Lycopene

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Lycopene
Accession Number
DB11231
Type
Small Molecule
Groups
Approved, Investigational
Description

Lycopene is a naturally occuring red carotenoid pigment that is responsible in red to pink colors seen in tomatoes, pink grapefruit, and other foods [1]. Having a chemical formula of C40H56, lycopene is a tetraterpene assembled from eight isoprene units that are solely composed of carbon and hydrogen. Lycophene may undergo extensive isomerization that allows 1056 theoretical cis-trans configurations; however the all-trans configuration of lycopene is the most predominant isomer found in foods [1, 2] that gives the red hue. Lycopene is a non-essential human nutrient that is classified as a non-provitamin A carotenoid pigment since it lacks a terminal beta ionone ring [1] and does not mediate vitamin A activity. However lycophene is a potent antioxidant molecule that scavenges reactive oxygen species (ROS) singlet oxygen. Tomato lycopene extract is used as a color additive in food products.

Structure
Thumb
Synonyms
Not Available
External IDs
E-160D(III) / FEMA NO. 4110 / INS NO.160D(III) / INS-160D(III) / NSC-407322
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
IQQU Advanced Sunscreen SPF 50Lycopene (0.3 g/0.01g) + D-alpha-Tocopherol acetate (0.3 g/0.01g) + Jojoba oil (1.5 g/0.05g) + Octinoxate (0.9 g/0.03g) + Saccharide isomerate (0.3 g/0.01g) + Titanium dioxide (0.9 g/0.03g)LotionTopicalIqqu Usa Co.2010-07-01Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
PreQue 10Lycopene (5 mg/1) + Ascorbic acid (30 mg/1) + Cholecalciferol (120 [iU]/1) + Cupric oxide (1 mg/1) + Cyanocobalamin (1 ug/1) + Doconexent (50 mg/1) + Docusate sodium (25 mg/1) + Folic Acid (0.5 mg/1) + Iron (15 mg/1) + Magnesium oxide (10 mg/1) + Riboflavin (1.7 mg/1) + Selenium (7.5 ug/1) + Thiamine chloride (1 mg/1) + Ubidecarenone (50 mg/1) + Vitamin A (1250 [iU]/1) + Vitamin E (15 [iU]/1) + Zinc oxide (12.5 mg/1)TabletOralActavis Pharma Company2011-11-01Not applicableUs
PreQue 10Lycopene (5 mg/1) + Ascorbic acid (30 mg/1) + Cholecalciferol (120 [iU]/1) + Cupric oxide (1 mg/1) + Cyanocobalamin (1 ug/1) + Doconexent (50 mg/1) + Docusate sodium (25 mg/1) + Folic Acid (0.5 mg/1) + Iron (15 mg/1) + Magnesium oxide (10 mg/1) + Riboflavin (1.7 mg/1) + Selenium (7.5 ug/1) + Thiamine mononitrate (1 mg/1) + Ubidecarenone (50 mg/1) + Vitamin A (1250 [iU]/1) + Zinc oxide (12.5 mg/1) + alpha-Tocopherol succinate (15 [iU]/1)TabletOralPhysicians Total Care, Inc.2011-11-012013-02-11Us
RE FAC-xLycopene (500 ug/1) + Ascorbic acid (200 mg/1) + Biotin (200 ug/1) + Cholecalciferol (400 [iU]/1) + Chromium picolinate (200 ug/1) + Cupric sulfate pentahydrate (2.5 mg/1) + Cyanocobalamin (2500 ug/1) + Folic Acid (2800 ug/1) + Lutein (500 ug/1) + Magnesium (100 mg/1) + Manganese sulfate (2.5 mg/1) + Nicotinamide (100 mg/1) + Calcium pantothenate (10 mg/1) + Pyridoxine hydrochloride (25 mg/1) + Riboflavin (20 mg/1) + Selenomethionine (100 ug/1) + Thiamine mononitrate (20 mg/1) + Vitamin A (5000 [iU]/1) + Vitamin E (100 [iU]/1) + Zinc (15 mg/1)TabletOralRiver’s Edge Pharmaceuticals, LLC2007-07-012011-01-13Us
Categories
UNII
SB0N2N0WV6
CAS number
502-65-8
Weight
Average: 536.888
Monoisotopic: 536.438201803
Chemical Formula
C40H56
InChI Key
OAIJSZIZWZSQBC-GYZMGTAESA-N
InChI
InChI=1S/C40H56/c1-33(2)19-13-23-37(7)27-17-31-39(9)29-15-25-35(5)21-11-12-22-36(6)26-16-30-40(10)32-18-28-38(8)24-14-20-34(3)4/h11-12,15-22,25-32H,13-14,23-24H2,1-10H3/b12-11+,25-15+,26-16+,31-17+,32-18+,35-21+,36-22+,37-27+,38-28+,39-29+,40-30+
IUPAC Name
(6E,8E,10E,12E,14E,16E,18E,20E,22E,24E,26E)-2,6,10,14,19,23,27,31-octamethyldotriaconta-2,6,8,10,12,14,16,18,20,22,24,26,30-tridecaene
SMILES
CC(C)=CCC\C(C)=C\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C=C(/C)CCC=C(C)C

Pharmacology

Indication
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Lycopene.
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Lycopene.
AncestimThe risk or severity of cytotoxicity can be increased when Ancestim is combined with Lycopene.
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Lycopene.
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Lycopene.
CymarinCymarin may decrease the cardiotoxic activities of Lycopene.
DeslanosideDeslanoside may decrease the cardiotoxic activities of Lycopene.
DigitoxinDigitoxin may decrease the cardiotoxic activities of Lycopene.
DigoxinDigoxin may decrease the cardiotoxic activities of Lycopene.
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Lycopene.
Food Interactions
Not Available

References

General References
  1. Story EN, Kopec RE, Schwartz SJ, Harris GK: An update on the health effects of tomato lycopene. Annu Rev Food Sci Technol. 2010;1:189-210. doi: 10.1146/annurev.food.102308.124120. [PubMed:22129335]
  2. Shi J, Le Maguer M: Lycopene in tomatoes: chemical and physical properties affected by food processing. Crit Rev Food Sci Nutr. 2000 Jan;40(1):1-42. [PubMed:10674200]
  3. Agarwal S, Rao AV: Tomato lycopene and its role in human health and chronic diseases. CMAJ. 2000 Sep 19;163(6):739-44. [PubMed:11022591]
External Links
Human Metabolome Database
HMDB0003000
KEGG Compound
C05432
PubChem Compound
446925
PubChem Substance
347827946
ChemSpider
394156
ChEBI
15948
ChEMBL
CHEMBL501174
HET
LYC
Wikipedia
Lycopene
PDB Entries
1lgh

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedPreventionProstatic Intraepithelial Neoplasia1
1CompletedTreatmentAdenocarcinoma of the Prostate1
1, 2CompletedTreatmentPeriodontitis, Chronic1
2CompletedPreventionBenign Prostatic Hypertrophy (BPH)1
2CompletedPreventionIntraepithelial Prostatic Neoplasia / Prostatic Neoplasms1
2CompletedTreatmentAdenocarcinoma of the Prostate / Stage I Prostate Cancer / Stage II Prostate Cancer / Stage III Prostate Cancer1
2CompletedTreatmentLichen Planus, Oral1
2CompletedTreatmentProstate Cancer1
2RecruitingSupportive CareMetastatic Colorectal Cancers / Skin Toxicities1
2Unknown StatusPreventionAneurysms / Subarachnoid Hemorrhage1
2WithdrawnPreventionTransitional Cell Carcinoma1
4CompletedTreatmentOral Lichen Planus1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
LotionTopical
TabletOral
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000397 mg/mLALOGPS
logP9.16ALOGPS
logP11.93ChemAxon
logS-6.1ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 Å2ChemAxon
Rotatable Bond Count16ChemAxon
Refractivity197.81 m3·mol-1ChemAxon
Polarizability73.69 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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 carotenes. These are a type of unsaturated hydrocarbons containing eight consecutive isoprene units. They 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.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Prenol lipids
Sub Class
Tetraterpenoids
Direct Parent
Carotenes
Alternative Parents
Branched unsaturated hydrocarbons / Unsaturated aliphatic hydrocarbons / Acyclic olefins
Substituents
Carotene / Branched unsaturated hydrocarbon / Unsaturated aliphatic hydrocarbon / Unsaturated hydrocarbon / Olefin / Acyclic olefin / Hydrocarbon / Aliphatic acyclic compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
acyclic carotene (CHEBI:15948) / C40 isoprenoids (tetraterpenes), Carotenoids (C05432) / C40 isoprenoids (tetraterpenes) (LMPR01070257)

Drug created on December 03, 2015 09:51 / Updated on August 02, 2018 06:22