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Details

Stereochemistry ACHIRAL
Molecular Formula C18H16O4
Molecular Weight 296.3172
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUTANTRONE

SMILES

CCCC(=O)C1C2=CC=CC(O)=C2C(=O)C3=C(O)C=CC=C13

InChI

InChIKey=AHZXFRRDQXXPJD-UHFFFAOYSA-N
InChI=1S/C18H16O4/c1-2-5-12(19)15-10-6-3-8-13(20)16(10)18(22)17-11(15)7-4-9-14(17)21/h3-4,6-9,15,20-21H,2,5H2,1H3

HIDE SMILES / InChI

Molecular Formula C18H16O4
Molecular Weight 296.3172
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Butantrone is the 10-butyryl derivative of dithranol with antipsoriatic activity. When butantrone and dithranol were used in equimolar gradually increasing concentrations in short-contact therapy for psoriasis the efficacy of butantrone was somewhat lower compared to dithranol. Butantrone has an antipsoriatic activity almost equal to that of dithranol. When short contact treatment is used, erythema and staining with butantrone are weaker than with dithranol.

Approval Year

PubMed

PubMed

TitleDatePubMed

Sample Use Guides

In Vivo Use Guide
Curator's Comment: An open clinical trial was carried out using butantrone ointment in the treatment of 10 patients with psoriasis in order to assess staining and irritation in relation to efficacy. At 0.5% and 1.0% strengths, butantrone produced significant levels of irritation and staining with minimal clinical response and poor patient compliance. https://www.ncbi.nlm.nih.gov/pubmed/2428761
To see whether the efficacy of butantrone in short-contact therapy could be increased by starting with a single high-concentration directly, 20 psoriatic patients were treated with dithranol (0.1,-0.5,-1.0,-2.0%) and butantrone (3.9%) short-contact therapy as a right-left comparison. With these treatment modalities the antipsoriatic effects of dithranol and butantrone were similar. Although the efficacy of 3.9% butantrone was better than the previously used butantrone therapy with gradually increasing doses, there was a parallel increase in side-effects.
Route of Administration: Topical
In Vitro Use Guide
Non-confluent monolayers of HeLa cells were treated with various concentrations (10(-5)-10(-8) M) of dithranol or butantrone for 45 min. The cells were then cultivated for up to 48 h and treated with 10 microM bromodeoxyuridine (BrdU) and 10 microM fluorodeoxyuridine for 30 min before harvesting. Both drugs at concentrations of 10(-6) and 10(-5) M inhibited the BrdU uptake of HeLa cells, but did not cause any significant change in the proportion of cells in S-phase. The highest (10(-5) M) concentration of butantrone caused an abrupt decrease in cell number.
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:11:08 GMT 2023
Edited
by admin
on Sat Dec 16 17:11:08 GMT 2023
Record UNII
9P148IBA8M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BUTANTRONE
INN   WHO-DD  
INN  
Official Name English
Butantrone [WHO-DD]
Common Name English
butantrone [INN]
Common Name English
10-BUTYRYL-1,8-DIHYDROXYANTHRONE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C29708
Created by admin on Sat Dec 16 17:11:08 GMT 2023 , Edited by admin on Sat Dec 16 17:11:08 GMT 2023
Code System Code Type Description
CAS
75464-11-8
Created by admin on Sat Dec 16 17:11:08 GMT 2023 , Edited by admin on Sat Dec 16 17:11:08 GMT 2023
PRIMARY
SMS_ID
100000088479
Created by admin on Sat Dec 16 17:11:08 GMT 2023 , Edited by admin on Sat Dec 16 17:11:08 GMT 2023
PRIMARY
MESH
C038464
Created by admin on Sat Dec 16 17:11:08 GMT 2023 , Edited by admin on Sat Dec 16 17:11:08 GMT 2023
PRIMARY
INN
5258
Created by admin on Sat Dec 16 17:11:08 GMT 2023 , Edited by admin on Sat Dec 16 17:11:08 GMT 2023
PRIMARY
ChEMBL
CHEMBL130968
Created by admin on Sat Dec 16 17:11:08 GMT 2023 , Edited by admin on Sat Dec 16 17:11:08 GMT 2023
PRIMARY
FDA UNII
9P148IBA8M
Created by admin on Sat Dec 16 17:11:08 GMT 2023 , Edited by admin on Sat Dec 16 17:11:08 GMT 2023
PRIMARY
PUBCHEM
53271
Created by admin on Sat Dec 16 17:11:08 GMT 2023 , Edited by admin on Sat Dec 16 17:11:08 GMT 2023
PRIMARY
NCI_THESAURUS
C74164
Created by admin on Sat Dec 16 17:11:08 GMT 2023 , Edited by admin on Sat Dec 16 17:11:08 GMT 2023
PRIMARY
EPA CompTox
DTXSID10226395
Created by admin on Sat Dec 16 17:11:08 GMT 2023 , Edited by admin on Sat Dec 16 17:11:08 GMT 2023
PRIMARY
EVMPD
SUB06006MIG
Created by admin on Sat Dec 16 17:11:08 GMT 2023 , Edited by admin on Sat Dec 16 17:11:08 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY