RETINOL

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

Structure Search

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+

HIDE SMILES / InChI

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 1447
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 661
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 661
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 661

Conditions

Condition	Modality	Highest Phase	Product
Vitamin A deficiency 4 Sources: https://clinicaltrials.gov/ct2/show/NCT00211341	Preventing	Phase III 665	Unknown Approved Use Unknown
Maternal morbidity 4 Sources: https://clinicaltrials.gov/ct2/show/NCT00211341	Preventing	Phase III 665	Unknown Approved Use Unknown
Maternal mortality 4 Sources: https://clinicaltrials.gov/ct2/show/NCT00211341	Preventing	Phase III 665	Unknown Approved Use Unknown
Vitamin A deficiency 4 Sources: https://www.drugs.com/monograph/vitamin-a.html	Primary	Approved 8583	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 1949
Measles 4 Sources: https://www.drugs.com/monograph/vitamin-a.html	Palliative	Approved 8583	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 1949
Skin photodamage 4 Sources: https://clinicaltrials.gov/ct2/show/NCT01283464	Primary	Phase II 1147	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
Vitamin A abuse: development of cirrhosis despite cessation of vitamin A. A six-year clinical and histopathologic follow-up.	1992 Dec	1470008
Use of vitamin supplements and cataract: the Blue Mountains Eye Study.	2001 Jul	11438049
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.	2001 Nov	11792017
The anemia of vitamin A deficiency: epidemiology and pathogenesis.	2002 Apr	11965502
DNA microarray technology reveals similar gene expression patterns in rats with vitamin a deficiency and chemically induced colitis.	2002 Aug	12163651
[Treatment of acne with consequences -- pseudotumor cerebri due to hypervitaminosis A].	2002 Jan 9	11824142
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
PPARbeta regulates vitamin A metabolism-related gene expression in hepatic stellate cells undergoing activation.	2003 Feb	12576510
Vitamin A deficiency leads to increased cell proliferation in olfactory epithelium of mature rats.	2003 Mar	12555267
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
What is the safe dose of vitamin A in children with measles?	2005 Apr	15818308
Retinoid receptor mRNA expression profiles in human bladder cancer specimens.	2005 Apr	15754000
Fortification of maize meal improved the nutritional status of 1-3-year-old African children.	2005 Aug	16153327
Effects of prenatal vitamins A, E, and C on the hypoplastic hearts of fetal rats with diaphragmatic hernia.	2005 Aug	16080930
Phospho-STAT5 accumulation in nuclear fractions from vitamin A-deficient rat liver.	2005 Jul 4	15963505
Effect of vitamin A content in cafeteria diet on the expression of nuclear receptors in rat subcutaneous adipose tissue.	2005 Jun	16180333
Vitamin a deficiency and anaemia in young children living in a malaria endemic district of western Kenya.	2005 Jun	16175781
Vitamin A deficiency induces prooxidant environment and inflammation in rat aorta.	2005 Jun	16036340
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
Vitamin A regulation of BMP4 expression in the male germ line.	2005 Oct 1	16120438
Mutation of key residues of RPE65 abolishes its enzymatic role as isomerohydrolase in the visual cycle.	2005 Sep 20	16150724
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
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
Vitamin A inhibits pancreatic stellate cell activation: implications for treatment of pancreatic fibrosis.	2006 Jan	16043492

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.

Name

Type

Language

NSC-122759

Preferred Name

English

RETINOL

Official Name

English

Retinol [WHO-DD]

Common Name

English

VITAMIN A ALCOHOL

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

Classification Tree Code System Code

WHO-VATC

QR01AX02