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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

Molecular Formula C20H30O
Molecular Weight 286.4523
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 4
Optical Activity NONE

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
[Review of acute hydrocephalus caused by administration of vitamin A in massive doses in nursing infants; based on 100 cases].
1957 Feb
Vitamin A induced benign intracranial hypertension.
1976 Feb
Effect of avitaminosis A and hypervitaminosis A on urinary bladder carcinogenicity of N-(4-(5-Nitro-2-furyl)-2-thiazolyl)formamide.
1976 Jul
Vitamin A abuse: development of cirrhosis despite cessation of vitamin A. A six-year clinical and histopathologic follow-up.
1992 Dec
McCollum Award Lecture, 1992: vitamin A absorption, transport, cellular uptake, and storage.
1992 Oct
Zinc transporters in the rat mammary gland respond to marginal zinc and vitamin A intakes during lactation.
2002 Nov
[Basic aspects and measurement of the antioxidant vitamins A and E].
2002 Sep
Retinoids regulate the repairing process of the podocytes in puromycin aminonucleoside-induced nephrotic rats.
2003 Apr
Retinoid receptors and vitamin A deficiency: differential patterns of transcription during early avian development and the rapid induction of RARs by retinoic acid.
2003 Aug 15
PPARbeta regulates vitamin A metabolism-related gene expression in hepatic stellate cells undergoing activation.
2003 Feb
Impact of 'Mad Cow Disease' publicity on trends in meat and total vitamin A consumption in Geneva between 1993 and 2000.
2003 Jan
Redistribution of vitamin A after iron supplementation in Indonesian infants.
2003 Mar
Vitamin A deficiency leads to increased cell proliferation in olfactory epithelium of mature rats.
2003 Mar
Pharmacology of all-trans-retinoic acid in children with acute promyelocytic leukemia.
2003 May
Vitamin A deficiency and relational memory deficit in adult mice: relationships with changes in brain retinoid signalling.
2003 Oct 17
Retinol-induced mdr1 and mdr3 modulation in cultured rat Sertoli cells is attenuated by free radical scavengers.
2004
Modulation of resistin expression by retinoic acid and vitamin A status.
2004 Apr
Metabolism of retinoids and arachidonic acid by human and mouse cytochrome P450 1b1.
2004 Aug
Vitamin A regulates proliferation and apoptosis of human T- and B-cells.
2004 Dec
Inverse gene expression patterns for macrophage activating hepatotoxicants and peroxisome proliferators in rat liver.
2004 Jun 1
Safety and efficacy of dose-intensive oral vitamin A in subjects with sun-damaged skin.
2004 Mar 15
Age differences in vitamin A intake among Canadian Inuit.
2004 Nov-Dec
Ocular side effects from herbal medicines and nutritional supplements.
2004 Oct
Differential effects of vitamin A on fetal lung growth and diaphragmatic formation in nitrofen-induced rat model.
2005
Alcohol, vitamin A, and cancer.
2005 Apr
Retinoid receptor mRNA expression profiles in human bladder cancer specimens.
2005 Apr
Effects of prenatal vitamins A, E, and C on the hypoplastic hearts of fetal rats with diaphragmatic hernia.
2005 Aug
beta-cryptoxanthin stimulates cell differentiation and mineralization in osteoblastic MC3T3-E1 cells.
2005 Aug 15
Vitamin A deficiency induces prooxidant environment and inflammation in rat aorta.
2005 Jun
Vitamin A supplementation for extremely low birth weight infants: outcome at 18 to 22 months.
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
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
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
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
Role of retinoic acid receptors alpha1 and gamma in the response of murine limbs to retinol in vitro.
2006 Jan
Vitamin A inhibits pancreatic stellate cell activation: implications for treatment of pancreatic fibrosis.
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.
Substance Class Chemical
Created
by admin
on Sat Jun 26 13:20:32 UTC 2021
Edited
by admin
on Sat Jun 26 13:20:32 UTC 2021
Record UNII
G2SH0XKK91
Record Status Validated (UNII)
Record Version
  • Download
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
Related Record Type Details
ACTIVE MOIETY