VITAMIN A ACETATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H32O2
Molecular Weight	328.4883
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	4
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(=O)OC\C=C(C)\C=C\C=C(C)\C=C\C1=C(C)CCCC1(C)C

InChI

InChIKey=QGNJRVVDBSJHIZ-QHLGVNSISA-N

InChI=1S/C22H32O2/c1-17(9-7-10-18(2)14-16-24-20(4)23)12-13-21-19(3)11-8-15-22(21,5)6/h7,9-10,12-14H,8,11,15-16H2,1-6H3/b10-7+,13-12+,17-9+,18-14+

HIDE SMILES / InChI

Molecular Formula	C22H32O2
Molecular Weight	328.4883
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 1430
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 656	Unknown Approved Use Unknown
Maternal morbidity 4 Sources: https://clinicaltrials.gov/ct2/show/NCT00211341	Preventing	Phase III 656	Unknown Approved Use Unknown
Maternal mortality 4 Sources: https://clinicaltrials.gov/ct2/show/NCT00211341	Preventing	Phase III 656	Unknown Approved Use Unknown
Vitamin A deficiency 4 Sources: https://www.drugs.com/monograph/vitamin-a.html	Primary	Approved 8429	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 8429	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 1132	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
Low serum retinol levels are associated with hepatocellular carcinoma in patients with chronic liver disease.	2000 Oct	11012474
[Hypercalcemia due to chronic vitamin A use by an elderly patient with renal insufficiency].	2001 Jan 13	11225264
Influence of vitamin A status on the regulation of uridine (5'-)diphosphate-glucuronosyltransferase (UGT) 1A1 and UGT1A6 expression by L-triiodothyronine.	2001 Mar	11299074
The anemia of vitamin A deficiency: epidemiology and pathogenesis.	2002 Apr	11965502
Retinoids regulate the repairing process of the podocytes in puromycin aminonucleoside-induced nephrotic rats.	2003 Apr	12660332
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
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	15203375
Carotenoids and their metabolites are naturally occurring activators of gene expression via the pregnane X receptor.	2004 Dec	15309450
Ocular side effects from herbal medicines and nutritional supplements.	2004 Oct	15488795
Protein and m-RNA expression of farnesyl-transferases, RhoA and RhoB in rat liver hepatocytes: action of perillyl alcohol and vitamin A in vivo.	2005	15959631
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
beta-cryptoxanthin stimulates cell differentiation and mineralization in osteoblastic MC3T3-E1 cells.	2005 Aug 15	15962303
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
Serum and CSF vitamin A concentrations in idiopathic intracranial hypertension.	2005 Jun 14	15955940
Extra-hepatic vitamin A concentrations in captive Rhesus (Macaca mulatta) and Marmoset (Callithrix jacchus) monkeys fed excess vitamin A.	2005 Mar	15929633
Vitamin A supplementation for extremely low birth weight infants: outcome at 18 to 22 months.	2005 Mar	15713907
Development of a versatile reporter assay for studies of retinol uptake and metabolism in vivo.	2005 Nov 1	16150442
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
Mutation of key residues of RPE65 abolishes its enzymatic role as isomerohydrolase in the visual cycle.	2005 Sep 20	16150724
Transmembrane protein GDE2 induces motor neuron differentiation in vivo.	2005 Sep 30	16195461
Effects of nitrofen and vitamins A, C and E on maturation of cultured human H441 pneumocytes.	2006	16490937
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 `Fri Dec 15 15:06:55 GMT 2023` Edited by `admin` on `Fri Dec 15 15:06:55 GMT 2023`
Record UNII	3LE3D9D6OY
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

VITAMIN A ACETATE

Common Name

English

RO-1-5275

Code

English

VITAMIN A (AS ACETATE & BETA CAROTENE) [VANDF]

Common Name

English

NSC-122760

Code

English

VITAMIN A ACETATE [VANDF]

Common Name

English

RETINYL ACETATE [INCI]

Common Name

English

ORISTAR RA

Brand Name

English

VITAMIN A ACETATE [MI]

Common Name

English

RETINYL ACETATE [USP-RS]

Common Name

English

NSC-122045

Code

English

RETINYL ACETATE

Official Name

English

ALL-(E)-RETINOL ACETATE [WHO-IP]

Common Name

English

VITAMIN A (AS ACETATE) [VANDF]

Common Name

English

Retinol acetate [WHO-DD]

Common Name

English

VITAMIN A ACETATE 1.5 M.I.U./G

Brand Name

English

RETINOL ACETATE [JAN]

Common Name

English

RETINOL ACETATE

Common Name

English

Classification Tree Code System Code

DSLD

3238 (Number of products:173)