Details
Stereochemistry | ACHIRAL |
Molecular Formula | C20H28O2 |
Molecular Weight | 300.4351 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 4 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C(C)=C/C(O)=O
InChI
InChIKey=SHGAZHPCJJPHSC-YCNIQYBTSA-N
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+
Alitretinoin, or 9-cis-retinoic acid, is a form of vitamin A. It is also used in medicine as an antineoplastic (anti-cancer) agent developed by Ligand Pharmaceuticals. Alitretinoin (9-cis-retinoic acid) is a naturally-occurring endogenous retinoid indicated for topical treatment of cutaneous lesions in patients with AIDS-related Kaposi's sarcoma. Alitretinoin inhibits the growth of Kaposi's sarcoma (KS) cells in vitro. Alitretinoin binds to and activates all known intracellular retinoid receptor subtypes (RARa, RARb, RARg, RXRa, RXRb and RXRg). Once activated these receptors function as transcription factors that regulate the expression of genes that control the process of cellular differentiation and proliferation in both normal and neoplastic cells. In the United States, topical alitretinoin (in the form of a gel; trade name Panretin) is indicated for the treatment of skin lesions in AIDS-related Kaposi's sarcoma.
Originator
Approval Year
PubMed
Title | Date | PubMed |
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Effects of xenobiotics and peroxisome proliferator-activated receptor-alpha on the human UDPglucose dehydrogenase gene expression. | 2005 |
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The detection of differentiation-inducing chemicals by using green fluorescent protein expression in genetically engineered teratocarcinoma cells. | 2005 Apr |
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[Receptor-related mechanism of proliferation inhibilion and apoptosis induetion of human tongue squamous cell line Tca8113 by retinoids]. | 2005 Aug |
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Retinoic acid induces VEGF gene expression in human retinal pigment epithelial cells (ARPE-19). | 2005 Dec |
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Coactivation of liver receptor homologue-1 by peroxisome proliferator-activated receptor gamma coactivator-1alpha on aromatase promoter II and its inhibition by activated retinoid X receptor suggest a novel target for breast-specific antiestrogen therapy. | 2005 Dec 15 |
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Retinoid x receptor agonists increase bcl2a1 expression and decrease apoptosis of naive T lymphocytes. | 2005 Dec 15 |
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Nuclear import of the retinoid X receptor, the vitamin D receptor, and their mutual heterodimer. | 2005 Dec 2 |
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Open-label pilot study of alitretinoin gel 0.1% in the treatment of photoaging. | 2005 Jul |
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A new retinoid-like compound that activates peroxisome proliferator-activated receptors and lowers blood glucose in diabetic mice. | 2005 Jul |
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Specificity of receptor-ligand interactions and their effect on dimerisation as observed by electrospray mass spectrometry: bile acids form stable adducts to the RXRalpha. | 2005 Nov |
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Effect of retinoic acid on murine preosteoblastic MC3T3-E1 cells. | 2005 Oct |
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Regulation of a highly specific retinoic acid-4-hydroxylase (CYP26A1) enzyme and all-trans-retinoic acid metabolism in human intestinal, liver, endothelial, and acute promyelocytic leukemia cells. | 2005 Oct |
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Hepatocyte growth factor receptor signaling mediates the anti-fibrotic action of 9-cis-retinoic acid in glomerular mesangial cells. | 2005 Oct |
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Arsenic trioxide inhibits nuclear receptor function via SEK1/JNK-mediated RXRalpha phosphorylation. | 2005 Oct |
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Liver X receptor and retinoic X receptor agonists modulate the expression of genes involved in lipid metabolism in human endothelial cells. | 2005 Oct |
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The human ABCG1 gene: identification of LXR response elements that modulate expression in macrophages and liver. | 2005 Oct |
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Physiological and receptor-selective retinoids modulate interferon gamma signaling by increasing the expression, nuclear localization, and functional activity of interferon regulatory factor-1. | 2005 Oct 28 |
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VPAC1 expression is regulated by FXR agonists in the human gallbladder epithelium. | 2005 Sep |
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Regulation of adiponectin receptor 1 in human hepatocytes by agonists of nuclear receptors. | 2005 Sep 2 |
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The human tumor antigen PRAME is a dominant repressor of retinoic acid receptor signaling. | 2005 Sep 23 |
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Regression of NMU-induced mammary tumors with the combination of melatonin and 9-cis-retinoic acid. | 2005 Sep 8 |
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Organ-specific expression profiles of rat mammary gland, liver, and lung tissues treated with targretin, 9-cis retinoic acid, and 4-hydroxyphenylretinamide. | 2006 Apr |
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Effects of PPAR and RXR ligands in semaphorin 6B gene expression of human MCF-7 breast cancer cells. | 2006 Apr |
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Organotin compounds enhance 17beta-hydroxysteroid dehydrogenase type I activity in human choriocarcinoma JAr cells: potential promotion of 17beta-estradiol biosynthesis in human placenta. | 2006 Apr 28 |
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Differential regulation of CC chemokine receptors by 9-cis retinoic acid in the human mast cell line, HMC-1. | 2006 Aug 22 |
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TGIF inhibits retinoid signaling. | 2006 Feb |
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9-Cis-retinoic acid suppresses inflammatory responses of microglia and astrocytes. | 2006 Feb |
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Nonclassical action of retinoic acid on the activation of the cAMP response element-binding protein in normal human bronchial epithelial cells. | 2006 Feb |
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Prostate cancer cell type-specific involvement of the VDR and RXR in regulation of the human PTHrP gene via a negative VDRE. | 2006 Feb |
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Retinoid-mediated stimulation of steroid sulfatase activity in myeloid leukemic cell lines requires RARalpha and RXR and involves the phosphoinositide 3-kinase and ERK-MAP kinase pathways. | 2006 Feb 1 |
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Analysis of ligand binding and protein dynamics of human retinoid X receptor alpha ligand-binding domain by nuclear magnetic resonance. | 2006 Feb 14 |
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Investigation of the mechanisms by which EB1089 abrogates apoptosis induced by 9-cis retinoic acid in pancreatic cancer cells. | 2006 Jan |
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Vitamin A inhibits pancreatic stellate cell activation: implications for treatment of pancreatic fibrosis. | 2006 Jan |
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Retinoic acid receptors and tissue-transglutaminase mediate short-term effect of retinoic acid on migration and invasion of neuroblastoma SH-SY5Y cells. | 2006 Jan 12 |
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Effects of 9-cis retinoic acid on human homeobox gene NKX3.1 expression in prostate cancer cell line LNCaP. | 2006 Jul |
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Retinoic acids increase P2X2 receptor expression through the 5'-flanking region of P2rx2 gene in rat phaeochromocytoma PC-12 cells. | 2006 Jul |
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Retinoids activate the RXR/SXR-mediated pathway and induce the endogenous CYP3A4 activity in Huh7 human hepatoma cells. | 2006 Jul |
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Peroxisome proliferator-activated receptor-gamma and retinoic acid X receptor alpha represses the TGFbeta1 gene via PTEN-mediated p70 ribosomal S6 kinase-1 inhibition: role for Zf9 dephosphorylation. | 2006 Jul |
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A novel cytochrome P450, zebrafish Cyp26D1, is involved in metabolism of all-trans retinoic acid. | 2006 Jul |
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Thiazolidinediones and rexinoids induce peroxisome proliferator-activated receptor-coactivator (PGC)-1alpha gene transcription: an autoregulatory loop controls PGC-1alpha expression in adipocytes via peroxisome proliferator-activated receptor-gamma coactivation. | 2006 Jun |
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Efficacy of new retinoids in the prevention of mammary cancers and correlations with short-term biomarkers. | 2006 Jun |
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CYP4A11 is repressed by retinoic acid in human liver cells. | 2006 Jun 12 |
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Co-resistance to retinoic acid and TRAIL by insertion mutagenesis into RAM. | 2006 Jun 22 |
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Effects of rexinoids on thyrotrope function and the hypothalamic-pituitary-thyroid axis. | 2006 Mar |
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Receptor-selective retinoids inhibit the growth of normal and malignant breast cells by inducing G1 cell cycle blockade. | 2006 Mar |
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The phosphoinositide 3-kinase/Akt pathway is essential for the retinoic acid-induced differentiation of F9 cells. | 2006 Mar 30 |
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Retinoic acid exerts dual regulatory actions on the expression and nuclear localization of interferon regulatory factor-1. | 2006 May |
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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. | 2006 Nov 28 |
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Molecular cloning of the rat beta-carotene 15,15'-monooxygenase gene and its regulation by retinoic acid. | 2006 Sep |
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Unsaturated fatty acids suppress the expression of the ATP-binding cassette transporter G1 (ABCG1) and ABCA1 genes via an LXR/RXR responsive element. | 2007 Mar |
Patents
Sample Use Guides
Panretin (Alitretinoin) gel should initially be applied two (2) times a day to cutaneous KS lesions. The application frequency can be gradually increased to three (3) or four (4) times a day according to individual lesion tolerance.
Route of Administration:
Topical
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000007700
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NDF-RT |
N0000175607
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NCI_THESAURUS |
C68299
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WHO-VATC |
QL01XX14
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FDA ORPHAN DRUG |
71692
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NCI_THESAURUS |
C804
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FDA ORPHAN DRUG |
5785
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FDA ORPHAN DRUG |
165802
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WHO-VATC |
QD10AD51
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FDA ORPHAN DRUG |
50990
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WHO-ATC |
D10AD51
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NDF-RT |
N0000007700
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NDF-RT |
N0000007700
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WHO-ATC |
D10AD01
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WHO-VATC |
QD10AD01
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WHO-ATC |
L01XX14
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NDF-RT |
N0000007700
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NDF-RT |
N0000007700
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LIVERTOX |
993
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CHEMBL38
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M9558
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2875
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221175
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C900
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TRETINOIN
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10753
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302-79-4
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DB00755
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302-79-4
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302-79-4
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SUB11246MIG
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302-79-4
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206-129-0
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D014212
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ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)
PARENT (METABOLITE)
SALT/SOLVATE (PARENT)