Vitamin A

Identification

Summary

Vitamin A is a vitamin important for retinal function that is used clinically to correct vitamin A deficiency.

Brand Names
Aquasol A, Infuvite, Infuvite Pediatric, Mvc-fluoride, Mvi Pediatric, Vitafol-one
Generic Name
Vitamin A
DrugBank Accession Number
DB00162
Background

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
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.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatDeficiency, vitamin aCombination Product in combination with: Vitamin E (DB00163)•••••••••••••••••••• •••••• ••••••
Used in combination to treatDeficiency, vitamin aCombination Product in combination with: Fish oil (DB13961)•••••••••••••••••••
Used in combination to treatDeficiency, vitamin dCombination Product in combination with: Fish oil (DB13961)•••••••••••••••••••
Used in combination to treatDegenerative retinal disordersCombination Product in combination with: D-alpha-Tocopherol acetate (DB14002)••••••••••••••••••• ••••••
Used in combination to treatDisorder of the epitheliumCombination Product in combination with: D-alpha-Tocopherol acetate (DB14002)••••••••••••••••••• ••••••
Associated Therapies
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
UApolipoprotein D
ligand
Humans
UProstaglandin-H2 D-isomerase
ligand
Humans
URetinol dehydrogenase 12
substrate
Humans
U11-cis retinol dehydrogenase
substrate
Humans
URetinol dehydrogenase 13
substrate
Humans
URetinal dehydrogenase 2
substrate
Humans
URetinal dehydrogenase 1
substrate
Humans
ULecithin retinol acyltransferase
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
Absorption

Readily absorbed from the normal gastrointestinal tract

Volume of distribution

Not Available

Protein binding

Less than 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.

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Route of elimination

Not Available

Half-life

1.9 hours

Clearance

Not Available

Adverse Effects
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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

Pathways
PathwayCategory
Retinol MetabolismMetabolic
Vitamin A DeficiencyDisease
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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 can be increased when Vitamin A is combined with Demeclocycline.
Food Interactions
No interactions found.

Products

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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/1mLIntramuscularCasper Pharma Llc2020-10-01Not applicableUS flag
Aquasol AInjection, solution15 mg/1mLIntramuscularHospira, Inc.2014-07-182021-10-01US flag
Aquasol A Cap 25000unitCapsule25000 unit / capOralRhone Poulenc Rorer1992-12-311996-09-09Canada flag
Aquasol A Cap 50000unitCapsule50000 unit / capOralRhone Poulenc Rorer1992-12-311996-09-09Canada flag
Vitamin A Cap 25000iuCapsule25000 unit / capOralStanley Pharmaceuticals, A Division Of Vita Health Products Inc.1957-12-312002-07-31Canada flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
400 Vitamin A 10000iuCapsule10000 unit / capOralHerbes Universelles Inc.1972-12-312009-07-15Canada flag
A Caps 10000 I.U.Capsule10000 unitOralTwin Laboratories Inc.1995-12-311999-11-10Canada flag
A Mulsion 10Emulsion10000 unit / .04 mLOralSeroyal International Inc.1982-12-312008-10-09Canada flag
Arovit Vitamine A Tab 10000unitTablet10000 unitOralLes Laboratoires Bio SantÉ Inc.1986-12-311996-09-10Canada flag
C-Mask PackPatch0.57 g/19gTopicalNeoBiotech Global Corporation2018-02-10Not applicableUS flag
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 / g) + Ascorbic acid (7 mg / g)Powder, for solutionOralStandard Process Inc.Not applicableNot applicableCanada flag
A + D OintmentVitamin A palmitate (2000 unit / g) + Cholecalciferol (500 unit / g)OintmentTopicalNational Care Products Ltd.1993-12-312002-10-10Canada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
AbaviteVitamin A palmitate (0.33 mg/1) + Ascorbic acid (60 mg/1) + Cholecalciferol (0.025 mg/1) + DL-alpha tocopheryl acetate (13.5 mg/1) + Ferrous sulfate (30 mg/1) + Folic acid (1 mg/1) + Magnesium oxide (25 mg/1) + Mecobalamin (0.5 mg/1) + Niacin (15 mg/1) + Calcium pantothenate (5 mg/1) + Potassium Iodide (0.25 mg/1) + Riboflavin (1.8 mg/1) + Thiamine mononitrate (1.6 mg/1) + Zinc oxide (15 mg/1)TabletOralABACOS HEALTH2021-03-31Not applicableUS flag
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
DavimetVitamin A (750 ug/1) + Ascorbic acid (24 mg/1) + Cholecalciferol (10 ug/1) + Cyanocobalamin (4.5 ug/1) + DL-alpha tocopheryl acetate (10 mg/1) + Folic acid (1667 ug/1) + Niacin (13.5 mg/1) + Pyridoxine hydrochloride (1.05 mg/1) + Riboflavin (1.2 mg/1) + Sodium ascorbate (36 mg/1) + Thiamine mononitrate (1.05 mg/1)Tablet, chewableOralPureTek Corporation2022-09-19Not applicableUS flag
Davimet-MVitamin A (750 ug/1) + Ascorbic acid (24 mg/1) + Cholecalciferol (10 ug/1) + DL-alpha tocopheryl acetate (10 mg/1) + Levomefolate calcium (1000 ug/1) + Mecobalamin (4.5 ug/1) + Niacin (13.5 mg/1) + Pyridoxine hydrochloride (1.05 mg/1) + Riboflavin (1.2 mg/1) + Sodium ascorbate (36 mg/1) + Thiamine mononitrate (1.05 mg/1)Tablet, chewableOralPureTek Corporation2023-11-30Not 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)
Affected organisms
  • Humans and other mammals

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. [Article]
  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. [Article]
  3. Olson JM, Ameer MA, Goyal A: Vitamin A Toxicity . [Article]
  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
PDB Entries
1aqb / 1brp / 1crb / 1eii / 1fbm / 1fmj / 1fml / 1gx8 / 1hbp / 1iiu
show 23 more
MSDS
Download (74.8 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
4CompletedOtherIntrinsic Aging of Skin1
4CompletedPreventionDeath / Morbidity3
4CompletedPreventionDiarrhea / Pneumonia / Upper Respiratory Tract Infection1
4CompletedPreventionLung Cancer1
4CompletedPreventionPremature Births / Retinopathy of Prematurity (ROP)1

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
OintmentTopical
CapsuleOral10000 unit
EmulsionOral10000 unit / .04 mL
SyrupOral
SolutionOral2000 UI
Injection, solutionIntramuscular; Oral
Injection, solutionIntramuscular15 mg/1mL
CapsuleOral25000 unit / cap
CapsuleOral50000 unit / cap
CapsuleOral600 UI
Injection, solutionIntramuscular
Solution / dropsOral
Tablet, coatedOral
Tablet, coatedOral50 IU
TabletOral10000 unit
SolutionIntravenous1.914 mg
Capsule, gelatin coated30 mg
Tablet, coatedOral25000 iu
SolutionOral687.5 mg
CreamTopical
PatchTopical0.57 g/19g
TabletOral1500 unit / tab
Injection, powder, for solutionIntramuscular; Intravenous
Injection, powder, for solutionParenteral
Injection, solutionIntramuscular; Intravenous
Injection, powder, for solutionIntravenous
Solution / dropsNasal
Tablet, film coated
Tablet
Capsule
EmulsionOral2662.5 IU
Powder, for solutionIntravenous
LozengeOral
TabletOral700 unit / tab
GelOral
Capsule, delayed releaseOral
Tablet, coatedOral150 mcg
Tablet, coatedOral
PowderOral
Capsule, coatedOral
StickTopical
Injection, solution, concentrate; kitIntravenous
Injection, powder, lyophilized, for solutionIntravenous
KitIntravenous
ElixirOral
Liquid; tabletOral
Tablet, chewableOral
SolutionIntravenous
SolutionOral
Tablet, sugar coatedOral
TabletOral
LiquidIntravenous
SolutionParenteral
Capsule, liquid filledOral25000 IU
GelOphthalmic10 mg/g
KitOral
SolutionConjunctival; Ophthalmic5000 IU
SolutionConjunctival; Ophthalmic
Powder
Injection, solution; kitIntravenous
Injection, solutionIntravenous
Solution / dropsOral
Tablet, film coatedOral
Capsule; kit; tabletOral
Solution / dropsOral5000 unit / .06 mL
OintmentCutaneous100000 UI
Capsule, gelatin coatedOral
Tablet, effervescentOral
Capsule, liquid filledOral29.4083 mg
CapsuleOral58.824 MG
Syrup
EmulsionOral
Capsule; kit; tablet, coatedOral
ClothTopical0.005 mg/1
Injection, powder, for solutionIntravenous100 mg
Tablet, extended releaseOral
Powder, for solutionIntramuscular; Intravenous
Capsule; liquidOral
Suspension / dropsOral
LiquidOral
Powder, for solutionOral
Injection, powder, lyophilized, for solutionIntramuscular; Intravenous
TabletOral
OintmentOphthalmic
Solution / drops; suspension / dropsOral30.2 mg/mL
CapsuleOral
Capsule, liquid filled; kitOral
Capsule, liquid filledOral
InjectionIntravenous330 iu/ml
Injection, solution, concentrateIntravenous
InjectionIntravenous230 iu/ml
Injection, emulsionIntravenous
EmulsionIntravenous
CapsuleOral
Tablet, sugar coatedOral
Tablet, sugar coatedOral100 mg
CapsuleOral10000 unit / tab
CapsuleOral30000 IE
TabletOral5000 unit / tab
CapsuleOral10000 unit / cap
CapsuleOral25000 unit
CapsuleOral50000 unit
CapsuleOral117.64 MG
CapsuleOral58.82 MG
TabletOral10000 unit / tab
TabletOral2000 unit / tab
OintmentOphthalmic250 IU/g
CapsuleOral10000 IU
Capsule, liquid filledOral10000 IU
Capsule, liquid filledOral50000 IU
Capsule, coatedOral50000 IU
Capsule, coatedOral5000000000 IU
Tablet, film coatedOral90 mg
GranuleOral
Tablet, sugar coatedOral50000 IU
CapsuleOral25000 IU
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-MSsplash10-00di-1190000000-7c2230ee88e04e8f3741
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/MSsplash10-016v-0960000000-528a5f4aa375c8ecb2df
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4l-0090000000-41f441fad2158160fb38
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0pvu-0190000000-f43383d756b5f117cb16
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00rt-1930000000-65d472a8c4915adc55ec
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0kdi-1790000000-3625d49135458bd1fe52
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-05ox-3910000000-f8a5c82210c7016d3815
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-016v-0960000000-528a5f4aa375c8ecb2df
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4l-0090000000-41f441fad2158160fb38
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00rt-1930000000-65d472a8c4915adc55ec
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0pvu-0190000000-f43383d756b5f117cb16
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0kdi-1790000000-3625d49135458bd1fe52
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-05ox-3910000000-f8a5c82210c7016d3815
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-202.6109289
predicted
DarkChem Lite v0.1.0
[M-H]-203.0449289
predicted
DarkChem Lite v0.1.0
[M-H]-202.5888289
predicted
DarkChem Lite v0.1.0
[M-H]-202.3235289
predicted
DarkChem Lite v0.1.0
[M-H]-185.7355
predicted
DeepCCS 1.0 (2019)
[M-H]-202.6109289
predicted
DarkChem Lite v0.1.0
[M-H]-203.0449289
predicted
DarkChem Lite v0.1.0
[M-H]-202.5888289
predicted
DarkChem Lite v0.1.0
[M-H]-202.3235289
predicted
DarkChem Lite v0.1.0
[M-H]-185.7355
predicted
DeepCCS 1.0 (2019)
[M+H]+204.7211289
predicted
DarkChem Lite v0.1.0
[M+H]+204.0586289
predicted
DarkChem Lite v0.1.0
[M+H]+203.5388289
predicted
DarkChem Lite v0.1.0
[M+H]+203.3750289
predicted
DarkChem Lite v0.1.0
[M+H]+188.0935
predicted
DeepCCS 1.0 (2019)
[M+H]+204.7211289
predicted
DarkChem Lite v0.1.0
[M+H]+204.0586289
predicted
DarkChem Lite v0.1.0
[M+H]+203.5388289
predicted
DarkChem Lite v0.1.0
[M+H]+203.3750289
predicted
DarkChem Lite v0.1.0
[M+H]+188.0935
predicted
DeepCCS 1.0 (2019)
[M+Na]+202.4290289
predicted
DarkChem Lite v0.1.0
[M+Na]+203.3937289
predicted
DarkChem Lite v0.1.0
[M+Na]+203.1978289
predicted
DarkChem Lite v0.1.0
[M+Na]+203.2812289
predicted
DarkChem Lite v0.1.0
[M+Na]+194.8832
predicted
DeepCCS 1.0 (2019)
[M+Na]+202.4290289
predicted
DarkChem Lite v0.1.0
[M+Na]+203.3937289
predicted
DarkChem Lite v0.1.0
[M+Na]+203.1978289
predicted
DarkChem Lite v0.1.0
[M+Na]+203.2812289
predicted
DarkChem Lite v0.1.0
[M+Na]+194.8832
predicted
DeepCCS 1.0 (2019)

Targets

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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. [Article]
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. [Article]
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. [Article]
  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. [Article]
  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. [Article]
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
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. [Article]
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
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. [Article]
  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. [Article]
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. [Article]
  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. [Article]
  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. [Article]
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]

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. [Article]
  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. [Article]
  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. [Article]

Carriers

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. [Article]
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
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. [Article]
  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. [Article]
  3. Harrison EH: Mechanisms of digestion and absorption of dietary vitamin A. Annu Rev Nutr. 2005;25:87-103. [Article]
  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. [Article]
  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. [Article]
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. [Article]
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. [Article]
  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. [Article]
  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. [Article]
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
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. [Article]

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. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55