LAWSONE

US Previously Marketed

Details

Stereochemistry	ACHIRAL
Molecular Formula	C10H6O3
Molecular Weight	174.1528
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=CC(=O)C2=C(C=CC=C2)C1=O

InChI

InChIKey=CSFWPUWCSPOLJW-UHFFFAOYSA-N

InChI=1S/C10H6O3/c11-8-5-9(12)10(13)7-4-2-1-3-6(7)8/h1-5,12H

HIDE SMILES / InChI

Molecular Formula	C10H6O3
Molecular Weight	174.1528
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18498522 | https://clinicaltrials.gov/ct2/show/NCT01751893 | https://www.ncbi.nlm.nih.gov/pubmed/24374273

Lawsone (aka hennatannic acid) is a red-orange dye present in the leaves of the henna plant as well as the flower of water hyacinth. Henna extracts have been used by humans as hair and skin dyes for more than 5000 years. Henna extracts have been clinically investigated as a method of reducing dose-limiting Chemotherapy-Induced Palmoplantar Erythrodysesthesia.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Tyrosinase 41 Target ID: P14679 Gene ID: 7299.0 Gene Symbol: TYR Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/25584612	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Chemotherapy-induced palmoplantar erythrodysesthesia 1 Sources: https://clinicaltrials.gov/ct2/show/NCT01751893	Secondary	Not Provided 504	Unknown Approved Use Unknown
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24374273	Primary	Basic research	Unknown Approved Use Unknown
Skin cancer 23 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25584612	Primary	Basic research	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:44401	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:44401
ChemicalBook	CB2493073	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB2493073
MolPort	MolPort-000-726-184	https://www.molport.com/shop/molecule-link/MolPort-000-726-184
ZINC	ZINC000004632115	http://zinc15.docking.org/substances/ZINC000004632115
eMolecules	539195	https://www.emolecules.com/cgi-bin/more?vid=539195

PubMed

Title	Date	PubMed
Hydroxyquinones are competitive non-peptide inhibitors of HIV-1 proteinase.	1995 Nov 15	7492599
Antiretroviral agents as inhibitors of both human immunodeficiency virus type 1 integrase and protease.	1996 Jun 21	8691444
Discovery, total synthesis, HRV 3C-protease inhibitory activity, and structure-activity relationships of 2-methoxystypandrone and its analogues.	2001 Dec 17	11720861
Structure-activity relationships of anthraquinones on the suppression of DNA-binding activity of the aryl hydrocarbon receptor induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin.	2009 Mar	19269596
Biological evaluation of hydroxynaphthoquinones as anti-malarials.	2013 Jul 10	23841934

Patents

Sample Use Guides

In Vivo Use Guide

In a mouse skin carcinogen model, mice that were fed lawsone (0.0025%) for 10 weeks decreased tumor incidence by 72% and multiplicity by 50%. The trend continued throughout the 20 week testing period.

Route of Administration: Oral

In Vitro Use Guide

Lawsone was investigated for growth inhibitory activity against a panel of 6 human cancer cell lines exhibiting different levels of resistance to pro-apoptotic stimuli using the MTT colorimetric assay; including U373, A549, Hs683, SKMEL-28, PC3, LoVo. Lawsone demonstrated IC50 values of 58 microM against A549 cells and 31 microM against Hs683 cells. The IC50 values for other cell lines were reported as > 100 microM.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:42:35 UTC 2023` Edited by `admin` on `Fri Dec 15 15:42:35 UTC 2023`
Record UNII	TLH4A6LV1W
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LAWSONE

Official Name

English

1,4-NAPHTHOQUINONE, 2-HYDROXY-

Systematic Name

English

NSC-52500

Code

English

C.I. NATURAL ORANGE 6

Common Name

English

NSC-8625

Code

English

NSC-27285

Code

English

HENNA (DYE)

Common Name

English

LAWSONE [INCI]

Common Name

English

LAWSONE [MI]

Common Name

English

2-HYDROXY-1,4-NAPHTHALENEDIONE

Systematic Name

English

Q 0

Common Name

English

LAWSONE [MART.]

Common Name

English

IMEXINE OG

Brand Name

English

1,4-NAPHTHALENEDIONE, 2-HYDROXY-

Systematic Name

English

2-HYDROXY-1,4-NAPTHOQUINONE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C461