Identification
- Generic Name
- Lutein
- DrugBank Accession Number
- DB00137
- Background
Lutein is an xanthophyll and one of 600 known naturally occurring carotenoids. Lutein is synthesized only by plants and like other xanthophylls is found in high quantities in green leafy vegetables such as spinach, kale and yellow carrots. In green plants, xanthophylls act to modulate light energy and serve as non-photochemical quenching agents to deal with triplet chlorophyll (an excited form of chlorophyll), which is overproduced at very high light levels, during photosynthesis.
- Type
- Small Molecule
- Groups
- Approved, Investigational, Nutraceutical
- Structure
Structure for Lutein (DB00137)
- Weight
- Average: 568.886
Monoisotopic: 568.428031043 - Chemical Formula
- C40H56O2
- Synonyms
- Xanthophyll
- Xantofyl
- External IDs
- E 161
- E-161B
- E-161B(I)
- INS NO.161B(I)
- INS-161B(I)
Pharmacology
- Indication
Xanthophylls are taken for nutritional supplementation, and also for treating dietary shortage or imbalance.
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- Contraindications & Blackbox Warnings
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Lutein was found to be present in a concentrated area of the macula, a small area of the retina responsible for central vision. The hypothesis for the natural concentration is that lutein helps protect from oxidative stress and high-energy light. Several studies show that an increase in macula pigmentation decreases the risk for eye diseases such as Age-related Macular Degeneration (AMD).
- Mechanism of action
Xanthophylls have antioxidant activity and react with active oxygen species, producing biologically active degradation products. They also can inhibit peroxidation of membrane phospholipids and reduce lipofuscin formation, both of which contribute to their antioxidant properties. Lutein is naturally present in the macula of the human retina. It filters out potentially phototoxic blue light and near-ultraviolet radiation from the macula. The protective effect is due in part, to the reactive oxygen species quenching ability of these carotenoids. Lutein is more stable to decomposition by pro-oxidants than are other carotenoids such as beta-carotene and lycopene. Lutein is abundant in the region surrounding the fovea, and lutein is the predominant pigment at the outermost periphery of the macula. Zeaxanthin, which is fully conjugated (lutein is not), may offer somewhat better protection than lutein against phototoxic damage caused by blue and near-ultraviolet light radiation. Lutein is one of only two carotenoids that have been identified in the human lens, may be protective against age-related increases in lens density and cataract formation. Again, the possible protection afforded by lutein may be accounted for, in part, by its reactive oxygen species scavenging abilities. Carotenoids also provide protection from cancer. One of the mechanisms of this is by increasing the expression of the protein connexin-43, thereby stimulating gap junctional communication and preventing unrestrained cell proliferation.
- Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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Not Available
- Pathways
- Not Available
- 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.Not Available
- Food Interactions
- Take with foods containing vitamin C. Taking lutein with vitamin C may increase the rate of absorption of lutein. Taking lutein with carotenoids or naringenin may reduce lutein absorption.
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.- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Doctor Super Lutein Capsule 20 g/100g Oral Health-Love Co. 2016-01-30 2018-02-12 US 
Noon for Kids Powder 10 mg/2g Oral Wholesum Brands Co., Ltd. 2022-03-01 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Furryden Dental Easy Green Lutein (0.01 g/100mL) + Chicken (6 g/100mL) Gum, chewing Oral Welpenschutz Inc. 2023-02-17 Not applicable US Ocuvite Lutein Lutein (2 mg) + Ascorbic acid (200 mg) + Copper (2 mg) + Selenium (55 mcg) + Vitamin A (1000 IU) + Vitamin E (60 IU) + Zinc (40 mg) Tablet Oral Bausch & Lomb (Malaysia) Sdn. Bhd. 2015-12-17 2017-01-19 Malaysia 
Vista Advanced AREDS2 Formula Lutein (5 mg/966.47mg) + Ascorbic acid (250 mg/966.47mg) + Copper gluconate (1 mg/966.47mg) + Glutathione (25 mg/966.47mg) + Selenium (0.0275 mg/966.47mg) + Vitamin E (137.5 mg/966.47mg) + Zeaxanthin (1 mg/966.47mg) Capsule Oral Red Wedding LLC 2020-09-01 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Doctor Super Lutein Lutein (20 g/100g) Capsule Oral Health-Love Co. 2016-01-30 2018-02-12 US Furryden Dental Easy Green Lutein (0.01 g/100mL) + Chicken (6 g/100mL) Gum, chewing Oral Welpenschutz Inc. 2023-02-17 Not applicable US Macuvex Lutein (5 mg/1) + Ascorbic acid (250 mg/1) + Copper (1 mg/1) + Folic acid (1 mg/1) + Zeaxanthin (1 mg/1) + Zinc oxide (40 mg/1) + alpha-Tocopherol acetate (200 [iU]/1) Capsule Oral Sterling-knight Pharmaceuticals,LLC 2014-11-16 2015-07-28 US Macuzin Lutein (10 mg/1) + Ascorbic acid (500 mg/1) + Copper (2 mg/1) + DL-alpha tocopheryl acetate (400 [iU]/1) + Folic acid (1 mg/1) + Zeaxanthin (2 mg/1) + Zinc oxide (80 mg/1) Capsule Oral Sterling-Knight Pharmaceuticals, LLC 2015-04-30 2018-07-30 US Noon for Kids Lutein (10 mg/2g) Powder Oral Wholesum Brands Co., Ltd. 2022-03-01 Not applicable US
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Prenol lipids
- Sub Class
- Tetraterpenoids
- Direct Parent
- Xanthophylls
- Alternative Parents
- Secondary alcohols / Hydrocarbon derivatives
- Substituents
- Alcohol / Aliphatic homomonocyclic compound / Hydrocarbon derivative / Organic oxygen compound / Organooxygen compound / Secondary alcohol / Xanthophyll
- Molecular Framework
- Aliphatic homomonocyclic compounds
- External Descriptors
- carotenol (CHEBI:28838) / C40 isoprenoids (tetraterpenes), Carotenoids (C08601) / C40 isoprenoids (tetraterpenes) (LMPR01070274)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- X72A60C9MT
- CAS number
- 127-40-2
- InChI Key
- KBPHJBAIARWVSC-RGZFRNHPSA-N
- InChI
- InChI=1S/C40H56O2/c1-29(17-13-19-31(3)21-23-37-33(5)25-35(41)27-39(37,7)8)15-11-12-16-30(2)18-14-20-32(4)22-24-38-34(6)26-36(42)28-40(38,9)10/h11-25,35-37,41-42H,26-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t35-,36+,37-/m0/s1
- IUPAC Name
- (1R,4R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-3,5,5-trimethylcyclohex-2-en-1-ol
- SMILES
- C\C(\C=C\C=C(/C)\C=C\[C@H]1C(C)=C[C@H](O)CC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)C[C@@H](O)CC1(C)C
References
- Synthesis Reference
Helmut Auweter, Heribert Bohn, Erik Luddecke, "Stable, aqueous dispersions and stable, water-dispersible dry xanthophyll powder, their production and use." U.S. Patent US6296877, issued September, 1994.
US6296877- General References
- Namitha KK, Negi PS: Chemistry and biotechnology of carotenoids. Crit Rev Food Sci Nutr. 2010 Sep;50(8):728-60. doi: 10.1080/10408398.2010.499811. [Article]
- Ma L, Lin XM: Effects of lutein and zeaxanthin on aspects of eye health. J Sci Food Agric. 2010 Jan 15;90(1):2-12. doi: 10.1002/jsfa.3785. [Article]
- External Links
- Human Metabolome Database
- HMDB0003233
- KEGG Compound
- C08601
- PubChem Compound
- 5281243
- PubChem Substance
- 46508835
- ChemSpider
- 4444655
- 11359
- ChEBI
- 28838
- ChEMBL
- CHEMBL173929
- ZINC
- ZINC000008221225
- PharmGKB
- PA164748318
- PDBe Ligand
- LUT
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Xanthophyll
- MSDS
- Download (73.1 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 Prevention Macular Pigment Optical Density 1 3 Completed Treatment Age - Related Macular Degeneration (AMD) / Cataracts 1 3 Completed Treatment Retinitis Pigmentosa (RP) 1 2 Completed Prevention Nutrient Deficiency / Pregnancy Related 1 2 Completed Treatment Macular Degeneration 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet, coated Oral Capsule Oral 20 g/100g Gum, chewing Oral Powder Oral 10 mg/2g Capsule Oral Tablet Oral Capsule, gelatin coated Oral Capsule, liquid filled Oral - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Liquid
- Experimental Properties
Property Value Source melting point (°C) 196 °C PhysProp water solubility Insoluble Not Available logP 7.9 Not Available - Predicted Properties
Property Value Source Water Solubility 0.000732 mg/mL ALOGPS logP 8.29 ALOGPS logP 8.55 Chemaxon logS -5.9 ALOGPS pKa (Strongest Acidic) 18.22 Chemaxon pKa (Strongest Basic) -0.91 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 40.46 Å2 Chemaxon Rotatable Bond Count 10 Chemaxon Refractivity 195.06 m3·mol-1 Chemaxon Polarizability 73.81 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9972 Blood Brain Barrier + 0.6588 Caco-2 permeable + 0.7904 P-glycoprotein substrate Substrate 0.5199 P-glycoprotein inhibitor I Inhibitor 0.5819 P-glycoprotein inhibitor II Non-inhibitor 0.8202 Renal organic cation transporter Non-inhibitor 0.876 CYP450 2C9 substrate Non-substrate 0.8299 CYP450 2D6 substrate Non-substrate 0.8408 CYP450 3A4 substrate Substrate 0.6607 CYP450 1A2 substrate Non-inhibitor 0.9079 CYP450 2C9 inhibitor Non-inhibitor 0.7723 CYP450 2D6 inhibitor Non-inhibitor 0.9368 CYP450 2C19 inhibitor Inhibitor 0.5225 CYP450 3A4 inhibitor Non-inhibitor 0.8808 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6267 Ames test Non AMES toxic 0.8391 Carcinogenicity Non-carcinogens 0.7489 Biodegradation Not ready biodegradable 0.9655 Rat acute toxicity 2.5006 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9273 hERG inhibition (predictor II) Non-inhibitor 0.8259
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 323.3535396 predictedDarkChem Lite v0.1.0 [M-H]- 324.8932396 predictedDarkChem Lite v0.1.0 [M-H]- 272.0651 predictedDeepCCS 1.0 (2019) [M+H]+ 325.5485396 predictedDarkChem Lite v0.1.0 [M+H]+ 327.3002396 predictedDarkChem Lite v0.1.0 [M+H]+ 273.7183 predictedDeepCCS 1.0 (2019) [M+Na]+ 325.2195396 predictedDarkChem Lite v0.1.0 [M+Na]+ 279.87515 predictedDeepCCS 1.0 (2019)
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- 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
- Zsila F, Nadolski G, Lockwood SF: Association studies of aggregated aqueous lutein diphosphate with human serum albumin and alpha1-acid glycoprotein in vitro: evidence from circular dichroism and electronic absorption spectroscopy. Bioorg Med Chem Lett. 2006 Jul 15;16(14):3797-801. Epub 2006 May 5. [Article]
- Yemelyanov AY, Katz NB, Bernstein PS: Ligand-binding characterization of xanthophyll carotenoids to solubilized membrane proteins derived from human retina. Exp Eye Res. 2001 Apr;72(4):381-92. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 21, 2024 02:33