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

Details

Stereochemistry RACEMIC
Molecular Formula C26H22Cl2N2O3
Molecular Weight 481.37
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DOCONAZOLE

SMILES

ClC1=CC(Cl)=C(C=C1)[C@@]3(CN2C=CN=C2)OC[C@H](COC4=CC=C(C=C4)C5=CC=CC=C5)O3

InChI

InChIKey=GNZHVEIGGFMLSP-OZXSUGGESA-N
InChI=1S/C26H22Cl2N2O3/c27-21-8-11-24(25(28)14-21)26(17-30-13-12-29-18-30)32-16-23(33-26)15-31-22-9-6-20(7-10-22)19-4-2-1-3-5-19/h1-14,18,23H,15-17H2/t23-,26-/m0/s1

HIDE SMILES / InChI

Molecular Formula C26H22Cl2N2O3
Molecular Weight 481.37
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Doconazole is the antifungal agent. It is the first of the dioxolane series, which was later to produce ketoconazole, to appear as a potential drug. Antifungal activity of doconazole was compared with miconazole and amphotericin B activity against a number of pathogenic filamentous fungi. Doconazole was found to be more active than miconazole only against Coccidioides immitis and less active against A.fumigatus, B. dermatitidis, H.capsulatum and S.schenckii. Doconazole has been described as the drug of choice for oral treatment of murine coccidioidomycosis but was dropped because it produced glaucoma in dogs. Doconazole is used for the treatment of infections of the skin and mucous membranes caused by the Herpes simplex type 1 virus, including herpes of lips. Docosanol affects the fusion of the virus with the plasma membrane, which inhibits the penetration of the virus into the cell and its subsequent replication. Side effects are: dry skin, pruritus, rash, short-term redness, soreness, peeling, burning or tingling.

Approval Year

Sample Use Guides

The drug is recommended to be applied in a thin layer on the affected and bordering areas of the skin to adults and children over 12 years of age 5 times a day (approximately every 3 hours) as soon as possible after the onset of infection.
Route of Administration: Topical
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:28:30 GMT 2023
Edited
by admin
on Fri Dec 15 15:28:30 GMT 2023
Record UNII
VR021VC9TY
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DOCONAZOLE
INN   USAN  
USAN   INN  
Official Name English
DOCONAZOLE, (±)-
Common Name English
DOCONAZOLE [USAN]
Common Name English
(±)-DOCONAZOLE
Common Name English
cis-1-[[4-[(4-Biphenyloxy)methyl]-2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl]methyl]imidazole
Common Name English
R 34,000
Code English
doconazole [INN]
Common Name English
R-34000
Code English
1H-IMIDAZOLE, 1-((4-(((1,1'-BIPHENYL)-4-YLOXY)METHYL)-2-(2,4-DICHLOROPHENYL)-1,3-DIOXOLAN-2-YL)METHYL)-, CIS-
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C514
Created by admin on Fri Dec 15 15:28:30 GMT 2023 , Edited by admin on Fri Dec 15 15:28:30 GMT 2023
Code System Code Type Description
INN
4254
Created by admin on Fri Dec 15 15:28:30 GMT 2023 , Edited by admin on Fri Dec 15 15:28:30 GMT 2023
PRIMARY
FDA UNII
VR021VC9TY
Created by admin on Fri Dec 15 15:28:30 GMT 2023 , Edited by admin on Fri Dec 15 15:28:30 GMT 2023
PRIMARY
ChEMBL
CHEMBL2104312
Created by admin on Fri Dec 15 15:28:30 GMT 2023 , Edited by admin on Fri Dec 15 15:28:30 GMT 2023
PRIMARY
CAS
59831-63-9
Created by admin on Fri Dec 15 15:28:30 GMT 2023 , Edited by admin on Fri Dec 15 15:28:30 GMT 2023
PRIMARY
EVMPD
SUB06346MIG
Created by admin on Fri Dec 15 15:28:30 GMT 2023 , Edited by admin on Fri Dec 15 15:28:30 GMT 2023
PRIMARY
NCI_THESAURUS
C65454
Created by admin on Fri Dec 15 15:28:30 GMT 2023 , Edited by admin on Fri Dec 15 15:28:30 GMT 2023
PRIMARY
PUBCHEM
15942727
Created by admin on Fri Dec 15 15:28:30 GMT 2023 , Edited by admin on Fri Dec 15 15:28:30 GMT 2023
PRIMARY
SMS_ID
100000080755
Created by admin on Fri Dec 15 15:28:30 GMT 2023 , Edited by admin on Fri Dec 15 15:28:30 GMT 2023
PRIMARY
EPA CompTox
DTXSID701024238
Created by admin on Fri Dec 15 15:28:30 GMT 2023 , Edited by admin on Fri Dec 15 15:28:30 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY