Details
Stereochemistry | ACHIRAL |
Molecular Formula | C23H30O3 |
Molecular Weight | 354.4825 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 4 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCOC(=O)\C=C(C)\C=C\C=C(C)\C=C\C1=C(C)C(C)=C(OC)C=C1C
InChI
InChIKey=HQMNCQVAMBCHCO-DJRRULDNSA-N
InChI=1S/C23H30O3/c1-8-26-23(24)14-17(3)11-9-10-16(2)12-13-21-18(4)15-22(25-7)20(6)19(21)5/h9-15H,8H2,1-7H3/b11-9+,13-12+,16-10+,17-14+
Molecular Formula | C23H30O3 |
Molecular Weight | 354.4825 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 4 |
Optical Activity | NONE |
DescriptionSources: https://www.drugbank.ca/drugs/DB00926Curator's Comment: description was created based on several sources, including
http://www.tabletwise.com/us/tegison-capsule | https://www.ncbi.nlm.nih.gov/pubmed/12723955 | https://www.drugs.com/mmx/etretinate.html
Sources: https://www.drugbank.ca/drugs/DB00926
Curator's Comment: description was created based on several sources, including
http://www.tabletwise.com/us/tegison-capsule | https://www.ncbi.nlm.nih.gov/pubmed/12723955 | https://www.drugs.com/mmx/etretinate.html
Etretinate (trade name Tegison) is a medication developed by Hoffmann–La Roche that was approved by the FDA in 1986 to treat severe psoriasis. It is a second-generation retinoid. It was subsequently removed from the Canadian market in 1996 and the United States market in 1998 due to the high risk of birth defects. Etretinate remains on the market in Japan as Tigason. 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. Etretinate activates retinoid receptors, causing an induction of cell differentiation, inhibition of cell proliferation, and inhibition of tissue infiltration by inflammatory cells.
CNS Activity
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/754925
Curator's Comment: # Hoffmann–La Roche
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2792 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12723955 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | TEGISON Approved UseUnknown Launch Date1986 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
100 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9703120 |
50 mg 1 times / day steady-state, oral dose: 50 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ETRETINATE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
100 mg single, oral Studied dose |
healthy, 20-32 years n = 12 Health Status: healthy Age Group: 20-32 years Sex: M Population Size: 12 Sources: |
Other AEs: Headache... |
50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, 57,1 ± 14,2 years (range 23±83 years) n = 86 Health Status: unhealthy Condition: psoriasis vulgaris Age Group: 57,1 ± 14,2 years (range 23±83 years) Sex: M+F Population Size: 86 Sources: |
Disc. AE: Palpitations, Edema face... AEs leading to discontinuation/dose reduction: Palpitations (2 patients) Sources: Edema face (2 patients) Transaminases increased (3 patients) Hypertriglyceridemia (1 patient) Hyperglycaemia (1 patient) |
75 mg 1 times / day multiple, oral Dose: 75 mg, 1 times / day Route: oral Route: multiple Dose: 75 mg, 1 times / day Sources: |
unhealthy, 75 years n = 1 Health Status: unhealthy Condition: psoriasis Age Group: 75 years Sex: M Population Size: 1 Sources: |
Disc. AE: Ectropion... AEs leading to discontinuation/dose reduction: Ectropion (1 patient) Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Headache | mild, 1 patient | 100 mg single, oral Studied dose |
healthy, 20-32 years n = 12 Health Status: healthy Age Group: 20-32 years Sex: M Population Size: 12 Sources: |
Hyperglycaemia | 1 patient Disc. AE |
50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, 57,1 ± 14,2 years (range 23±83 years) n = 86 Health Status: unhealthy Condition: psoriasis vulgaris Age Group: 57,1 ± 14,2 years (range 23±83 years) Sex: M+F Population Size: 86 Sources: |
Hypertriglyceridemia | 1 patient Disc. AE |
50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, 57,1 ± 14,2 years (range 23±83 years) n = 86 Health Status: unhealthy Condition: psoriasis vulgaris Age Group: 57,1 ± 14,2 years (range 23±83 years) Sex: M+F Population Size: 86 Sources: |
Edema face | 2 patients Disc. AE |
50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, 57,1 ± 14,2 years (range 23±83 years) n = 86 Health Status: unhealthy Condition: psoriasis vulgaris Age Group: 57,1 ± 14,2 years (range 23±83 years) Sex: M+F Population Size: 86 Sources: |
Palpitations | 2 patients Disc. AE |
50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, 57,1 ± 14,2 years (range 23±83 years) n = 86 Health Status: unhealthy Condition: psoriasis vulgaris Age Group: 57,1 ± 14,2 years (range 23±83 years) Sex: M+F Population Size: 86 Sources: |
Transaminases increased | 3 patients Disc. AE |
50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: |
unhealthy, 57,1 ± 14,2 years (range 23±83 years) n = 86 Health Status: unhealthy Condition: psoriasis vulgaris Age Group: 57,1 ± 14,2 years (range 23±83 years) Sex: M+F Population Size: 86 Sources: |
Ectropion | 1 patient Disc. AE |
75 mg 1 times / day multiple, oral Dose: 75 mg, 1 times / day Route: oral Route: multiple Dose: 75 mg, 1 times / day Sources: |
unhealthy, 75 years n = 1 Health Status: unhealthy Condition: psoriasis Age Group: 75 years Sex: M Population Size: 1 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Malformations of the maxillofacial region induced by retinoids in an experimental system. | 1990 Jun |
|
[Successful use of isotretinoin in type Zumbusch generalized pustular psoriasis following recovered etretinate-induced hepatitis]. | 1991 Sep |
|
Renal impairment probably induced by etretinate. | 1992 |
|
Peripheral neuropathy during etretinate therapy for psoriasis. | 1993 Feb |
|
Joint pains with psoriasis and long-term systemic etretinate therapy: a case report and summary of 12 cases. | 1993 Oct |
|
Prevention of etretinate-induced craniofacial malformations by vitamin B6 in the rat. | 1996 Oct-Dec |
|
Dramatic improvement of psoriatic erythroderma after acute hepatitis: analysis of cytokine synthesis capability in peripheral blood T cells. | 2006 Aug |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/mmx/etretinate.html
Initial: 0.75 mg to 1 mg per kg of body weight per day in divided doses. Maintenance: 0.5 to 0.75 mg per kg of body weight per day may be initiated after initial response, generally after 8 to 16 weeks of therapy.
Usual adult prescribing limits 1.5 mg per kg of body weight per day.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11448476
Erythrocytes were isolated from fresh blood by centrifugation. Etretinate (as DMSO solution) was added to the suspensions of erythrocytes. The final concentration of etretinate was 1.4nM. Erythrocyte suspensions were incubated for 30 min at 370C. After treatment with etretinate, a significant increase in erythrocyte membrane fluidity and in antioxidant activity as well as a decrease in lipid peroxidation were observed in erythrocytes from patients.
Substance Class |
Chemical
Created
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admin
on
Edited
Fri Dec 15 15:16:47 GMT 2023
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on
Fri Dec 15 15:16:47 GMT 2023
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Record UNII |
65M2UDR9AG
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C804
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LIVERTOX |
391
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WHO-VATC |
QD05BB01
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WHO-ATC |
D05BB01
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m5206
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C29036
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DB00926
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1011029
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5282375
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SUB07346MIG
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4913
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7599
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ETRETINATE
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D005050
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DTXSID0023036
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4182
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54350-48-0
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100000082135
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259-119-3
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297936
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1116
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CHEMBL464
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Related Record | Type | Details | ||
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PARENT -> METABOLITE |
Clinical evidence has shown that etretinate (a retinoid with a much longer half-life, see below) can be formed with concurrent ingestion of acitretin and ethanol.
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METABOLITE ACTIVE -> PRODRUG |
URINE
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Related Record | Type | Details | ||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Tmax | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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