Details
Stereochemistry | ACHIRAL |
Molecular Formula | C20H28O2 |
Molecular Weight | 300.4359 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 4 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C/C(=C(\[H])/C(/[H])=C(\[H])/C(=C(\[H])/C(=O)O)/C)/C(/[H])=C(\[H])/C1=C(C)CCCC1(C)C
InChI
InChIKey=SHGAZHPCJJPHSC-ZVCIMWCZSA-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+
DescriptionSources: http://www.drugbank.ca/drugs/DB00523Curator's Comment:: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/1999/20886lbl.pdf
Sources: http://www.drugbank.ca/drugs/DB00523
Curator's Comment:: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/1999/20886lbl.pdf
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
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2061 |
10.0 nM [EC50] | ||
Target ID: CHEMBL2003 |
50.0 nM [EC50] | ||
Target ID: CHEMBL2061 |
195.0 nM [EC50] | ||
Target ID: CHEMBL2008 |
3.0 nM [EC50] | ||
Target ID: CHEMBL2004 |
140.0 nM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | ACCUTANE Approved UseAccutane is indicated for the treatment of severe recalcitrant nodular acne. Nodules are inflammatory lesions with a diameter of 5 mm or greater. The nodules may become suppurative or hemorrhagic. “Severe,” by definition, means “many” as opposed to “few or several” nodules. Because of significant adverse effects associated with its use, Accutane should be reserved for patients with severe nodular acne who are unresponsive to conventional therapy, including systemic antibiotics. In addition, Accutane is indicated only for those female patients who are not pregnant, because Accutane can cause severe birth defects. Launch Date3.89491196E11 |
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Primary | Panretin gel Approved UsePanretin gel is indicated for topical treatment of cutaneous lesions in patients with AIDS-related Kaposi’s sarcoma. Launch Date9.1782722E11 |
PubMed
Title | Date | PubMed |
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Generation of radical oxygen species by neural crest cells treated in vitro with isotretinoin and 4-oxo-isotretinoin. | 1990 |
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Taste and olfactory disturbances after treatment for acne with isotretinoin, a 13-cis-isomer of retinoic acid. | 1990 |
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Acute depression from isotretinoin. | 1990 Jun |
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[Acne fulminans triggered by isotretinoin therapy]. | 1991 |
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Acute depression from isotretinoin. | 1991 Jul |
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Isotretinoin therapy induces DNA oxidative damage. | 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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Retinoic acid induces VEGF gene expression in human retinal pigment epithelial cells (ARPE-19). | 2005 Dec |
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All-trans-retinoic acid accelerates the differentiation of human B lymphocytes maturing into plasma cells. | 2005 Dec |
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[Erectile dysfunction during isotretinoin therapy]. | 2005 Nov-Dec |
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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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Matrix metalloproteinases of epithelial origin in facial sebum of patients with acne and their regulation by isotretinoin. | 2005 Oct |
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Mechanism of retinoid receptors in inhibiting proliferation and inducing apoptosis of human melanoma cell line A375. | 2005 Sep 5 |
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Differential regulation of Toll-like receptor and CD14 pathways by retinoids and corticosteroids in human sebocytes. | 2006 |
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Low-dose isotretinoin in the treatment of acne vulgaris. | 2006 Apr |
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Increased use of mental health services related to isotretinoin treatment: a 5-year analysis. | 2006 Aug |
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Incidence of depression related to isotretinoin treatment in 100 acne vulgaris patients. | 2006 Dec |
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The results and side effects of systemic isotretinoin treatment in 100 patients with acne vulgaris. | 2006 Dec |
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[Panic attacks in a patient treated with isotretinoin for acne. Report of one case]. | 2006 Dec |
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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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Angioedema and urticaria due to isotretinoin therapy. | 2006 Jan |
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[From the Cochrane Library: Improvement of photodamaged skin with retinoid creams and not with other local treatments]. | 2006 Jan 21 |
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Small molecule RPE65 antagonists limit the visual cycle and prevent lipofuscin formation. | 2006 Jan 24 |
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[Mechanism of receptor for retinoids inducing apoptosis of human melanoma cell line A375]. | 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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A novel cytochrome P450, zebrafish Cyp26D1, is involved in metabolism of all-trans retinoic acid. | 2006 Jul |
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A rare side-effect of systemic isotretinoin treatment: hoarseness. | 2006 Nov |
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13-cis Retinoic acid induces apoptosis and cell cycle arrest in human SEB-1 sebocytes. | 2006 Oct |
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Chronic administration of 13-cis-retinoic acid increases depression-related behavior in mice. | 2006 Sep |
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Cytodifferentiation by retinoids, a novel therapeutic option in oncology: rational combinations with other therapeutic agents. | 2007 |
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Atrial tachycardia associated with isotretinoin use. | 2007 Aug |
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Isotretinoin-induced pleuritic chest pain. | 2007 Feb |
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Isotretinoin, pregnancies, abortions and birth defects: a population-based perspective. | 2007 Feb |
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Antitumor effect of the histone deacetylase inhibitor LAQ824 in combination with 13-cis-retinoic acid in human malignant melanoma. | 2007 Jan |
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Cerebral ischemia probably related to isotretinoin. | 2007 Jun |
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Molecular targeting of retinoic acid metabolism in neuroblastoma: the role of the CYP26 inhibitor R116010 in vitro and in vivo. | 2007 Jun 4 |
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Acneiform eruptions associated with epidermal growth factor receptor-targeted chemotherapy. | 2007 Mar |
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CD69 on CD56+ NK cells and response to chemoimmunotherapy in metastatic melanoma. | 2007 Nov |
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No association found between patients receiving isotretinoin for acne and the development of depression in a Canadian prospective cohort. | 2007 Summer |
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Hypercalcemia induced by 13 cis-retinoic acid in patients with neuroblastoma. | 2008 Apr |
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Use of oral isotretinoin in photoaging therapy. | 2008 Jan-Feb |
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Sacroiliitis and polyneuropathy during isotretinoin treatment. | 2008 Mar |
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A cerebellar demyelinating lesion following treatment of acne with isotretinoin. | 2008 Mar |
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Isotretinoin (13-cis-retinoic acid)-associated premature ventricular contractions. | 2009 Jul-Aug |
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Giant cobblestone-like papillae during isotretinoin therapy. | 2009 Sep-Oct |
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Retinoids activate RXR/CAR-mediated pathway and induce CYP3A. | 2010 Jan 15 |
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Onset of Kleine-Levin Syndrome in association with isotretinoin treatment. | 2010 Jun |
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Psychiatric reactions to isotretinoin in patients with bipolar disorder. | 2010 May |
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Isotretinoin-induced encephalopathy. | 2010 Nov |
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Chemical genomics profiling of environmental chemical modulation of human nuclear receptors. | 2011 Aug |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21368300
The addition of 5 nM Alitretinoin to the maturation medium was beneficial for parthenogenetic pig embryo production.
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WHO-ATC |
D11AX19
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WHO-VATC |
QL01XX22
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WHO-VATC |
QD11AH04
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NDF-RT |
N0000007700
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NCI_THESAURUS |
C804
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NDF-RT |
N0000007700
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FDA ORPHAN DRUG |
101296
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WHO-ATC |
D11AH04
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EMA ASSESSMENT REPORTS |
PANRETIN (AUTHORIZED: SARCOMA, KAPOSI)
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NDF-RT |
N0000007700
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NDF-RT |
N0000007700
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FDA ORPHAN DRUG |
110998
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WHO-ATC |
L01XX22
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NDF-RT |
N0000175607
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FDA ORPHAN DRUG |
66592
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NDF-RT |
N0000007700
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FDA ORPHAN DRUG |
708819
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C1574
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7781
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7186
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CHEMBL705
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M1511
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3862
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M9558
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C103303
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5300-03-8
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5300-03-8
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DB00523
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81864
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2645
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ALITRETINOIN
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SUB00344MIG
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449171
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1UA8E65KDZ
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ACTIVE MOIETY