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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 9-HYDROXY CHRYSAROBIN

SMILES

CC1=CC(O)=C2C(=C1)C=C3C=CC=C(O)C3=C2O

InChI

InChIKey=JBGKVNQFVAJOGC-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/h2-7,16-18H,1H3

HIDE SMILES / InChI

Description
Curator's Comment: Description was created using several sources including: https://www.google.com/patents/US5852060; https://worldwide.espacenet.com/publicationDetails/biblio?FT=D&date=20020626&DB=&locale=&CC=EP&NR=0906114B1&KC=B1&ND=1; http://proz92.com/Research.html; https://www.ncbi.nlm.nih.gov/pubmed/20748534; https://www.ncbi.nlm.nih.gov/pubmed/?term=8597533; https://www.ncbi.nlm.nih.gov/pubmed/?term=21533367; https://www.ncbi.nlm.nih.gov/pubmed/10365914; http://www.fda.gov/downloads/drugs/developmentapprovalprocess/developmentresources/over-the-counterotcdrugs/statusofotcrulemakings/ucm181724.pdf; http://proz92.com/customercare.html

9-Hydroxy chrysarobin or 3-methylanthralin is a pure product of chrysophanic acid reduction. The compound 3-methylanthralin is listed in the Merck Index as an antipsoriatic. Chrysarobin is a mixture of compounds derived from Goa powder, and includes 3-methylanthralin. Goa powder (Araboba) is derived from the wood and bark of Andria Araroba Aguiar (Leguminosae). Literature references describing the isolation of chrysarobin date back to the second part of 1800s. A method of reducing chrysarobin to obtain 3-methylanthralin was known as early as 1931. At present chrysarobin is used in the topical antipsoriatic compositions with natural plant extracts and as a homeopatic product. Pure 3-methylanthralin when tested on mice in vivo was found to play an important role in skin hyperplasia and promotion of skin carcinogenesis by effecting the expression of several gap-junctional proteins connexins (Cxs) and inhibiting glucocorticoid receptor expression in mouse epidermis specifically in keranocytes. Chrysarobin is approved by FDA as an over-the-counter drug. ProZ92 is a trade name a patented botanical formula, topical marketed in Israel which primary anti-psoriatic agents are: 3-methylanthralin, chrysophanol, aloe-emodin and aloe-emodin acetate.

Originator

Curator's Comment: Liebermann and Siedler, are authority for the statement that chrysophanic acid does not exist ready-formed in araroba, but is formed by oxidation of a natural constituent to which the name chrysarobin was given

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ProZ92

Approved Use

skin/scalp psoriasis from moderate to severe psoriasis form
PubMed

PubMed

TitleDatePubMed
Inhibition of the glucocorticoid receptor expression by diverse tumor promoters in SENCAR mouse epidermis.
1997-02
Effect of diverse tumor promoters on the expression of gap-junctional proteins connexin (Cx)26, Cx31.1, and Cx43 in SENCAR mouse epidermis.
1996-03
Patents

Sample Use Guides

In Vivo Use Guide
Treat the site at night before going to bed. Shake the Pro Z92 bottle well. Using a cotton swab, apply a light coating of the compound to the affected area. Do not overuse. One dip of a cotton swab is enough to cover a 2x2 inch area. For larger areas, you may use a cotton ball. (See note below on treating psoriasis on 30% or more of the body.) Do not apply on wounds or cracked skin. Do not wash the treated area for at least three hours. Treated areas may itch or burn for a few minutes. Do not scratch at any time during the treatment. This will worsen your symptoms and increase the time required to heal. You may use sweet almond oil or wheat germ oil to relieve the itching and soften the skin. Administer the treatment at about the same time each day for the first week. Starting the second week, apply Pro Z92 every other day. For Extra strength ProZ92 use it once every 3 days. Stop treatment after your skin becomes clear of psoriasis. This normally takes between 2 and 18 weeks. For some, the treatment period may be longer.
Route of Administration: Topical
In Vitro Use Guide
Unknown
Name Type Language
3-METHYLANTHRALIN
Preferred Name English
9-HYDROXY CHRYSAROBIN
Common Name English
CHRYSAROBIN 9-HYDROXY ANALOG [MI]
Common Name English
CHRYSOPHANIC ACID ANTHRANOL
Common Name English
PURIFIED ARAROBA
Common Name English
3-METHYL-1,8,9-ANTHRACENETRIOL
Systematic Name English
1,8,9-TRIHYDROXY-3-METHYLANTHRACENE
Systematic Name English
Code System Code Type Description
CAS
491-59-8
Created by admin on Mon Mar 31 21:18:30 GMT 2025 , Edited by admin on Mon Mar 31 21:18:30 GMT 2025
PRIMARY
FDA UNII
0433FJV3CI
Created by admin on Mon Mar 31 21:18:30 GMT 2025 , Edited by admin on Mon Mar 31 21:18:30 GMT 2025
PRIMARY
PUBCHEM
10288
Created by admin on Mon Mar 31 21:18:30 GMT 2025 , Edited by admin on Mon Mar 31 21:18:30 GMT 2025
PRIMARY
MERCK INDEX
m3527
Created by admin on Mon Mar 31 21:18:30 GMT 2025 , Edited by admin on Mon Mar 31 21:18:30 GMT 2025
PRIMARY Merck Index
EPA CompTox
DTXSID1048671
Created by admin on Mon Mar 31 21:18:30 GMT 2025 , Edited by admin on Mon Mar 31 21:18:30 GMT 2025
PRIMARY