WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 100020
Description: 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.
MedKoo Cat#: 100020
Chemical Formula: C20H28O2
Exact Mass: 300.20893
Molecular Weight: 300.43
Elemental Analysis: C, 79.96; H, 9.39; O, 10.65
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
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.
|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: 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. PubMed PMID: 20507802.
2: Molin S, Ruzicka T. [Treatment for chronic hand eczema]. MMW Fortschr Med. 2009 May 7;151(19):35-7. Review. German. PubMed PMID: 19827442.
3: 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. Review. PubMed PMID: 19678713.
4: Stege H. [Ultraviolet therapy in patients with chronic hand eczema]. Hautarzt. 2008 Sep;59(9):696-702. Review. German. PubMed PMID: 18712324.
5: Molin S, Ruzicka T. [Alitretinoin: a new treatment option for chronic refractory hand eczema]. Hautarzt. 2008 Sep;59(9):703-4, 706-9. Review. German. PubMed PMID: 18704345.
6: Wollina U. Pompholyx: what's new? Expert Opin Investig Drugs. 2008 Jun;17(6):897-904. Review. PubMed PMID: 18491990.
7: Szabo E. Proliferative changes in chemoprevention trials: learning from secondary endpoints. J Natl Cancer Inst. 2007 Nov 7;99(21):1565-7. Epub 2007 Oct 30. PubMed PMID: 17971524.
8: Al-Wadei HA, Schuller HM. Cyclic adenosine monophosphate-dependent cell type-specific modulation of mitogenic signaling by retinoids in normal and neoplastic lung cells. Cancer Detect Prev. 2006;30(5):403-11. Epub 2006 Oct 25. PubMed PMID: 17067750; PubMed Central PMCID: PMC1761122.
9: Mernitz H, Smith DE, Zhu AX, Wang XD. 9-cis-Retinoic acid inhibition of lung carcinogenesis in the A/J mouse model is accompanied by increased expression of RAR-beta but no change in cyclooxygenase-2. Cancer Lett. 2006 Nov 28;244(1):101-8. Epub 2006 Jan 18. PubMed PMID: 16413115.
10: Baumann L, Vujevich J, Halem M, Martin LK, Kerdel F, Lazarus M, Pacheco H, Black L, Bryde J. Open-label pilot study of alitretinoin gel 0.1% in the treatment of photoaging. Cutis. 2005 Jul;76(1):69-73. PubMed PMID: 16144296.
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.