Terconazole

Identification

Summary

Terconazole is an antifungal drug used in the treatment of vulvovaginal candidiasis.

Brand Names
Terazol 3
Generic Name
Terconazole
DrugBank Accession Number
DB00251
Background

Terconazole is an anti-fungal drug that is mainly used to treat vaginal yeast infections (or vaginal candidiasis). It is classified as a triazole ketal derivative.2 Terconazole was initially approved by the FDA in 1987.Label This drug is available in cream and suppository forms and both have demonstrated high levels of safety, efficacy, and tolerability in clinical trials. 1

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 532.462
Monoisotopic: 531.180395297
Chemical Formula
C26H31Cl2N5O3
Synonyms
  • Terconazole

Pharmacology

Indication

For the treatment of candidiasis (a yeast-like fungal infection) of the vulva and vagina.

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Terconazole is a triazole antifungal agent available for intravaginal use. It is structurally related to imidazole-derivative antifungal agents, although terconazole and other triazoles have 3 nitrogens in the azole ring. By inhibiting the 14-alpha-demethylase (lanosterol 14-alpha-demethylase), Terconazole inhibits ergosterol synthesis. Depletion of ergosterol in fungal membrane disrupts the structure and many functions of fungal membrane leading to inhibition of fungal growth.

Mechanism of action

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.

TargetActionsOrganism
ACytochrome P450 51
antagonist
Yeast
Absorption

Following intravaginal administration of terconazole in humans, absorption ranged from 5-8% in three hysterectomized subjects and 12-16% in two non-hysterectomized subjects with tubal ligations

Volume of distribution

Not Available

Protein binding

94.9%

Metabolism

Systemically absorbed drug appears to be rapidly and extensively metabolized. Terconazole primarily undergoes oxidatative N- and O-dealkylation, dioxolane ring cleavage, and conjugation.

Route of elimination

Following oral (30 mg) administration of 14C-labelled terconazole, excretion of radioactivity was both by renal (32-56%) and fecal (47-52%) routes.

Half-life

6.9 hours (range 4.0-11.3)

Clearance

Not Available

Adverse Effects
Medicalerrors
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Toxicity

The oral LD50 values were found to be 1741 and 849 mg/kg for the male and female in rat.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
No interactions found.
Food Interactions
No interactions found.

Products

Products
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International/Other Brands
Terazol
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Terazol 3Cream8 mg/1gVaginalOrtho Mc Neil Pharmaceuticals1991-02-212016-02-29US flag
Terazol 3Suppository80 mg/1VaginalPhysicians Total Care, Inc.1996-07-242012-06-30US flag
Terazol 3Suppository80 mg/1VaginalJanssen Pharmaceuticals, Inc.1988-05-242020-06-15US flag
Terazol 3Cream8 mg/1gVaginalPhysicians Total Care, Inc.1994-09-012012-07-16US flag
Terazol 3Suppository80 mg/1VaginalOrtho Mc Neil Pharmaceuticals1988-06-272014-03-31US flag
Terazol 3Cream8 mg/1gVaginalA S Medication Solutions1991-02-21Not applicableUS flag
Terazol 3Cream8 mg/1gVaginalJanssen Pharmaceuticals, Inc.1991-02-212020-06-15US flag
Terazol 3 Vaginal Cream 0.8%Cream0.8 %VaginalJanssen Pharmaceuticals1992-12-312007-08-11Canada flag
Terazol 3 Vaginal Ovules 80mgInsert80 mgVaginalJanssen Pharmaceuticals1991-12-312008-08-08Canada flag
Terazol 7Cream4 mg/1gVaginalJanssen Pharmaceuticals, Inc.1987-12-312020-06-15US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Taro-terconazole CreamCream0.4 %VaginalTaro Pharmaceuticals, Inc.2004-09-21Not applicableCanada flag
TerconazoleCream8 mg/1gVaginalREMEDYREPACK INC.2018-05-142020-05-19US flag
TerconazoleCream4 mg/1gVaginalTaro Pharmaceuticals U.S.A., Inc.2005-01-19Not applicableUS flag
TerconazoleCream4 mg/1gVaginalRpk Pharmaceuticals, Inc.2005-01-19Not applicableUS flag
TerconazoleCream8 mg/1gVaginalPhysicians Total Care, Inc.2004-11-18Not applicableUS flag
TerconazoleSuppository80 mg/1VaginalTaro Pharmaceuticals U.S.A., Inc.2007-03-09Not applicableUS flag
TerconazoleSuppository80 mg/1VaginalCosette Pharmaceuticals, Inc.2015-09-25Not applicableUS flag
TerconazoleCream8 mg/1gVaginalNucare Pharmaceuticals,inc.2004-04-06Not applicableUS flag
TerconazoleCream8 mg/1gVaginalA-S Medication Solutions2004-04-012016-10-31US flag
TerconazoleSuppository80 mg/1VaginalPerrigo New York Inc2006-08-28Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Terazol 3 Dual PakTerconazole (80 mg) + Terconazole (0.8 %)Cream; Insert; KitVaginalJanssen Pharmaceuticals1994-12-312014-03-19Canada flag
Terazol 3 Dual PakTerconazole (80 mg) + Terconazole (0.8 %)Cream; Insert; KitVaginalJanssen Pharmaceuticals1994-12-312014-03-19Canada flag
TEREX-3Terconazole (0.8 g) + Dexamethasone acetate (3.58 mg)CreamVaginalLABORATORIOS CHALVER DE COLOMBIA S.A.2018-06-20Not applicableColombia flag
VAGICORT� CREMA VAGINALTerconazole (0.8 g) + Dexamethasone acetate (3.58 mg)CreamVaginalLABORATORIO FRANCO COLOMBIANO LAFRANCOL S.A.S.2010-03-10Not applicableColombia flag

Categories

ATC Codes
G01AG02 — Terconazole
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenylpiperazines. These are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Diazinanes
Sub Class
Piperazines
Direct Parent
Phenylpiperazines
Alternative Parents
N-arylpiperazines / Aminophenyl ethers / Phenoxy compounds / Dichlorobenzenes / Dialkylarylamines / Aniline and substituted anilines / Alkyl aryl ethers / N-alkylpiperazines / Ketals / Aryl chlorides
show 9 more
Substituents
1,2,4-triazole / 1,3-dichlorobenzene / Acetal / Alkyl aryl ether / Amine / Aminophenyl ether / Aniline or substituted anilines / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide
show 28 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
1-(4-\{[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy\}phenyl)-4-isopropylpiperazine (CHEBI:82980)
Affected organisms
  • Fungi

Chemical Identifiers

UNII
0KJ2VE664U
CAS number
67915-31-5
InChI Key
BLSQLHNBWJLIBQ-OZXSUGGESA-N
InChI
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-/m0/s1
IUPAC Name
1-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-(propan-2-yl)piperazine
SMILES
CC(C)N1CCN(CC1)C1=CC=C(OC[C@H]2CO[C@@](CN3C=NC=N3)(O2)C2=C(Cl)C=C(Cl)C=C2)C=C1

References

General References
  1. Thomason JL: Clinical evaluation of terconazole. United states experience. J Reprod Med. 1989 Aug;34(8 Suppl):597-601. [Article]
  2. Pfaller MA, Gerarden T: Susceptibility of clinical isolates of Candida spp. to terconazole and other azole antifungal agents. Diagn Microbiol Infect Dis. 1989 Nov-Dec;12(6):467-71. [Article]
Human Metabolome Database
HMDB0014396
KEGG Drug
D00888
KEGG Compound
C08080
PubChem Compound
441383
PubChem Substance
46505257
ChemSpider
390122
BindingDB
50375318
RxNav
37806
ChEBI
82980
ChEMBL
CHEMBL1306
ZINC
ZINC000003873936
Therapeutic Targets Database
DAP000629
PharmGKB
PA164768834
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Terconazole
FDA label
Download (105 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentVulvovaginal Candidiasis1
3CompletedTreatmentVaginal Infections2
3Unknown StatusTreatmentVaginal Candidiasis1
1CompletedNot AvailableHIV, Prevention1
0CompletedTreatmentVaginal Inflammation1
Not AvailableCompletedTreatmentVulvovaginal Candidiasis1
Not AvailableNot Yet RecruitingTreatmentVulvovaginal Candidiasis1

Pharmacoeconomics

Manufacturers
  • Ortho mcneil janssen pharmaceuticals inc
  • Altana inc
  • Nycomed us inc
  • Taro pharmaceuticals usa inc
  • Ortho mcneil janssen pharmaceutical inc
  • Perrigo new york inc
Packagers
  • A-S Medication Solutions LLC
  • Dept Health Central Pharmacy
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • E. Fougera and Co.
  • Lake Erie Medical and Surgical Supply
  • Nycomed Inc.
  • Ortho Mcneil Janssen Pharmaceutical Inc.
  • Ortho-McNeil-Janssen Pharmaceuticals Inc.
  • Perrigo Co.
  • Pharmaderm
  • Pharmedix
  • Physicians Total Care Inc.
  • Rebel Distributors Corp.
  • Stat Rx Usa
  • Taro Pharmaceuticals USA
  • Watson Pharmaceuticals
Dosage Forms
FormRouteStrength
CreamVaginal0.8 g
InsertVaginal80 mg
InsertVaginal
CreamVaginal0.4 %
SuppositoryVaginal80 mg/1
Cream; insert; kitVaginal
CreamVaginal0.8 %
CreamVaginal4 mg / g
CreamVaginal
CreamVaginal4 mg/1g
CreamVaginal8 mg/1g
CreamVaginal
Prices
Unit descriptionCostUnit
Terazol 3 0.8% Cream 20 gm Tube55.99USD tube
Terazol 7 0.4% Cream 45 gm Tube54.0USD tube
Terazol 3 3 80 mg Suppository Box53.99USD box
Terconazole 3 80 mg Suppository Box50.9USD box
Terconazole 0.4% Cream 45 gm Tube42.57USD tube
Terconazole 0.8% Cream 20 gm Tube42.57USD tube
Terazol 3 cream2.64USD g
Zazole 0.8% vaginal cream2.54USD g
Terconazole 0.8% cream2.35USD g
Terazol 7 cream1.17USD g
Terconazole 0.4% cream0.96USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)126.3 °CNot Available
logP4.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0116 mg/mLALOGPS
logP4.58ALOGPS
logP5.37ChemAxon
logS-4.7ALOGPS
pKa (Strongest Basic)8.41ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area64.88 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity153.19 m3·mol-1ChemAxon
Polarizability56.15 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9926
Blood Brain Barrier+0.6657
Caco-2 permeable+0.6081
P-glycoprotein substrateSubstrate0.7064
P-glycoprotein inhibitor IInhibitor0.8563
P-glycoprotein inhibitor IIInhibitor0.7891
Renal organic cation transporterInhibitor0.5272
CYP450 2C9 substrateNon-substrate0.8484
CYP450 2D6 substrateNon-substrate0.8227
CYP450 3A4 substrateSubstrate0.6986
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.923
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorInhibitor0.796
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8354
Ames testNon AMES toxic0.5825
CarcinogenicityNon-carcinogens0.7686
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.8114 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6633
hERG inhibition (predictor II)Inhibitor0.603
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00o0-3971230000-dd66741ee49b1efec5ef

Targets

Drugtargets
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Kind
Protein
Organism
Yeast
Pharmacological action
Yes
Actions
Antagonist
General Function
Sterol 14-demethylase activity
Specific Function
Catalyzes C14-demethylation of lanosterol which is critical for ergosterol biosynthesis. It transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol.
Gene Name
ERG11
Uniprot ID
P10613
Uniprot Name
Lanosterol 14-alpha demethylase
Molecular Weight
60674.965 Da
References
  1. Vanden Bossche H, Marichal P: Mode of action of anti-Candida drugs: focus on terconazole and other ergosterol biosynthesis inhibitors. Am J Obstet Gynecol. 1991 Oct;165(4 Pt 2):1193-9. [Article]
  2. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
  3. Cauwenbergh G, Vanden Bossche H: Terconazole. Pharmacology of a new antimycotic agent. J Reprod Med. 1989 Aug;34(8 Suppl):588-92. [Article]

Drug created on June 13, 2005 13:24 / Updated on July 29, 2021 06:27