U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C15H12O3
Molecular Weight 240.254
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CHRYSAROBIN

SMILES

CC1=CC(O)=C2C(=O)C3=C(CC2=C1)C=CC=C3O

InChI

InChIKey=ZZBWSNKBZKPGAK-UHFFFAOYSA-N
InChI=1S/C15H12O3/c1-8-5-10-7-9-3-2-4-11(16)13(9)15(18)14(10)12(17)6-8/h2-6,16-17H,7H2,1H3

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including http://www.drugfuture.com/chemdata/chrysarobin.html | http://www.google.com/patents/US4007271 | http://www.henriettes-herb.com/eclectic/kings/chrysarobin.html | https://www.ncbi.nlm.nih.gov/pubmed/1401327 | https://www.ncbi.nlm.nih.gov/pubmed/3135955 | https://www.ncbi.nlm.nih.gov/pubmed/3986797

Chrysarobin was originally extracted from Goa powder, a substance deposited in the wood of Andira Araroba, Aguiar (Nat. Ord.—Leguminosae). Chrysarobin (1,8-dihydroxy-3-methyl-9-anthrone) has enol tautomer of 1,8,9-trihydroxy-3-methyl-anthracene. Chrysarobin exerts antipsoriatic action. The use of chrysarobin has a number of quite serious disadvantages, not the least of which is that it can result in severe staining and irritation of the skin. Chrysarobin is an anthrone skin tumor promoter.

Originator

Approval Year

1921
1467
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Activator
1430
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
Unknown

Approved Use

Unknown
Sourcing

Sourcing

Vendor/AggregatorIDURL
Compound Cloud
68111
HongKong Chemhere
SCD43078
ZINC
ZINC000002040462
http://zinc15.docking.org/substances/ZINC000002040462
PubMed

PubMed

TitleDatePubMed
History of the treatment of psoriasis.
1992 Oct
Patents

Patents

EP0083359B1
1
US4699929
1

Sample Use Guides

In Vivo Use Guide
Chrysarobin was used in the form of 1-5% ointment
Route of Administration: Topical
In Vitro Use Guide
Curator's Comment: In V79 cells, the concentration of anthraquinones and structurally related compounds including chrysarobin causing 50% inhibition ranged from 0.21 to 21.6 mug/ml for cloning efficiency and from 0.86 to 14.6 mug/ml for MTT reduction.
Unknown
Name Type Language
CHRYSAROBIN
MI   WHO-DD  
Common Name English
CHRYSOPHANOL-9-ANTHRONE
Common Name English
Chrysarobin [WHO-DD]
Common Name English
CHRYSOPHANOL ANTHRONE
Common Name English
CHRYSAROBINUM
HPUS  
Common Name English
CHRYSAROBIN [MI]
Common Name English
1,8-DIHYDROXY-3-METHYL-9-ANTHRONE
Systematic Name English
1,8-DIHYDROXY-3-METHYL-9(10H)-ANTHRACENONE
Systematic Name English
CHRYSOPHANOLANTHRONE
Common Name English
CHRYSAROBINUM [HPUS]
Common Name English
CHRYSOPHANIC ACID 9-ANTHRONE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C761
Created by admin on Fri Dec 15 15:20:30 UTC 2023 , Edited by admin on Fri Dec 15 15:20:30 UTC 2023
NCI_THESAURUS C514
Created by admin on Fri Dec 15 15:20:30 UTC 2023 , Edited by admin on Fri Dec 15 15:20:30 UTC 2023
Code System Code Type Description
CHEBI
3686
Created by admin on Fri Dec 15 15:20:30 UTC 2023 , Edited by admin on Fri Dec 15 15:20:30 UTC 2023
PRIMARY
EPA CompTox
DTXSID20197683
Created by admin on Fri Dec 15 15:20:30 UTC 2023 , Edited by admin on Fri Dec 15 15:20:30 UTC 2023
PRIMARY
NCI_THESAURUS
C372
Created by admin on Fri Dec 15 15:20:30 UTC 2023 , Edited by admin on Fri Dec 15 15:20:30 UTC 2023
PRIMARY
MERCK INDEX
m3527
Created by admin on Fri Dec 15 15:20:30 UTC 2023 , Edited by admin on Fri Dec 15 15:20:30 UTC 2023
PRIMARY Merck Index
SMS_ID
100000080087
Created by admin on Fri Dec 15 15:20:30 UTC 2023 , Edited by admin on Fri Dec 15 15:20:30 UTC 2023
PRIMARY
DAILYMED
6307EF51M1
Created by admin on Fri Dec 15 15:20:30 UTC 2023 , Edited by admin on Fri Dec 15 15:20:30 UTC 2023
PRIMARY
CAS
491-58-7
Created by admin on Fri Dec 15 15:20:30 UTC 2023 , Edited by admin on Fri Dec 15 15:20:30 UTC 2023
PRIMARY
RXCUI
1860418
Created by admin on Fri Dec 15 15:20:30 UTC 2023 , Edited by admin on Fri Dec 15 15:20:30 UTC 2023
PRIMARY
EVMPD
SUB13367MIG
Created by admin on Fri Dec 15 15:20:30 UTC 2023 , Edited by admin on Fri Dec 15 15:20:30 UTC 2023
PRIMARY
MESH
C013883
Created by admin on Fri Dec 15 15:20:30 UTC 2023 , Edited by admin on Fri Dec 15 15:20:30 UTC 2023
PRIMARY
ECHA (EC/EINECS)
207-740-5
Created by admin on Fri Dec 15 15:20:30 UTC 2023 , Edited by admin on Fri Dec 15 15:20:30 UTC 2023
PRIMARY
FDA UNII
6307EF51M1
Created by admin on Fri Dec 15 15:20:30 UTC 2023 , Edited by admin on Fri Dec 15 15:20:30 UTC 2023
PRIMARY
PUBCHEM
68111
Created by admin on Fri Dec 15 15:20:30 UTC 2023 , Edited by admin on Fri Dec 15 15:20:30 UTC 2023
PRIMARY
ACTIVE MOIETY
Structure of CHRYSAROBIN
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966