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Details

Stereochemistry ACHIRAL
Molecular Formula C23H30O3
Molecular Weight 354.4834
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 4
Charge 0

SHOW SMILES / InChI
Structure of ETRETINATE

SMILES

CCOC(=O)/C(/[H])=C(\C)/C(/[H])=C(\[H])/C(/[H])=C(\C)/C(/[H])=C(\[H])/c1c(C)cc(c(C)c1C)OC

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+

HIDE SMILES / InChI

Description
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.

Originator

Curator's Comment:: # Hoffmann–La Roche

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TEGISON

Approved Use

Unknown

Launch Date

5.28422404E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
100 ng/mL
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

Doses

DosePopulationAdverse events​
100 mg single, oral
Studied dose
Dose: 100 mg
Route: oral
Route: single
Dose: 100 mg
Sources:
healthy, 20-32 years
n = 12
Health Status: healthy
Age Group: 20-32 years
Sex: M
Population Size: 12
Sources:
Other AEs: Headache...
Other AEs:
Headache (mild, 1 patient)
Sources:
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)
Edema face (2 patients)
Transaminases increased (3 patients)
Hypertriglyceridemia (1 patient)
Hyperglycaemia (1 patient)
Sources:
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

AEs

AESignificanceDosePopulation
Headache mild, 1 patient
100 mg single, oral
Studied dose
Dose: 100 mg
Route: oral
Route: single
Dose: 100 mg
Sources:
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

PubMed

TitleDatePubMed
A rosacea-like eruption induced by Tigason (Ro 10-9359) treatment.
1982
Intracranial hypertension with etretinate.
1983 Oct 22
Impaired renal function and hypercalcaemia associated with etretinate.
1984 Nov 10
Differential hepatotoxicity of two oral retinoids (etretinate and isotretinoin) in a patient with palmoplantar psoriasis.
1985
The effect of etretinate compared with different regimens of PUVA in the treatment of persistent palmoplantar pustulosis.
1985 Apr
Cholestatic jaundice, an unusual side effect of etretinate.
1985 Oct
Benign intracranial hypertension during etretinate therapy for mycosis fungoides.
1985 Sep
[Retinoids and lipid metabolism].
1986 Jun
Increased muscle tone during etretinate therapy.
1986 May
Etretinate-induced skeletal muscle damage.
1987 May
Hepatocanalicular injury associated with vitamin A derivative etretinate. An idiosyncratic hypersensitivity reaction.
1987 Oct
A new syndrome of axial muscle rigidity associated with etretinate therapy.
1988
Depression induced by etretinate.
1989 Apr 8
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
Teratological studies on craniofacial malformations.
1997
Patents

Patents

Sample Use Guides

In Vivo Use Guide
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
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.
Name Type Language
ETRETINATE
HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
ETRETINATE [VANDF]
Common Name English
ACITRETIN RELATED COMPOUND B [USP-RS]
Common Name English
NSC-297936
Code English
ACITRETIN IMPURITY B [EP]
Common Name English
RO-109359
Code English
TEGISON
Brand Name English
ETHYL (ALL-E)-9-(4-METHOXY-2,3,6-TRIMETHYLPHENYL)-3,7-DIMETHYL-2,4,6,8-NONATETRAENOATE
Common Name English
ETRETINATE [INN]
Common Name English
2,4,6,8-NONATETRAENOIC ACID, 9-(4-METHOXY-2,3,6-TRIMETHYLPHENYL)-, ETHYL ESTER, (ALL-E-)
Common Name English
ETRETINATE [JAN]
Common Name English
ETRETINATE [ORANGE BOOK]
Common Name English
ETRETINATE [HSDB]
Common Name English
ACITRETIN RELATED COMPOUND B [USP]
USP-RS  
Common Name English
RO-10-9359
Code English
RO 10-9359
Code English
ETRETINATE [USAN]
Common Name English
ETRETINATE [MI]
Common Name English
ETRETINATE [MART.]
Common Name English
ETRETINATE [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C804
Created by admin on Sat Jun 26 11:42:35 UTC 2021 , Edited by admin on Sat Jun 26 11:42:35 UTC 2021
LIVERTOX 391
Created by admin on Sat Jun 26 11:42:35 UTC 2021 , Edited by admin on Sat Jun 26 11:42:35 UTC 2021
WHO-VATC QD05BB01
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WHO-ATC D05BB01
Created by admin on Sat Jun 26 11:42:35 UTC 2021 , Edited by admin on Sat Jun 26 11:42:35 UTC 2021
Code System Code Type Description
MERCK INDEX
M5206
Created by admin on Sat Jun 26 11:42:35 UTC 2021 , Edited by admin on Sat Jun 26 11:42:35 UTC 2021
PRIMARY Merck Index
NCI_THESAURUS
C29036
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PRIMARY
DRUG BANK
DB00926
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PRIMARY
PUBCHEM
5282375
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PRIMARY
EVMPD
SUB07346MIG
Created by admin on Sat Jun 26 11:42:35 UTC 2021 , Edited by admin on Sat Jun 26 11:42:35 UTC 2021
PRIMARY
IUPHAR
7599
Created by admin on Sat Jun 26 11:42:35 UTC 2021 , Edited by admin on Sat Jun 26 11:42:35 UTC 2021
PRIMARY
WIKIPEDIA
ETRETINATE
Created by admin on Sat Jun 26 11:42:35 UTC 2021 , Edited by admin on Sat Jun 26 11:42:35 UTC 2021
PRIMARY
MESH
D005050
Created by admin on Sat Jun 26 11:42:35 UTC 2021 , Edited by admin on Sat Jun 26 11:42:35 UTC 2021
PRIMARY
EPA CompTox
54350-48-0
Created by admin on Sat Jun 26 11:42:35 UTC 2021 , Edited by admin on Sat Jun 26 11:42:35 UTC 2021
PRIMARY
FDA UNII
65M2UDR9AG
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PRIMARY
RXCUI
4182
Created by admin on Sat Jun 26 11:42:35 UTC 2021 , Edited by admin on Sat Jun 26 11:42:35 UTC 2021
PRIMARY RxNorm
CAS
54350-48-0
Created by admin on Sat Jun 26 11:42:35 UTC 2021 , Edited by admin on Sat Jun 26 11:42:35 UTC 2021
PRIMARY
ECHA (EC/EINECS)
259-119-3
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PRIMARY
INN
4658
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PRIMARY
HSDB
7185
Created by admin on Sat Jun 26 11:42:35 UTC 2021 , Edited by admin on Sat Jun 26 11:42:35 UTC 2021
PRIMARY
DRUG CENTRAL
1116
Created by admin on Sat Jun 26 11:42:35 UTC 2021 , Edited by admin on Sat Jun 26 11:42:35 UTC 2021
PRIMARY
ChEMBL
CHEMBL464
Created by admin on Sat Jun 26 11:42:35 UTC 2021 , Edited by admin on Sat Jun 26 11:42:35 UTC 2021
PRIMARY
USP_CATALOG
1011029
Created by admin on Sat Jun 26 11:42:35 UTC 2021 , Edited by admin on Sat Jun 26 11:42:35 UTC 2021
PRIMARY USP-RS