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Etretinate

Etretinate structure

CAS No:
54350-48-0
Formula:
C23H30O3
Chemical Name:
Etretinate
Synonyms:
2,4,6,8-Nonatetraenoic acid,9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-,ethyl ester,(2E,4E,6E,8E)-;2,4,6,8-Nonatetraenoic acid,9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-,ethyl ester,(all-E)-;Ethyl all-trans-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoate;Ro 10-9359;Etretinate;Tigason;Ethyl etrinoate;Tigasone;Tegison;71833-61-9
Categories:
Active Pharmaceutical Ingredients > Specialty Drugs

Description

Etretinate(Ro 10-9359) is a second-generation retinoid to treat severe psoriasis; has been replaced by acitretin, a safer metabolite of etretinate.

Etretinate is a medication used to treat severe psoriasis. It is a synthetic aromatic retinoid. The mechanism of action of etretinate is still incompletely understood although, like retinoic acid, it is thought to interfere with the terminal differentiation of keratinocytes. It is thought to bind to the retinoic acid receptors. Etretinate is also believed to enhance the binding of cAMP to the regulatory RI subunit of cAMP dependent protein kinases. Etretinate was taken off the market in Canada in 1996 and America in 1998 due to the risk of birth defects. Etretinate is now used to treat T-cell lymphomas. It also appears to inhibit NADH oxidase activity.

Etretinate Basic Attributes

Molecular Weight：

354.48

Exact Mass：

354.48

EC Number：

259-119-3

HScode：

2918992090

Characteristics

PSA：

35.5

XLogP3：

8.43 /Estimated/

Density：

1.0±0.1 g/cm3

Melting Point：

104-105 °C

Boiling Point：

506.4±38.0 °C at 760 mmHg

Flash Point：

219.4±21.4 °C

Refractive Index：

1.544

Storage Conditions：

Amber Vial, -20°C Freezer

Vapor Pressure：

2.2X10-7 mm Hg @ 25 deg C /Estimated/

Toxicity：

LD50 in mice (1 day): >4000 mg/kg i.p. (Bollag); LD50 (20 day) in mice, rats (mg/kg): 1176, >2000 i.p.; >2000, >4000 orally (Kamm)

Safety Information

Transport codes：

NONH for all modes of transport

Precautionary statement(s)：

P201, P202, P261, P264, P271, P273, P280, P281, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P332+P313, P337+P313, P362, P391, P403+P233, P405, P501

Hazard Statements：

H315

Toxicity

Toxicity Summary：

Symptoms of overdose include headache and vertigo.

Protein Binding：

More than 99% bound to plasma proteins, predominantly lipoproteins, whereas its active metabolite, acetretin (etretin), is predominantly bound to albumin.

Drug Information

Drug Indication：

For the treatment of severe psoriasis in adults.

Pharmacology：

The active metabolite responsible for etretinate's effects, acitretin, is a retinoid. Retinoids have a structure similar to vitamin A and are involved in the normal growth of skin cells. Acitretin works by inhibiting the excessive cell growth and keratinisation (process by which skin cells become thickened due to the deposition of a protein within them) seen in psoriasis. It therefore reduces the thickening of the skin, plaque formation and scaling.

Absorption：

Absorbed in the small intestine. Studies in normal volunteers indicate that the absorption of etretinate is greater in patients consuming whole milk or a high-fat diet than in patients in a fasting state.

Metabolism/Metabolites：

Extensively metabolized, with significant first-pass metabolism to the pharmacologically active acid form. Subsequent metabolism results in the inactive 13-cis acid form, chain-shortened breakdown products, and conjugates that are ultimately excreted.

Biological Half-Life：

In one study, the apparent terminal half-life of etretinate after 6 months of therapy was approximately 120 days. In another study of 47 patients who had undergone chronic therapy with etretinate, 5 patients had detectable serum drug concentrations (0.5 to 12 ng/mL) 2.1 to 2.9 years after therapy was completed.

Mechanism of Action：

The mechanism of action of the active metabolite, acitretin, is unknown, however it is believed to work by targeting specific receptors (retinoid receptors) in the skin which help normalize the growth cycle of skin cells.

Etretinate Use and Manufacturing

Aromatic analog of Retinoic Acid. Immunomodulator. Antipsoriatic

Computed Properties

Molecular Weight:354.5
XLogP3:6.8
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:8
Exact Mass:354.21949481
Monoisotopic Mass:354.21949481
Topological Polar Surface Area:35.5
Heavy Atom Count:26
Complexity:568
Undefined Bond Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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CAS No.: 54350-48-0

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CAS No.: 54350-48-0

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