Details
Stereochemistry | ACHIRAL |
Molecular Formula | C40H56 |
Molecular Weight | 536.8726 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 11 |
Charge | 0 |
SHOW SMILES / InChI
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
InChI
InChIKey=OAIJSZIZWZSQBC-GYZMGTAESA-N
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+
Molecular Formula | C40H56 |
Molecular Weight | 536.8726 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 11 |
Optical Activity | NONE |
DescriptionSources: https://www.drugs.com/npc/lycopene.htmlCurator's Comment: description was created based on several sources, including:
http://www.fda.gov/ohrms/dockets/dockets/04q0201/04q-0201-qhc0002-04-Section-B-02-vol1.pdf
http://www.rxlist.com/lycopene-page2/supplements.htm
Sources: https://www.drugs.com/npc/lycopene.html
Curator's Comment: description was created based on several sources, including:
http://www.fda.gov/ohrms/dockets/dockets/04q0201/04q-0201-qhc0002-04-Section-B-02-vol1.pdf
http://www.rxlist.com/lycopene-page2/supplements.htm
Lycopene is the fat-soluble pigment that gives tomatoes, watermelon, pink grapefruit, and other foods their red color. Bioavailability of lycopene is enhanced in the presence of lipids and thermal processing. Lycopene accounts for about 50% of the carotenoids found in human serum and is among the major carotenoids present in human milk. The antioxidant activity of lycopene and its use in cancer prevention and cardiovascular disease have been widely documented. The scientific literature documents some adverse reactions, such as diarrhea, dyspepsia, gas, nausea, and vomiting. One trial documented a cancer-related hemorrhage in a patient taking lycopene, although causality is unclear. Lycopene interacts with some cancer chemotherapy agents, as well as with ciprofloxacin and olestra.
CNS Activity
Curator's Comment: Lycopene was shown to cross the blood brain barrier and be present in the central nervous system in low concentrations.
Deficiency of a series of anti-oxidation nutrients including lycopene is related to such neurodegenerative diseases as Parkinson’s disease, vascular dementia, Alzheimer disease, etc.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: GO:0006979 |
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Target ID: 2697.0 Gene Symbol: GJA1 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Preventing | Ateronon Approved UseUnknown |
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Preventing | Ateronon Approved UseUnknown |
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Preventing | Ateronon Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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4.03 μg/dL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15159319/ |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
LYCOPENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
8.76 μg/dL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15159319/ |
30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered: |
LYCOPENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
9.26 μg/dL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15159319/ |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
LYCOPENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
10.74 μg/dL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15159319/ |
90 mg single, oral dose: 90 mg route of administration: Oral experiment type: SINGLE co-administered: |
LYCOPENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
11.27 μg/dL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15159319/ |
120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered: |
LYCOPENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
273.9 μg × h/dL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15159319/ |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
LYCOPENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
450.8 μg × h/dL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15159319/ |
30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered: |
LYCOPENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
517.3 μg × h/dL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15159319/ |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
LYCOPENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1047.7 μg × h/dL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15159319/ |
90 mg single, oral dose: 90 mg route of administration: Oral experiment type: SINGLE co-administered: |
LYCOPENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
969.8 μg × h/dL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15159319/ |
120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered: |
LYCOPENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
28.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15159319/ |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
LYCOPENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
28.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15159319/ |
30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered: |
LYCOPENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
36.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15159319/ |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
LYCOPENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
61.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15159319/ |
90 mg single, oral dose: 90 mg route of administration: Oral experiment type: SINGLE co-administered: |
LYCOPENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
40.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15159319/ |
120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered: |
LYCOPENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
120 mg single, oral Highest studied dose |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: |
|
30 mg 1 times / day multiple, oral Studied dose Dose: 30 mg, 1 times / day Route: oral Route: multiple Dose: 30 mg, 1 times / day Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
PubMed
Title | Date | PubMed |
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cis-trans isomers of lycopene and beta-carotene in human serum and tissues. | 1992 Apr |
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Skin lycopene is destroyed preferentially over beta-carotene during ultraviolet irradiation in humans. | 1995 Jul |
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The potential role of lycopene for human health. | 1997 Apr |
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The anti-carcinogenic role of lycopene, abundantly present in tomato. | 1999 Aug |
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Intestinal absorption of lycopene from different matrices and interactions to other carotenoids, the lipid status, and the antioxidant capacity of human plasma. | 1999 Jun |
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Lymphocyte lycopene concentration and DNA protection from oxidative damage is increased in women after a short period of tomato consumption. | 2000 Feb |
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Stimulation of gap junctional communication: comparison of acyclo-retinoic acid and lycopene. | 2000 Jan 1 |
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Correlation of chemopreventive efficacy data from the human epidermal cell assay with in vivo data. | 2000 Jan-Feb |
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Lycopene and cardiovascular disease. | 2000 Jun |
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Antioxidant and pro-oxidant effects of lycopene in comparison with beta-carotene on oxidant-induced damage in Hs68 cells. | 2000 Nov |
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Carotenoids and protection against solar UV radiation. | 2002 Sep-Oct |
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Antioxidant status of rats receiving lycopene in different doses. | 2003 Apr |
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Summary of safety studies conducted with synthetic lycopene. | 2003 Apr |
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Lycopene in serum, skin and adipose tissues after tomato-oleoresin supplementation in patients undergoing haemorrhoidectomy or peri-anal fistulotomy. | 2003 Oct |
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Lycopene and vitamin E interfere with autocrine/paracrine loops in the Dunning prostate cancer model. | 2004 Jun |
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Noninvasive selective detection of lycopene and beta-carotene in human skin using Raman spectroscopy. | 2004 Mar-Apr |
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Lycopene and vitamin C concentrations increase in plasma and lymphocytes after tomato intake. Effects on cellular antioxidant protection. | 2004 Oct |
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Upregulation of connexin 43 by retinoids but not by non-provitamin A carotenoids requires RARs. | 2005 |
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Combination of S-allylcysteine and lycopene induces apoptosis by modulating Bcl-2, Bax, Bim and caspases during experimental gastric carcinogenesis. | 2005 Aug |
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Supplementation with tomato-based products increases lycopene, phytofluene, and phytoene levels in human serum and protects against UV-light-induced erythema. | 2005 Jan |
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Inhibitory effects of lycopene on in vitro platelet activation and in vivo prevention of thrombus formation. | 2005 Oct |
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Dietary lycopene downregulates carotenoid 15,15'-monooxygenase and PPAR-gamma in selected rat tissues. | 2006 Apr |
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Lycopene inhibition of IGF-induced cancer cell growth depends on the level of cyclin D1. | 2006 Aug |
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Protective effect of lycopene on adriamycin-induced cardiotoxicity and nephrotoxicity. | 2006 Feb 1 |
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Gene signature of breast cancer cell lines treated with lycopene. | 2006 Jul |
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Retinoids activate the RXR/SXR-mediated pathway and induce the endogenous CYP3A4 activity in Huh7 human hepatoma cells. | 2006 Jul |
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Lycopene differentially induces quiescence and apoptosis in androgen-responsive and -independent prostate cancer cell lines. | 2007 Apr |
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Oral administration of lycopene reverses cadmium-suppressed body weight loss and lipid peroxidation in rats. | 2007 Aug |
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Lycopene and other carotenoids inhibit estrogenic activity of 17beta-estradiol and genistein in cancer cells. | 2007 Aug |
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Gene expression profiling of aging in multiple mouse strains: identification of aging biomarkers and impact of dietary antioxidants. | 2009 Aug |
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Studies on the protective role of lycopene against polychlorinated biphenyls (Aroclor 1254)-induced changes in StAR protein and cytochrome P450 scc enzyme expression on Leydig cells of adult rats. | 2009 Jan |
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Lycopene: An antioxidant and radioprotector against gamma-radiation-induced cellular damages in cultured human lymphocytes. | 2009 Jul 28 |
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Differential effects of several phytochemicals and their derivatives on murine keratinocytes in vitro and in vivo: implications for skin cancer prevention. | 2009 Jun |
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Modulatory effects of lycopene and ellagic acid on reproductive dysfunction induced by polychlorinated biphenyl (Aroclor 1254) in male rats. | 2010 Jun |
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The protective role of procyanidins and lycopene against mercuric chloride renal damage in rats. | 2011 Oct |
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Neurohepatic toxicity of subacute manganese chloride exposure and potential chemoprotective effects of lycopene. | 2012 Jan |
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An interaction between carotene-15,15'-monooxygenase expression and consumption of a tomato or lycopene-containing diet impacts serum and testicular testosterone. | 2012 Jul 15 |
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Inhibitory effects of lycopene on HMGB1-mediated pro-inflammatory responses in both cellular and animal models. | 2012 Jun |
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Protection against chemotaxis in the anti-inflammatory effect of bioactives from tomato ketchup. | 2014 |
|
Lycopene protects against acute zearalenone-induced oxidative, endocrine, inflammatory and reproductive damages in male mice. | 2015 Mar 25 |
Sample Use Guides
As a pure compound it has been studied in clinical trials at dosages of 13 to 75 mg/day. Dosage guidelines from manufacturers ranging from 10 to 30 mg taken twice daily with meals. For example, as an antioxidant, lycopene has been taken in doses of 6.5, 15, and 30 milligrams daily for eight weeks.
To treat asthma caused by exercise, 30 milligrams of lycopene has been taken daily for one week.
Route of Administration:
Oral
In Vitro Use Guide
Sources: http://www.rjpbcs.com/pdf/2012_3(3)/[129].pdf
The lycopene showed significant antioxidant activity against nitric oxide radical with IC50 value of 57.879 ug/ml and antioxidant activity against reducing power method with IC50 value of 45.609 ug/ml respectively.
Substance Class |
Chemical
Created
by
admin
on
Edited
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by
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Record UNII |
SB0N2N0WV6
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Record Status |
Validated (UNII)
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Record Version |
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JECFA EVALUATION |
INS-160D(III)
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DSLD |
164 (Number of products:1777)
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LOINC |
27075-1
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DSLD |
1297 (Number of products:1)
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CODEX ALIMENTARIUS (GSFA) |
INS-160D(III)
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NCI_THESAURUS |
C68307
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15948
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207-949-1
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LYCOPENE
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446925
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407322
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C2226
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1370881
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C015329
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SUB21639
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DB11231
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m6951
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29008
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ACTIVE MOIETY |
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