CAS 55079-83-9|Acitretin
Introduction：Basic information about CAS 55079-83-9|Acitretin, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Acitretin | ||
|---|---|---|---|
| CAS Number | 55079-83-9 | Molecular Weight | 326.429 |
| Density | 1.1±0.1 g/cm3 | Boiling Point | 521.3±38.0 °C at 760 mmHg |
| Molecular Formula | C21H26O3 | Melting Point | 228-230ºC |
| MSDS | USA | Flash Point | 180.3±20.3 °C |
| Symbol | GHS07, GHS08, GHS09 | Signal Word | Danger |
Names
| Name | all-trans-acitretin |
|---|---|
| Synonym | More Synonyms |
Acitretin BiologicalActivity
| Description | Acitretin(Ro 10-1670) is a second-generation, systemic retinoid that has been used in the treatment of psoriasis.Target: RAR/RXRAcitretin is a second-generation, systemic retinoid that has been approved for the treatment of psoriasis since 1997. It can be considered one of the treatments of choice for pustular and erythrodermic psoriasis. However, the efficacy of acitretin as a monotherapy for plaque psoriasis is less, although it is often used in combination therapy with other systemic psoriasis therapies, especially ultraviolet B or psoralen plus ultraviolet A phototherapy, to increase efficacy. Such combination treatments may potentially minimise toxicity by using lower doses of each of the two agent [1].Thirty-nine male adult Wistar albino rats were divided into 3 groups as two experimental groups and one control group. The first group consisting 14 rats were applied orally standard dose (0.75 mg/kg/day) acitretin and the second group consisting 16 rats were applied high dose (1.5 mg/kg/day) acitretin.Acitretin was given within dimetil sulphoxide (DMSO), which was diluted with saline solution as a ratio of 1/10, in order to increase its solubility. The control group consisting 9 rats were given only saline solution including DMSO for 8 weeks. After 8 weeks of the administration, half of the rats in the first and second groups and the entire control group were sacrificed under deep ether anaesthesia and bilateral orchiectomy was made. The remainingrats were compared with the control group using a similar method at the end of 8 weeks of wash-off period. The orchiectomy materials were histopathologically evaluated under the light microscope for spermatogenesis according to parameters including spermatogenetic activity, spermatogenetic organization, seminiferous tubular diameter, interstitial Leydig cells and fibroblasts. In our study it was concluded that the standard and high doses of acitretin do not have any effect on the spermatogenesis of threats [2].Clinical indications: PsoriasisFDA Approved Date: Toxicity: nausea; headache; itching; red or flaky skin; dry or red eyes; dry mouth; depression; 0cystitis acne or hair loss |
|---|---|
| Related Catalog | Signaling Pathways >>Metabolic Enzyme/Protease >>RAR/RXRResearch Areas >>Inflammation/Immunology |
| References | [1]. Lee CS, et al. A review of acitretin, a systemic retinoid for the treatment of psoriasis. Expert Opin Pharmacother. 2005 Aug;6(10):1725-34. [2]. Seng?r B, et al. Effects of acitretin on spermatogenesis of rats. J Eur Acad Dermatol Venereol. 2006 Jul;20(6):689-92. |
Chemical & Physical Properties
| Density | 1.1±0.1 g/cm3 |
|---|---|
| Boiling Point | 521.3±38.0 °C at 760 mmHg |
| Melting Point | 228-230ºC |
| Molecular Formula | C21H26O3 |
| Molecular Weight | 326.429 |
| Flash Point | 180.3±20.3 °C |
| Exact Mass | 326.188202 |
| PSA | 46.53000 |
| LogP | 5.73 |
| Vapour Pressure | 0.0±1.4 mmHg at 25°C |
| Index of Refraction | 1.570 |
| InChIKey | IHUNBGSDBOWDMA-AQFIFDHZSA-N |
| SMILES | COc1cc(C)c(C=CC(C)=CC=CC(C)=CC(=O)O)c(C)c1C |
| Storage condition | 2-8°C |
| Stability | LIGHT SENSITIVE |
Toxicological Information
CHEMICAL IDENTIFICATION |
ACUTE TOXICITY DATA - TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- >4 gm/kg
- TOXIC EFFECTS :
- Gastrointestinal - hypermotility, diarrhea
- REFERENCE :
- YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 10,5033,1982
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 700 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #4105681 ** REPRODUCTIVE DATA **
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Unreported
- DOSE :
- 68 mg/kg
- SEX/DURATION :
- female 10-78 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Specific Developmental Abnormalities - eye/ear Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - musculoskeletal system
- REFERENCE :
- TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 52,215,1995
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 300 mg/kg
- SEX/DURATION :
- female 7-16 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Effects on Newborn - weaning or lactation index (e.g., # alive at weaning per # alive at day 4)
- REFERENCE :
- ARTODN Archives of Toxicology. (Springer-Verlag, Heidelberger Pl. 3, D-1000 Berlin 33, Fed. Rep. Ger.) V.32- 1974- Volume(issue)/page/year: 58,50,1985
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 150 mg/kg
- SEX/DURATION :
- female 7-16 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Specific Developmental Abnormalities - musculoskeletal system Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive)
- REFERENCE :
- ARTODN Archives of Toxicology. (Springer-Verlag, Heidelberger Pl. 3, D-1000 Berlin 33, Fed. Rep. Ger.) V.32- 1974- Volume(issue)/page/year: 58,50,1985
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 150 mg/kg
- SEX/DURATION :
- female 7-16 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive)
- REFERENCE :
- ARTODN Archives of Toxicology. (Springer-Verlag, Heidelberger Pl. 3, D-1000 Berlin 33, Fed. Rep. Ger.) V.32- 1974- Volume(issue)/page/year: 58,50,1985
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 300 mg/kg
- SEX/DURATION :
- female 7-16 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Effects on Newborn - weaning or lactation index (e.g., # alive at weaning per # alive at day 4)
- REFERENCE :
- ARTODN Archives of Toxicology. (Springer-Verlag, Heidelberger Pl. 3, D-1000 Berlin 33, Fed. Rep. Ger.) V.32- 1974- Volume(issue)/page/year: 58,50,1985
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 30 mg/kg
- SEX/DURATION :
- female 7-16 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - musculoskeletal system
- REFERENCE :
- ARTODN Archives of Toxicology. (Springer-Verlag, Heidelberger Pl. 3, D-1000 Berlin 33, Fed. Rep. Ger.) V.32- 1974- Volume(issue)/page/year: 58,50,1985
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 100 mg/kg
- SEX/DURATION :
- female 7-16 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
- REFERENCE :
- ARTODN Archives of Toxicology. (Springer-Verlag, Heidelberger Pl. 3, D-1000 Berlin 33, Fed. Rep. Ger.) V.32- 1974- Volume(issue)/page/year: 58,50,1985
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 100 mg/kg
- SEX/DURATION :
- female 11 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - musculoskeletal system
- REFERENCE :
- TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 41,707,1990
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 100 mg/kg
- SEX/DURATION :
- female 11 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Specific Developmental Abnormalities - other developmental abnormalities
- REFERENCE :
- TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 34,417,1986
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 26 mg/kg
- SEX/DURATION :
- female 7-19 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - musculoskeletal system
- REFERENCE :
- ARTODN Archives of Toxicology. (Springer-Verlag, Heidelberger Pl. 3, D-1000 Berlin 33, Fed. Rep. Ger.) V.32- 1974- Volume(issue)/page/year: 58,50,1985
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 2600 ug/kg
- SEX/DURATION :
- female 7-19 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
- REFERENCE :
- ARTODN Archives of Toxicology. (Springer-Verlag, Heidelberger Pl. 3, D-1000 Berlin 33, Fed. Rep. Ger.) V.32- 1974- Volume(issue)/page/year: 58,50,1985
Safety Information
| Symbol | GHS07, GHS08, GHS09 |
|---|---|
| Signal Word | Danger |
| Hazard Statements | H315-H319-H360-H410 |
| Precautionary Statements | P201-P273-P305 + P351 + P338-P308 + P313-P501 |
| Hazard Codes | T:Toxic |
| Risk Phrases | R36/38;R61;R50/53 |
| Safety Phrases | S53-S37/39-S45-S60-S61 |
| RIDADR | UN 3077 |
| WGK Germany | 3 |
| RTECS | RA8460000 |
| Packaging Group | III |
| Hazard Class | 9.0 |
Articles55
More Articles| Comparative effectiveness of less commonly used systemic monotherapies and common combination therapies for moderate to severe psoriasis in the clinical setting. J. Am. Acad. Dermatol. 71(6) , 1167-75, (2014) The effectiveness of psoriasis therapies in real-world settings remains relatively unknown.We sought to compare the effectiveness of less commonly used systemic therapies and commonly used combination... | |
| Acitretin exhibits inhibitory effects towards UDP-glucuronosyltransferase (UGT)1A9-mediated 4-methylumbelliferone (4-MU) and propofol glucuronidation reaction. Pharmazie 68(6) , 449-52, (2013) The present study aimed to evaluate the potential risk of drug-drug interactions associated with acitretin which is a drug for therapy of psoriasis approved by the Food and Drug Administration (FDA). ... | |
| IgA pemphigus: case series with emphasis on therapeutic response. J. Am. Acad. Dermatol. 70(1) , 200-1, (2014) |
Synonyms
| 13-cis Acitretin |
| retinoidetretin |
| 2,4,6,8-Noneatetraenoic acid, 9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-, (Z,E,E,E)- |
| Acetretin |
| ro10-1670 |
| SORIATANE |
| etretin |
| (2Z,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid |
| Acitreti |
| (2Z,4E,6E,8E)-9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic acid |
| 2,4,6,8-Nonatetraenoic acid, 9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-, (2Z,4E,6E,8E)- |
| Acitretin |
| Acritretin |
| all-trans-etretin |
| EINECS 259-474-4 |
| MFCD00866632 |
| 13-cis-Acitretin |
| NEOTIGASON |
