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
Structure for Vitamin A (DB00162)
- 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.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to treat Deficiency, vitamin a Combination Product in combination with: Vitamin E (DB00163) •••••••••••• •••••••• •••••• •••••• Used in combination to treat Deficiency, vitamin a Combination Product in combination with: Fish oil (DB13961) •••••••••••• ••••••• Used in combination to treat Deficiency, vitamin d Combination Product in combination with: Fish oil (DB13961) •••••••••••• ••••••• Used in combination to treat Degenerative retinal disorders Combination Product in combination with: D-alpha-Tocopherol acetate (DB14002) •••••••••••• ••••••• •••••• Used in combination to treat Disorder of the epithelium Combination Product in combination with: D-alpha-Tocopherol acetate (DB14002) •••••••••••• ••••••• •••••• - Associated Therapies
- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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.
Target Actions Organism UApolipoprotein D ligandHumans UProstaglandin-H2 D-isomerase ligandHumans URetinol dehydrogenase 12 substrateHumans U11-cis retinol dehydrogenase substrateHumans URetinol dehydrogenase 13 substrateHumans URetinal dehydrogenase 2 substrateHumans URetinal dehydrogenase 1 substrateHumans ULecithin retinol acyltransferase substrateHumans UShort-chain dehydrogenase/reductase 3 substrateHumans UAldehyde dehydrogenase family 1 member A3 substrateHumans UAll-trans-retinol 13,14-reductase substrateHumans URetinol dehydrogenase 11 substrateHumans UDehydrogenase/reductase SDR family member 4 substrateHumans URetinol dehydrogenase 14 substrateHumans URetinol dehydrogenase 8 substrateHumans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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
Pathway Category Retinol Metabolism Metabolic Vitamin A Deficiency Disease - 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcitretin The risk or severity of adverse effects can be increased when Vitamin A is combined with Acitretin. Alitretinoin The risk or severity of adverse effects can be increased when Vitamin A is combined with Alitretinoin. Bexarotene The risk or severity of adverse effects can be increased when Vitamin A is combined with Bexarotene. Cyproterone acetate The therapeutic efficacy of Cyproterone acetate can be decreased when used in combination with Vitamin A. Demeclocycline The risk or severity of pseudotumor cerebri can be increased when Vitamin A is combined with Demeclocycline. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Vitamin A acetate 3LE3D9D6OY 127-47-9 QGNJRVVDBSJHIZ-QHLGVNSISA-N Vitamin A palmitate 1D1K0N0VVC 79-81-2 VYGQUTWHTHXGQB-FFHKNEKCSA-N - Active Moieties
Name Kind UNII CAS InChI Key Beta carotene unknown 01YAE03M7J 7235-40-7 OENHQHLEOONYIE-JLTXGRSLSA-N - Product Images
- International/Other Brands
- Alphalin / Chocola A
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Aquasol A Injection, solution 15 mg/1mL Intramuscular Casper Pharma Llc 2020-10-01 Not applicable US 
Aquasol A Injection, solution 15 mg/1mL Intramuscular Hospira, Inc. 2014-07-18 2021-10-01 US Aquasol A Cap 25000unit Capsule 25000 unit / cap Oral Rhone Poulenc Rorer 1992-12-31 1996-09-09 Canada 
Aquasol A Cap 50000unit Capsule 50000 unit / cap Oral Rhone Poulenc Rorer 1992-12-31 1996-09-09 Canada Vitamin A Cap 25000iu Capsule 25000 unit / cap Oral Stanley Pharmaceuticals, A Division Of Vita Health Products Inc. 1957-12-31 2002-07-31 Canada - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image 400 Vitamin A 10000iu Capsule 10000 unit / cap Oral Herbes Universelles Inc. 1972-12-31 2009-07-15 Canada A Caps 10000 I.U. Capsule 10000 unit Oral Twin Laboratories Inc. 1995-12-31 1999-11-10 Canada A Mulsion 10 Emulsion 10000 unit / .04 mL Oral Seroyal International Inc. 1982-12-31 2008-10-09 Canada Arovit Vitamine A Tab 10000unit Tablet 10000 unit Oral Les Laboratoires Bio SantÉ Inc. 1986-12-31 1996-09-10 Canada C-Mask Pack Patch 0.57 g/19g Topical NeoBiotech Global Corporation 2018-02-10 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image 24 Multivitamins + Minerals Vitamin 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) Tablet Oral Stanley Pharmaceuticals, A Division Of Vita Health Products Inc. 1997-04-30 2002-07-31 Canada 50 Plus Vitamin 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) Tablet Oral Quest Vitamins A Div Of Purity Life Health Products 1998-08-04 2001-07-06 Canada 50 Plus Multiple Vitamins & Minerals Vitamin 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) Tablet Oral Gfr Pharma Ltd. 2002-10-20 2004-06-15 Canada A & C Powder Vitamin A (930 unit / g) + Ascorbic acid (7 mg / g) Powder, for solution Oral Standard Process Inc. Not applicable Not applicable Canada A + D Ointment Vitamin A palmitate (2000 unit / g) + Cholecalciferol (500 unit / g) Ointment Topical National Care Products Ltd. 1993-12-31 2002-10-10 Canada - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Abavite Vitamin 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) Tablet Oral ABACOS HEALTH 2021-03-31 Not applicable US Bacmin Vitamin 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, coated Oral Marnel Pharmaceuticals, Llc 2000-04-01 Not applicable US C-Mask Pack Vitamin A (0.57 g/19g) Patch Topical NeoBiotech Global Corporation 2018-02-10 Not applicable US Davimet Vitamin 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, chewable Oral PureTek Corporation 2022-09-19 Not applicable US Davimet-M Vitamin 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, chewable Oral PureTek Corporation 2023-11-30 Not applicable US
Categories
- ATC Codes
- S01XA02 — Retinol
- S01XA — Other ophthalmologicals
- S01X — OTHER OPHTHALMOLOGICALS
- S01 — OPHTHALMOLOGICALS
- S — SENSORY ORGANS
- D10AD — Retinoids for topical use in acne
- D10A — ANTI-ACNE PREPARATIONS FOR TOPICAL USE
- D10 — ANTI-ACNE PREPARATIONS
- D — DERMATOLOGICALS
- R01AX — Other nasal preparations
- R01A — DECONGESTANTS AND OTHER NASAL PREPARATIONS FOR TOPICAL USE
- R01 — NASAL PREPARATIONS
- R — RESPIRATORY SYSTEM
- Drug Categories
- Adjuvants, Immunologic
- Alimentary Tract and Metabolism
- Alkenes
- Anti-Acne Preparations
- Anti-Acne Preparations for Topical Use
- Anticarcinogenic Agents
- Antioxidants
- Biological Factors
- Carotenoids
- Compounds used in a research, industrial, or household setting
- Cyclohexanes
- Cyclohexenes
- Cycloparaffins
- Dermatologicals
- Diagnostic Agents
- Diet, Food, and Nutrition
- Diterpenes
- Esters
- Food
- Growth Substances
- Immunologic Factors
- Micronutrients
- Nasal Preparations
- Ophthalmologicals
- Physiological Phenomena
- Pigments, Biological
- Polyenes
- Protective Agents
- Retinoids
- Retinoids for Topical Use in Acne
- Sensory Organs
- Terpenes
- Tests for Fat Absorption
- Vitamin A
- Vitamins
- Vitamins (Fat Soluble)
- 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
- Roncone DP: Xerophthalmia secondary to alcohol-induced malnutrition. Optometry. 2006 Mar;77(3):124-33. [Article]
- 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]
- Olson JM, Ameer MA, Goyal A: Vitamin A Toxicity . [Article]
- Health Canada: Dietary Reference Intakes [Link]
- External Links
- Human Metabolome Database
- HMDB0000305
- KEGG Drug
- D00069
- KEGG Compound
- C17276
- PubChem Compound
- 445354
- PubChem Substance
- 46508191
- ChemSpider
- 393012
- BindingDB
- 50092056
- 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);">
Phase Status Purpose Conditions Count 4 Completed Other Intrinsic Aging of Skin 1 4 Completed Prevention Death / Morbidity 3 4 Completed Prevention Diarrhea / Pneumonia / Upper Respiratory Tract Infection 1 4 Completed Prevention Lung Cancer 1 4 Completed Prevention Premature 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
Form Route Strength Ointment Topical Capsule Oral 10000 unit Emulsion Oral 10000 unit / .04 mL Syrup Oral Solution Oral 2000 UI Injection, solution Intramuscular; Oral Injection, solution Intramuscular 15 mg/1mL Capsule Oral 25000 unit / cap Capsule Oral 50000 unit / cap Capsule Oral 600 UI Injection, solution Intramuscular Solution / drops Oral Tablet, coated Oral Tablet, coated Oral 50 IU Tablet Oral 10000 unit Solution Intravenous 1.914 mg Capsule, gelatin coated 30 mg Tablet, coated Oral 25000 iu Solution Oral 687.5 mg Cream Topical Patch Topical 0.57 g/19g Tablet Oral 1500 unit / tab Injection, powder, for solution Intramuscular; Intravenous Injection, powder, for solution Parenteral Injection, solution Intramuscular; Intravenous Injection, powder, for solution Intravenous Solution / drops Nasal Tablet, film coated Tablet Capsule Emulsion Oral 2662.5 IU Powder, for solution Intravenous Lozenge Oral Tablet Oral 700 unit / tab Gel Oral Capsule, delayed release Oral Tablet, coated Oral 150 mcg Tablet, coated Oral Powder Oral Capsule, coated Oral Stick Topical Injection, solution, concentrate; kit Intravenous Injection, powder, lyophilized, for solution Intravenous Kit Intravenous Elixir Oral Liquid; tablet Oral Tablet, chewable Oral Solution Intravenous Solution Oral Tablet, sugar coated Oral Tablet Oral Liquid Intravenous Solution Parenteral Capsule, liquid filled Oral 25000 IU Gel Ophthalmic 10 mg/g Kit Oral Solution Conjunctival; Ophthalmic 5000 IU Solution Conjunctival; Ophthalmic Powder Injection, solution; kit Intravenous Injection, solution Intravenous Solution / drops Oral Tablet, film coated Oral Capsule; kit; tablet Oral Solution / drops Oral 5000 unit / .06 mL Ointment Cutaneous 100000 UI Capsule, gelatin coated Oral Tablet, effervescent Oral Capsule, liquid filled Oral 29.4083 mg Capsule Oral 58.824 MG Syrup Emulsion Oral Capsule; kit; tablet, coated Oral Cloth Topical 0.005 mg/1 Injection, powder, for solution Intravenous 100 mg Tablet, extended release Oral Powder, for solution Intramuscular; Intravenous Capsule; liquid Oral Suspension / drops Oral Liquid Oral Powder, for solution Oral Injection, powder, lyophilized, for solution Intramuscular; Intravenous Tablet Oral Ointment Ophthalmic Solution / drops; suspension / drops Oral 30.2 mg/mL Capsule Oral Capsule, liquid filled; kit Oral Capsule, liquid filled Oral Injection Intravenous 330 iu/ml Injection, solution, concentrate Intravenous Injection Intravenous 230 iu/ml Injection, emulsion Intravenous Emulsion Intravenous Capsule Oral Tablet, sugar coated Oral Tablet, sugar coated Oral 100 mg Capsule Oral 10000 unit / tab Capsule Oral 30000 IE Tablet Oral 5000 unit / tab Capsule Oral 10000 unit / cap Capsule Oral 25000 unit Capsule Oral 50000 unit Capsule Oral 117.64 MG Capsule Oral 58.82 MG Tablet Oral 10000 unit / tab Tablet Oral 2000 unit / tab Ointment Ophthalmic 250 IU/g Capsule Oral 10000 IU Capsule, liquid filled Oral 10000 IU Capsule, liquid filled Oral 50000 IU Capsule, coated Oral 50000 IU Capsule, coated Oral 5000000000 IU Tablet, film coated Oral 90 mg Granule Oral Tablet, sugar coated Oral 50000 IU Capsule Oral 25000 IU - Prices
Unit description Cost Unit Avita 0.025% Cream 45 gm Tube 149.39USD tube Avita 0.025% Gel 45 gm Tube 149.39USD tube Avita 0.025% Cream 20 gm Tube 69.21USD tube Vitamin a palmitate liquid 22.33USD ml Aquasol a 50000 unit/ml vial 17.69USD ml Vitamin a acetate crystals 1.99USD g Gordon's vite a creme 0.13USD g Vitamin a palm 10000 unit tablet 0.06USD tablet Vitamin a cream 0.03USD g Vitamin a 10000 unit tablet 0.02USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 63.5 °C PhysProp water solubility 0.671 mg/L Not Available logP 5.68 BIOBYTE (1995) - Predicted Properties
Property Value Source Water Solubility 0.00758 mg/mL ALOGPS logP 6.38 ALOGPS logP 4.69 Chemaxon logS -4.6 ALOGPS pKa (Strongest Acidic) 16.44 Chemaxon pKa (Strongest Basic) -2.2 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 20.23 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 97.92 m3·mol-1 Chemaxon Polarizability 36.54 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9938 Blood Brain Barrier + 0.9665 Caco-2 permeable + 0.7272 P-glycoprotein substrate Non-substrate 0.5939 P-glycoprotein inhibitor I Non-inhibitor 0.8205 P-glycoprotein inhibitor II Non-inhibitor 0.5631 Renal organic cation transporter Non-inhibitor 0.7646 CYP450 2C9 substrate Non-substrate 0.8193 CYP450 2D6 substrate Non-substrate 0.8324 CYP450 3A4 substrate Substrate 0.5522 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.907 CYP450 2D6 inhibitor Non-inhibitor 0.923 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Non-inhibitor 0.842 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7388 Ames test AMES toxic 0.6952 Carcinogenicity Non-carcinogens 0.7004 Biodegradation Ready biodegradable 0.5504 Rat acute toxicity 2.1249 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8563 hERG inhibition (predictor II) Non-inhibitor 0.8853
Spectra
- Mass Spec (NIST)
- Download (10.5 KB)
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 202.6109289 predictedDarkChem Lite v0.1.0 [M-H]- 203.0449289 predictedDarkChem Lite v0.1.0 [M-H]- 202.5888289 predictedDarkChem Lite v0.1.0 [M-H]- 202.3235289 predictedDarkChem Lite v0.1.0 [M-H]- 185.7355 predictedDeepCCS 1.0 (2019) [M-H]- 202.6109289 predictedDarkChem Lite v0.1.0 [M-H]- 203.0449289 predictedDarkChem Lite v0.1.0 [M-H]- 202.5888289 predictedDarkChem Lite v0.1.0 [M-H]- 202.3235289 predictedDarkChem Lite v0.1.0 [M-H]- 185.7355 predictedDeepCCS 1.0 (2019) [M+H]+ 204.7211289 predictedDarkChem Lite v0.1.0 [M+H]+ 204.0586289 predictedDarkChem Lite v0.1.0 [M+H]+ 203.5388289 predictedDarkChem Lite v0.1.0 [M+H]+ 203.3750289 predictedDarkChem Lite v0.1.0 [M+H]+ 188.0935 predictedDeepCCS 1.0 (2019) [M+H]+ 204.7211289 predictedDarkChem Lite v0.1.0 [M+H]+ 204.0586289 predictedDarkChem Lite v0.1.0 [M+H]+ 203.5388289 predictedDarkChem Lite v0.1.0 [M+H]+ 203.3750289 predictedDarkChem Lite v0.1.0 [M+H]+ 188.0935 predictedDeepCCS 1.0 (2019) [M+Na]+ 202.4290289 predictedDarkChem Lite v0.1.0 [M+Na]+ 203.3937289 predictedDarkChem Lite v0.1.0 [M+Na]+ 203.1978289 predictedDarkChem Lite v0.1.0 [M+Na]+ 203.2812289 predictedDarkChem Lite v0.1.0 [M+Na]+ 194.8832 predictedDeepCCS 1.0 (2019) [M+Na]+ 202.4290289 predictedDarkChem Lite v0.1.0 [M+Na]+ 203.3937289 predictedDarkChem Lite v0.1.0 [M+Na]+ 203.1978289 predictedDarkChem Lite v0.1.0 [M+Na]+ 203.2812289 predictedDarkChem Lite v0.1.0 [M+Na]+ 194.8832 predictedDeepCCS 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
- 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
- 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
- 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]
- 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]
- 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
- 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]
- 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]
- 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]
- 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]
- 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
- 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
- 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]
- 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]
- 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]
- 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]
- 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
- 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]
- 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]
- 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]
- 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]
- 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
- 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]
- 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
- 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]
- 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]
- 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
- 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]
- 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]
- 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]
- 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
- 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
- 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
- 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
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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]
- 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]
- 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]
- 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
- SubstrateInducer
- 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
- 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]
- 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]
- 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
- 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
- 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]
- 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]
- 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]
- 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
- 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]
- 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]
- 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]
- 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]
- 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
- 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]
- 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]
- Harrison EH: Mechanisms of digestion and absorption of dietary vitamin A. Annu Rev Nutr. 2005;25:87-103. [Article]
- 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]
- 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
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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]
- 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
- 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]
- 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]
- 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]
- 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]
- 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
- 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
- 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