9-cis-Retinoic Acid

  • CAT Number: R000404
  • CAS Number: 5300-03-8
  • Molecular Formula: C20H28O2
  • Molecular Weight: 300.442
  • Purity: ≥95%
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In the United States, topical alitretinoin is indicated for the treatment of skin lesions in AIDS-related Kaposi/’s sarcoma. Alitretinoin is not indicated when systemic therapy against Kaposi/’s sarcoma is required. It has received EMA and FDA approval for this indication. Under the trade name Toctino it has been granted prescription rights in the UK for oral use in chronic hand eczema. In May 2009 the National Institute for Health and Clinical Excellence (NICE) issued preliminary guidance on the use of Alitretinoin for the treatment of severe chronic hand eczema in adults. The recommendation stated that only patients with severe chronic hand eczema who are unresponsive to potent topical corticosteroids, oral immunosuppressants or phototherapy should receive the drug.

Catalog Number R000404
CAS Number 5300-03-8
Molecular Formula

C20H28O2

Purity 95%
Target RAR/RXR
Solubility Soluble in DMSO
Storage Store at -20C
IUPAC Name (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid
InChI 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+
InChIKey SHGAZHPCJJPHSC-ZVCIMWCZSA-N
SMILES CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CC(=O)O)C)C
Reference

</br>1:9-cis Retinoic acid modulates myotrophin expression and its miR in physiological and pathophysiological cell models. Perri M, Caroleo MC, Liu N, Gallelli L, De Sarro G, Kagechika H, Cione E.Exp Cell Res. 2017 May 1;354(1):25-30. doi: 10.1016/j.yexcr.2017.03.022. Epub 2017 Mar 12. PMID: 28300567 </br>2:Stimulation of Phospholipid Scrambling of the Erythrocyte Membrane by 9-Cis-Retinoic Acid. Abed M, Alzoubi K, Lang F, Al Mamun Bhuayn A.Cell Physiol Biochem. 2017;41(2):543-554. doi: 10.1159/000457014. Epub 2017 Jan 31. PMID: 28214868 Free Article</br>3:Interactive effects of 9-cis-retinoic acid and androgen on proliferation, differentiation, and apoptosis of LNCaP prostate cancer cells. Eskra JN, Kuiper JW, Walden PD, Bosland MC, Özten N.Eur J Cancer Prev. 2017 Jan;26(1):71-77. PMID: 26886237 </br>4:Evaluation of 9-cis retinoic acid and mitotane as antitumoral agents in an adrenocortical xenograft model. Nagy Z, Baghy K, Hunyadi-Gulyás É, Micsik T, Nyírő G, Rácz G, Butz H, Perge P, Kovalszky I, Medzihradszky KF, Rácz K, Patócs A, Igaz P.Am J Cancer Res. 2015 Nov 15;5(12):3645-58. eCollection 2015. PMID: 26885453 Free PMC Article</br>5:187 9-cis RETINOIC ACID IMPROVES MATURATION RATE AND ALTERS GENE EXPRESSION OF IN VITRO-MATURED OOCYTES IN EGYPTIAN BUFFALO. Gad A, Abu Hamed S, Khalifa M, El-Sayed A, Swiefy SA, El-Assal S.Reprod Fertil Dev. 2016 Jan;29(1):202. doi: 10.1071/RDv29n1Ab187. PMID: 28278984 </br>6:Prevention of Postsurgical Lymphedema by 9-cis Retinoic Acid. Bramos A, Perrault D, Yang S, Jung E, Hong YK, Wong AK.Ann Surg. 2016 Aug;264(2):353-61. doi: 10.1097/SLA.0000000000001525. PMID: 26655920 </br>7:9-cis-retinoic acid improves sensitivity to platelet-derived growth factor-BB via RXRα and SHP-1 in diabetic retinopathy. Chen Y, Wang W, Liu F, Tang L, Tang R, Li W.Biochem Biophys Res Commun. 2015 Oct 2;465(4):810-6. doi: 10.1016/j.bbrc.2015.08.093. Epub 2015 Aug 24. PMID: 26310807 </br>8:Correction. 9-Cis retinoic acid promotes lymphangiogenesis and enhances lymphatic vessel regeneration: therapeutic implications of 9-Cis retinoic acid for secondary lymphedema. Choi.Circulation. 2015 Apr 7;131(14):e401-2. doi: 10.1161/CIR.0000000000000200. No abstract available. PMID: 25847986 Free Article</br>9:RXR agonist modulates TR: corepressor dissociation upon 9-cis retinoic acid treatment. Fattori J, Campos JL, Doratioto TR, Assis LM, Vitorino MT, Polikarpov I, Xavier-Neto J, Figueira AC.Mol Endocrinol. 2015 Feb;29(2):258-73. doi: 10.1210/me.2014-1251. Epub 2014 Dec 26. PMID: 25541638 Free PMC Article</br>10:Proteomic analysis of changes in the protein composition of MCF-7 human breast cancer cells induced by all-trans retinoic acid, 9-cis retinoic acid, and their combination. Flodrova D, Benkovska D, Macejova D, Bialesova L, Hunakova L, Brtko J, Bobalova J.Toxicol Lett. 2015 Jan 5;232(1):226-32. doi: 10.1016/j.toxlet.2014.09.030. Epub 2014 Oct 16. PMID: 25455455

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