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. 1Due to the existence of 2 stereocentres, there are 4 possible stereoisomers for terconazole.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Terconazole (DB00251)
- Weight
- Average: 532.47
Monoisotopic: 531.1803953 - Chemical Formula
- C26H31Cl2N5O3
- Synonyms
- Terconazole
Pharmacology
- Indication
For the treatment of candidiasis (a yeast-like fungal infection) of the vulva and vagina.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Vulvovaginal candidiasis •••••••••••• - Contraindications & Blackbox Warnings
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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.
Target Actions Organism ACytochrome P450 51 antagonistYeast - 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
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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
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Terazol
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Terazol 3 Cream 8 mg/1g Vaginal Janssen Pharmaceuticals, Inc. 1991-02-21 2020-06-15 US 
Terazol 3 Suppository 80 mg/1 Vaginal Physicians Total Care, Inc. 1996-07-24 2012-06-30 US Terazol 3 Suppository 80 mg/1 Vaginal Janssen Pharmaceuticals, Inc. 1988-05-24 2020-06-15 US Terazol 3 Cream 8 mg/1g Vaginal Physicians Total Care, Inc. 1994-09-01 2012-07-16 US Terazol 3 Cream 8 mg/1g Vaginal A S Medication Solutions 1991-02-21 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Taro-terconazole Cream 0.4 % Vaginal Taro Pharmaceuticals, Inc. 2004-09-21 Not applicable Canada 
Terconazole Cream 4 mg/1g Vaginal E. Fougera & Co. a division of Fougera Pharmaceuticals Inc. 2005-02-18 Not applicable US Terconazole Cream 4 mg/1g Vaginal A-S Medication Solutions 2005-01-19 Not applicable US Terconazole Cream 4 mg/1g Vaginal Rpk Pharmaceuticals, Inc. 2005-01-19 Not applicable US Terconazole Cream 8 mg/1g Vaginal A-S Medication Solutions 2004-04-06 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Terazol 3 Dual Pak Terconazole (80 mg) + Terconazole (0.8 %) Cream; Insert; Kit Vaginal Janssen Pharmaceuticals 1994-12-31 2014-03-19 Canada Terazol 3 Dual Pak Terconazole (80 mg) + Terconazole (0.8 %) Cream; Insert; Kit Vaginal Janssen Pharmaceuticals 1994-12-31 2014-03-19 Canada TEREX-3 Terconazole (0.8 g) + Dexamethasone acetate (3.58 mg) Cream Vaginal LABORATORIOS CHALVER DE COLOMBIA S.A. 2018-06-20 Not applicable Colombia 
VAGICORT® CREMA VAGINAL Terconazole (0.8 g) + Dexamethasone acetate (3.58 mg) Cream Vaginal LABORATORIO FRANCO COLOMBIANO - LAFRANCOL S.A.S. 2010-03-10 Not applicable Colombia
Categories
- ATC Codes
- G01AG02 — Terconazole
- Drug Categories
- Classification
- Not classified
- Affected organisms
- Fungi
Chemical Identifiers
- UNII
- 0KJ2VE664U
- CAS number
- 67915-31-5
- InChI Key
- BLSQLHNBWJLIBQ-ZEQKJWHPSA-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-/m1/s1
- IUPAC Name
- 1-(4-{[(2S,4R)-2-(2,4-dichlorophenyl)-2-[(1H-1,2,4-triazol-1-yl)methyl]-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
- Thomason JL: Clinical evaluation of terconazole. United states experience. J Reprod Med. 1989 Aug;34(8 Suppl):597-601. [Article]
- 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]
- FDA Approved Drug Products: TERAZOL (terconazole) cream and suppositories [Link]
- External Links
- Human Metabolome Database
- HMDB0014396
- KEGG Drug
- D00888
- KEGG Compound
- C08080
- PubChem Compound
- 441383
- PubChem Substance
- 46505257
- ChemSpider
- 421966
- BindingDB
- 31769
- 37806
- ChEBI
- 82981
- ChEMBL
- CHEMBL1410669
- ZINC
- ZINC000000897382
- 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
Phase Status Purpose Conditions Count 4 Completed Treatment Vulvovaginal Candidiasis 1 3 Completed Treatment Vaginal Infections 2 3 Unknown Status Treatment Vaginal Candidiasis 1 1 Completed Not Available HIV, Prevention 1 0 Completed Treatment Vaginal Inflammation 1
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
Form Route Strength Cream Vaginal 0.8 g Insert Vaginal Cream Vaginal 0.4 % Suppository Vaginal 80 mg/1 Cream; insert; kit Vaginal Cream Vaginal 0.8 % Insert Vaginal 80 mg Cream Vaginal 4 mg / g Cream Vaginal Cream Vaginal 4 mg/1g Cream Vaginal 8 mg/1g Cream Vaginal - Prices
Unit description Cost Unit Terazol 3 0.8% Cream 20 gm Tube 55.99USD tube Terazol 7 0.4% Cream 45 gm Tube 54.0USD tube Terazol 3 3 80 mg Suppository Box 53.99USD box Terconazole 3 80 mg Suppository Box 50.9USD box Terconazole 0.4% Cream 45 gm Tube 42.57USD tube Terconazole 0.8% Cream 20 gm Tube 42.57USD tube Terazol 3 cream 2.64USD g Zazole 0.8% vaginal cream 2.54USD g Terconazole 0.8% cream 2.35USD g Terazol 7 cream 1.17USD g Terconazole 0.4% cream 0.96USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 126.3 °C Not Available logP 4.5 Not Available - Predicted Properties
Property Value Source Water Solubility 0.0116 mg/mL ALOGPS logP 4.58 ALOGPS logP 5.37 Chemaxon logS -4.7 ALOGPS pKa (Strongest Basic) 8.41 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 64.88 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 153.19 m3·mol-1 Chemaxon Polarizability 56.59 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9926 Blood Brain Barrier + 0.6657 Caco-2 permeable + 0.6081 P-glycoprotein substrate Substrate 0.7064 P-glycoprotein inhibitor I Inhibitor 0.8563 P-glycoprotein inhibitor II Inhibitor 0.7891 Renal organic cation transporter Inhibitor 0.5272 CYP450 2C9 substrate Non-substrate 0.8484 CYP450 2D6 substrate Non-substrate 0.8227 CYP450 3A4 substrate Substrate 0.6986 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.907 CYP450 2D6 inhibitor Non-inhibitor 0.923 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Inhibitor 0.796 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8354 Ames test Non AMES toxic 0.5825 Carcinogenicity Non-carcinogens 0.7686 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.8114 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.6633 hERG inhibition (predictor II) Inhibitor 0.603
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Not Available
Targets
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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
- 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]
- 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]
- 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 at June 13, 2005 13:24 / Updated at April 18, 2024 09:15