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Details

Stereochemistry RACEMIC
Molecular Formula C26H31Cl2N5O3
Molecular Weight 532.4629
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TERCONAZOLE

SMILES

CC(C)N1CCN(CC1)c2ccc(cc2)OC[C@]3([H])CO[C@@](Cn4cncn4)(c5ccc(cc5Cl)Cl)O3

InChI

InChIKey=BLSQLHNBWJLIBQ-ZEQKJWHPSA-N
InChI=1S/C26H31Cl2N5O3/c1-19(2)31-9-11-32(12-10-31)21-4-6-22(7-5-21)34-14-23-15-35-26(36-23,16-33-18-29-17-30-33)24-8-3-20(27)13-25(24)28/h3-8,13,17-19,23H,9-12,14-16H2,1-2H3/t23-,26-/m1/s1

HIDE SMILES / InChI

Description
Curator's Comment:: description was created based on several sources, including http://reference.medscape.com/drug/terazol-3-terconazole-vaginal-342596 | https://www.drugs.com/cdi/terconazole-cream.html | https://www.drugbank.ca/drugs/DB00251 | https://www.ncbi.nlm.nih.gov/pubmed/3891537

Terconazole is an antifungal drug used to treat vaginal yeast infection. Terconazole may exert its antifungal activity by disrupting normal fungal cell membrane permeability. Terconazole and other triazole antifungal agents inhibit cytochrome P450 "14-alpha-demethylase" in susceptible fungi, which leads to the accumulation of lanosterol and other methylated sterols and a decrease in ergosterol concentration. Depletion of ergosterol in the membrane disrupts the structure and function of the fungal cell leading to a decrease or inhibition of fungal growth. During controlled clinical studies conducted in the United States, 521 patients with vulvovaginal candidiasis were treated with terconazole 0.4% vaginal cream. Based on comparative analyses with placebo, the adverse experiences considered most likely related to terconazole 0.4% vaginal cream were a headache and body pain. Fever and chills, vulvovaginal burning, itching, and irritation have also been reported. The adverse drug experience on terconazole most frequently causing discontinuation was vulvovaginal itching.

Originator

Sources: Research report. Naval Medical Research Institute (U.S.) (1945), (2), 1-6.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
8.9 µM [EC50]
3.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
TERAZOL 7

Approved Use

Terconazole vaginal cream 0.4% is indicated for the local treatment of vulvovaginal candidiasis (moniliasis). As terconazole vaginal cream 0.4% is effective only for vulvovaginitis caused by the genus Candida, the diagnosis should be confirmed by KOH smears and/or cultures.

Launch Date

5.6790719E11
Preventing
TERAZOL 7

Approved Use

Terconazole vaginal cream 0.4% is indicated for the local treatment of vulvovaginal candidiasis (moniliasis). As terconazole vaginal cream 0.4% is effective only for vulvovaginitis caused by the genus Candida, the diagnosis should be confirmed by KOH smears and/or cultures.

Launch Date

5.6790719E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
5.9 ng/mL
40 mg 1 times / day multiple, vaginal
dose: 40 mg
route of administration: Vaginal
experiment type: MULTIPLE
co-administered:
TERCONAZOLE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
6.9 h
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TERCONAZOLE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
5.1%
TERCONAZOLE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
0.8 % 1 times / day multiple, vaginal
Recommended
Dose: 0.8 %, 1 times / day
Route: vaginal
Route: multiple
Dose: 0.8 %, 1 times / day
Sources:
unhealthy, adult
n = 243
Health Status: unhealthy
Condition: vulvovaginal candidiasis
Age Group: adult
Sex: F
Population Size: 243
Sources:
Disc. AE: Allergic reaction, Vaginitis...
AEs leading to
discontinuation/dose reduction:
Allergic reaction
Vaginitis
Sources:
AEs

AEs

AESignificanceDosePopulation
Allergic reaction Disc. AE
0.8 % 1 times / day multiple, vaginal
Recommended
Dose: 0.8 %, 1 times / day
Route: vaginal
Route: multiple
Dose: 0.8 %, 1 times / day
Sources:
unhealthy, adult
n = 243
Health Status: unhealthy
Condition: vulvovaginal candidiasis
Age Group: adult
Sex: F
Population Size: 243
Sources:
Vaginitis Disc. AE
0.8 % 1 times / day multiple, vaginal
Recommended
Dose: 0.8 %, 1 times / day
Route: vaginal
Route: multiple
Dose: 0.8 %, 1 times / day
Sources:
unhealthy, adult
n = 243
Health Status: unhealthy
Condition: vulvovaginal candidiasis
Age Group: adult
Sex: F
Population Size: 243
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes
PubMed

PubMed

TitleDatePubMed
Topical treatment for vaginal candidiasis (thrush) in pregnancy.
2001
Paecilomyces lilacinus vaginitis in an immuno-competent patient.
2003 Sep
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Enantiomeric separation of ketoconazole and terconazole antifungals by electrokinetic chromatography: Rapid quantitative analysis of ketoconazole in pharmaceutical formulations.
2005 Oct
Inhibition of the enzymatic activity of heme oxygenases by azole-based antifungal drugs.
2006 Oct
Anti-inflammatory and anti-itch activity of sertaconazole nitrate.
2006 Sep
Fungistatic activity of freshly killed termite, Nasutitermes acajutlae, soldiers in the Caribbean.
2007
Enantioselective separation of azole compounds by EKC. Reversal of migration order of enantiomers with CD concentration.
2007 Aug
Chromatographic/mass spectrometric method for the estimation of itraconazole and its metabolite in human plasma. Application to a bioequivalence study.
2009
About the role of enantioselective selector-selectand interactions and the mobilities of diastereomeric associates in enantiomer separations using CE.
2009 Aug
Identification of antifungal compounds active against Candida albicans using an improved high-throughput Caenorhabditis elegans assay.
2009 Sep 14
5-(4-Chloro-phen-yl)-3-(2,4-dimethyl-thiazol-5-yl)-1,2,4-triazolo[3,4-a]isoquinoline.
2010 Apr 10
Chemical combinations elucidate pathway interactions and regulation relevant to Hepatitis C replication.
2010 Jun 8
Chromatographic and electrophoretic techniques used in the analysis of triazole antifungal agents-a review.
2010 Sep 15
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
Elucidating mechanisms of toxicity using phenotypic data from primary human cell systems--a chemical biology approach for thrombosis-related side effects.
2015 Jan 5
Patents

Sample Use Guides

One full applicator (5 g) of TERAZOL® 7 Vaginal Cream (20 mg terconazole) should be administered intravaginally once daily at bedtime for seven consecutive days. One full applicator (5 g) of TERAZOL® 3 Vaginal Cream (40 mg terconazole) should be administered intravaginally once daily at bedtime for three consecutive days. One TERAZOL® 3 Vaginal Suppository (80 mg terconazole) should be administered intravaginally once daily at bedtime for three consecutive days.
Route of Administration: Vaginal
In Vitro Use Guide
Terconazole was dissolved in methyl alcohol to a final concentration of 250 mkg/ml. 20 mkl of these solutions were added to 6 mm blank antibiotic discs (BBL) and dried at room temperature to yield 5 mkg/disk. The disks were applied to the inoculated surface of a two-layer agar assay plate (150 mm dia.). The base uninoculated layer contained 42 ml of the supplemented agar selected for the study. The agar selected was TSA containing 16 mkg/ml biotin, sodium chloride. 1.5% (w/v), pH 7.4. The inoculated top layer consisted of 8 ml of the same agar. The final cell count was 6.4 X 10^4 colony-forming units (CFU)/ml of agar. Within 30 min of preparation of the agar plate, disks of each of the test compounds were placed on the agar surface and the plates incubated 48 h at 37.5 °C. The zones of inhibition were measured to the nearest 0.5 mm
Name Type Language
TERCONAZOLE
EP   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
R-42,470
Code English
R-42470
Code English
PIPERAZINE, 1-(4-((2-(2,4-DICHLOROPHENYL)-2-(1H-1,2,4-TRIAZOL-1-YLMETHYL)-1,3-DIOXOLAN-4-YL)METHOXY)PHENYL)-4-(1-METHYLETHYL)-, CIS
Common Name English
TERCONAZOLE [INN]
Common Name English
TERCONAZOLE [VANDF]
Common Name English
FUNGISTAT
Brand Name English
TERCONAZOLE [USP-RS]
Common Name English
TERCONAZOLE [WHO-DD]
Common Name English
TERMAYAZOLE
Brand Name English
TRIACONAZOLE
Common Name English
CIS-1-(P-((2-(2,4-DICHLOROPHENYL)-2-(1H-1,2,4-TRIAZOL-1-YLMETHYL)-1,3-DIOXOLAN-4-YL)METHOXY)PHENYL)-4-ISOPROPYLPIPERAZINE
Common Name English
TERCONAZOLE [USP MONOGRAPH]
Common Name English
TERCONAZOLE [EP MONOGRAPH]
Common Name English
TERCONAZOLE [MART.]
Common Name English
TERCOSPOR
Brand Name English
TERAZOL 3
Brand Name English
R 42470
Code English
NSC-331942
Code English
TERCONAZOLE [ORANGE BOOK]
Common Name English
TERCONAZOLE [USAN]
Common Name English
TERCONAZOLE [MI]
Common Name English
TERAZOL
Systematic Name English
Classification Tree Code System Code
WHO-VATC QG01AG02
Created by admin on Fri Jun 25 20:52:38 UTC 2021 , Edited by admin on Fri Jun 25 20:52:38 UTC 2021
WHO-ATC G01AG02
Created by admin on Fri Jun 25 20:52:38 UTC 2021 , Edited by admin on Fri Jun 25 20:52:38 UTC 2021
NCI_THESAURUS C514
Created by admin on Fri Jun 25 20:52:38 UTC 2021 , Edited by admin on Fri Jun 25 20:52:38 UTC 2021
NDF-RT N0000008217
Created by admin on Fri Jun 25 20:52:38 UTC 2021 , Edited by admin on Fri Jun 25 20:52:38 UTC 2021
NDF-RT N0000175487
Created by admin on Fri Jun 25 20:52:38 UTC 2021 , Edited by admin on Fri Jun 25 20:52:38 UTC 2021
Code System Code Type Description
ECHA (EC/EINECS)
267-751-6
Created by admin on Fri Jun 25 20:52:38 UTC 2021 , Edited by admin on Fri Jun 25 20:52:38 UTC 2021
PRIMARY
DRUG BANK
DB00251
Created by admin on Fri Jun 25 20:52:38 UTC 2021 , Edited by admin on Fri Jun 25 20:52:38 UTC 2021
PRIMARY
LACTMED
Terconazole
Created by admin on Fri Jun 25 20:52:38 UTC 2021 , Edited by admin on Fri Jun 25 20:52:38 UTC 2021
PRIMARY
USP_CATALOG
1643703
Created by admin on Fri Jun 25 20:52:38 UTC 2021 , Edited by admin on Fri Jun 25 20:52:38 UTC 2021
PRIMARY USP-RS
CAS
67915-31-5
Created by admin on Fri Jun 25 20:52:38 UTC 2021 , Edited by admin on Fri Jun 25 20:52:38 UTC 2021
PRIMARY
MERCK INDEX
M10573
Created by admin on Fri Jun 25 20:52:38 UTC 2021 , Edited by admin on Fri Jun 25 20:52:38 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
TERCONAZOLE
Created by admin on Fri Jun 25 20:52:38 UTC 2021 , Edited by admin on Fri Jun 25 20:52:38 UTC 2021
PRIMARY
ChEMBL
CHEMBL1306
Created by admin on Fri Jun 25 20:52:38 UTC 2021 , Edited by admin on Fri Jun 25 20:52:38 UTC 2021
PRIMARY
EVMPD
SUB10917MIG
Created by admin on Fri Jun 25 20:52:38 UTC 2021 , Edited by admin on Fri Jun 25 20:52:38 UTC 2021
PRIMARY
MESH
C037815
Created by admin on Fri Jun 25 20:52:38 UTC 2021 , Edited by admin on Fri Jun 25 20:52:38 UTC 2021
PRIMARY
PUBCHEM
480953
Created by admin on Fri Jun 25 20:52:38 UTC 2021 , Edited by admin on Fri Jun 25 20:52:38 UTC 2021
PRIMARY
EPA CompTox
67915-31-5
Created by admin on Fri Jun 25 20:52:38 UTC 2021 , Edited by admin on Fri Jun 25 20:52:38 UTC 2021
PRIMARY
INN
4815
Created by admin on Fri Jun 25 20:52:38 UTC 2021 , Edited by admin on Fri Jun 25 20:52:38 UTC 2021
PRIMARY
FDA UNII
0KJ2VE664U
Created by admin on Fri Jun 25 20:52:38 UTC 2021 , Edited by admin on Fri Jun 25 20:52:38 UTC 2021
PRIMARY
DRUG CENTRAL
2599
Created by admin on Fri Jun 25 20:52:38 UTC 2021 , Edited by admin on Fri Jun 25 20:52:38 UTC 2021
PRIMARY
RXCUI
37806
Created by admin on Fri Jun 25 20:52:38 UTC 2021 , Edited by admin on Fri Jun 25 20:52:38 UTC 2021
PRIMARY RxNorm
NCI_THESAURUS
C29493
Created by admin on Fri Jun 25 20:52:38 UTC 2021 , Edited by admin on Fri Jun 25 20:52:38 UTC 2021
PRIMARY