RETINOL

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 Search

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
Sources: http://www.drugbank.ca/drugs/DB00162https://www.drugs.com/monograph/vitamin-a.html
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Superoxide dismutase 4 Target ID: CHEMBL2354 Sources: https://www.ncbi.nlm.nih.gov/pubmed/30972178	Activator 1343
Lecithin retinol acyltransferase 4 Target ID: O95237 Gene ID: 9227.0 Gene Symbol: LRAT Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/19920137 \| https://www.ncbi.nlm.nih.gov/pubmed/10819989	Substrate 609
Retinol dehydrogenase 12 4 Target ID: Q96NR8 Gene ID: 145226.0 Gene Symbol: RDH12 Target Organism: Homo sapiens (Human) Sources: https://www.drugbank.ca/drugs/DB00162	Substrate 609
11-cis retinol dehydrogenase 5 Target ID: Q92781 Gene ID: 5959.0 Gene Symbol: RDH5 Target Organism: Homo sapiens (Human) Sources: https://www.drugbank.ca/drugs/DB00162	Substrate 609

Conditions

Condition	Modality	Highest Phase	Product
Vitamin A deficiency 4 Sources: https://clinicaltrials.gov/ct2/show/NCT00211341	Preventing	Phase III 643	Unknown Approved Use Unknown
Maternal morbidity 4 Sources: https://clinicaltrials.gov/ct2/show/NCT00211341	Preventing	Phase III 643	Unknown Approved Use Unknown
Maternal mortality 4 Sources: https://clinicaltrials.gov/ct2/show/NCT00211341	Preventing	Phase III 643	Unknown Approved Use Unknown
Vitamin A deficiency 4 Sources: https://www.drugs.com/monograph/vitamin-a.html	Primary	Approved 8043	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
Measles 4 Sources: https://www.drugs.com/monograph/vitamin-a.html	Palliative	Approved 8043	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
Skin photodamage 4 Sources: https://clinicaltrials.gov/ct2/show/NCT01283464	Primary	Phase II 1101	Unknown Approved Use Unknown
Skin aging 5 Sources: https://clinicaltrials.gov/ct2/show/NCT02906566	Primary	Phase IV 63	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
[Review of acute hydrocephalus caused by administration of vitamin A in massive doses in nursing infants; based on 100 cases].	1957 Feb	13410607
Vitamin A induced benign intracranial hypertension.	1976 Feb	130200
Effect of avitaminosis A and hypervitaminosis A on urinary bladder carcinogenicity of N-(4-(5-Nitro-2-furyl)-2-thiazolyl)formamide.	1976 Jul	1277139
Vitamin A abuse: development of cirrhosis despite cessation of vitamin A. A six-year clinical and histopathologic follow-up.	1992 Dec	1470008
McCollum Award Lecture, 1992: vitamin A absorption, transport, cellular uptake, and storage.	1992 Oct	1414975
Zinc transporters in the rat mammary gland respond to marginal zinc and vitamin A intakes during lactation.	2002 Nov	12421840
[Basic aspects and measurement of the antioxidant vitamins A and E].	2002 Sep	12229281
Retinoids regulate the repairing process of the podocytes in puromycin aminonucleoside-induced nephrotic rats.	2003 Apr	12660332
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	12921748
PPARbeta regulates vitamin A metabolism-related gene expression in hepatic stellate cells undergoing activation.	2003 Feb	12576510
Impact of 'Mad Cow Disease' publicity on trends in meat and total vitamin A consumption in Geneva between 1993 and 2000.	2003 Jan	12548314
Redistribution of vitamin A after iron supplementation in Indonesian infants.	2003 Mar	12600856
Vitamin A deficiency leads to increased cell proliferation in olfactory epithelium of mature rats.	2003 Mar	12555267
Pharmacology of all-trans-retinoic acid in children with acute promyelocytic leukemia.	2003 May	12652617
Vitamin A deficiency and relational memory deficit in adult mice: relationships with changes in brain retinoid signalling.	2003 Oct 17	14529804
Retinol-induced mdr1 and mdr3 modulation in cultured rat Sertoli cells is attenuated by free radical scavengers.	2004	15327746
Modulation of resistin expression by retinoic acid and vitamin A status.	2004 Apr	15047602
Metabolism of retinoids and arachidonic acid by human and mouse cytochrome P450 1b1.	2004 Aug	15258110
Vitamin A regulates proliferation and apoptosis of human T- and B-cells.	2004 Dec	15506942
Inverse gene expression patterns for macrophage activating hepatotoxicants and peroxisome proliferators in rat liver.	2004 Jun 1	15135310
Safety and efficacy of dose-intensive oral vitamin A in subjects with sun-damaged skin.	2004 Mar 15	15041701
Age differences in vitamin A intake among Canadian Inuit.	2004 Nov-Dec	15622799
Ocular side effects from herbal medicines and nutritional supplements.	2004 Oct	15488795
Differential effects of vitamin A on fetal lung growth and diaphragmatic formation in nitrofen-induced rat model.	2005	15707848
Alcohol, vitamin A, and cancer.	2005 Apr	16054987
Retinoid receptor mRNA expression profiles in human bladder cancer specimens.	2005 Apr	15754000
Effects of prenatal vitamins A, E, and C on the hypoplastic hearts of fetal rats with diaphragmatic hernia.	2005 Aug	16080930
beta-cryptoxanthin stimulates cell differentiation and mineralization in osteoblastic MC3T3-E1 cells.	2005 Aug 15	15962303
Vitamin A deficiency induces prooxidant environment and inflammation in rat aorta.	2005 Jun	16036340
Vitamin A supplementation for extremely low birth weight infants: outcome at 18 to 22 months.	2005 Mar	15713907
Inhibitory effects of vitamin A on TCDD-induced cytochrome P-450 1A1 enzyme activity and expression.	2005 May	15728703
Megalin-mediated reuptake of retinol in the kidneys of mice is essential for vitamin A homeostasis.	2005 Nov	16251603
Expression of nuclear receptor and target genes in liver and intestine of neonatal calves fed colostrum and vitamin A.	2005 Nov	16230703
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	16267017
Retinoid metabolism during development of liver cirrhosis.	2005 Nov 15	16248980
Vitamin A supplementation induces adipose tissue loss through apoptosis in lean but not in obese rats of the WNIN/Ob strain.	2005 Oct	16216918
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	16194896
Comparison of indices of vitamin A status in children with chronic liver disease.	2005 Oct	16175620
Acyl coenzyme A dependent retinol esterification by acyl coenzyme A: diacylglycerol acyltransferase 1.	2005 Oct 15	16214399
Retinol induces permeability transition and cytochrome c release from rat liver mitochondria.	2005 Oct 30	16202537
Transmembrane protein GDE2 induces motor neuron differentiation in vivo.	2005 Sep 30	16195461
Hypervitaminosis A resulting in DNA aberration in fetal transgenic mice (Muta Mouse).	2005 Sep 5	16054864
Effects of nitrofen and vitamins A, C and E on maturation of cultured human H441 pneumocytes.	2006	16490937
The effect of vitamin A on CCl4-induced hepatic injuries in rats: a histochemical, immunohistochemical and ultrastructural study.	2006	16256175
Vitamin A improves Pax3 expression that is decreased in the heart of rats with experimental diaphragmatic hernia.	2006 Feb	16481245
The acute and chronic toxic effects of vitamin A.	2006 Feb	16469975
Role of retinoic acid receptors alpha1 and gamma in the response of murine limbs to retinol in vitro.	2006 Jan	16397886
Vitamin A inhibits pancreatic stellate cell activation: implications for treatment of pancreatic fibrosis.	2006 Jan	16043492
Hypervitaminosis A-induced liver fibrosis: stellate cell activation and daily dose consumption.	2006 Mar	16448456
Retinol palmitate protects against myocardial ischemia/reperfusion injury via reducing oxidative stress and inhibiting apoptosis.	2019	30972178

Patents

Sample Use Guides

In Vivo Use Guide

Weekly single oral dose 7000 micrograms

Route of Administration: Oral

In Vitro Use Guide

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

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