VITAMIN A PALMITATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C36H60O2
Molecular Weight	524.8604
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	4
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=VYGQUTWHTHXGQB-FFHKNEKCSA-N

InChI=1S/C36H60O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-25-35(37)38-30-28-32(3)23-20-22-31(2)26-27-34-33(4)24-21-29-36(34,5)6/h20,22-23,26-28H,7-19,21,24-25,29-30H2,1-6H3/b23-20+,27-26+,31-22+,32-28+

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
[Review of acute hydrocephalus caused by administration of vitamin A in massive doses in nursing infants; based on 100 cases].	1957 Feb	13410607
Effect of avitaminosis A and hypervitaminosis A on urinary bladder carcinogenicity of N-(4-(5-Nitro-2-furyl)-2-thiazolyl)formamide.	1976 Jul	1277139
Bilateral transverse sinus obstruction in benign intracranial hypertension due to hypervitaminosis A.	1978 Aug	151668
McCollum Award Lecture, 1992: vitamin A absorption, transport, cellular uptake, and storage.	1992 Oct	1414975
Hepatic hyper-vitaminosis A: importance of retinyl ester level determination.	2000 Mar	10750659
Low serum retinol levels are associated with hepatocellular carcinoma in patients with chronic liver disease.	2000 Oct	11012474
Effects of excess vitamin A on development of cranial neural crest-derived structures: a neonatal and embryologic study.	2000 Oct	10992263
[Hypercalcemia due to chronic vitamin A use by an elderly patient with renal insufficiency].	2001 Jan 13	11225264
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
Restoring effects of vitamin A on surfactant synthesis in nitrofen-induced congenital diaphragmatic hernia in rats.	2001 Sep 15	11588001
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
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
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
Modulation of resistin expression by retinoic acid and vitamin A status.	2004 Apr	15047602
Vitamin A regulates proliferation and apoptosis of human T- and B-cells.	2004 Dec	15506942
A palmitoylation switch mechanism in the regulation of the visual cycle.	2004 Jun 11	15186777
Age differences in vitamin A intake among Canadian Inuit.	2004 Nov-Dec	15622799
Differential effects of vitamin A on fetal lung growth and diaphragmatic formation in nitrofen-induced rat model.	2005	15707848
Brain tissue fragments in the amniotic fluid of rats with neural tube defect.	2005 Apr	16028844
beta-cryptoxanthin stimulates cell differentiation and mineralization in osteoblastic MC3T3-E1 cells.	2005 Aug 15	15962303
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
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
Megalin-mediated reuptake of retinol in the kidneys of mice is essential for vitamin A homeostasis.	2005 Nov	16251603
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
Development of a versatile reporter assay for studies of retinol uptake and metabolism in vivo.	2005 Nov 1	16150442
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
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
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
Comparative ligand-binding analysis of ten human lipocalins.	2006 Feb	16461020
Nonclassical action of retinoic acid on the activation of the cAMP response element-binding protein in normal human bronchial epithelial cells.	2006 Feb	16280361
Expression of Connexin 43 in the hearts of rat embryos exposed to nitrofen and effects of vitamin A on it.	2006 Jan	16292552
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

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 PALMITATE

Common Name

English

RETINOL, HEXADECANOATE

Common Name

English

RETINOL PALMITATE [JAN]

Common Name

English

NSC-758478

Code

English

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

Common Name

English

RETINOL PALMITATE

Common Name

English

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

Common Name

English

RETINOL, PALMITATE, ALL-TRANS

Common Name

English

RETINYL PALMITATE [VANDF]

Common Name

English

VITAMIN A PALMITATE [MI]

Common Name

English

VITAMIN A PALMITATE [ORANGE BOOK]

Common Name

English

RETINYL PALMITATE

Official Name

English

RETINYL PALMITATE [USP-RS]

Common Name

English

VITAMIN A PALMITATE [VANDF]

Common Name

English

VITAMIN A PALMITATE (SOLUBILIZED) [VANDF]

Common Name

English

Retinol palmitate [WHO-DD]

Common Name

English

RETINYL PALMITATE [INCI]

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

525116