Fenretinide structure

CAS No:
65646-68-6
Formula:
C26H33NO2
Chemical Name:
Fenretinide
Synonyms:
Retinamide,N-(4-hydroxyphenyl)-;N-(4-Hydroxyphenyl)retinamide;N-(4-Hydroxyphenyl)-all-trans-retinamide;Retinoic acid p-hydroxyphenylamide;Fenretinide;all-trans-N-(4-Hydroxyphenyl)retinamide;(4-Hydroxyphenyl)retinamide;Ro 22-4667;4-HPR;all-trans-4′-Hydroxyretinanilide;RII retinamide;MK 4016;Retinoic acid p-hydroxyanilide;1006055-28-2;2321387-54-4
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

Description

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 antineoplastic agent and an antioxidant. It is a retinoid and a monocarboxylic acid amide. It derives from an all-trans-retinoic acid.|A synthetic retinoid that is used orally as a chemopreventive against prostate cancer and in women at risk of developing contralateral breast cancer. It is also effective as an antineoplastic agent.|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. (NCI04)

Fenretinide Basic Attributes

Molecular Weight：

391.55

Exact Mass：

391.55

EC Number：

200-256-5

UNII：

187EJ7QEXL

NSC Number：

760419|374551

DSSTox ID：

DTXSID2032005

NCI Thesaurus Code：

C1098

Characteristics

Density：

1.081±0.06 g/cm3

Melting Point：

173-175 °C

Boiling Point：

597.6±42.0 °C(Predicted)

PKA：

9.98±0.26

Collision Cross Section：

200.5 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Safety Information

wgk germany：

hazard class code：

60-61-20/21/22-36/37/38

safety instructions：

53-26-36/37/39-45-52

RTECS Number：

VH6420000

Marks：

GHS Classification：

|Danger|H302 (97.67%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P308+P313, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 43 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Toxicity Summary：

"Mechanism of fenretinide (4-HPR)-induced cell death"

Drug Information

Drug Indication：

Investigated for use/treatment in macular degeneration.

MeSH：

Agents that reduce the frequency or rate of spontaneous or induced tumors independently of the mechanism involved. (See all compounds classified as Anticarcinogenic Agents.)|Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

Metabolism/Metabolites：

Fenretinide has known human metabolites that include (2S,3S,4S,5R)-6-[4-[[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoyl]amino]phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid.

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 Entry Terms：

13-cis-Isomer Fenretinide

Fenretinide Use and Manufacturing

Uses

4-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

Use Classification：

Human drugs -> Rare disease (orphan)

Computed Properties

Molecular Weight:391.5
XLogP3:7.3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:6
Exact Mass:391.251129295
Monoisotopic Mass:391.251129295
Topological Polar Surface Area:49.3
Heavy Atom Count:29
Complexity:726
Defined Bond Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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65646-68-6 (2E,4E,6E,8E)-N-(4-hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenamide

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