Identification

Name
Vitamin A
Accession Number
DB00162
Description

Retinol and derivatives of retinol that play an essential role in metabolic functioning of the retina, the growth of and differentiation of epithelial tissue, the growth of bone, reproduction, and the immune response. Dietary vitamin A is derived from a variety of carotenoids found in plants. It is enriched in the liver, egg yolks, and the fat component of dairy products.

Type
Small Molecule
Groups
Approved, Nutraceutical, Vet approved
Structure
Thumb
Weight
Average: 286.4516
Monoisotopic: 286.229665582
Chemical Formula
C20H30O
Synonyms
  • (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol
  • all-trans-retinol
  • all-trans-retinyl alcohol
  • all-trans-vitamin A alcohol
  • Retinol
  • Retinolum
  • Vitamin A1
External IDs
  • 11103-57-4

Pharmacology

Indication

For the treatment of vitamin A deficiency.

Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

Vitamin A is effective for the treatment of Vitamin A deficiency. Vitamin A refers to a group of fat-soluble substances that are structurally related to and possess the biological activity of the parent substance of the group called all-trans retinol or retinol. Vitamin A plays vital roles in vision, epithelial differentiation, growth, reproduction, pattern formation during embryogenesis, bone development, hematopoiesis and brain development. It is also important for the maintenance of the proper functioning of the immune system.

Mechanism of action

Vision:Vitamin A (all-trans retinol) is converted in the retina to the 11-cis-isomer of retinaldehyde or 11-cis-retinal. 11-cis-retinal functions in the retina in the transduction of light into the neural signals necessary for vision. 11-cis-retinal, while attached to opsin in rhodopsin is isomerized to all-trans-retinal by light. This is the event that triggers the nerve impulse to the brain which allows for the perception of light. All-trans-retinal is then released from opsin and reduced to all-trans-retinol. All-trans-retinol is isomerized to 11-cis-retinol in the dark, and then oxidized to 11-cis-retinal. 11-cis-retinal recombines with opsin to re-form rhodopsin. Night blindness or defective vision at low illumination results from a failure to re-synthesize 11-cis retinal rapidly.
Epithelial differentiation: The role of Vitamin A in epithelial differentiation, as well as in other physiological processes, involves the binding of Vitamin A to two families of nuclear retinoid receptors (retinoic acid receptors, RARs; and retinoid-X receptors, RXRs). These receptors function as ligand-activated transcription factors that modulate gene transcription. When there is not enough Vitamin A to bind these receptors, natural cell differentiation and growth are interrupted.

TargetActionsOrganism
URetinol dehydrogenase 12
substrate
Humans
UShort-chain dehydrogenase/reductase 3
substrate
Humans
UAldehyde dehydrogenase family 1 member A3
substrate
Humans
UAll-trans-retinol 13,14-reductase
substrate
Humans
URetinol dehydrogenase 11
substrate
Humans
UDehydrogenase/reductase SDR family member 4
substrate
Humans
URetinol dehydrogenase 14
substrate
Humans
URetinol dehydrogenase 8
substrate
Humans
ULecithin retinol acyltransferase
substrate
Humans
U11-cis retinol dehydrogenase
substrate
Humans
URetinol dehydrogenase 13
substrate
Humans
URetinal dehydrogenase 2
substrate
Humans
URetinal dehydrogenase 1
substrate
Humans
UApolipoprotein D
ligand
Humans
UProstaglandin-H2 D-isomerase
ligand
Humans
Absorption

Readily absorbed from the normal gastrointestinal tract

Volume of distribution
Not Available
Protein binding

<5% of circulating vitamin A is bound to lipoproteins in blood in normal condition, but may be up to 65% when hepatic stores are saturated because of excessive intake. When released from liver, vitamin A is bound to retinol-binding protein (RBP). Most vitamin A circulates in the form of retinol bound to RBP.

Metabolism

Hepatic. Retinol is conjugated with glucuronic acid; the B-glucuronide undergoes enterohepatic circulation and oxidation to retinol and retinoic acid. Retinoic acid undergoes decarboxylation and conjugation with glucuronic acid.

Hover over products below to view reaction partners

Route of elimination
Not Available
Half-life

1.9 hours

Clearance
Not Available
Adverse Effects
Learn about our commercial Adverse Effects data.
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Toxicity

Acute toxicity to vitamin A can occur when adults or children ingest >100x or >20x the RDA, respectively, over a period of hours or a few days.2 The RDA for vitamin A differs depending on age and sex and can range from 300 - 900 μg retinol activity equivalents (RAE) per day.4 Symptoms of acute systemic toxicity generally include mucocutaneous involvement (e.g. xerosis, cheilitis, skin peeling) and may involve mental status changes.3 Children are typically more susceptible to acute vitamin A toxicity - daily intakes of as little as 1500 IU/kg have been observed to result in toxicity.2

Chronic vitamin A toxicity can develop following the long-term ingestion of high vitamin A doses. While there is a wide variation in the lowest toxic vitamin A dose, the ingestion of >25 000 IU daily for 6 years or 100,000 IU daily for 6 months is considered to be toxic.2 Chronic vitamin A toxicity can affect many organ systems and can lead to the development of osteoporosis and CNS effects (e.g. headaches).3

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Retinol MetabolismMetabolic
Vitamin A DeficiencyDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcitretinThe risk or severity of adverse effects can be increased when Vitamin A is combined with Acitretin.
AlitretinoinThe risk or severity of adverse effects can be increased when Vitamin A is combined with Alitretinoin.
BexaroteneThe risk or severity of adverse effects can be increased when Vitamin A is combined with Bexarotene.
Cyproterone acetateThe therapeutic efficacy of Cyproterone acetate can be decreased when used in combination with Vitamin A.
DemeclocyclineThe risk or severity of pseudotumor cerebri and elevated intracranial pressure can be increased when Vitamin A is combined with Demeclocycline.
DesogestrelThe therapeutic efficacy of Desogestrel can be decreased when used in combination with Vitamin A.
DienogestThe therapeutic efficacy of Dienogest can be decreased when used in combination with Vitamin A.
DiethylstilbestrolThe therapeutic efficacy of Diethylstilbestrol can be decreased when used in combination with Vitamin A.
DoxycyclineThe risk or severity of pseudotumor cerebri and elevated intracranial pressure can be increased when Vitamin A is combined with Doxycycline.
DrospirenoneThe therapeutic efficacy of Drospirenone can be decreased when used in combination with Vitamin A.
Additional Data Available
  • Extended Description
    Extended Description
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    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity
    Available for Purchase

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level
    Available for Purchase

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action
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    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
No interactions found.

Products

Purchasing individual compounds or compound libraries for your research?
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Product Ingredients
IngredientUNIICASInChI Key
Vitamin A acetate3LE3D9D6OY127-47-9QGNJRVVDBSJHIZ-QHLGVNSISA-N
Vitamin A palmitate1D1K0N0VVC79-81-2VYGQUTWHTHXGQB-FFHKNEKCSA-N
Active Moieties
NameKindUNIICASInChI Key
Beta caroteneunknown01YAE03M7J7235-40-7OENHQHLEOONYIE-JLTXGRSLSA-N
Product Images
International/Other Brands
Alphalin / Chocola A
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Aquasol AInjection, solution15 mg/1mLIntramuscularHospira, Inc.2014-07-182021-07-01US flag
Aquasol AInjection, solution15 mg/1mLIntramuscularCasper Pharma Llc2020-10-01Not applicableUS flag
Aquasol A Cap 25000unitCapsuleOralRhone Poulenc Rorer1992-12-311996-09-09Canada flag
Aquasol A Cap 50000unitCapsuleOralRhone Poulenc Rorer1992-12-311996-09-09Canada flag
Vitamin A Cap 25000iuCapsuleOralNovopharm Limited1967-12-312015-10-26Canada flag
Vitamin A Cap 25000iuCapsuleOralStanley Pharmaceuticals, A Division Of Vita Health Products Inc.1957-12-312002-07-31Canada flag
Vitamin A Cap 50000iuCapsuleOralStanley Pharmaceuticals, A Division Of Vita Health Products Inc.1957-12-312002-07-31Canada flag
Vitamin A Cap 50000iuCapsuleOralNovopharm Limited1967-12-312015-10-26Canada flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code
    Available for Purchase

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
400 Vitamin A 10000iuCapsuleOralHerbes Universelles Inc.1972-12-312009-07-15Canada flag
A Caps 10000 I.U.CapsuleOralTwin Laboratories Inc.1995-12-311999-11-10Canada flag
A Mulsion 10EmulsionOralSeroyal International Inc.1982-12-312008-10-09Canada flag
Arovit Vitamine A Tab 10000unitTabletOralLes Laboratoires Bio SantÉ Inc.1986-12-311996-09-10Canada flag
C-Mask PackPatch0.57 g/19gTopicalNeoBiotech Global Corporation2018-02-10Not applicableUS flag
Pro-sol A Liq 5000unit/minSolution / dropsOralProfessional Health Products1990-12-311998-08-13Canada flag
SkineezCloth0.01 1/1TopicalCAUSE FOR CHANGE LLC2019-07-22Not applicableUS flag
Super A 40CapsuleOralFrega Inc.1979-12-312008-07-09Canada flag
Vitamin ACapsuleOralSeroyal International Inc.1996-12-312009-07-06Canada flag
Vitamin A 10000I.U. CapCapsuleOralNutricorp International1993-12-312009-08-05Canada flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code
    Available for Purchase

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
24 Multivitamins + MineralsVitamin A palmitate (5000 unit) + Ascorbic acid (150 mg) + Beta carotene (10000 unit) + Biotin (25 mcg) + Calcium (130 mg) + Cholecalciferol (400 unit) + Choline bitartrate (25 mg) + Chromium (20 mcg) + Copper (1 mg) + Cyanocobalamin (25 mcg) + Ferrous fumarate (15 mg) + Folic acid (.8 mg) + Inositol (25 mg) + Magnesium (65 mg) + Manganese (2 mg) + Molybdenum (20 mcg) + Niacin (25 mg) + Calcium pantothenate (25 mg) + Potassium (15 mg) + Potassium Iodide (.1 mg) + Pyridoxine hydrochloride (25 mg) + Racemethionine (25 mg) + Riboflavin (25 mg) + Selenium (20 mcg) + Thiamine hydrochloride (25 mg) + Vanadium (20 mcg) + Vitamin E (50 unit) + Zinc (10 mg)TabletOralStanley Pharmaceuticals, A Division Of Vita Health Products Inc.1997-04-302002-07-31Canada flag
50 PlusVitamin A palmitate (10000 unit) + Ascorbic acid (200 mg) + Biotin (20 mcg) + Choline bitartrate (20 mg) + Cyanocobalamin (20 mcg) + Folic acid (.2 mg) + Inositol (20 mg) + Niacin (20 mg) + Calcium pantothenate (20 mg) + Pyridoxine hydrochloride (20 mg) + Racemethionine (20 mg) + Riboflavin (20 mg) + Thiamine hydrochloride (20 mg) + Vitamin D (400 unit) + Vitamin E (20 unit)TabletOralQuest Vitamins A Div Of Purity Life Health Products1998-08-042001-07-06Canada flag
50 Plus Multiple Vitamins & MineralsVitamin A palmitate (6000 unit) + Ascorbic acid (90 mg) + Biotin (45 mcg) + Calcium (200 mg) + Cholecalciferol (400 unit) + Chromium (10 mcg) + Copper (2 mg) + Cyanocobalamin (25 mcg) + Folic acid (0.4 mg) + Magnesium (100 mg) + Manganese (5 mg) + Molybdenum (25 mcg) + Nicotinamide (40 mg) + Pantothenic acid (10 mg) + Potassium Iodide (0.15 mg) + Pyridoxine hydrochloride (3 mg) + Riboflavin (3.2 mg) + Selenium (25 mcg) + Thiamine mononitrate (2.25 mg) + Vanadium (10 mcg) + Zinc (15 mg)TabletOralGfr Pharma Ltd.2002-10-202004-06-15Canada flag
A & C PowderVitamin A (930 unit) + Ascorbic acid (7 mg)Powder, for solutionOralStandard Process Inc.Not applicableNot applicableCanada flag
A + D OintmentVitamin A palmitate (2000 unit) + Cholecalciferol (500 unit)OintmentTopicalNational Care Products Ltd.1993-12-312002-10-10Canada flag
A + ZincVitamin A (10000 unit) + Zinc (15 mg)TabletOralNutrilite, A Division Of Access Business Group, Llc2000-09-012007-07-06Canada flag
A and D OintmentVitamin A (1500 unit) + Vitamin D (213 unit)OintmentTopicalSchering Plough1951-12-312002-07-12Canada flag
A D Calcium TabVitamin A (5000 unit) + Calcium (126 mg) + Vitamin D (400 unit)TabletOralStar Pharmaceuticals, Llc1979-12-311999-07-21Canada flag
A-D Calcium CapVitamin A (2500 unit) + Calcium (170 mg) + Vitamin D (133 unit)CapsuleOralVitalab1990-12-312005-07-12Canada flag
Aces TabVitamin A (5000 unit) + Calcium ascorbate (350 mg) + Cholecalciferol (200 unit) + Chromium (25 mcg) + Selenium (100 mcg) + Vitamin E (200 unit) + Zinc (25 mg)TabletOralNu Life Nutrition Ltd.1987-12-312005-03-15Canada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
BacminVitamin A acetate (2000 [iU]/1) + Ascorbic acid (500 mg/1) + Biotin (150 ug/1) + Chromium Cr-51 chloride (0.1 mg/1) + Cupric oxide (3 mg/1) + Cyanocobalamin (50 ug/1) + Ferrous fumarate (27 mg/1) + Flavone (50 mg/1) + Folic acid (1 mg/1) + Magnesium oxide (50 mg/1) + Manganese gluconate (5 mg/1) + Nicotinamide (100 mg/1) + Calcium pantothenate (25 mg/1) + Pyridoxine hydrochloride (25 mg/1) + Riboflavin (20 mg/1) + Selenomethionine (50 ug/1) + Thiamine mononitrate (20 mg/1) + Zinc oxide (22.5 mg/1) + alpha-Tocopherol acetate (30 [iU]/1)Tablet, coatedOralMarnel Pharmaceuticals, Llc2000-04-01Not applicableUS flag
C-Mask PackVitamin A (0.57 g/19g)PatchTopicalNeoBiotech Global Corporation2018-02-10Not applicableUS flag
EscaviteVitamin A acetate (1000 [iU]/1) + Ascorbic acid (100 mg/1) + Biotin (45 ug/1) + Cholecalciferol (400 [iU]/1) + Copper (1 mg/1) + Cyanocobalamin (9 ug/1) + Folic acid (0.4 mg/1) + Iron (7.5 mg/1) + Magnesium (60 mg/1) + Nicotinamide (20 mg/1) + Calcium pantothenate (10 mg/1) + Pyridoxine hydrochloride (2 mg/1) + Riboflavin (1.7 mg/1) + Sodium fluoride (0.25 mg/1) + Thiamine mononitrate (1.5 mg/1) + Zinc (7.4 mg/1) + alpha-Tocopherol acetate (30 [iU]/1)Tablet, chewableOralGm Pharmaceuticals2012-02-01Not applicableUS flag
Escavite LqVitamin A palmitate (1500 [iU]/1mL) + Ascorbic acid (35 mg/1mL) + Cholecalciferol (400 [iU]/1mL) + Cyanocobalamin (0.9 ug/1mL) + D-alpha-Tocopherol acetate (7.5 [iU]/1mL) + Ferric pyrophosphate (5 mg/1mL) + Ferrous cysteine glycinate (1 mg/1mL) + Niacin (8 mg/1mL) + Pyridoxine hydrochloride (0.4 mg/1mL) + Riboflavin (0.6 mg/1mL) + Sodium fluoride (0.25 mg/1mL) + Thiamine hydrochloride (0.5 mg/1mL)LiquidOralGM Pharmaceuticals, INC2013-08-202018-10-03US flag
FlorivaVitamin A acetate (1000 [iU]/1) + Ascorbic acid (75 mg/1) + Beta carotene (1000 [iU]/1) + Biotin (40 ug/1) + Cholecalciferol (600 [iU]/1) + Cupric oxide (1 mg/1) + Cyanocobalamin (6 ug/1) + Folic acid (100 ug/1) + Levomefolate glucosamine (162 ug/1) + Nicotinamide (15 mg/1) + Pyridoxine (1.8 mg/1) + Riboflavin (1.5 mg/1) + Sodium fluoride (0.5 mg/1) + Thiamine chloride (1.3 mg/1) + Vitamin E (20 [iU]/1) + Zinc gluconate (5 mg/1)Tablet, chewableOralBonGeo Pharmaceuticals, Inc.2014-10-15Not applicableUS flag
FlorivaVitamin A acetate (1000 [iU]/1) + Ascorbic acid (75 mg/1) + Beta carotene (1000 [iU]/1) + Biotin (40 ug/1) + Cholecalciferol (600 [iU]/1) + Cupric oxide (1 mg/1) + Cyanocobalamin (6 ug/1) + Folic acid (100 ug/1) + Levomefolate glucosamine (162 ug/1) + Nicotinamide (15 mg/1) + Pyridoxine (1.8 mg/1) + Riboflavin (1.5 mg/1) + Sodium fluoride (1 mg/1) + Thiamine chloride (1.3 mg/1) + Vitamin E (20 [iU]/1) + Zinc gluconate (5 mg/1)Tablet, chewableOralBonGeo Pharmaceuticals, Inc.2014-10-15Not applicableUS flag
FlorivaVitamin A acetate (1000 [iU]/1) + Ascorbic acid (75 mg/1) + Beta carotene (1000 [iU]/1) + Biotin (40 ug/1) + Cholecalciferol (600 [iU]/1) + Cupric oxide (1 mg/1) + Cyanocobalamin (6 ug/1) + Folic acid (100 ug/1) + Levomefolate glucosamine (162 ug/1) + Nicotinamide (15 mg/1) + Pyridoxine (1.8 mg/1) + Riboflavin (1.5 mg/1) + Sodium fluoride (0.25 mg/1) + Thiamine chloride (1.3 mg/1) + Vitamin E (20 [iU]/1) + Zinc gluconate (5 mg/1)Tablet, chewableOralBonGeo Pharmaceuticals, Inc.2015-09-10Not applicableUS flag
Floriva PlusVitamin A acetate (1150 [iU]/1mL) + Ascorbic acid (32 mg/1mL) + Biotin (3 ug/1mL) + Cholecalciferol (400 [iU]/1mL) + Cyanocobalamin (2 ug/1mL) + Riboflavin 5'-phosphate sodium (0.6 mg/1mL) + Levomefolate glucosamine (29.7 ug/1mL) + Nicotinamide (2 mg/1mL) + Pantothenic acid (1 mg/1mL) + Pyridoxine hydrochloride (0.4 mg/1mL) + Sodium fluoride (0.25 mg/1mL) + Thiamine hydrochloride (0.5 mg/1mL) + Vitamin E (5 [iU]/1mL)Solution / dropsOralBonGeo Pharmaceuticals, Inc.2016-06-202020-01-21US flag
Inatal AdvanceVitamin A (2700 [iU]/1) + Ascorbic acid (120 mg/1) + Calcium carbonate (200 mg/1) + Cholecalciferol (400 [iU]/1) + Cupric oxide (2 mg/1) + Cyanocobalamin (12 ug/1) + Docusate sodium (50 mg/1) + Folic acid (1 mg/1) + Iron (90 mg/1) + Magnesium oxide (30 mg/1) + Nicotinamide (20 mg/1) + Pyridoxine hydrochloride (20 mg/1) + Riboflavin (3.4 mg/1) + Thiamine mononitrate (3 mg/1) + Zinc oxide (25 mg/1) + alpha-Tocopherol acetate (30 [iU]/1)Tablet, coatedOralNnodum Pharmaceuticals2005-06-10Not applicableUS flag
INATAL UltraVitamin A (2700 [iU]/1) + Ascorbic acid (120 mg/1) + Calcium citrate tetrahydrate (200 mg/1) + Cholecalciferol (400 [iU]/1) + Cupric oxide (2 mg/1) + Cyanocobalamin (12 ug/1) + Docusate sodium (50 mg/1) + Folic acid (1 mg/1) + Iron (90 mg/1) + Nicotinamide (20 mg/1) + Potassium Iodide (150 ug/1) + Pyridoxine hydrochloride (20 mg/1) + Riboflavin (3.4 mg/1) + Thiamine mononitrate (3 mg/1) + Zinc oxide (25 mg/1) + alpha-Tocopherol acetate (30 [iU]/1)Tablet, coatedOralNnodum Pharmaceuticals2005-06-20Not applicableUS flag

Categories

ATC Codes
S01XA02 — RetinolV04CB01 — Vitamin a concentratesD10AD02 — RetinolR01AX02 — RetinolA11CA01 — Retinol (vit a)
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Prenol lipids
Sub Class
Retinoids
Direct Parent
Retinoids
Alternative Parents
Diterpenoids / Fatty alcohols / Primary alcohols / Hydrocarbon derivatives
Substituents
Alcohol / Aliphatic homomonocyclic compound / Diterpenoid / Fatty acyl / Fatty alcohol / Hydrocarbon derivative / Organic oxygen compound / Organooxygen compound / Primary alcohol / Retinoid skeleton
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
retinol (CHEBI:17336) / Retinoids, Fat-soluble vitamins (C00473) / Retinoids (LMPR01090000)

Chemical Identifiers

UNII
G2SH0XKK91
CAS number
68-26-8
InChI Key
FPIPGXGPPPQFEQ-OVSJKPMPSA-N
InChI
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+
IUPAC Name
(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol
SMILES
C\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C

References

Synthesis Reference

William Oroshnik, "Synthesis of Vitamin A, intermediates and conversion thereof to Vitamin A." U.S. Patent US4092366, issued May, 1948.

US4092366
General References
  1. Roncone DP: Xerophthalmia secondary to alcohol-induced malnutrition. Optometry. 2006 Mar;77(3):124-33. [PubMed:16513513]
  2. Penniston KL, Tanumihardjo SA: The acute and chronic toxic effects of vitamin A. Am J Clin Nutr. 2006 Feb;83(2):191-201. doi: 10.1093/ajcn/83.2.191. [PubMed:16469975]
  3. Olson JM, Ameer MA, Goyal A: Vitamin A Toxicity . [PubMed:30422511]
  4. Health Canada: Dietary Reference Intakes [Link]
Human Metabolome Database
HMDB0000305
KEGG Drug
D00069
KEGG Compound
C17276
PubChem Compound
445354
PubChem Substance
46508191
ChemSpider
393012
BindingDB
50092056
RxNav
11246
ChEBI
17336
ChEMBL
CHEMBL986
ZINC
ZINC000003831417
Therapeutic Targets Database
DNC001498
PharmGKB
PA451884
PDBe Ligand
RTL
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Vitamin_A
AHFS Codes
  • 88:04.00 — Vitamin A
PDB Entries
1aqb / 1brp / 1crb / 1eii / 1fbm / 1fmj / 1fml / 1gx8 / 1hbp / 1iiu
show 23 more
MSDS
Download (74.8 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedOtherIntrinsic Aging of Skin1
4CompletedPreventionAcute Upper Respiratory Tract Infections / Diarrhea / Pneumonia1
4CompletedPreventionDeath / Morbidity3
4CompletedPreventionLung Cancers1
4CompletedPreventionPremature Births / Retinopathy of Prematurity1
4CompletedPreventionVillage Children1
4CompletedScreeningType 2 Diabetes Mellitus1
4CompletedTreatmentAnemia / Worm Infections1
4CompletedTreatmentHyperemesis Gravidarum / Morning Sickness / Nausea / Pregnancy / Vomiting1
4CompletedTreatmentSepsis1

Pharmacoeconomics

Manufacturers
  • Astrazeneca lp
  • Banner pharmacaps inc
  • Chase chemical co lp
  • Everylife
  • Impax laboratories inc
  • West ward pharmaceutical corp
  • Sterling winthrop inc
  • Eli lilly and co
  • Del ray laboratories inc
  • Bayer pharmaceuticals corp
  • Bristol myers squibb co
  • Elkins sinn div ah robins co inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Mk laboratories inc
  • Wharton laboratories inc div us ethicals
  • Arcum pharmaceutical corp
  • Teva pharmaceuticals usa inc
  • Hospira inc
  • Bel mar laboratories inc
Packagers
  • Ambix Labs
  • A-S Medication Solutions LLC
  • AstraZeneca Inc.
  • Breckenridge Pharmaceuticals
  • Bristol-Myers Squibb Co.
  • Dispensing Solutions
  • Dofs Laboratories
  • Ethex Corp.
  • Freeda Vitamins
  • Gerber Products Co.
  • Gordon Pharmacy
  • Hi Tech Pharmacal Co. Inc.
  • Hospira Inc.
  • Laboratorios Magnachem International SA
  • Magno-Humphries Laboratories
  • Major Pharmaceuticals
  • Mucos Emulsion GmbH
  • Nextwave Pharmaceuticals Inc.
  • Pharmedix
  • Physicians Total Care Inc.
  • Qualitest
  • River's Edge Pharmaceuticals
  • Sancilio and Company Inc.
  • Spectrum Pharmaceuticals
  • Teral Laboratories
  • Tris Pharma Inc.
  • Vintage Pharmaceuticals Inc.
Dosage Forms
FormRouteStrength
Powder, for solutionOral
OintmentTopical
EmulsionOral
SyrupOral500 mg/100ml
Capsule; liquidOral
CapsuleOral5 mg
TabletOral3 mg
TabletOral2 mcg
Tablet, chewableOral5 mg
SyrupOral10 mg/5ml
TabletOral1500 IU
CapsuleOral0.4 mg
SyrupOral400 IU
SyrupOral0.35 mg
Injection, solutionIntramuscular15 mg/1mL
Capsule, gelatin coated30 mg
Tablet, coatedOral25000 iu
Tablet, coatedOral100000 iu
CapsuleOral5000 IU
TabletOral4 mcg
Tablet, film coatedOral5 mcg
TabletOral582.5 IU
CapsuleOral400 mcg
CreamTopical
PatchTopical0.57 g/19g
Capsule, gelatin coatedOral27 mg
Capsule15 mg
Tablet, coatedOral100 mg
Injection, powder, for solutionParenteral125 mg
Injection, powder, for solutionIntravenous5.8 mg
Tablet, chewableOral2 mcg
Tablet, chewableOral0.5 mg
Tablet, chewableOral1500 IU
Tablet, chewableOral0.25 mg
Tablet, chewableOral50 mg
Solution / dropsNasal8.25 mg/ml
Solution / dropsOral200000 IU/mL
SyrupOral200 iu/5mL
Tablet, coatedOral5 mg
Tablet, film coated8000 IU
SyrupOral2000 IU/5ml
Tablet4000 IU
Capsule4000 IU
TabletOral15 mg
Solution / dropsOral2000 IU/mL
SyrupOral400 mg/100ml
TabletOral0.1 mg
Tablet, film coatedOral500 IU
Tablet, film coatedOral125 mg
TabletOral4000 IU
EmulsionOral2662.5 IU
Tablet, coatedOral60 mg
LozengeOral
TabletOral25 mg
TabletOral6.5 mg
Capsule60 mg
Capsule, delayed releaseOral0.6 mg
Capsule, gelatin coatedOral40 mg
TabletOral82.5 mg
Capsule, gelatin coatedOral1250 IU
CapsuleOral400 IU
Tablet, coatedOral150 mcg
CapsuleOral4 mg
Tablet, coatedOral113 mg
Tablet, coatedOral
PowderOral
Tablet, chewableOral2500 IU
StickTopical
Capsule, liquid filledOral150 mg
Injection, powder, lyophilized, for solutionIntravenous
KitIntravenous
Syrup400 iu/5mL
Capsule, liquid filledOral7500 IU
Tablet, coatedOral30 mg
Tablet, film coatedOral1200 mcg
TabletOral8.3 mg
CapsuleOral750 mcg
OintmentTopical8 g
SolutionIntravenous
ElixirOral1 mg/5ml
Liquid; tabletOral
Tablet, chewableOral
SolutionIntravenous140 mcg
Solution / dropsOral300 mcg/ml
SolutionOral
Tablet, sugar coatedOral1 mg
SyrupOral2500 IU/5ml
CapsuleOral1828 µg
Capsule, liquid filledOral0.25 mg
TabletOral
LiquidIntravenous
Tablet, coatedOral75 mg
Capsule, liquid filledOral0.6 mg
CapsuleOral8000 iu
Tablet, chewableOral200 mcg
CapsuleOral1.16 mg
LiquidOral2500 IU/5ml
CapsuleOral3000 IU
KitOral
TabletOral150 mg
TabletOral5 mg
SolutionConjunctival; Ophthalmic12 mg
Capsule, delayed releaseOral150 mg
SyrupOral
InjectionIntravenous
Injection, solutionIntravenous
SolutionOral100 mg
CapsuleOral2000 IU
Syrup5 mg/100mL
Syrup5 mg/5mL
CapsuleOral2667 IU
CapsuleOral50 mcg
SyrupOral1500 IU
Solution / dropsOral
Tablet, coatedOral50 mg
CapsuleOral4000 IU
Tablet, film coatedOral
Solution / dropsOral
TabletOral0.5 mg
Capsule, gelatin coatedOral
Tablet, effervescentOral2333 IU
Capsule, liquid filledOral29.4083 mg
CapsuleOral0.1 mg
Syrup1250 IU
Syrup150 ml
EmulsionOral850 IU
Tablet, film coatedOral400 mcg
SyrupOral1.7 mg/10ml
Tablet, chewableOral15 IU
CapsuleOral1 mg
CapsuleOral10 mg
Tablet, film coatedOral100 mcg
ClothTopical0.01 1/1
TabletOral40 mcg
Syrup2500 IU
Capsule, liquid filledOral562.85 mg
TabletOral2 mg
Syrup100 iu/5mL
Tablet, extended releaseOral
CapsuleOral50000 IU
Powder, for solutionIntramuscular; Intravenous3500 IU
Suspension / dropsOral
LiquidOral
Capsule, liquid filledOral1 mg
Tablet50 mg
SyrupOral0.25 mg/5ml
Injection, powder, lyophilized, for solutionIntramuscular; Intravenous3500 IU
Tablet, chewableOral5000 IU
Injection, powder, for solutionParenteral9.11 mg
Capsule, liquid filledOral25 mg
Capsule, liquid filledOral200 mg
TabletOral6000 IU
OintmentOphthalmic25000 UI/100G
SyrupOral1250 IU/5mL
Capsule75 mg
Tablet, coatedOral400 iu
Solution / drops; suspension / dropsOral30.2 mg/mL
CapsuleOral
Capsule, liquid filledOral
Tablet, chewableOral10 IU
Capsule, gelatin coatedOral0.5 mg
SolutionIntravenous0.15 mg
SolutionIntravenous0.2 mg
Injection, emulsionIntravenous10 iu
Injection, solution, concentrateIntravenous15 mcg/ml
Injection, emulsionIntravenous7 iu
Injection, solution, concentrateIntravenous20 mcg/ml
Injection, emulsionIntravenous99 mcg/mL
Injection, emulsionIntravenous69 mcg/mL
EmulsionIntravenous2300 IU
EmulsionIntravenous3300 IU
CapsuleOral200 IU
CapsuleOral25000 iu
Tablet, sugar coatedOral
CapsuleOral30000 IE
CapsuleOral
CapsuleOral100 IU
TabletOral
OintmentOphthalmic250 IU/g
CapsuleOral300 mg
CapsuleOral10000 IU
Capsule, liquid filledOral50000 IU
Capsule, coatedOral50000 IU
SyrupOral320 mg
Tablet, chewableOral7.33 mg
Solution / dropsOral2000 IU
Tablet, chewableOral1250 IU
Tablet, coatedOral15 mg
Syrup20 mg/5mL
Capsule, liquid filledOral250 mg
TabletOral200 mg
Tablet, film coatedOral200 mg
GranuleOral70 mcg
Prices
Unit descriptionCostUnit
Avita 0.025% Cream 45 gm Tube149.39USD tube
Avita 0.025% Gel 45 gm Tube149.39USD tube
Avita 0.025% Cream 20 gm Tube69.21USD tube
Vitamin a palmitate liquid22.33USD ml
Aquasol a 50000 unit/ml vial17.69USD ml
Vitamin a acetate crystals1.99USD g
Gordon's vite a creme0.13USD g
Vitamin a palm 10000 unit tablet0.06USD tablet
Vitamin a cream0.03USD g
Vitamin a 10000 unit tablet0.02USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)63.5 °CPhysProp
water solubility0.671 mg/LNot Available
logP5.68BIOBYTE (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.00758 mg/mLALOGPS
logP6.38ALOGPS
logP4.69ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)16.44ChemAxon
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity97.92 m3·mol-1ChemAxon
Polarizability36.54 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9938
Blood Brain Barrier+0.9665
Caco-2 permeable+0.7272
P-glycoprotein substrateNon-substrate0.5939
P-glycoprotein inhibitor INon-inhibitor0.8205
P-glycoprotein inhibitor IINon-inhibitor0.5631
Renal organic cation transporterNon-inhibitor0.7646
CYP450 2C9 substrateNon-substrate0.8193
CYP450 2D6 substrateNon-substrate0.8324
CYP450 3A4 substrateSubstrate0.5522
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.923
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.842
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7388
Ames testAMES toxic0.6952
CarcinogenicityNon-carcinogens0.7004
BiodegradationReady biodegradable0.5504
Rat acute toxicity2.1249 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8563
hERG inhibition (predictor II)Non-inhibitor0.8853
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (10.5 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-052r-2950000000-c24ec8ff8d0ba6c1f23f
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-000i-0290000000-25c523b646154b291da8
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-05gj-3900000000-a63c286f931608f650a3
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-05mo-9700000000-e627db30469c74bb037f
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Retinol dehydrogenase activity
Specific Function
Exhibits an oxidoreductive catalytic activity towards retinoids. Most efficient as an NADPH-dependent retinal reductase. Displays high activity toward 9-cis and all-trans-retinol. Also involved in ...
Gene Name
RDH12
Uniprot ID
Q96NR8
Uniprot Name
Retinol dehydrogenase 12
Molecular Weight
35093.455 Da
References
  1. Maeda A, Maeda T, Imanishi Y, Sun W, Jastrzebska B, Hatala DA, Winkens HJ, Hofmann KP, Janssen JJ, Baehr W, Driessen CA, Palczewski K: Retinol dehydrogenase (RDH12) protects photoreceptors from light-induced degeneration in mice. J Biol Chem. 2006 Dec 8;281(49):37697-704. Epub 2006 Oct 10. [PubMed:17032653]
  2. Thompson DA, Janecke AR, Lange J, Feathers KL, Hubner CA, McHenry CL, Stockton DW, Rammesmayer G, Lupski JR, Antinolo G, Ayuso C, Baiget M, Gouras P, Heckenlively JR, den Hollander A, Jacobson SG, Lewis RA, Sieving PA, Wissinger B, Yzer S, Zrenner E, Utermann G, Gal A: Retinal degeneration associated with RDH12 mutations results from decreased 11-cis retinal synthesis due to disruption of the visual cycle. Hum Mol Genet. 2005 Dec 15;14(24):3865-75. Epub 2005 Nov 3. [PubMed:16269441]
  3. Keller B, Adamski J: RDH12, a retinol dehydrogenase causing Leber's congenital amaurosis, is also involved in steroid metabolism. J Steroid Biochem Mol Biol. 2007 May;104(3-5):190-4. Epub 2007 Mar 23. [PubMed:17512723]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Retinol dehydrogenase activity
Specific Function
Catalyzes the reduction of all-trans-retinal to all-trans-retinol in the presence of NADPH.
Gene Name
DHRS3
Uniprot ID
O75911
Uniprot Name
Short-chain dehydrogenase/reductase 3
Molecular Weight
33548.115 Da
References
  1. Haeseleer F, Huang J, Lebioda L, Saari JC, Palczewski K: Molecular characterization of a novel short-chain dehydrogenase/reductase that reduces all-trans-retinal. J Biol Chem. 1998 Aug 21;273(34):21790-9. [PubMed:9705317]
  2. Cerignoli F, Guo X, Cardinali B, Rinaldi C, Casaletto J, Frati L, Screpanti I, Gudas LJ, Gulino A, Thiele CJ, Giannini G: retSDR1, a short-chain retinol dehydrogenase/reductase, is retinoic acid-inducible and frequently deleted in human neuroblastoma cell lines. Cancer Res. 2002 Feb 15;62(4):1196-204. [PubMed:11861404]
  3. Chai Z, Brereton P, Suzuki T, Sasano H, Obeyesekere V, Escher G, Saffery R, Fuller P, Enriquez C, Krozowski Z: 17 beta-hydroxysteroid dehydrogenase type XI localizes to human steroidogenic cells. Endocrinology. 2003 May;144(5):2084-91. [PubMed:12697717]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Thyroid hormone binding
Specific Function
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early...
Gene Name
ALDH1A3
Uniprot ID
P47895
Uniprot Name
Aldehyde dehydrogenase family 1 member A3
Molecular Weight
56107.995 Da
References
  1. Nakazawa N, Montedonico S, Takayasu H, Paradisi F, Puri P: Disturbance of retinol transportation causes nitrofen-induced hypoplastic lung. J Pediatr Surg. 2007 Feb;42(2):345-9. [PubMed:17270546]
  2. Everts HB, Sundberg JP, Ong DE: Immunolocalization of retinoic acid biosynthesis systems in selected sites in rat. Exp Cell Res. 2005 Aug 15;308(2):309-19. [PubMed:15950969]
  3. Halilagic A, Ribes V, Ghyselinck NB, Zile MH, Dolle P, Studer M: Retinoids control anterior and dorsal properties in the developing forebrain. Dev Biol. 2007 Mar 1;303(1):362-75. Epub 2006 Nov 17. [PubMed:17184764]
  4. Maden M, Blentic A, Reijntjes S, Seguin S, Gale E, Graham A: Retinoic acid is required for specification of the ventral eye field and for Rathke's pouch in the avian embryo. Int J Dev Biol. 2007;51(3):191-200. [PubMed:17486539]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxidoreductase activity
Specific Function
Retinol saturase carrying out the saturation of the 13-14 double bond of all-trans-retinol to produce all-trans-13,14-dihydroretinol. Has activity toward all-trans-retinol as substrate. Does not us...
Gene Name
RETSAT
Uniprot ID
Q6NUM9
Uniprot Name
All-trans-retinol 13,14-reductase
Molecular Weight
66818.935 Da
References
  1. Moise AR, Isken A, Dominguez M, de Lera AR, von Lintig J, Palczewski K: Specificity of zebrafish retinol saturase: formation of all-trans-13,14-dihydroretinol and all-trans-7,8- dihydroretinol. Biochemistry. 2007 Feb 20;46(7):1811-20. Epub 2007 Jan 25. [PubMed:17253779]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Retinol dehydrogenase activity
Specific Function
Exhibits an oxidoreductive catalytic activity towards retinoids. Most efficient as an NADPH-dependent retinal reductase. Displays high activity towards 9-cis and all-trans-retinol. Also involved in...
Gene Name
RDH11
Uniprot ID
Q8TC12
Uniprot Name
Retinol dehydrogenase 11
Molecular Weight
35385.955 Da
References
  1. Gallego O, Belyaeva OV, Porte S, Ruiz FX, Stetsenko AV, Shabrova EV, Kostereva NV, Farres J, Pares X, Kedishvili NY: Comparative functional analysis of human medium-chain dehydrogenases, short-chain dehydrogenases/reductases and aldo-keto reductases with retinoids. Biochem J. 2006 Oct 1;399(1):101-9. [PubMed:16787387]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Receptor binding
Specific Function
Reduces all-trans-retinal and 9-cis retinal. Can also catalyze the oxidation of all-trans-retinol with NADP as co-factor, but with much lower efficiency. Reduces alkyl phenyl ketones and alpha-dica...
Gene Name
DHRS4
Uniprot ID
Q9BTZ2
Uniprot Name
Dehydrogenase/reductase SDR family member 4
Molecular Weight
29536.885 Da
References
  1. Du K, Liu GF, Xie JP, Song XH, Li R, Liang B, Huang DY: A 27.368 kDa retinal reductase in New Zealand white rabbit liver cytosol encoded by the peroxisomal retinol dehydrogenase-reductase cDNA: purification and characterization of the enzyme. Biochem Cell Biol. 2007 Apr;85(2):209-17. [PubMed:17534402]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Alcohol dehydrogenase (nadp+) activity
Specific Function
Exhibits an oxidoreductive catalytic activity towards retinoids. Most efficient as an NADPH-dependent retinal reductase. Displays high activity toward 9-cis and all-trans-retinol. No steroid dehydr...
Gene Name
RDH14
Uniprot ID
Q9HBH5
Uniprot Name
Retinol dehydrogenase 14
Molecular Weight
36864.355 Da
References
  1. Belyaeva OV, Kedishvili NY: Human pancreas protein 2 (PAN2) has a retinal reductase activity and is ubiquitously expressed in human tissues. FEBS Lett. 2002 Nov 20;531(3):489-93. doi: 10.1016/s0014-5793(02)03588-3. [PubMed:12435598]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Retinol dehydrogenase activity
Specific Function
Retinol dehydrogenase with a clear preference for NADP. Converts all-trans-retinal to all-trans-retinol. May play a role in the regeneration of visual pigment at high light intensity (By similarity).
Gene Name
RDH8
Uniprot ID
Q9NYR8
Uniprot Name
Retinol dehydrogenase 8
Molecular Weight
33755.02 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Han W, Shen Y, Wang J, Yip S, Yap MK: [Establishing the linkage disequilibrium pattern for the all-trans-retinol dehydrogenase (RDH8) gene]. Zhonghua Yan Ke Za Zhi. 2006 Jul;42(7):642-8. [PubMed:17081426]
  4. Han W, Yip SP, Wang J, Yap MK: Using denaturing HPLC for SNP discovery and genotyping, and establishing the linkage disequilibrium pattern for the all-trans-retinol dehydrogenase (RDH8) gene. J Hum Genet. 2004;49(1):16-23. Epub 2003 Dec 6. [PubMed:14661078]
  5. Fishman GA, Roberts MF, Derlacki DJ, Grimsby JL, Yamamoto H, Sharon D, Nishiguchi KM, Dryja TP: Novel mutations in the cellular retinaldehyde-binding protein gene (RLBP1) associated with retinitis punctata albescens: evidence of interfamilial genetic heterogeneity and fundus changes in heterozygotes. Arch Ophthalmol. 2004 Jan;122(1):70-5. [PubMed:14718298]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Transferase activity, transferring acyl groups
Specific Function
Transfers the acyl group from the sn-1 position of phosphatidylcholine to all-trans retinol, producing all-trans retinyl esters. Retinyl esters are storage forms of vitamin A. LRAT plays a critical...
Gene Name
LRAT
Uniprot ID
O95237
Uniprot Name
Lecithin retinol acyltransferase
Molecular Weight
25702.635 Da
References
  1. Kaschula CH, Jin MH, Desmond-Smith NS, Travis GH: Acyl CoA:retinol acyltransferase (ARAT) activity is present in bovine retinal pigment epithelium. Exp Eye Res. 2006 Jan;82(1):111-21. Epub 2005 Jul 27. [PubMed:16054134]
  2. Liu L, Gudas LJ: Disruption of the lecithin:retinol acyltransferase gene makes mice more susceptible to vitamin A deficiency. J Biol Chem. 2005 Dec 2;280(48):40226-34. Epub 2005 Sep 20. [PubMed:16174770]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Retinol dehydrogenase activity
Specific Function
Stereospecific 11-cis retinol dehydrogenase, which catalyzes the final step in the biosynthesis of 11-cis retinaldehyde, the universal chromophore of visual pigments. Also able to oxidize 9-cis-ret...
Gene Name
RDH5
Uniprot ID
Q92781
Uniprot Name
11-cis retinol dehydrogenase
Molecular Weight
34978.425 Da
References
  1. Zhang M, Hu P, Krois CR, Kane MA, Napoli JL: Altered vitamin A homeostasis and increased size and adiposity in the rdh1-null mouse. FASEB J. 2007 Sep;21(11):2886-96. Epub 2007 Apr 13. [PubMed:17435174]
  2. Maeda A, Maeda T, Imanishi Y, Golczak M, Moise AR, Palczewski K: Aberrant metabolites in mouse models of congenital blinding diseases: formation and storage of retinyl esters. Biochemistry. 2006 Apr 4;45(13):4210-9. [PubMed:16566595]
  3. Dalfo D, Marques N, Albalat R: Analysis of the NADH-dependent retinaldehyde reductase activity of amphioxus retinol dehydrogenase enzymes enhances our understanding of the evolution of the retinol dehydrogenase family. FEBS J. 2007 Jul;274(14):3739-52. Epub 2007 Jul 2. [PubMed:17608724]
  4. Gidlof AC, Ocaya P, Olofsson PS, Torma H, Sirsjo A: Differences in retinol metabolism and proliferative response between neointimal and medial smooth muscle cells. J Vasc Res. 2006;43(4):392-8. Epub 2006 Jul 6. [PubMed:16837774]
  5. Belyaeva OV, Kedishvili NY: Comparative genomic and phylogenetic analysis of short-chain dehydrogenases/reductases with dual retinol/sterol substrate specificity. Genomics. 2006 Dec;88(6):820-30. Epub 2006 Jul 24. [PubMed:16860536]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxidoreductase activity
Specific Function
Does not exhibit retinol dehydrogenase (RDH) activity in vitro.
Gene Name
RDH13
Uniprot ID
Q8NBN7
Uniprot Name
Retinol dehydrogenase 13
Molecular Weight
35931.85 Da
References
  1. Keller B, Adamski J: RDH12, a retinol dehydrogenase causing Leber's congenital amaurosis, is also involved in steroid metabolism. J Steroid Biochem Mol Biol. 2007 May;104(3-5):190-4. Epub 2007 Mar 23. [PubMed:17512723]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Retinal dehydrogenase activity
Specific Function
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Does metabolize octanal and decanal but does not metabolize citral, benzaldehyde, acetaldehyde and propanal...
Gene Name
ALDH1A2
Uniprot ID
O94788
Uniprot Name
Retinal dehydrogenase 2
Molecular Weight
56723.495 Da
References
  1. Isken A, Holzschuh J, Lampert JM, Fischer L, Oberhauser V, Palczewski K, von Lintig J: Sequestration of retinyl esters is essential for retinoid signaling in the zebrafish embryo. J Biol Chem. 2007 Jan 12;282(2):1144-51. Epub 2006 Nov 10. [PubMed:17098734]
  2. Halilagic A, Ribes V, Ghyselinck NB, Zile MH, Dolle P, Studer M: Retinoids control anterior and dorsal properties in the developing forebrain. Dev Biol. 2007 Mar 1;303(1):362-75. Epub 2006 Nov 17. [PubMed:17184764]
  3. Asson-Batres MA, Smith WB: Localization of retinaldehyde dehydrogenases and retinoid binding proteins to sustentacular cells, glia, Bowman's gland cells, and stroma: potential sites of retinoic acid synthesis in the postnatal rat olfactory organ. J Comp Neurol. 2006 May 10;496(2):149-71. [PubMed:16538685]
  4. Szatmari I, Pap A, Ruhl R, Ma JX, Illarionov PA, Besra GS, Rajnavolgyi E, Dezso B, Nagy L: PPARgamma controls CD1d expression by turning on retinoic acid synthesis in developing human dendritic cells. J Exp Med. 2006 Oct 2;203(10):2351-62. Epub 2006 Sep 18. [PubMed:16982809]
  5. Nakazawa N, Montedonico S, Takayasu H, Paradisi F, Puri P: Disturbance of retinol transportation causes nitrofen-induced hypoplastic lung. J Pediatr Surg. 2007 Feb;42(2):345-9. [PubMed:17270546]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Retinal dehydrogenase activity
Specific Function
Binds free retinal and cellular retinol-binding protein-bound retinal. Can convert/oxidize retinaldehyde to retinoic acid (By similarity).
Gene Name
ALDH1A1
Uniprot ID
P00352
Uniprot Name
Retinal dehydrogenase 1
Molecular Weight
54861.44 Da
References
  1. Asson-Batres MA, Smith WB: Localization of retinaldehyde dehydrogenases and retinoid binding proteins to sustentacular cells, glia, Bowman's gland cells, and stroma: potential sites of retinoic acid synthesis in the postnatal rat olfactory organ. J Comp Neurol. 2006 May 10;496(2):149-71. [PubMed:16538685]
  2. Chambers D, Wilson L, Maden M, Lumsden A: RALDH-independent generation of retinoic acid during vertebrate embryogenesis by CYP1B1. Development. 2007 Apr;134(7):1369-83. Epub 2007 Feb 28. [PubMed:17329364]
  3. Gyamfi MA, Kocsis MG, He L, Dai G, Mendy AJ, Wan YJ: The role of retinoid X receptor alpha in regulating alcohol metabolism. J Pharmacol Exp Ther. 2006 Oct;319(1):360-8. Epub 2006 Jul 7. [PubMed:16829625]
  4. Maden M, Blentic A, Reijntjes S, Seguin S, Gale E, Graham A: Retinoic acid is required for specification of the ventral eye field and for Rathke's pouch in the avian embryo. Int J Dev Biol. 2007;51(3):191-200. [PubMed:17486539]
  5. Huq MD, Tsai NP, Gupta P, Wei LN: Regulation of retinal dehydrogenases and retinoic acid synthesis by cholesterol metabolites. EMBO J. 2006 Jul 12;25(13):3203-13. Epub 2006 Jun 8. [PubMed:16763553]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Ligand
General Function
Lipid transporter activity
Specific Function
APOD occurs in the macromolecular complex with lecithin-cholesterol acyltransferase. It is probably involved in the transport and binding of bilin. Appears to be able to transport a variety of liga...
Gene Name
APOD
Uniprot ID
P05090
Uniprot Name
Apolipoprotein D
Molecular Weight
21275.37 Da
References
  1. Breustedt DA, Schonfeld DL, Skerra A: Comparative ligand-binding analysis of ten human lipocalins. Biochim Biophys Acta. 2006 Feb;1764(2):161-73. Epub 2006 Jan 6. [PubMed:16461020]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Ligand
General Function
Catalyzes the conversion of PGH2 to PGD2, a prostaglandin involved in smooth muscle contraction/relaxation and a potent inhibitor of platelet aggregation. Involved in a variety of CNS functions, such as sedation, NREM sleep and PGE2-induced allodynia, and may have an anti-apoptotic role in oligodendrocytes. Binds small non-substrate lipophilic molecules, including biliverdin, bilirubin, retinal, retinoic acid and thyroid hormone, and may act as a scavenger for harmful hydrophobic molecules and as a secretory retinoid and thyroid hormone transporter. Possibly involved in development and maintenance of the blood-brain, blood-retina, blood-aqueous humor and blood-testis barrier. It is likely to play important roles in both maturation and maintenance of the central nervous system and male reproductive system.
Specific Function
Fatty acid binding
Gene Name
PTGDS
Uniprot ID
P41222
Uniprot Name
Prostaglandin-H2 D-isomerase
Molecular Weight
21028.665 Da
References
  1. Breustedt DA, Schonfeld DL, Skerra A: Comparative ligand-binding analysis of ten human lipocalins. Biochim Biophys Acta. 2006 Feb;1764(2):161-73. Epub 2006 Jan 6. [PubMed:16461020]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inducer
General Function
Retinoic acid binding
Specific Function
Plays a key role in retinoic acid metabolism. Acts on retinoids, including all-trans-retinoic acid (RA) and its stereoisomer 9-cis-RA. Capable of both 4-hydroxylation and 18-hydroxylation. Responsi...
Gene Name
CYP26A1
Uniprot ID
O43174
Uniprot Name
Cytochrome P450 26A1
Molecular Weight
56198.11 Da
References
  1. Abu-Abed S, Dolle P, Metzger D, Beckett B, Chambon P, Petkovich M: The retinoic acid-metabolizing enzyme, CYP26A1, is essential for normal hindbrain patterning, vertebral identity, and development of posterior structures. Genes Dev. 2001 Jan 15;15(2):226-40. doi: 10.1101/gad.855001. [PubMed:11157778]
  2. Ross AC, Zolfaghari R: Cytochrome P450s in the regulation of cellular retinoic acid metabolism. Annu Rev Nutr. 2011 Aug 21;31:65-87. doi: 10.1146/annurev-nutr-072610-145127. [PubMed:21529158]
  3. Topletz AR, Tripathy S, Foti RS, Shimshoni JA, Nelson WL, Isoherranen N: Induction of CYP26A1 by metabolites of retinoic acid: evidence that CYP26A1 is an important enzyme in the elimination of active retinoids. Mol Pharmacol. 2015;87(3):430-41. doi: 10.1124/mol.114.096784. Epub 2014 Dec 9. [PubMed:25492813]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Transporter activity
Specific Function
Intracellular transport of retinol.
Gene Name
RBP5
Uniprot ID
P82980
Uniprot Name
Retinol-binding protein 5
Molecular Weight
15931.17 Da
References
  1. O'Byrne SM, Wongsiriroj N, Libien J, Vogel S, Goldberg IJ, Baehr W, Palczewski K, Blaner WS: Retinoid absorption and storage is impaired in mice lacking lecithin:retinol acyltransferase (LRAT). J Biol Chem. 2005 Oct 21;280(42):35647-57. Epub 2005 Aug 22. [PubMed:16115871]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Transporter activity
Specific Function
Intracellular transport of retinol.
Gene Name
RBP7
Uniprot ID
Q96R05
Uniprot Name
Retinoid-binding protein 7
Molecular Weight
15535.585 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Caprioli A, Zhu H, Sato TN: CRBP-III:lacZ expression pattern reveals a novel heterogeneity of vascular endothelial cells. Genesis. 2004 Nov;40(3):139-45. [PubMed:15493015]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Retinol transporter activity
Specific Function
Delivers retinol from the liver stores to the peripheral tissues. In plasma, the RBP-retinol complex interacts with transthyretin, this prevents its loss by filtration through the kidney glomeruli.
Gene Name
RBP4
Uniprot ID
P02753
Uniprot Name
Retinol-binding protein 4
Molecular Weight
23009.8 Da
References
  1. Goodman AB: Retinoid receptors, transporters, and metabolizers as therapeutic targets in late onset Alzheimer disease. J Cell Physiol. 2006 Dec;209(3):598-603. [PubMed:17001693]
  2. Ziouzenkova O, Orasanu G, Sharlach M, Akiyama TE, Berger JP, Viereck J, Hamilton JA, Tang G, Dolnikowski GG, Vogel S, Duester G, Plutzky J: Retinaldehyde represses adipogenesis and diet-induced obesity. Nat Med. 2007 Jun;13(6):695-702. Epub 2007 May 27. [PubMed:17529981]
  3. Wolf G: Serum retinol-binding protein: a link between obesity, insulin resistance, and type 2 diabetes. Nutr Rev. 2007 May;65(5):251-6. [PubMed:17566551]
  4. Liden M, Eriksson U: Development of a versatile reporter assay for studies of retinol uptake and metabolism in vivo. Exp Cell Res. 2005 Nov 1;310(2):401-8. Epub 2005 Sep 8. [PubMed:16150442]
  5. Hinterhuber G, Cauza K, Dingelmaier-Hovorka R, Diem E, Horvat R, Wolff K, Foedinger D: Expression of RPE65, a putative receptor for plasma retinol-binding protein, in nonmelanocytic skin tumours. Br J Dermatol. 2005 Oct;153(4):785-9. [PubMed:16181461]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Transporter activity
Specific Function
Intracellular transport of retinol.
Gene Name
RBP2
Uniprot ID
P50120
Uniprot Name
Retinol-binding protein 2
Molecular Weight
15706.595 Da
References
  1. Suruga K, Kitagawa M, Yasutake H, Takase S, Goda T: Diet-related variation in cellular retinol-binding protein type II gene expression in rat jejunum. Br J Nutr. 2005 Dec;94(6):890-5. [PubMed:16351764]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Karnaukhova E: Interactions of human serum albumin with retinoic acid, retinal and retinyl acetate. Biochem Pharmacol. 2007 Mar 15;73(6):901-10. Epub 2006 Dec 2. [PubMed:17217919]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Transporter activity
Specific Function
Soluble retinoid carrier essential the proper function of both rod and cone photoreceptors. Participates in the regeneration of active 11-cis-retinol and 11-cis-retinaldehyde, from the inactive 11-...
Gene Name
RLBP1
Uniprot ID
P12271
Uniprot Name
Retinaldehyde-binding protein 1
Molecular Weight
36474.02 Da
References
  1. Muniz A, Villazana-Espinoza ET, Thackeray B, Tsin AT: 11-cis-Acyl-CoA:retinol O-acyltransferase activity in the primary culture of chicken Muller cells. Biochemistry. 2006 Oct 10;45(40):12265-73. [PubMed:17014079]
  2. Wenzel A, von Lintig J, Oberhauser V, Tanimoto N, Grimm C, Seeliger MW: RPE65 is essential for the function of cone photoreceptors in NRL-deficient mice. Invest Ophthalmol Vis Sci. 2007 Feb;48(2):534-42. [PubMed:17251447]
  3. Vogel JS, Bullen EC, Teygong CL, Howard EW: Identification of the RLBP1 gene promoter. Invest Ophthalmol Vis Sci. 2007 Aug;48(8):3872-7. [PubMed:17652763]
  4. Salvador-Silva M, Ghosh S, Bertazolli-Filho R, Boatright JH, Nickerson JM, Garwin GG, Saari JC, Coca-Prados M: Retinoid processing proteins in the ocular ciliary epithelium. Mol Vis. 2005 May 18;11:356-65. [PubMed:15928609]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Serine-type peptidase activity
Specific Function
IRBP shuttles 11-cis and all trans retinoids between the retinol isomerase in the pigment epithelium and the visual pigments in the photoreceptor cells of the retina.
Gene Name
RBP3
Uniprot ID
P10745
Uniprot Name
Retinol-binding protein 3
Molecular Weight
135361.46 Da
References
  1. Qtaishat NM, Wiggert B, Pepperberg DR: Interphotoreceptor retinoid-binding protein (IRBP) promotes the release of all-trans retinol from the isolated retina following rhodopsin bleaching illumination. Exp Eye Res. 2005 Oct;81(4):455-63. Epub 2005 Jun 2. [PubMed:15935345]
  2. Wu Q, Blakeley LR, Cornwall MC, Crouch RK, Wiggert BN, Koutalos Y: Interphotoreceptor retinoid-binding protein is the physiologically relevant carrier that removes retinol from rod photoreceptor outer segments. Biochemistry. 2007 Jul 24;46(29):8669-79. Epub 2007 Jun 30. [PubMed:17602665]
  3. Kolesnikov AV, Ala-Laurila P, Shukolyukov SA, Crouch RK, Wiggert B, Estevez ME, Govardovskii VI, Cornwall MC: Visual cycle and its metabolic support in gecko photoreceptors. Vision Res. 2007 Feb;47(3):363-74. Epub 2006 Oct 16. [PubMed:17049961]
  4. Duncan T, Fariss RN, Wiggert B: Confocal immunolocalization of bovine serum albumin, serum retinol-binding protein, and interphotoreceptor retinoid-binding protein in bovine retina. Mol Vis. 2006 Dec 22;12:1632-9. [PubMed:17200663]
  5. Salvador-Silva M, Ghosh S, Bertazolli-Filho R, Boatright JH, Nickerson JM, Garwin GG, Saari JC, Coca-Prados M: Retinoid processing proteins in the ocular ciliary epithelium. Mol Vis. 2005 May 18;11:356-65. [PubMed:15928609]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Transporter activity
Specific Function
Intracellular transport of retinol.
Gene Name
RBP1
Uniprot ID
P09455
Uniprot Name
Retinol-binding protein 1
Molecular Weight
15850.13 Da
References
  1. Yapi HF, Ahiboh H, Ago K, Ake M, Monnet D: [Protein profile and vitamin A in children of school age in Ivory Coast]. Ann Biol Clin (Paris). 2005 May-Jun;63(3):291-5. [PubMed:15951260]
  2. Quadro L, Hamberger L, Gottesman ME, Wang F, Colantuoni V, Blaner WS, Mendelsohn CL: Pathways of vitamin A delivery to the embryo: insights from a new tunable model of embryonic vitamin A deficiency. Endocrinology. 2005 Oct;146(10):4479-90. Epub 2005 Jun 30. [PubMed:15994349]
  3. Harrison EH: Mechanisms of digestion and absorption of dietary vitamin A. Annu Rev Nutr. 2005;25:87-103. [PubMed:16011460]
  4. Paci E, Greene LH, Jones RM, Smith LJ: Characterization of the molten globule state of retinol-binding protein using a molecular dynamics simulation approach. FEBS J. 2005 Sep;272(18):4826-38. [PubMed:16156801]
  5. Folli C, Viglione S, Busconi M, Berni R: Biochemical basis for retinol deficiency induced by the I41N and G75D mutations in human plasma retinol-binding protein. Biochem Biophys Res Commun. 2005 Nov 4;336(4):1017-22. [PubMed:16157297]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Functions as retinol transporter. Accepts all-trans retinol from the extracellular retinol-binding protein RBP4, facilitates retinol transport across the cell membrane, and then transfers retinol to the cytoplasmic retinol-binding protein RBP1 (PubMed:9452451, PubMed:18316031, PubMed:22665496). Retinol uptake is enhanced by LRAT, an enzyme that converts retinol to all-trans retinyl esters, the storage forms of vitamin A (PubMed:18316031, PubMed:22665496). Contributes to the activation of a signaling cascade that depends on retinol transport and LRAT-dependent generation of retinol metabolites that then trigger activation of JAK2 and its target STAT5, and ultimately increase the expression of SOCS3 and inhibit cellular responses to insulin (PubMed:21368206, PubMed:22665496). Important for the homeostasis of vitamin A and its derivatives, such as retinoic acid (PubMed:18316031). STRA6-mediated transport is particularly important in the eye, and under conditions of dietary vitamin A deficiency (Probable). Does not transport retinoic acid (PubMed:18316031).
Specific Function
Retinal binding
Gene Name
STRA6
Uniprot ID
Q9BX79
Uniprot Name
Receptor for retinol uptake STRA6
Molecular Weight
73502.13 Da
References
  1. Kawaguchi R, Zhong M, Kassai M, Ter-Stepanian M, Sun H: Vitamin A Transport Mechanism of the Multitransmembrane Cell-Surface Receptor STRA6. Membranes (Basel). 2015 Aug 28;5(3):425-53. doi: 10.3390/membranes5030425. [PubMed:26343735]

Drug created on June 13, 2005 07:24 / Updated on November 30, 2020 13:38

Covid drug repurpose