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Details

Stereochemistry ACHIRAL
Molecular Formula C20H30O
Molecular Weight 286.4523
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 4
Charge 0

SHOW SMILES / InChI
Structure of RETINOL

SMILES

C/C(=C(/[H])\C(\[H])=C(/[H])\C(=C(/[H])\CO)\C)/C(/[H])=C(\[H])/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+

HIDE SMILES / InChI

Description
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.

CNS Activity

Curator's Comment:: Evidence indicates that retinol is transported by retinol binding protein across the blood–brain barrier and blood–CSF barrier to the CNS

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: O95237
Gene ID: 9227.0
Gene Symbol: LRAT
Target Organism: Homo sapiens (Human)
Target ID: Q96NR8
Gene ID: 145226.0
Gene Symbol: RDH12
Target Organism: Homo sapiens (Human)
Target ID: Q92781
Gene ID: 5959.0
Gene Symbol: RDH5
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
Primary
AQUASOL A

Approved Use

Used 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
Palliative
AQUASOL A

Approved Use

Children 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
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Retinol-induced mdr1 and mdr3 modulation in cultured rat Sertoli cells is attenuated by free radical scavengers.
2004
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
Modulation of resistin expression by retinoic acid and vitamin A status.
2004 Apr
Vitamin A regulates proliferation and apoptosis of human T- and B-cells.
2004 Dec
Carotenoids and their metabolites are naturally occurring activators of gene expression via the pregnane X receptor.
2004 Dec
Inverse gene expression patterns for macrophage activating hepatotoxicants and peroxisome proliferators in rat liver.
2004 Jun 1
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
Hypercalcaemia from non-prescription vitamin A.
2004 Nov
Ocular side effects from herbal medicines and nutritional supplements.
2004 Oct
Effects of 2,3,7,8-tetrachlorodibenzo-p-dioxin on vitamin A metabolism in mice.
2005
Alcohol, vitamin A, and cancer.
2005 Apr
Brain tissue fragments in the amniotic fluid of rats with neural tube defect.
2005 Apr
Retinoid receptor mRNA expression profiles in human bladder cancer specimens.
2005 Apr
Fortification of maize meal improved the nutritional status of 1-3-year-old African children.
2005 Aug
Effects of prenatal vitamins A, E, and C on the hypoplastic hearts of fetal rats with diaphragmatic hernia.
2005 Aug
Vitamin A status in mice affects the histone code of the phosphoenolpyruvate carboxykinase gene in liver.
2005 Dec
Retinal degeneration associated with RDH12 mutations results from decreased 11-cis retinal synthesis due to disruption of the visual cycle.
2005 Dec 15
Phospho-STAT5 accumulation in nuclear fractions from vitamin A-deficient rat liver.
2005 Jul 4
Effect of vitamin A content in cafeteria diet on the expression of nuclear receptors in rat subcutaneous adipose tissue.
2005 Jun
Vitamin a deficiency and anaemia in young children living in a malaria endemic district of western Kenya.
2005 Jun
Serum and CSF vitamin A concentrations in idiopathic intracranial hypertension.
2005 Jun 14
Extra-hepatic vitamin A concentrations in captive Rhesus (Macaca mulatta) and Marmoset (Callithrix jacchus) monkeys fed excess vitamin A.
2005 Mar
Inhibitory effects of vitamin A on TCDD-induced cytochrome P-450 1A1 enzyme activity and expression.
2005 May
Megalin-mediated reuptake of retinol in the kidneys of mice is essential for vitamin A homeostasis.
2005 Nov
Expression of nuclear receptor and target genes in liver and intestine of neonatal calves fed colostrum and vitamin A.
2005 Nov
Retinol inhibits the growth of all-trans-retinoic acid-sensitive and all-trans-retinoic acid-resistant colon cancer cells through a retinoic acid receptor-independent mechanism.
2005 Nov 1
Development of a versatile reporter assay for studies of retinol uptake and metabolism in vivo.
2005 Nov 1
Retinoid metabolism during development of liver cirrhosis.
2005 Nov 15
Vitamin A supplementation induces adipose tissue loss through apoptosis in lean but not in obese rats of the WNIN/Ob strain.
2005 Oct
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
Comparison of indices of vitamin A status in children with chronic liver disease.
2005 Oct
Vitamin A regulation of BMP4 expression in the male germ line.
2005 Oct 1
Acyl coenzyme A dependent retinol esterification by acyl coenzyme A: diacylglycerol acyltransferase 1.
2005 Oct 15
Retinol induces permeability transition and cytochrome c release from rat liver mitochondria.
2005 Oct 30
Mutation of key residues of RPE65 abolishes its enzymatic role as isomerohydrolase in the visual cycle.
2005 Sep 20
Transmembrane protein GDE2 induces motor neuron differentiation in vivo.
2005 Sep 30
Hypervitaminosis A resulting in DNA aberration in fetal transgenic mice (Muta Mouse).
2005 Sep 5
Effects of nitrofen and vitamins A, C and E on maturation of cultured human H441 pneumocytes.
2006
The effect of vitamin A on CCl4-induced hepatic injuries in rats: a histochemical, immunohistochemical and ultrastructural study.
2006
Vitamin A improves Pax3 expression that is decreased in the heart of rats with experimental diaphragmatic hernia.
2006 Feb
The acute and chronic toxic effects of vitamin A.
2006 Feb
Comparative ligand-binding analysis of ten human lipocalins.
2006 Feb
Nonclassical action of retinoic acid on the activation of the cAMP response element-binding protein in normal human bronchial epithelial cells.
2006 Feb
Retinoic acid regulates sex-specific timing of meiotic initiation in mice.
2006 Feb 21
RPE65 is an iron(II)-dependent isomerohydrolase in the retinoid visual cycle.
2006 Feb 3
Role of retinoic acid receptors alpha1 and gamma in the response of murine limbs to retinol in vitro.
2006 Jan
Renal pathology and retinol status in multiple myeloma patients.
2006 Jan
Expression of Connexin 43 in the hearts of rat embryos exposed to nitrofen and effects of vitamin A on it.
2006 Jan
Hypervitaminosis A-induced liver fibrosis: stellate cell activation and daily dose consumption.
2006 Mar
Retinol palmitate protects against myocardial ischemia/reperfusion injury via reducing oxidative stress and inhibiting apoptosis.
2019
Patents

Sample Use Guides

Weekly single oral dose 7000 micrograms
Route of Administration: Oral
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.
Name Type Language
RETINOL
HSDB   INCI   INN   WHO-DD  
INN   INCI  
Official Name English
NSC-122759
Code English
VITAMIN A ALCOHOL
Common Name English
RETINOL [WHO-DD]
Common Name English
(2E,4E,6E,8E)-3,7-DIMETHYL-9-(2,6,6-TRIMETHYLCYCLOHEX-1-EN-1-YL)NONA-2,4,6,8-TETRAEN-1-OL
Systematic Name English
ALL-TRANS-RETINOL
Common Name English
RETINOL [INN]
Common Name English
VITAMIN A [MI]
Common Name English
RETINOL [HSDB]
Common Name English
RETINOL [INCI]
Common Name English
Classification Tree Code System Code
WHO-VATC QR01AX02
Created by admin on Sat Jun 26 13:20:32 UTC 2021 , Edited by admin on Sat Jun 26 13:20:32 UTC 2021
LOINC 20947-8
Created by admin on Sat Jun 26 13:20:32 UTC 2021 , Edited by admin on Sat Jun 26 13:20:32 UTC 2021
LOINC 14905-4
Created by admin on Sat Jun 26 13:20:32 UTC 2021 , Edited by admin on Sat Jun 26 13:20:32 UTC 2021
WHO-VATC QS01XA02
Created by admin on Sat Jun 26 13:20:32 UTC 2021 , Edited by admin on Sat Jun 26 13:20:32 UTC 2021
NCI_THESAURUS C68299
Created by admin on Sat Jun 26 13:20:32 UTC 2021 , Edited by admin on Sat Jun 26 13:20:32 UTC 2021
NCI_THESAURUS C938
Created by admin on Sat Jun 26 13:20:32 UTC 2021 , Edited by admin on Sat Jun 26 13:20:32 UTC 2021
WHO-VATC QD10AD02
Created by admin on Sat Jun 26 13:20:32 UTC 2021 , Edited by admin on Sat Jun 26 13:20:32 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 27
Created by admin on Sat Jun 26 13:20:32 UTC 2021 , Edited by admin on Sat Jun 26 13:20:32 UTC 2021
LOINC 20948-6
Created by admin on Sat Jun 26 13:20:32 UTC 2021 , Edited by admin on Sat Jun 26 13:20:32 UTC 2021
DSLD 3441 (Number of products:6)
Created by admin on Sat Jun 26 13:20:32 UTC 2021 , Edited by admin on Sat Jun 26 13:20:32 UTC 2021
WHO-ATC S01XA02
Created by admin on Sat Jun 26 13:20:32 UTC 2021 , Edited by admin on Sat Jun 26 13:20:32 UTC 2021
WHO-ATC A11CA01
Created by admin on Sat Jun 26 13:20:32 UTC 2021 , Edited by admin on Sat Jun 26 13:20:32 UTC 2021
EU-Orphan Drug EU/3/17/1895
Created by admin on Sat Jun 26 13:20:32 UTC 2021 , Edited by admin on Sat Jun 26 13:20:32 UTC 2021
LOINC 20946-0
Created by admin on Sat Jun 26 13:20:32 UTC 2021 , Edited by admin on Sat Jun 26 13:20:32 UTC 2021
LOINC 87673-0
Created by admin on Sat Jun 26 13:20:32 UTC 2021 , Edited by admin on Sat Jun 26 13:20:32 UTC 2021
LOINC 2923-1
Created by admin on Sat Jun 26 13:20:32 UTC 2021 , Edited by admin on Sat Jun 26 13:20:32 UTC 2021
WHO-ATC D10AD02
Created by admin on Sat Jun 26 13:20:32 UTC 2021 , Edited by admin on Sat Jun 26 13:20:32 UTC 2021
WHO-ATC R01AX02
Created by admin on Sat Jun 26 13:20:32 UTC 2021 , Edited by admin on Sat Jun 26 13:20:32 UTC 2021
WHO-VATC QA11CA01
Created by admin on Sat Jun 26 13:20:32 UTC 2021 , Edited by admin on Sat Jun 26 13:20:32 UTC 2021
LOINC 2922-3
Created by admin on Sat Jun 26 13:20:32 UTC 2021 , Edited by admin on Sat Jun 26 13:20:32 UTC 2021
Code System Code Type Description
DRUG CENTRAL
2831
Created by admin on Sat Jun 26 13:20:32 UTC 2021 , Edited by admin on Sat Jun 26 13:20:32 UTC 2021
PRIMARY
EPA CompTox
68-26-8
Created by admin on Sat Jun 26 13:20:32 UTC 2021 , Edited by admin on Sat Jun 26 13:20:32 UTC 2021
PRIMARY
CAS
68-26-8
Created by admin on Sat Jun 26 13:20:32 UTC 2021 , Edited by admin on Sat Jun 26 13:20:32 UTC 2021
PRIMARY
RXCUI
1367187
Created by admin on Sat Jun 26 13:20:32 UTC 2021 , Edited by admin on Sat Jun 26 13:20:32 UTC 2021
PRIMARY RxNorm
PUBCHEM
445354
Created by admin on Sat Jun 26 13:20:32 UTC 2021 , Edited by admin on Sat Jun 26 13:20:32 UTC 2021
PRIMARY
DRUG BANK
DB00162
Created by admin on Sat Jun 26 13:20:32 UTC 2021 , Edited by admin on Sat Jun 26 13:20:32 UTC 2021
PRIMARY
HSDB
815
Created by admin on Sat Jun 26 13:20:32 UTC 2021 , Edited by admin on Sat Jun 26 13:20:32 UTC 2021
PRIMARY
ChEMBL
CHEMBL986
Created by admin on Sat Jun 26 13:20:32 UTC 2021 , Edited by admin on Sat Jun 26 13:20:32 UTC 2021
PRIMARY
INN
2243
Created by admin on Sat Jun 26 13:20:32 UTC 2021 , Edited by admin on Sat Jun 26 13:20:32 UTC 2021
PRIMARY
WIKIPEDIA
RETINOL
Created by admin on Sat Jun 26 13:20:32 UTC 2021 , Edited by admin on Sat Jun 26 13:20:32 UTC 2021
PRIMARY
FDA UNII
G2SH0XKK91
Created by admin on Sat Jun 26 13:20:32 UTC 2021 , Edited by admin on Sat Jun 26 13:20:32 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-683-7
Created by admin on Sat Jun 26 13:20:32 UTC 2021 , Edited by admin on Sat Jun 26 13:20:32 UTC 2021
PRIMARY
EVMPD
SUB16102MIG
Created by admin on Sat Jun 26 13:20:32 UTC 2021 , Edited by admin on Sat Jun 26 13:20:32 UTC 2021
PRIMARY
NCI_THESAURUS
C68302
Created by admin on Sat Jun 26 13:20:32 UTC 2021 , Edited by admin on Sat Jun 26 13:20:32 UTC 2021
PRIMARY
MERCK INDEX
M11481
Created by admin on Sat Jun 26 13:20:32 UTC 2021 , Edited by admin on Sat Jun 26 13:20:32 UTC 2021
PRIMARY Merck Index