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Identification
NameTerconazole
Accession NumberDB00251  (APRD00659)
TypeSmall Molecule
GroupsApproved
Description

Terconazole is an anti-fungal medication, primarily used to treat vaginal fungal infections. [Wikipedia]

Structure
Thumb
Synonyms
Terazol 3
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Taro-terconazole Creamcream0.4 %vaginalTaro Pharmaceuticals Inc2004-09-21Not applicableCanada
Terazol 3cream8 mg/gvaginalA S Medication Solutions Llc1991-02-21Not applicableUs
Terazol 3cream8 mg/gvaginalJanssen Pharmaceuticals, Inc.1991-02-21Not applicableUs
Terazol 3cream8 mg/gvaginalOrtho Mc Neil Janssen Pharmaceutical1991-02-21Not applicableUs
Terazol 3suppository80 mg/1vaginalJanssen Pharmaceuticals, Inc.1988-05-24Not applicableUs
Terazol 3suppository80 mg/1vaginalOrtho Mc Neil Janssen Pharmaceutical1988-06-27Not applicableUs
Terazol 3 Vaginal Cream 0.8%cream0.8 %vaginalJanssen Inc1992-12-312007-08-11Canada
Terazol 3 Vaginal Ovules 80mgovule80 mgvaginalJanssen Inc1991-12-312008-08-08Canada
Terazol 7cream4 mg/gvaginalOrtho Mc Neil Janssen Pharmaceutical1988-06-27Not applicableUs
Terazol 7cream4 mg/gvaginalJanssen Pharmaceuticals, Inc.1987-12-31Not applicableUs
Terazol 7 Vaginal Cream 0.4%cream4 mgvaginalJanssen Inc1991-12-31Not applicableCanada
Terconazolecream8 mg/gvaginalDispensing Solutions, Inc.2004-04-01Not applicableUs
Terconazolecream8 mg/gvaginalActavis Pharma, Inc2004-04-01Not applicableUs
Terconazolecream4 mg/gvaginalActavis Pharma, Inc2004-04-01Not applicableUs
Terconazolecream4 mg/gvaginalH.J. Harkins Company, Inc.2004-04-01Not applicableUs
Terconazolecream8 mg/gvaginalRebel Distributors Corp2004-04-01Not applicableUs
Terconazole Vaginal Cream 0.8%cream8 mg/gvaginalE. FOUGERA & CO. A division of Nycomed US Inc.2004-10-01Not applicableUs
Zazolecream8 mg/gvaginalPharmaDerm, A division of Nycomed US Inc.2009-10-02Not applicableUs
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Terconazolecream4 mg/gvaginalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2005-02-18Not applicableUs
Terconazolecream8 mg/gvaginalTaro Pharmaceuticals U.S.A., Inc.2004-04-06Not applicableUs
Terconazolesuppository80 mg/1vaginalPerrigo New York Inc2006-08-28Not applicableUs
Terconazolecream4 mg/gvaginalRebel Distributors Corp2005-01-19Not applicableUs
Terconazolecream4 mg/gvaginalPhysicians Total Care, Inc.2010-08-24Not applicableUs
Terconazolesuppository80 mg/1vaginalG & W LABORATORIES, INC.2015-09-25Not applicableUs
Terconazolecream8 mg/gvaginalPhysicians Total Care, Inc.2004-11-18Not applicableUs
Terconazolesuppository80 mg/1vaginalTaro Pharmaceuticals U.S.A., Inc.2007-03-09Not applicableUs
Terconazolecream4 mg/gvaginalTaro Pharmaceuticals U.S.A., Inc.2005-01-19Not applicableUs
Zazolesuppository80 mg/1vaginalPharma Derm A Division Of Fougera Pharmaceuticals Inc.2006-07-12Not applicableUs
Zazolecream4 mg/gvaginalPharma Derm A Division Of Fougera Pharmaceuticals Inc.2005-02-18Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
TerazolNot Available
Brand mixtures
NameLabellerIngredients
Terazol 3 Dual PakJanssen Inc
SaltsNot Available
Categories
UNII0KJ2VE664U
CAS number67915-31-5
WeightAverage: 532.462
Monoisotopic: 531.180395297
Chemical FormulaC26H31Cl2N5O3
InChI KeyInChIKey=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[[email protected]]2CO[C@@](CN3C=NC=N3)(O2)C2=C(Cl)C=C(Cl)C=C2)C=C1
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazinanes
Sub ClassPiperazines
Direct ParentPhenylpiperazines
Alternative Parents
Substituents
  • N-arylpiperazine
  • Phenylpiperazine
  • Substituted aniline
  • Dialkylarylamine
  • Phenol ether
  • 1,3-dichlorobenzene
  • N-alkylpiperazine
  • Glycerol ether
  • Halobenzene
  • Chlorobenzene
  • Aniline
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl chloride
  • Heteroaromatic compound
  • 1,2,4-triazole
  • Azole
  • Meta-dioxolane
  • Tertiary aliphatic amine
  • Tertiary amine
  • Oxacycle
  • Azacycle
  • Ether
  • Acetal
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the treatment of candidiasis (a yeast-like fungal infection) of the vulva and vagina.
PharmacodynamicsTerconazole 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 actionTerconazole 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.
Related Articles
AbsorptionFollowing 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 distributionNot Available
Protein binding94.9%
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 eliminationFollowing oral (30 mg) administration of 14C-labelled terconazole, excretion of radioactivity was both by renal (32-56%) and fecal (47-52%) routes.
Half life6.9 hours (range 4.0-11.3)
ClearanceNot Available
ToxicityThe oral LD50 values were found to be 1741 and 849 mg/kg for the male and female in rat.
Affected organisms
  • Fungi
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
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
Dosage forms
FormRouteStrength
Creamvaginal0.4 %
Creamvaginal8 mg/g
Suppositoryvaginal80 mg/1
Ovule; kit; creamvaginal
Creamvaginal0.8 %
Ovulevaginal80 mg
Creamvaginal4 mg/g
Creamvaginal4 mg
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.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point126.3 °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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesG01AG02
AHFS Codes
  • 84:04.08.08
PDB EntriesNot Available
FDA labelDownload (33.8 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
ProgesteroneThe therapeutic efficacy of Progesterone can be decreased when used in combination with Terconazole.
Food InteractionsNot Available

Targets

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
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. [PubMed:1951574 ]
  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. [PubMed:10592235 ]
  3. Cauwenbergh G, Vanden Bossche H: Terconazole. Pharmacology of a new antimycotic agent. J Reprod Med. 1989 Aug;34(8 Suppl):588-92. [PubMed:2677363 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23