Acitretin
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MedKoo CAT#: 317157

CAS#: 55079-83-9

Description: Acitretin is an oral synthetic retinoid effective in the treatment of psoriasis. It is the major metabolite of etretinate (sc-205689). It has demonstrated an ability to suppress the development of chemically-induced epithelial tumors, as well as squamous cell carcinoma. Acitretin has potential antineoplastic, chemopreventive, anti-psoratic, and embryotoxic properties. Acitretin activates nuclear retinoic acid receptors (RAR), resulting in induction of cell differentiation, inhibition of cell proliferation, and inhibition of tissue infiltration by inflammatory cells. This agent may also inhibit tumor angiogenesis.


Chemical Structure

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Acitretin
CAS# 55079-83-9

Theoretical Analysis

MedKoo Cat#: 317157
Name: Acitretin
CAS#: 55079-83-9
Chemical Formula: C21H26O3
Exact Mass: 326.18819
Molecular Weight: 326.44
Elemental Analysis: C, 77.27; H, 8.03; O, 14.70

Price and Availability

Size Price Availability Quantity
100.0mg USD 150.0 Same Day
200.0mg USD 250.0 Same Day
500.0mg USD 450.0 Same Day
1.0g USD 750.0 Same Day
2.0g USD 1250.0 Same Day
5.0g USD 2250.0 Same Day
20.0g USD 4650.0 2 Weeks
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Synonym: Ro 10-1670; Ro-10-1670; Ro10-1670; Ro 10-1670/000; U0279; Acitretin; Soriatane; Etretin; Neotigason.

IUPAC/Chemical Name: (2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid

InChi Key: IHUNBGSDBOWDMA-AQFIFDHZSA-N

InChi Code: InChI=1S/C21H26O3/c1-14(8-7-9-15(2)12-21(22)23)10-11-19-16(3)13-20(24-6)18(5)17(19)4/h7-13H,1-6H3,(H,22,23)/b9-7+,11-10+,14-8+,15-12+

SMILES Code: CC1=CC(=C(C(=C1C=CC(=CC=CC(=CC(=O)O)C)C)C)C)OC

Appearance: Yellow solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Biological target: Acitretin(Ro 10-1670) targets RAR/RXR.
In vitro activity: This study investigated the effects of acitretin on cell proliferation in SCL-1 and HaCaT at five different concentrations of acitretin for 3 days and 10−5 M of acitretin for 1, 3, 5 days using a MTT assay (Fig. 1A and B). The results showed that acitretin inhibited cell growth of SCL-1 in a dose- and time-dependent manner. In contrast, acitretin exhibited a few inhibitory effects on the proliferation of HaCaT cells, indicating that acitretin showed less toxicity to non-malignant keratinocytes. Reference: J Cell Mol Med. 2009 Sep; 13(9a): 2888–2898. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4498944/
In vivo activity: After the IMQ-induced model mice were treated with acitretin for 6 days, the scaling and thickness of the skin on the back of the mice were significantly alleviated, which was confirmed by the histological evaluation showing a significant decrease in epidermal thickness; the PASI score was also significantly decreased (Figures 2B,C, Supplementary Figures 2A–D). Besides, the expression of PCNA and K17 (the makers of cell proliferation) significantly decreased in the skin lesion of the acitretin treatment group. In contrast, the expression of K10 (the markers of keratinization) increased in the skin lesion of the acitretin treatment group compared with the IMQ groups (Supplementary Figures 2E–G). The number of MDSCs and M-MDSCs in the spleen and skin lesions was decreased significantly in the acitretin treatment group compared with the IMQ groups (Figures 2D,E). However, there was no significant difference in the number of G-MDSCs after acitretin treatment (Figures 2D,E). Therefore, these results indicated that acitretin reduced the number of MDSCs and M-MDSCs in the psoriasis patients and psoriasis-like model mice. Reference: Front Med (Lausanne). 2021; 8: 625130. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8021725/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 10.5 32.17
DMF 5.0 15.32
DMF:PBS (pH 7.2) (1:4) 0.2 0.61

Preparing Stock Solutions

The following data is based on the product molecular weight 326.44 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Qin X, Chen C, Zhang Y, Zhang L, Mei Y, Long X, Tan R, Liang W, Sun L. Acitretin modulates HaCaT cells proliferation through STAT1- and STAT3-dependent signaling. Saudi Pharm J. 2017 May;25(4):620-624. doi: 10.1016/j.jsps.2017.04.034. Epub 2017 May 8. PMID: 28579901; PMCID: PMC5447439. 2. Lin XY, He CD, Xiao T, Jin X, Chen J, Wang YK, Liu M, Wang KB, Jiang Y, Wei HC, Chen HD. Acitretin induces apoptosis through CD95 signalling pathway in human cutaneous squamous cell carcinoma cell line SCL-1. J Cell Mol Med. 2009 Sep;13(9A):2888-98. doi: 10.1111/j.1582-4934.2008.00397.x. Epub 2009 Jun 20. PMID: 18624760; PMCID: PMC4498944. 3. Bragazzi Cunha J, Elenbaas JS, Maitra D, Kuo N, Azuero-Dajud R, Ferguson AC, Griffin MS, Lentz SI, Shavit JA, Omary MB. Acitretin mitigates uroporphyrin-induced bone defects in congenital erythropoietic porphyria models. Sci Rep. 2021 May 5;11(1):9601. doi: 10.1038/s41598-021-88668-9. PMID: 33953217; PMCID: PMC8100164. 4. Liu P, Peng C, Chen X, Wu L, Yin M, Li J, Qin Q, Kuang Y, Zhu W. Acitretin Promotes the Differentiation of Myeloid-Derived Suppressor Cells in the Treatment of Psoriasis. Front Med (Lausanne). 2021 Mar 23;8:625130. doi: 10.3389/fmed.2021.625130. PMID: 33834031; PMCID: PMC8021725.
In vitro protocol: 1. Qin X, Chen C, Zhang Y, Zhang L, Mei Y, Long X, Tan R, Liang W, Sun L. Acitretin modulates HaCaT cells proliferation through STAT1- and STAT3-dependent signaling. Saudi Pharm J. 2017 May;25(4):620-624. doi: 10.1016/j.jsps.2017.04.034. Epub 2017 May 8. PMID: 28579901; PMCID: PMC5447439. 2. Lin XY, He CD, Xiao T, Jin X, Chen J, Wang YK, Liu M, Wang KB, Jiang Y, Wei HC, Chen HD. Acitretin induces apoptosis through CD95 signalling pathway in human cutaneous squamous cell carcinoma cell line SCL-1. J Cell Mol Med. 2009 Sep;13(9A):2888-98. doi: 10.1111/j.1582-4934.2008.00397.x. Epub 2009 Jun 20. PMID: 18624760; PMCID: PMC4498944.
In vivo protocol: 1. Bragazzi Cunha J, Elenbaas JS, Maitra D, Kuo N, Azuero-Dajud R, Ferguson AC, Griffin MS, Lentz SI, Shavit JA, Omary MB. Acitretin mitigates uroporphyrin-induced bone defects in congenital erythropoietic porphyria models. Sci Rep. 2021 May 5;11(1):9601. doi: 10.1038/s41598-021-88668-9. PMID: 33953217; PMCID: PMC8100164. 2. Liu P, Peng C, Chen X, Wu L, Yin M, Li J, Qin Q, Kuang Y, Zhu W. Acitretin Promotes the Differentiation of Myeloid-Derived Suppressor Cells in the Treatment of Psoriasis. Front Med (Lausanne). 2021 Mar 23;8:625130. doi: 10.3389/fmed.2021.625130. PMID: 33834031; PMCID: PMC8021725.

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1: Almutawa F, Thusaringam T, Watters K, Gayden T, Jabado N, Sasseville D. Pachyonychia Congenita (K16) with Unusual Features and Good Response to Acitretin. Case Rep Dermatol. 2015 Aug 19;7(2):220-6. doi: 10.1159/000438920. eCollection 2015 May-Aug. PubMed PMID: 26464567; PubMed Central PMCID: PMC4592507.

2: Solak B, Kara RO, Kosem M. Palmoplantar lichen planus successfully treated with acitretin. BMJ Case Rep. 2015 Sep 7;2015. pii: bcr2015211115. doi: 10.1136/bcr-2015-211115. PubMed PMID: 26347237.

3: Yanik ME, Erfan G, Albayrak H, Tasolar K, Albayrak S, Gelincik I, Kulac M. Acitretin-induced spiny follicular hyperkeratosis. Cutan Ocul Toxicol. 2015 Sep 4:1-3. [Epub ahead of print] PubMed PMID: 26340416.

4: Yanik ME, Erfan G, Albayrak H, Tasolar K, Albayrak S, Gelincik I, Kulac M. Acitretin-induced spiny follicular hyperkeratosis. Cutan Ocul Toxicol. 2015 Aug 12:1-3. [Epub ahead of print] PubMed PMID: 26264531.

5: Geng S, Liu Y, Wang H, Yan H, Niu X, Toyohara JP, Xiao S. Hypertrophic Lichenoid Eruption in a Child Successfully Treated Using Acitretin and Surgery: A Case Report and Literature Review. Pediatr Dermatol. 2015 Jul 29. doi: 10.1111/pde.12658. [Epub ahead of print] PubMed PMID: 26227743.

6: Rossi AM, Hibler BP, Johnson-Jahangir H. Serum Sirolimus Level Elevation Induced by Acitretin: Report of a Novel Drug-Drug Interaction. J Drugs Dermatol. 2015 Jul;14(7):747-9. PubMed PMID: 26151793.

7: Rob F, Fialová J, Brejchová M, Džambová M, Sečníková Z, Zelenková D, Jiráková A, Hercogová J. Drug fever as an adverse effect of acitretin in complicated psoriasis patient. Dermatol Ther. 2015 Jul 2. doi: 10.1111/dth.12263. [Epub ahead of print] PubMed PMID: 26133643.

8: García-Arpa M, López-Nieto M, Santiago Sánchez-Mateos JL, Sánchez-Caminero MP. Thrombocytopenia Probably Induced by Acitretin. Actas Dermosifiliogr. 2015 Oct;106(8):692-693. doi: 10.1016/j.ad.2015.03.010. Epub 2015 Jun 10. English, Spanish. PubMed PMID: 26071907.

9: Parkins GJ, Brennan KM, Wylie G. Sixth cranial nerve palsy due to acitretin. Clin Exp Dermatol. 2015 May 21. doi: 10.1111/ced.12684. [Epub ahead of print] PubMed PMID: 25997624.

10: Byekova Y, Sami N. Successful response of refractory type I adult-onset pityriasis rubra pilaris with ustekinumab and acitretin combination therapy. J Dermatol. 2015 Aug;42(8):830-1. doi: 10.1111/1346-8138.12927. Epub 2015 May 18. PubMed PMID: 25982628.

Acitretin

100.0mg / USD 150.0