Details
Stereochemistry | ACHIRAL |
Molecular Formula | C20H30O |
Molecular Weight | 286.4516 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 4 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(=C/CO)\C=C\C=C(C)\C=C\C1=C(C)CCCC1(C)C
InChI
InChIKey=FPIPGXGPPPQFEQ-OVSJKPMPSA-N
InChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6+,12-11+,16-8+,17-13+
DescriptionCurator's Comment: description was created based on several sources, including:
https://en.wikipedia.org/wiki/Vitamin_A
Curator's Comment: description was created based on several sources, including:
https://en.wikipedia.org/wiki/Vitamin_A
Vitamin A is important for growth and development as well as maintenance of the immune system and good vision. Vitamin A is needed by the retina of the eye in the form of retinal, which combines with the protein opsin to form rhodopsin. Together Vitamin A and Rhodopsin form the light-absorbing molecule necessary for both low-light (scotopic vision) and color vision. Vitamin A also functions in a very different role as retinoic acid (an irreversibly oxidized form of retinol) which is an important hormone-like growth factor for epithelial and other cells. In foods of animal origin, the major form of vitamin A is an ester, primarily retinyl palmitate, which is converted to retinol (chemically an alcohol) in the small intestine. The retinol form functions as a storage form of the vitamin, and can be converted to and from its visually active aldehyde form, retinal. Vitamin A is effective for the treatment of Vitamin A deficiency. Vitamin A refers to a group of fat-soluble substances that are structurally related to and possess the biological activity of the parent substance of the group called all-trans retinol or retinol. Vitamin A plays vital roles in vision, epithelial differentiation, growth, reproduction, pattern formation during embryogenesis, bone development, hematopoiesis and brain development. It is also important for the maintenance of a proper functioning immune system. The precise mechanism of action of vitamin A differs based on the biological use case, and some mechanisms are better known than others. To facilitate vision Vitamin A (all-trans retinol) is converted in the retina to the 11-cis-isomer of retinaldehyde or 11-cis-retinal. 11-cis-retinal functions in the retina contributing to the transduction of light into the neural signals necessary for vision. While attached to opsin in rhodopsin 11-cis-retinal is isomerized to all-trans-retinal by light which triggers the nerve impulse to the brain allowing for the perception of light. All-trans-retinal is then released from opsin and reduced to all-trans-retinol. All-trans-retinol is isomerized to 11-cis-retinol in the absence of light and then oxidized to 11-cis-retinal. 11-cis-retinal recombines with opsin to re-form rhodopsin. Night blindness or defective vision at low illumination results from a failure to re-synthesize 11-cis retinal rapidly. During epithelial differentiation the role of Vitamin A (as in other physiological processes) involves the binding of Vitamin A to two families of nuclear retinoid receptors (retinoic acid receptors, RARs; and retinoid-X receptors, RXRs). These receptors function as ligand-activated transcription factors that modulate gene transcription. When there is not enough Vitamin A to bind these receptors, natural cell differentiation and growth are interrupted.
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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Vitamin A induced benign intracranial hypertension. | 1976 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 A abuse: development of cirrhosis despite cessation of vitamin A. A six-year clinical and histopathologic follow-up. | 1992 Dec |
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McCollum Award Lecture, 1992: vitamin A absorption, transport, cellular uptake, and storage. | 1992 Oct |
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Vitamin neurotoxicity. | 1992 Spring |
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Fruit and fertility in San Juan de la Manguana. | 1995 |
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Characterization of a novel airway epithelial cell-specific short chain alcohol dehydrogenase/reductase gene whose expression is up-regulated by retinoids and is involved in the metabolism of retinol. | 2001 Jun 29 |
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Influence of vitamin A status on the regulation of uridine (5'-)diphosphate-glucuronosyltransferase (UGT) 1A1 and UGT1A6 expression by L-triiodothyronine. | 2001 Mar |
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Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients. | 2001 Nov |
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The anemia of vitamin A deficiency: epidemiology and pathogenesis. | 2002 Apr |
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Retinoids regulate the repairing process of the podocytes in puromycin aminonucleoside-induced nephrotic rats. | 2003 Apr |
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PPARbeta regulates vitamin A metabolism-related gene expression in hepatic stellate cells undergoing activation. | 2003 Feb |
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Impact of 'Mad Cow Disease' publicity on trends in meat and total vitamin A consumption in Geneva between 1993 and 2000. | 2003 Jan |
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Redistribution of vitamin A after iron supplementation in Indonesian infants. | 2003 Mar |
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Vitamin A deficiency leads to increased cell proliferation in olfactory epithelium of mature rats. | 2003 Mar |
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Effects of supplementation with vitamins A, C, and E, selenium, and zinc on immune function in a murine sensitization model. | 2003 Nov-Dec |
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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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Modulation of resistin expression by retinoic acid and vitamin A status. | 2004 Apr |
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Metabolism of retinoids and arachidonic acid by human and mouse cytochrome P450 1b1. | 2004 Aug |
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Vitamin A regulates proliferation and apoptosis of human T- and B-cells. | 2004 Dec |
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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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Capillary leak syndrome induced by acitretin. | 2004 Jan |
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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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Use of the deuterated-retinol-dilution technique to monitor the vitamin A status of Nicaraguan schoolchildren 1 y after initiation of the Nicaraguan national program of sugar fortification with vitamin A. | 2004 Nov |
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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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Effects of 2,3,7,8-tetrachlorodibenzo-p-dioxin on vitamin A metabolism in mice. | 2005 |
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Differential effects of vitamin A on fetal lung growth and diaphragmatic formation in nitrofen-induced rat model. | 2005 |
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What is the safe dose of vitamin A in children with measles? | 2005 Apr |
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Retinoid receptor mRNA expression profiles in human bladder cancer specimens. | 2005 Apr |
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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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Retinal degeneration associated with RDH12 mutations results from decreased 11-cis retinal synthesis due to disruption of the visual cycle. | 2005 Dec 15 |
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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 supplementation for extremely low birth weight infants: outcome at 18 to 22 months. | 2005 Mar |
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Inhibitory effects of vitamin A on TCDD-induced cytochrome P-450 1A1 enzyme activity and expression. | 2005 May |
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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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Mutation of key residues of RPE65 abolishes its enzymatic role as isomerohydrolase in the visual cycle. | 2005 Sep 20 |
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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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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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RPE65 is an iron(II)-dependent isomerohydrolase in the retinoid visual cycle. | 2006 Feb 3 |
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Renal pathology and retinol status in multiple myeloma patients. | 2006 Jan |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/monograph/vitamin-a.html
Retinol should be administered orally or by intramuscular injection. For skin conditions retinol is applied topically.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10819989
Kinetic analyses of retinol esterification by lecithin retinol acyltransferase (LRAT) were carried out by measuring the rates of 3H-all-trans-retinyl ester formation under conditions where 3H-all-trans-retinol was varied at saturating lecithin concentrations. LRAT catalyzes esterification of retinol with Km of 0.94 uM.
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WHO-VATC |
QR01AX02
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20947-8
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14905-4
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WHO-VATC |
QS01XA02
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NCI_THESAURUS |
C68299
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NCI_THESAURUS |
C938
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WHO-VATC |
QD10AD02
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WHO-ESSENTIAL MEDICINES LIST |
27
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LOINC |
20948-6
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DSLD |
3441 (Number of products:6)
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WHO-ATC |
S01XA02
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WHO-ATC |
A11CA01
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EU-Orphan Drug |
EU/3/17/1895
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20946-0
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87673-0
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LOINC |
2923-1
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WHO-ATC |
D10AD02
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WHO-ATC |
R01AX02
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WHO-VATC |
QA11CA01
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LOINC |
2922-3
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2831
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1367187
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445354
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DB00162
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CHEMBL986
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50211
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2243
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RETINOL
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G2SH0XKK91
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17336
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200-683-7
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SUB16102MIG
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C68302
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G2SH0XKK91
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122759
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M11481
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PRIMARY | Merck Index |
ACTIVE MOIETY