Details
Stereochemistry | ACHIRAL |
Molecular Formula | C22H32O2 |
Molecular Weight | 328.4891 |
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])\COC(=O)C)\C)/C(/[H])=C(\[H])/C1=C(C)CCCC1(C)C
InChI
InChIKey=QGNJRVVDBSJHIZ-QHLGVNSISA-N
InChI=1S/C22H32O2/c1-17(9-7-10-18(2)14-16-24-20(4)23)12-13-21-19(3)11-8-15-22(21,5)6/h7,9-10,12-14H,8,11,15-16H2,1-6H3/b10-7+,13-12+,17-9+,18-14+
Molecular Formula | C22H32O2 |
Molecular Weight | 328.4891 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 4 |
Optical Activity | NONE |
DescriptionCurator's Comment:: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/8801161
Curator's Comment:: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/8801161
Retonol, also known as Vitamin A1, is a vitamin found in food and used as a dietary supplement. It is used to treat and prevent vitamin A deficiency. It is also used to prevent further issues in those who have measles. Retinol is used as a metabolic precursor of retinoic acid to treat skin-related conditions, such as cellulite, skin aging, photodamage.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2354 Sources: https://www.ncbi.nlm.nih.gov/pubmed/30972178 |
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Target ID: O95237 Gene ID: 9227.0 Gene Symbol: LRAT Target Organism: Homo sapiens (Human) |
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Target ID: Q96NR8 Gene ID: 145226.0 Gene Symbol: RDH12 Target Organism: Homo sapiens (Human) Sources: https://www.drugbank.ca/drugs/DB00162 |
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Target ID: Q92781 Gene ID: 5959.0 Gene Symbol: RDH5 Target Organism: Homo sapiens (Human) Sources: https://www.drugbank.ca/drugs/DB00162 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Preventing | Unknown Approved UseUnknown |
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Preventing | Unknown Approved UseUnknown |
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Preventing | Unknown Approved UseUnknown |
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Primary | AQUASOL A Approved UseUsed to treat and prevent symptoms of vitamin A deficiency such as xerophthalmia and night blindness. Used as a dietary supplement to prevent vitamin A deficiency in patients with GI diseases (e.g., malabsorption syndromes) and those with abnormal storage and transport of vitamin A (e.g., abetalipoproteinemia, protein deficiency, diabetes mellitus, hyperthyroidism, fever, liver disease, cystic fibrosis with hepatic involvement). Launch Date-6.5093763E11 |
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Palliative | AQUASOL A Approved UseChildren with severe measles have been found to have low serum concentrations of vitamin A; WHO and AAP recommend that vitamin A supplements be given to all children with acute measles, regardless of their country of residence. Launch Date-6.5093763E11 |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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[Review of acute hydrocephalus caused by administration of vitamin A in massive doses in nursing infants; based on 100 cases]. | 1957 Feb |
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[Renal tubular failure after treatment with high dose of vitamin A (author's transl)]. | 1976 Feb 6 |
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Effect of avitaminosis A and hypervitaminosis A on urinary bladder carcinogenicity of N-(4-(5-Nitro-2-furyl)-2-thiazolyl)formamide. | 1976 Jul |
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Vitamin neurotoxicity. | 1992 Spring |
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The anemia of vitamin A deficiency: epidemiology and pathogenesis. | 2002 Apr |
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[Treatment of acne with consequences -- pseudotumor cerebri due to hypervitaminosis A]. | 2002 Jan 9 |
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PPARbeta regulates vitamin A metabolism-related gene expression in hepatic stellate cells undergoing activation. | 2003 Feb |
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Vitamin A deficiency and relational memory deficit in adult mice: relationships with changes in brain retinoid signalling. | 2003 Oct 17 |
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Retinol-induced mdr1 and mdr3 modulation in cultured rat Sertoli cells is attenuated by free radical scavengers. | 2004 |
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Vitamin A prevents high fat diet-induced ACF development and modifies the pattern of expression of peroxisome proliferator and retinoic acid receptor m-RNA. | 2004 |
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Dietary vitamin A intakes of Filipino elders with adequate or low liver vitamin A concentrations as assessed by the deuterated-retinol-dilution method: implications for dietary requirements. | 2004 Apr |
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Carotenoids and their metabolites are naturally occurring activators of gene expression via the pregnane X receptor. | 2004 Dec |
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A palmitoylation switch mechanism in the regulation of the visual cycle. | 2004 Jun 11 |
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Safety and efficacy of dose-intensive oral vitamin A in subjects with sun-damaged skin. | 2004 Mar 15 |
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Hypercalcaemia from non-prescription vitamin A. | 2004 Nov |
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Age differences in vitamin A intake among Canadian Inuit. | 2004 Nov-Dec |
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Ocular side effects from herbal medicines and nutritional supplements. | 2004 Oct |
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Protein and m-RNA expression of farnesyl-transferases, RhoA and RhoB in rat liver hepatocytes: action of perillyl alcohol and vitamin A in vivo. | 2005 |
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Alcohol, vitamin A, and cancer. | 2005 Apr |
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What is the safe dose of vitamin A in children with measles? | 2005 Apr |
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Fortification of maize meal improved the nutritional status of 1-3-year-old African children. | 2005 Aug |
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Effects of prenatal vitamins A, E, and C on the hypoplastic hearts of fetal rats with diaphragmatic hernia. | 2005 Aug |
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beta-cryptoxanthin stimulates cell differentiation and mineralization in osteoblastic MC3T3-E1 cells. | 2005 Aug 15 |
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Vitamin A status in mice affects the histone code of the phosphoenolpyruvate carboxykinase gene in liver. | 2005 Dec |
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Phospho-STAT5 accumulation in nuclear fractions from vitamin A-deficient rat liver. | 2005 Jul 4 |
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Effect of vitamin A content in cafeteria diet on the expression of nuclear receptors in rat subcutaneous adipose tissue. | 2005 Jun |
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Vitamin a deficiency and anaemia in young children living in a malaria endemic district of western Kenya. | 2005 Jun |
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Vitamin A deficiency induces prooxidant environment and inflammation in rat aorta. | 2005 Jun |
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Serum and CSF vitamin A concentrations in idiopathic intracranial hypertension. | 2005 Jun 14 |
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Extra-hepatic vitamin A concentrations in captive Rhesus (Macaca mulatta) and Marmoset (Callithrix jacchus) monkeys fed excess vitamin A. | 2005 Mar |
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Megalin-mediated reuptake of retinol in the kidneys of mice is essential for vitamin A homeostasis. | 2005 Nov |
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Development of a versatile reporter assay for studies of retinol uptake and metabolism in vivo. | 2005 Nov 1 |
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Retinoid metabolism during development of liver cirrhosis. | 2005 Nov 15 |
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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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Comparison of indices of vitamin A status in children with chronic liver disease. | 2005 Oct |
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Vitamin A regulation of BMP4 expression in the male germ line. | 2005 Oct 1 |
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Acyl coenzyme A dependent retinol esterification by acyl coenzyme A: diacylglycerol acyltransferase 1. | 2005 Oct 15 |
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Retinol induces permeability transition and cytochrome c release from rat liver mitochondria. | 2005 Oct 30 |
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Expression of keratinocyte transglutaminase in cornea of vitamin A-deficient rats. | 2005 Sep |
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Transmembrane protein GDE2 induces motor neuron differentiation in vivo. | 2005 Sep 30 |
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Hypervitaminosis A resulting in DNA aberration in fetal transgenic mice (Muta Mouse). | 2005 Sep 5 |
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Effects of nitrofen and vitamins A, C and E on maturation of cultured human H441 pneumocytes. | 2006 |
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Vitamin A improves Pax3 expression that is decreased in the heart of rats with experimental diaphragmatic hernia. | 2006 Feb |
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The acute and chronic toxic effects of vitamin A. | 2006 Feb |
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Comparative ligand-binding analysis of ten human lipocalins. | 2006 Feb |
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Retinoic acid regulates sex-specific timing of meiotic initiation in mice. | 2006 Feb 21 |
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Role of retinoic acid receptors alpha1 and gamma in the response of murine limbs to retinol in vitro. | 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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Hypervitaminosis A-induced liver fibrosis: stellate cell activation and daily dose consumption. | 2006 Mar |
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Retinol palmitate protects against myocardial ischemia/reperfusion injury via reducing oxidative stress and inhibiting apoptosis. | 2019 |
Patents
Sample Use Guides
The role of vitamin A (2.72 μM/7 ml culture), a naturally occurring antioxidant upon arsenic-induced genotoxicity; with respect to chromosomal aberrations (structural and numerical) and micronuclei. Whole blood cultures set for 72 h were exposed to test chemicals for a period of 24 h ahead of harvesting. Arsenic concentrations tested in the present study are 0.36, 0.72 and 1.4 μM/7 ml culture. Mitomycin C (MMC), the direct acting mutagen was used as positive control.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Jun 26 05:03:47 UTC 2021
by
admin
on
Sat Jun 26 05:03:47 UTC 2021
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Record UNII |
3LE3D9D6OY
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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DSLD |
3238 (Number of products:173)
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DSLD |
2650 (Number of products:125)
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NCI_THESAURUS |
C804
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Code System | Code | Type | Description | ||
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638034
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PRIMARY | |||
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127-47-9
Created by
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PRIMARY | |||
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CHEMBL986
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PRIMARY | |||
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DBSALT001720
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PRIMARY | |||
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VITAMIN A ACETATE
Created by
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PRIMARY | Description: A yellow to brownish yellow, oily liquid. Solubility: Practically insoluble in water; soluble or partly soluble in dehydrated ethanol R; miscible with organic solvents. Category: Vitamin.Storage: The oily form of Retinol concentrate should be kept in a well-closed and well-filled container, protected from light. Once the container has been opened its contents should be used as soon as possible; any part of the contents not used at once shouldbe protected by an atmosphere of inert gas. Labelling: The designation on the container should state the name of the retinol ester or esters, and their quantities expressed as the content of vitamin A in International Units (IU) per gram, whether any stabilizing agents are added and their quantities, as well as the method of restoring the solution if partial crystallization has occurred. Additional information: Even in the absence of light the oily form of Retinol concentrate is gradually degraded on exposure to ahumid atmosphere, the decomposition being faster at higher temperatures.Partial crystallization may occur in concentrated solutions and upon refrigeration. | ||
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3LE3D9D6OY
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M11481
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PRIMARY | Merck Index | ||
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C1216
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PRIMARY | |||
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35400
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PRIMARY | RxNorm | ||
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2372
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RETINYL ACETATE
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204-844-2
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C009166
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127-47-9
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1716002
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PRIMARY | USP-RS | ||
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SUB04224MIG
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PRIMARY |
Related Record | Type | Details | ||
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ACTIVE MOIETY |