MedKoo Cat#: 100020 | Name: Alitretinoin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Alitretinoin, or 9-cis-retinoic acid, is a form of vitamin A. Alitretinoin is an orally- and topically-active naturally-occurring retinoic acid with antineoplastic, chemopreventive, teratogenic, and embryotoxic activities. Alitretinoin binds to and activates nuclear retinoic acid receptors (RAR) and retinoid X receptors (RXR); these activated receptors act as transcription factors, regulating gene expression that results in the inhibition of cell proliferation, induction of cell differentiation, and apoptosis of both normal cells and tumor cells.

Chemical Structure

Alitretinoin
Alitretinoin
CAS#5300-03-8

Theoretical Analysis

MedKoo Cat#: 100020

Name: Alitretinoin

CAS#: 5300-03-8

Chemical Formula: C20H28O2

Exact Mass: 300.2089

Molecular Weight: 300.43

Elemental Analysis: C, 79.96; H, 9.39; O, 10.65

Price and Availability

Size Price Availability Quantity
5mg USD 350.00 2 Weeks
10mg USD 600.00 2 Weeks
25mg USD 1,150.00 2 Weeks
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Related CAS #
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Synonym
9-CRA. 9-cis-RA. ALRT1057; LGD1057; LGD-1057; LGD 1057; 9-cis-retinoic acid. Alitretinoin; Panretin. Panretyn; Panrexin
IUPAC/Chemical Name
(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
InChi Key
SHGAZHPCJJPHSC-ZVCIMWCZSA-N
InChi Code
InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8-,16-14+
SMILES Code
O=C(O)/C=C(C)/C=C/C=C(C)\C=C\C1=C(C)CCCC1(C)C
Appearance
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
2934.99.03.00
More Info
It is also used in medicine as an antineoplastic (anti-cancer) agent developed by Ligand Pharmaceuticals. It is a first generation retinoid. Ligand gained Food and Drug Administration (FDA) approval for alitretinoin in February 1999.

Preparing Stock Solutions

The following data is based on the product molecular weight 300.43 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
1: Cheer SM, Foster RH. Alitretinoin. Am J Clin Dermatol. 2000 Sep- Oct;1(5):307-14; discussion 315-6. doi: 10.2165/00128071-200001050-00005. PMID: 11702321. 2: Napolitano M, Potestio L, De Lucia M, Nocerino M, Fabbrocini G, Patruno C. Alitretinoin for the treatment of severe chronic eczema of the hands. Expert Opin Pharmacother. 2022 Feb;23(2):159-167. doi: 10.1080/14656566.2021.1998457. Epub 2021 Nov 18. PMID: 34789049. 3: Blair HA, Scott LJ. Alitretinoin: A Review in Severe Chronic Hand Eczema. Drugs. 2016 Sep;76(13):1271-1279. doi: 10.1007/s40265-016-0621-0. PMID: 27438290. 4: Schmitt-Hoffmann AH, Roos B, Schoetzau A, Leese PT, Meyer I, van de Wetering J, Kovacs P. Oral alitretinoin: a review of the clinical pharmacokinetics and pharmacodynamics. Expert Rev Clin Pharmacol. 2012 Jul;5(4):373-88. doi: 10.1586/ecp.12.26. PMID: 22943117. 5: Cheng C, Michaels J, Scheinfeld N. Alitretinoin: a comprehensive review. Expert Opin Investig Drugs. 2008 Mar;17(3):437-43. doi: 10.1517/13543784.17.3.437. PMID: 18321241. 6: Maqbool T, Kraft JN. Alitretinoin for prurigo nodularis. Clin Exp Dermatol. 2021 Mar;46(2):362-363. doi: 10.1111/ced.14385. Epub 2020 Oct 10. PMID: 33464627. 7: Garnock-Jones KP, Perry CM. Alitretinoin: in severe chronic hand eczema. Drugs. 2009 Aug 20;69(12):1625-34. doi: 10.2165/11202200-000000000-00000. PMID: 19678713. 8: Paulden M, Rodgers M, Griffin S, Slack R, Duffy S, Ingram JR, Woolacott N, Sculpher M. Alitretinoin for the treatment of severe chronic hand eczema. Health Technol Assess. 2010 May;14 Suppl 1:39-46. doi: 10.3310/hta14Suppl1/06. PMID: 20507802. 9: Rodgers M, Griffin S, Paulden M, Slack R, Duffy S, Ingram JR, Woolacott N, Sculpher M. Alitretinoin for severe chronic hand eczema: a NICE single technology appraisal. Pharmacoeconomics. 2010;28(5):351-62. doi: 10.2165/11532160-000000000-00000. PMID: 20131924. 10: Richard MA. Alitrétinoïne et eczéma chronique des mains: synthèse des essais cliniques [Alitretinoin in chronic hand eczema: summary of clinical trials]. Ann Dermatol Venereol. 2010 Nov;137 Suppl 3:S111-23. French. doi: 10.1016/S0151-9638(10)70038-7. PMID: 21185982. 11: Kim TH, Lee JW, Kim Y, Park TJ, Lee JY, Kang HY. Alitretinoin induces skin pigmentation: implications for melasma. Eur J Dermatol. 2022 Jan 1;32(1):140-142. English. doi: 10.1684/ejd.2022.4237. PMID: 35653092. 12: Gooderham MJ. Alitretinoin: An Update of Real-World Evidence in The Management of Chronic Hand Dermatitis. Skin Therapy Lett. 2018 Jul;23(4):1-4. PMID: 30086182. 13: Balestri R, Magnano M, Savoia F, Patrizi A, Neri I. Alitretinoin for palmoplantar keratodermas: A novel case and review of the literature. Dermatol Ther. 2019 Mar;32(2):e12794. doi: 10.1111/dth.12794. Epub 2018 Dec 26. PMID: 30515925. 14: Fritz K, Tiplica GS, Salavastru C, Onder M. Alitretinoin und Off-label-Use [Off-label use of alitretinoin]. Hautarzt. 2013 Oct;64(10):748-51. German. doi: 10.1007/s00105-013-2593-2. PMID: 24150823. 15: Kaemmerer T, Stadler PC, Helene Frommherz L, Guertler A, Einar French L, Reinholz M. Alitretinoin in the treatment of cutaneous T-cell lymphoma. Cancer Med. 2021 Oct;10(20):7071-7078. doi: 10.1002/cam4.4237. Epub 2021 Aug 25. PMID: 34435474; PMCID: PMC8525105. 16: Schmutz JL. Alitrétinoïne (Toctino®) : données récentes de pharmacovigilance [Alitretinoin (Toctino®): Recent pharmacovigilance data]. Ann Dermatol Venereol. 2020 Apr;147(4):329-330. French. doi: 10.1016/j.annder.2020.01.002. Epub 2020 Mar 4. PMID: 32145989. 17: Oral alitretinoin. Severe chronic hand eczema: this retinoid is too risky. Prescrire Int. 2010 Apr;19(106):62-3. PMID: 20568484. 18: Molin S, Ruzicka T. Alitretinoin: Die erste spezifisch zugelassene Therapie für das chronische Handekzem [Alitretinoin: a new treatment option for chronic refractory hand eczema]. Hautarzt. 2008 Sep;59(9):703-4, 706-9. German. doi: 10.1007/s00105-008-1559-2. PMID: 18704345. 19: Chung BY, Um JY, Kang SY, Jung MJ, Kim JC, Kwak IS, Park CW, Kim HO. Oral Alitretinoin for Patients with Refractory Prurigo. Medicina (Kaunas). 2020 Nov 9;56(11):599. doi: 10.3390/medicina56110599. PMID: 33182351; PMCID: PMC7695266. 20: Didona D, Pumnea T, von Braunmühl T, Wolf R. Effective use of alitretinoin in acitretin-refractory nail lichen planus. Int J Dermatol. 2022 May;61(5):e174-e176. doi: 10.1111/ijd.15993. Epub 2021 Nov 23. PMID: 34812508.