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Acitretin ( CASNO:55079-83-9 )

Identification and Related Records
CAS Registry number:
9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic acid
Molecular Formula:
Molecular Weight:
Canonical SMILES:
Isomers smiles:
Chemical and Physical Properties
crystalline solid
1.051 g/cm3
Melting Point:
228-230 °C
Boiling Point:
521.3 °C at 760 mmHg
Refractive Index:
Flash Point:
180.3 °C
Crystals from hexane
Yellow to greenish-yellow powder
Stable at normal temperatures and pressures.
Storage temp:
Computed Properties:
Molecular Weight:326.42934 [g/mol]
Molecular Formula:C21H26O3
H-Bond Donor:1
H-Bond Acceptor:3
Rotatable Bond Count:6
Exact Mass:326.188195
MonoIsotopic Mass:326.188195
Topological Polar Surface Area:46.5
Heavy Atom Count:24
Formal Charge:0
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:4
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:3
Feature 3D Anion Count:1
Feature 3D Hydrophobe Count:2
Feature 3D Ring Count:1
Effective Rotor Count:6
Conformer Sampling RMSD:0.8
CID Conformer Count:33
Safety and Handling
Hazard Codes:
Risk Statements:
Safety Statements:
Hazard Codes:?ToxicT,?DangerousN
Risk Statements: 61-36/38-50/53?
R61:May cause harm to the unborn child.?
R36/38:Irritating to eyes and skin.?
R50/53:Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Statements: 53-26-45-60-61-37/39?
S53:Avoid exposure - obtain special instructions before use.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)?
S60:This material and its container must be disposed of as hazardous waste.?
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.?
S37/39:Wear suitable gloves and eye/face protection.
RIDADR: UN 3077 9/PG 3
WGK Germany: 3
RTECS: RA8460000
F: 8-10-21
An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits acrid smoke and irritating fumes.
UN 3077
Exposure Standards and Regulations:
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl acitretin, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
?Acitretin (CAS NO.55079-83-9) is also named as (all-E)-9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic acid ; Acitretina ; Acitretina [Spanish] ; Acitretine ; Acitretine [French] ; Acitretinum ; Acitretinum [Latin] ; CCRIS 5534 ; Etretin ; HSDB 7187 ; Neotigason ; Retinoid etretin ; Ro 10-1670 ; Ro 10-1670/000 ; Soriatane ; TMMP ; U0279 ; UNII-LCH760E9T7 ; all-trans-3,7-Dimethyl-9-(4-methoxy-2,3,6-trimethylphenyl)-2,4,6,8-nonatetraenoic acid ; all-trans-Acitretin?.?Acitretin (CAS NO.55079-83-9) is crystalline solid.
Octanol/Water Partition Coefficient:
log Kow = 6.40
Disposal Methods:
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
Use and Manufacturing
A synthetic retinoid which is the major metabolite of etretinate (E938000).
Biomedical Effects and Toxicity
Pharmacological Action:
- Agents that soften, separate, and cause desquamation of the cornified epithelium or horny layer of skin. They are used to expose mycelia of infecting fungi or to treat corns, warts, and certain other skin diseases.
Therapeutic Uses:
Acitretin is indicated to treat symptoms of severe erythrodermic and generalized pustular psoriasis that involve more than 10% of the patient's body surface area, especially when psoriasis is physically, occupationally, or psychologically disabling. Acitretin is indicated for the treatment of localized palmoplantar pustulosis, but the localized condition is more recalcitrant to treatment than is generalized, severe psoriasis. /Included in US product labeling/
Acitretin is indicated to treat inherited disorders of keratinization,such as bullous or nonbullous ichthyosiform erythroderma, keratosis follicularis, and lamellar ichthyosis. Best results are obtained in treatment of keratosis follicularis (also called Darier's's disease), severe recessive X-linked ichthyosis, and nonbullous congenital ichthyosis, such as erythrodermic or non erythrodermic lamellar ichthyosis. Patients will bullous ichthyosiform erythroderma may experience improvement of their condition under less aggressive treatment with a low-dose regimen. /NOT included in US product labeling/
Acitretin has been used in conjunction with interferon-alpha 2a to treat cutaneous T-cell lymphoma when there was no known internal organ involvement.
/Exper Ther/ Small studies have been done using acitretin prophylactically in the treatment of keratotic skin lesions or skin cancer. Acitretin prevented development of new keratotic skin lesions in renal transplant patients who had a history of extensive keratotic skin lesions and/or recurrent squamous cell and basal cell carcinomas. Additional studies are needed.
Acitretin has been used as monotherapy in the treatment of psoriasis associated with human immunodeficiency virus (HIV) infection., Although acitretin dose not appear to have immunosuppressive properties capable of worsening a compromised immune system, additional studies are needed to assess acitretin's immunosuppressive properties in HIV-positive patients.
Biomedical Effects and Toxicity:
Patients receiving /an oral dose/ 30 mg of acitretin once a day for 30 days showed skin concentrations of acitretin that were 10 times higher than those observed in the plasma and 3 to 5 times higher than the skin concentrations of its metabolite, 13-cis acitretin. Concentrations of acitretin and 13-cis acitretin are higher in lesional skin than in uninvolved skin.
The mean absolute bioavailability of acitretin is 59% (range, 36-95%). The dose absorbed is linear up to 50 mg a day, but may become nonproportional or nonlinear for doses greater than 50 mg a day. The rate and extent of acitretin absorption are doubled when 50 mg of acitretin is given with food when compared with the absorption of the same dose given under fasting conditions.
Elimination: For acitretin or 13-cis acitretin conjugates, 34 to 54% renal and 16 to 53% fecal. No acitretin or 13-cis acitretin (active metabolite) was recovered in the urine.
It is not known if acitretin is distributed into human breast milk.
The mean accumulation ratio is 1.2 for acitretin and 6.6 for the cis-metabolite. Acitretin has not been shown to accumulate in any particular organ; however, etretinate (an active metabolite) does accumulate in fat and , to a lesser degree, in the liver; lower tissue concentrations are found in the kidneys, brain, and testes. Five hours after acitretin administration, etretinate concentrations in the subcutaneous fat exceed those found in the plasma; however, accumulation does not occur. In one patient given acitretin orally, the concentration of etretinate in the adrenal glands exceeded that found in the fat tissue.
The maximum acitretin concentration observed in human seminal fluid from systemic use of acitretin or etretinate was 12.5 ng/mL, which would transfer approximately 125 ng/mL of acitretin per 10 mL of ejaculate.
In the absence of transesterification to form etretinate, greater than 98% of the acitretin would be eliminated within 2 months, assuming a mean elimination half-life of 49 hours. In cases where etretinate is formed, as has been demonstrated with concomitant administration of acitretin and ethanol: greater than 98% of the etretinate formed would be eliminated in 2 years, assuming a mean elimination half-life of 120 days; greater than 98% of the etretinate formed would be eliminated in 3 years, bases on the longest demonstrated elimination half life of 168 days. However, etretinate was found in plasma and subcutaneous fat in one patient reported to have had sporadic alcohol intake, 52 months after she stopped acitretin therapy.
... 10 patients with severe psoriasis were treated with 30 mg acitretin daily for 3 months. Seven patients had detectable mean steady-state plasma etretinate concentrations in the range of 2.5 to 56.7 ng/ml. Four of the patients showed teratogenic levels of plasma etretinate. Consumption of alcohol appeared to be an important contributing factor for the formation of etretinate. As judged from the dose- and body-weight-normalized AUC values (AUCcor) there was a great inter-individual variation (sixfold) in the systemic availability of acitretin. After discontinuation of therapy, the rate of elimination of both acitretin (t1/2 range 1.0 to 25.4 d) and 13-cis-acitretin (t1/2 range 1.5 to 25.7 d) was found to be related to the observed mean steady-state level of etretinate as evidenced by a longer terminal t1/2 of patients with high levels of etretinate in plasma. A mean terminal elimination half-life of etretinate was found to be 45.7 d +/- 10.6 (mean +/- SD; range 27.0 to 59.3 d). [Larsen FG et al; J Invest Dermatol 100 (5): 623-7 (1993)] PubMed Abstract
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