Identification

Name
Lutein
Accession Number
DB00137  (NUTR00036, DB11138)
Type
Small Molecule
Groups
Approved, Nutraceutical
Description

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.

Structure
Thumb
Synonyms
  • Xanthophyll
  • Xantofyl
External IDs
E 161 / E-161B / E-161B(I) / INS NO.161B(I) / INS-161B(I)
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Doctor Super LuteinCapsule20 g/100gOralH Lscience Co Ltd2016-01-30Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
MacuzinLutein (10 mg/1) + Copper (2 mg/1) + Folic Acid (1 mg/1) + Vitamin C (500 mg/1) + Vitamin E (400 [iU]/1) + Zeaxanthin (2 mg/1) + Zinc oxide (80 mg/1)CapsuleOralSterling Knight Pharmaceuticals, Llc2015-04-302017-09-13Us
OcuvelLutein (10 mg/1) + Copper (2 mg/1) + Folic Acid (1 mg/1) + Vitamin C (500 mg/1) + Vitamin E acetate (400 [iU]/1) + Zeaxanthin (2 mg/1) + Zinc oxide (80 mg/1)CapsuleOralAdler Stern Pharmaceuticals, Llc2014-11-05Not applicableUs
OcuvelLutein (5 mg/1) + Copper (1 mg/1) + Folic Acid (.5 mg/1) + Vitamin C (250 mg/1) + Vitamin E acetate (200 [iU]/1) + Zeaxanthin (1 mg/1) + Zinc oxide (40 mg/1)CapsuleOralAdler Stern Pharmaceuticals, Llc2014-12-01Not applicableUs
Strovite One CapletsLutein (5 mg/1) + Biotin (100 ug/1) + Cholecalciferol (1000 [iU]/1) + Chromium (50 ug/1) + Cupric sulfate (1.5 mg/1) + Cyanocobalamin (50 ug/1) + Folic Acid (1 mg/1) + Lipoic Acid (15 mg/1) + Magnesium oxide (50 mg/1) + Manganese (1.5 mg/1) + Nicotinamide (25 mg/1) + Calcium pantothenate (15 mg/1) + Pyridoxine hydrochloride (25 mg/1) + Riboflavin (5 mg/1) + Selenium (100 ug/1) + Thiamine (20 mg/1) + Vitamin A (3000 [iU]/1) + Vitamin C (300 mg/1) + Vitamin E succinate (100 [iU]/1) + Zinc oxide (25 mg/1)TabletOralEverett Laboratories, Inc.2001-05-04Not applicableUs
TozalLutein (15 mg/31) + Cholecalciferol (1000 [iU]/31) + Copper (1.6 mg/31) + Cyanocobalamin (100 ug/31) + Folic Acid (1 mg/31) + Omega-3 fatty acids (600 mg/31) + Pyridoxine hydrochloride (20 mg/31) + Taurine (400 mg/31) + Vitamin A palmitate (10000 [iU]/31) + Vitamin C (452 mg/31) + Vitamin E (200 [iU]/31) + Zeaxanthin (3 mg/31) + Zinc picolinate (40 mg/31)Capsule, gelatin coatedOralFocus Laboratories, Inc.2013-06-012016-10-13Us
Categories
UNII
X72A60C9MT
CAS number
127-40-2
Weight
Average: 568.886
Monoisotopic: 568.428031043
Chemical Formula
C40H56O2
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\[[email protected]]1C(C)=C[[email protected]](O)CC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)C[[email protected]@H](O)CC1(C)C

Pharmacology

Indication

Xanthophylls are taken for nutritional supplementation, and also for treating dietary shortage or imbalance.

Structured Indications
Not Available
Pharmacodynamics

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
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

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
  1. 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. [PubMed:20830634]
  2. 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. [PubMed:20355006]
External Links
KEGG Compound
C08601
PubChem Compound
5281243
PubChem Substance
46508835
ChemSpider
4444655
ChEBI
28838
ChEMBL
CHEMBL173929
PharmGKB
PA164748318
HET
LUT
PDRhealth
PDRhealth Drug Page
Wikipedia
Xanthophyll
MSDS
Download (73.1 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentMacular Degeneration1
1, 2CompletedTreatmentRetinitis Pigmentosa (RP)1
1, 2Unknown StatusTreatmentAge-Related Macular Degeneration (ARMD)1
1, 2Unknown StatusTreatmentOxidative Stress in Healthy Subjects1
2CompletedTreatmentMacular Degeneration1
2CompletedTreatmentNon-Proliferative Diabetic Retinopathy / Type 2 Diabetes Mellitus1
3CompletedTreatmentAge-Related Macular Degeneration (ARMD) / Cataracts1
3CompletedTreatmentRetinitis Pigmentosa (RP)1
4CompletedPreventionMacular Pigment Optical Density1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
CapsuleOral20 g/100g
CapsuleOral
TabletOral
Capsule, gelatin coatedOral
Prices
Not Available
Patents
Not Available

Properties

State
Liquid
Experimental Properties
PropertyValueSource
melting point (°C)196 °CPhysProp
water solubilityInsolubleNot Available
logP7.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000732 mg/mLALOGPS
logP8.29ALOGPS
logP8.55ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)18.22ChemAxon
pKa (Strongest Basic)-0.91ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity195.06 m3·mol-1ChemAxon
Polarizability73.81 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9972
Blood Brain Barrier+0.6588
Caco-2 permeable+0.7904
P-glycoprotein substrateSubstrate0.5199
P-glycoprotein inhibitor IInhibitor0.5819
P-glycoprotein inhibitor IINon-inhibitor0.8202
Renal organic cation transporterNon-inhibitor0.876
CYP450 2C9 substrateNon-substrate0.8299
CYP450 2D6 substrateNon-substrate0.8408
CYP450 3A4 substrateSubstrate0.6607
CYP450 1A2 substrateNon-inhibitor0.9079
CYP450 2C9 inhibitorNon-inhibitor0.7723
CYP450 2D6 inhibitorNon-inhibitor0.9368
CYP450 2C19 inhibitorInhibitor0.5225
CYP450 3A4 inhibitorNon-inhibitor0.8808
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6267
Ames testNon AMES toxic0.8391
CarcinogenicityNon-carcinogens0.7489
BiodegradationNot ready biodegradable0.9655
Rat acute toxicity2.5006 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9273
hERG inhibition (predictor II)Non-inhibitor0.8259
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Xanthophyll / Secondary alcohol / Organic oxygen compound / Hydrocarbon derivative / Organooxygen compound / Alcohol / Aliphatic homomonocyclic compound
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
carotenol (CHEBI:28838) / C40 isoprenoids (tetraterpenes), Carotenoids (C08601) / C40 isoprenoids (tetraterpenes) (LMPR01070274)

Carriers

Kind
Protein
Organism
Human
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
  1. 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. [PubMed:16678417]
  2. 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. [PubMed:11273666]

Drug created on June 13, 2005 07:24 / Updated on November 07, 2017 01:33