LYCOPENE

First approved in 2007

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

Structure Search

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+

HIDE SMILES / InChI

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

Description
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
response to oxidative stress 20 Target ID: GO:0006979 Sources: http://www.fda.gov/ohrms/dockets/dockets/04q0201/04q-0201-qhc0002-04-Section-B-02-vol1.pdf	Modulator 828
gap junction protein alpha 1 1 Target ID: 2697.0 Gene Symbol: GJA1 Sources: http://www.ncbi.nlm.nih.gov/pubmed/12468619 \| http://www.ncbi.nlm.nih.gov/pubmed/12424335 \| http://www.fda.gov/ohrms/dockets/dockets/04q0201/04q-0201-qhc0002-04-Section-B-02-vol1.pdf	Activator 1430

Conditions

Condition	Modality	Highest Phase	Product
Prostate cancer 178 Sources: http://www.medscape.com/viewarticle/487510 http://www.fda.gov/ohrms/dockets/dockets/04q0201/04q-0201-qhc0002-04-Section-B-02-vol1.pdf http://www.fda.gov/Food/IngredientsPackagingLabeling/LabelingNutrition/ucm072767.htm	Preventing	Phase III 656	Ateronon Approved Use Unknown
Coronary heart disease 41 Sources: https://www.drugs.com/npp/lycopene.html http://www.ateronon.com/latest-news/ateronons-new-formula-lactolycopene-thiamine-and-selenium/	Preventing	Phase III 656	Ateronon Approved Use Unknown
Atherosclerosis 74 Sources: http://www.rxlist.com/lycopene/supplements.htm http://www.ncbi.nlm.nih.gov/pubmed/22023768	Preventing	Phase III 656	Ateronon Approved Use Unknown

PubMed

Title	Date	PubMed
Skin lycopene is destroyed preferentially over beta-carotene during ultraviolet irradiation in humans.	1995 Jul	7616301
The potential role of lycopene for human health.	1997 Apr	9100211
Intestinal absorption of lycopene from different matrices and interactions to other carotenoids, the lipid status, and the antioxidant capacity of human plasma.	1999 Jun	10443333
Stimulation of gap junctional communication: comparison of acyclo-retinoic acid and lycopene.	2000 Jan 1	10620348
Lycopene and cardiovascular disease.	2000 Jun	10837319
Antioxidant and pro-oxidant effects of lycopene in comparison with beta-carotene on oxidant-induced damage in Hs68 cells.	2000 Nov	11137891
Lycopene and vitamin E interfere with autocrine/paracrine loops in the Dunning prostate cancer model.	2004 Jun	15084515
Lycopene and vitamin C concentrations increase in plasma and lymphocytes after tomato intake. Effects on cellular antioxidant protection.	2004 Oct	15054415
Upregulation of connexin 43 by retinoids but not by non-provitamin A carotenoids requires RARs.	2005	16091010
Protective effect of lycopene on adriamycin-induced cardiotoxicity and nephrotoxicity.	2006 Feb 1	16325981
Differential effects of several phytochemicals and their derivatives on murine keratinocytes in vitro and in vivo: implications for skin cancer prevention.	2009 Jun	19329757
Modulatory effects of lycopene and ellagic acid on reproductive dysfunction induced by polychlorinated biphenyl (Aroclor 1254) in male rats.	2010 Jun	20074268
The protective role of procyanidins and lycopene against mercuric chloride renal damage in rats.	2011 Oct	22108423
Neurohepatic toxicity of subacute manganese chloride exposure and potential chemoprotective effects of lycopene.	2012 Jan	22192907
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	21935922
Inhibitory effects of lycopene on HMGB1-mediated pro-inflammatory responses in both cellular and animal models.	2012 Jun	22429818
Modulatory effect of lycopene on deltamethrin-induced testicular injury in rats.	2013 Apr	23076637
Lycopene modulates initiation of N-nitrosodiethylamine induced hepatocarcinogenesis: studies on chromosomal abnormalities, membrane fluidity and antioxidant defense system.	2013 Nov 25	24144777
Protection against chemotaxis in the anti-inflammatory effect of bioactives from tomato ketchup.	2014	25551565
Lycopene protects against acute zearalenone-induced oxidative, endocrine, inflammatory and reproductive damages in male mice.	2015 Mar 25	25682699

Patents

Sample Use Guides

In Vivo Use Guide

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

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 `Fri Dec 15 15:56:44 GMT 2023` Edited by `admin` on `Fri Dec 15 15:56:44 GMT 2023`
Record UNII	SB0N2N0WV6
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

LYCOPENE

Official Name

English

INS-160D(III)

Code

English

TOMAT-O-RED

Common Name

English

TOMATO LYCOPENE [FHFI]

Common Name

English

(ALL-TRANS)-LYCOPENE

Common Name

English

LYCORED

Common Name

English

LYCOPENE [MI]

Common Name

English

LYCOPENE [MART.]

Common Name

English

LYCOPENE PREPARATION [USP-RS]

Common Name

English

LYCOPENE EXTRACT FROM TOMATO [FCC]

Common Name

English

Solanorubin

Common Name

English

(ALL-E)-2,6,10,14,19,23,27,31-OCTAMETHYL-2,6,8,10,12,14,16,18,20,22,24,26,30-DOTRIACONTATRIDECAENE

Common Name

English

(ALL-E)-LYCOPENE (CONSTITUENT OF LYCOPENE AND TOMATO EXTRACT CONTAINING LYCOPENE) [DSC]

Common Name

English

FEMA NO. 4110

Code

English

CI 75125 [INCI]

Common Name

English

LYCOPENE FROM BLAKESLEA TRISPORA [FCC]

Common Name

English

NSC-407322

Code

English

LYCOPENE [INCI]

Common Name

English

BLAKESLEA TRISPORA

Common Name

English

ATERONON

Brand Name

English

REDIVIVO

Common Name

English

Lycopene [WHO-DD]

Common Name

English

LYCOPENE FROM BLAKESLEA TRISPORA

Common Name

English

E-160D(III)

Code

English

(ALL-E)-LYCOPENE

Common Name

English

INS NO.160D(III)

Code

English

LYCOPENE EXTRACT FROM TOMATO

Common Name

English

MEXORYL SAQ

Common Name

English

LYCOPENE [VANDF]

Common Name

English

AEC LYCOPENE

Brand Name

English

CI 75125

Official Name

English

Classification Tree Code System Code

JECFA EVALUATION

INS-160D(III)