Zeaxanthin

Identification

Generic Name

Zeaxanthin

DrugBank Accession Number

DB11176

Background

Zeaxanthin is a most common carotenoid alcohols found in nature that is involved in the xanthophyll cycle. As a coexistent isomer of lutein, zeaxanthin is synthesized in plants and some micro-organisms. It gives the distinct yellow color to many vegetables and other plants including paprika, corn, saffron and wolfberries. Zeaxanthin is one of the two primary xanthophyll carotenoids contained within the retina of the eye and plays a predominant component in the central macula. It is available as a dietary supplement for eye health benefits and potential prevention of age-related macular degeneration. Zeaxanthin is also added as a food dye.

Type

Small Molecule

Groups

Approved, Investigational

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Zeaxanthin (DB11176)

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Weight

Average: 568.886
Monoisotopic: 568.428031043

Chemical Formula

C₄₀H₅₆O₂

Synonyms

Not Available

External IDs

• E 161H
• E-161H(I)
• INS NO.161H(I)
• INS-161H(I)

Pharmacology

Indication

Not Available

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Associated Therapies

• Mineral supplementation therapy
• Oral Nutritional Supplementation
• Vitamin supplementation

Contraindications & Blackbox Warnings

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Pharmacodynamics

Not Available

Mechanism of action

Not Available

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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Toxicity

Not Available

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Not Available

Food Interactions

• Take with or without food.

Products

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Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Vista Advanced AREDS2 Formula	Zeaxanthin (1 mg/966.47mg) + Ascorbic acid (250 mg/966.47mg) + Copper gluconate (1 mg/966.47mg) + Glutathione (25 mg/966.47mg) + Lutein (5 mg/966.47mg) + Selenium (0.0275 mg/966.47mg) + Vitamin E (137.5 mg/966.47mg)	Capsule	Oral	Red Wedding LLC	2020-09-01	Not applicable

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Macuvex	Zeaxanthin (1 mg/1) + Ascorbic acid (250 mg/1) + Copper (1 mg/1) + Folic acid (1 mg/1) + Lutein (5 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
Macuzin	Zeaxanthin (2 mg/1) + Ascorbic acid (500 mg/1) + Copper (2 mg/1) + DL-alpha tocopheryl acetate (400 [iU]/1) + Folic acid (1 mg/1) + Lutein (10 mg/1) + Zinc oxide (80 mg/1)	Capsule	Oral	Sterling-Knight Pharmaceuticals, LLC	2015-04-30	2018-07-30
Ocuvel	Zeaxanthin (1 mg/1) + Ascorbic acid (250 mg/1) + Copper (1 mg/1) + Folic acid (0.5 mg/1) + Lutein (5 mg/1) + Zinc oxide (40 mg/1) + alpha-Tocopherol acetate (200 [iU]/1)	Capsule	Oral	Adler-Stern Pharmaceuticals, LLC	2014-12-01	Not applicable
Ocuvel	Zeaxanthin (2 mg/1) + Ascorbic acid (500 mg/1) + Copper (2 mg/1) + Folic acid (1 mg/1) + Lutein (10 mg/1) + Zinc oxide (80 mg/1) + alpha-Tocopherol acetate (400 [iU]/1)	Capsule	Oral	Adler-Stern Pharmaceuticals, LLC	2014-11-05	Not applicable
Tozal	Zeaxanthin (3 mg/31) + Ascorbic acid (452 mg/31) + Cholecalciferol (1000 [iU]/31) + Copper (1.6 mg/31) + Cyanocobalamin (100 ug/31) + Folic acid (1 mg/31) + Lutein (15 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 E (200 [iU]/31) + Zinc picolinate (40 mg/31)	Capsule, gelatin coated	Oral	Focus Laboratories, Inc.	2013-06-01	2015-07-15
Vista Advanced AREDS2 Formula	Zeaxanthin (1 mg/966.47mg) + Ascorbic acid (250 mg/966.47mg) + Copper gluconate (1 mg/966.47mg) + Glutathione (25 mg/966.47mg) + Lutein (5 mg/966.47mg) + Selenium (0.0275 mg/966.47mg) + Vitamin E (137.5 mg/966.47mg)	Capsule	Oral	Red Wedding LLC	2020-09-01	Not applicable

Categories

Drug Categories

• Alkenes
• Biological Factors
• Carotenoids
• Cyclohexanes
• Cyclohexenes
• Cycloparaffins
• Hydrocarbons, Acyclic
• Pigments, Biological
• Polyenes
• Terpenes
• Xanthophylls

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:27547) / C40 isoprenoids (tetraterpenes), Carotenoids (C06098) / C40 isoprenoids (tetraterpenes) (LMPR01070261)

Affected organisms

Not Available

Chemical Identifiers

UNII

CV0IB81ORO

CAS number

144-68-3

InChI Key

JKQXZKUSFCKOGQ-QAYBQHTQSA-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/h11-24,35-36,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t35-,36-/m1/s1

IUPAC Name

(1R)-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-3-en-1-ol

SMILES

C\C(\C=C\C=C(/C)\C=C\C1=C(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

General References

Not Available

External Links

Human Metabolome Database

HMDB0002789

KEGG Compound

C06098

PubChem Compound

5280899

PubChem Substance

347827933

ChemSpider

4444421

RxNav

39918

ChEBI

27547

ChEMBL

CHEMBL2359248

ZINC

ZINC000008220175

Wikipedia

Zeaxanthin

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
3	Completed	Treatment	Age - Related Macular Degeneration (AMD) / Cataracts	1
2	Completed	Prevention	Nutrient Deficiency / Pregnancy Related	1
2	Completed	Treatment	NPDR - Non Proliferative Diabetic Retinopathy / Type 2 Diabetes Mellitus	1
1	Recruiting	Treatment	Metastatic Cancer / Metastatic Solid Neoplasm	1
1, 2	Terminated	Other	Glaucoma	1
1, 2	Unknown Status	Treatment	Age - Related Macular Degeneration (AMD)	1
Not Available	Completed	Not Available	Idiopathic Juxtafoveal Telangiectasia	1
Not Available	Completed	Supportive Care	Age - Related Macular Degeneration (AMD) / Cognitive Dysfunctions	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Capsule	Oral
Capsule, gelatin coated	Oral
Tablet	Oral
Capsule, liquid filled	Oral

Prices

Not Available

Patents

Not Available

Properties

State

Not Available

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.000649 mg/mL	ALOGPS
logP	8.3	ALOGPS
logP	8.35	Chemaxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	18.91	Chemaxon
pKa (Strongest Basic)	-0.79	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	194.95 m3·mol-1	Chemaxon
Polarizability	73.47 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

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available

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Drug created at December 03, 2015 16:51 / Updated at June 12, 2020 16:53