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

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
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
Fruit and fertility in San Juan de la Manguana.	1995	12290005
Hepatic hyper-vitaminosis A: importance of retinyl ester level determination.	2000 Mar	10750659
Effects of beta-carotene and vitamin A on oval cell proliferation and connexin 43 expression during hepatic differentiation in the rat(1).	2001 Dec	12031251
Use of vitamin supplements and cataract: the Blue Mountains Eye Study.	2001 Jul	11438049
Characterization of a novel airway epithelial cell-specific short chain alcohol dehydrogenase/reductase gene whose expression is up-regulated by retinoids and is involved in the metabolism of retinol.	2001 Jun 29	11304534
Influence of vitamin A status on the regulation of uridine (5'-)diphosphate-glucuronosyltransferase (UGT) 1A1 and UGT1A6 expression by L-triiodothyronine.	2001 Mar	11299074
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.	2001 Nov	11792017
Simultaneous analysis of retinol, beta-carotene and tocopherol levels in serum of Vietnamese populations with different incomes.	2002	12074187
The anemia of vitamin A deficiency: epidemiology and pathogenesis.	2002 Apr	11965502
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
Hypercalcaemia from non-prescription vitamin A.	2004 Nov	15496578
Age differences in vitamin A intake among Canadian Inuit.	2004 Nov-Dec	15622799
Effects of 2,3,7,8-tetrachlorodibenzo-p-dioxin on vitamin A metabolism in mice.	2005	16292751
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
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 status in mice affects the histone code of the phosphoenolpyruvate carboxykinase gene in liver.	2005 Dec	16317119
Vitamin a deficiency and anaemia in young children living in a malaria endemic district of western Kenya.	2005 Jun	16175781
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
Inhibitory effects of vitamin A on TCDD-induced cytochrome P-450 1A1 enzyme activity and expression.	2005 May	15728703
Development of a versatile reporter assay for studies of retinol uptake and metabolism in vivo.	2005 Nov 1	16150442
Vitamin A regulation of BMP4 expression in the male germ line.	2005 Oct 1	16120438
Retinol induces permeability transition and cytochrome c release from rat liver mitochondria.	2005 Oct 30	16202537
Expression of keratinocyte transglutaminase in cornea of vitamin A-deficient rats.	2005 Sep	16146918
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
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
Nonclassical action of retinoic acid on the activation of the cAMP response element-binding protein in normal human bronchial epithelial cells.	2006 Feb	16280361
Retinoic acid regulates sex-specific timing of meiotic initiation in mice.	2006 Feb 21	16461896
RPE65 is an iron(II)-dependent isomerohydrolase in the retinoid visual cycle.	2006 Feb 3	16319067
Renal pathology and retinol status in multiple myeloma patients.	2006 Jan	16374440
Expression of Connexin 43 in the hearts of rat embryos exposed to nitrofen and effects of vitamin A on it.	2006 Jan	16292552

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

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)