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
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 317157
Name: Acitretin
CAS#: 55079-83-9
Chemical Formula: C21H26O3
Exact Mass: 326.19
Molecular Weight: 326.440
Elemental Analysis: C, 77.27; H, 8.03; O, 14.70

Price and Availability

Size Price Availability Quantity
50mg USD 90 Ready to ship
100mg USD 150 Ready to ship
200mg USD 250 Ready to ship
500g USD 550 Ready to ship
1g USD 850 Ready to ship
2g USD 1450 Ready to ship
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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

More Info:

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: Sarkar R, Chugh S, Garg VK. Acitretin in dermatology. Indian J Dermatol Venereol Leprol. 2013 Nov-Dec;79(6):759-71. doi: 10.4103/0378-6323.120721. PMID: 24177607.


2: Guenther LC, Kunynetz R, Lynde CW, Sibbald RG, Toole J, Vender R, Zip C. Acitretin Use in Dermatology. J Cutan Med Surg. 2017 Nov/Dec;21(3_suppl):2S-12S. doi: 10.1177/1203475417733414. Epub 2017 Sep 27. PMID: 28952335.


3: Tan MG, Shear NH, Walsh S, Alhusayen R. Acitretin. J Cutan Med Surg. 2017 Jan/Feb;21(1):48-53. doi: 10.1177/1203475416659858. Epub 2016 Jul 19. PMID: 27432818.


4: Ortiz NE, Nijhawan RI, Weinberg JM. Acitretin. Dermatol Ther. 2013 Sep- Oct;26(5):390-9. doi: 10.1111/dth.12086. PMID: 24099069.


5: Sbidian E; Groupe de recherche sur le psoriasis de la Société française de dermatologie. Acitrétine [Acitretin]. Ann Dermatol Venereol. 2019 Jun- Jul;146(6-7):454-458. French. doi: 10.1016/j.annder.2019.04.008. Epub 2019 Jun 20. PMID: 31229350.


6: Roenigk HH Jr. Acitretin combination therapy. J Am Acad Dermatol. 1999 Sep;41(3 Pt 2):S18-21. doi: 10.1016/s0190-9622(99)70361-0. PMID: 10459142.


7: Heath MS, Sahni DR, Curry ZA, Feldman SR. Pharmacokinetics of tazarotene and acitretin in psoriasis. Expert Opin Drug Metab Toxicol. 2018 Sep;14(9):919-927. doi: 10.1080/17425255.2018.1515198. Epub 2018 Sep 3. PMID: 30134735.


8: Ling MR. Acitretin: optimal dosing strategies. J Am Acad Dermatol. 1999 Sep;41(3 Pt 2):S13-7. doi: 10.1016/s0190-9622(99)70360-9. PMID: 10459141.


9: Booij MT, Van De Kerkhof PC. Acitretin revisited in the era of biologics. J Dermatolog Treat. 2011 Apr;22(2):86-9. doi: 10.3109/09546630903578582. Epub 2010 Aug 1. PMID: 20673152.


10: Dunn LK, Gaar LR, Yentzer BA, O'Neill JL, Feldman SR. Acitretin in dermatology: a review. J Drugs Dermatol. 2011 Jul;10(7):772-82. PMID: 21720660.


11: Nikam BP, Amladi S, Wadhwa SL. Acitretin. Indian J Dermatol Venereol Leprol. 2006 Mar-Apr;72(2):167-72. doi: 10.4103/0378-6323.25655. PMID: 16707835.


12: Dubertret L. Acitrétine [Acitretin]. Ann Dermatol Venereol. 2011 Dec;138(12):829-32. French. doi: 10.1016/j.annder.2011.10.001. Epub 2011 Nov 5. PMID: 22137620.


13: Gowda P, Shastry V, Ranugha PSS, Rangappa V. Acitretin-induced differentiation syndrome in a case of generalized pustular psoriasis. Indian J Dermatol Venereol Leprol. 2020 Mar-Apr;86(2):231. doi: 10.4103/ijdvl.IJDVL_318_18. PMID: 31089005.


14: Ezine E, Pedailles S, Dompmartin A, Morice C. Syndrome de fuite capillaire observé sous acitrétine : un cas et revue de la littérature [Acitretin-induced capillary leak syndrome: Case report and literature review]. Ann Dermatol Venereol. 2020 Sep;147(8-9):535-541. French. doi: 10.1016/j.annder.2020.04.021. Epub 2020 Jul 8. PMID: 32653219.


15: Dogra S, Yadav S. Acitretin in psoriasis: an evolving scenario. Int J Dermatol. 2014 May;53(5):525-38. doi: 10.1111/ijd.12365. Epub 2014 Mar 6. PMID: 24601982.


16: Nasr M, Abd-Elhamid N, Abd-Allah D, Elkholy B. Acitretin: Could it be a new therapeutic player in the field of onychomycosis? Mycoses. 2022 Apr;65(4):402-410. doi: 10.1111/myc.13424. Epub 2022 Feb 10. PMID: 35103343.


17: Lynde CW, Kraft JN, Lynde CB. Acitretin revisited. Skin Therapy Lett. 2011 Mar;16(3):1-4. PMID: 21611678.


18: Lee CS, Li K. A review of acitretin for the treatment of psoriasis. Expert Opin Drug Saf. 2009 Nov;8(6):769-79. doi: 10.1517/14740330903393732. PMID: 19998529.


19: Geng A, Pei T, Zhao X, Jia B. A Meta-analysis of Xiaoyin Granules Combined with Acitretin Capsule in the Treatment of Psoriasis Vulgaris. Comput Math Methods Med. 2022 Jul 27;2022:7360975. doi: 10.1155/2022/7360975. PMID: 35936361; PMCID: PMC9348960.


20: Lebwohl M. Acitretin in combination with UVB or PUVA. J Am Acad Dermatol. 1999 Sep;41(3 Pt 2):S22-4. doi: 10.1016/s0190-9622(99)70362-2. PMID: 10459143.