Butoconazole
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Overview
- Description
- A medication used to treat yeast infections.
- Description
- A medication used to treat yeast infections.
- DrugBank ID
- DB00639
- Type
- Small Molecule
- Clinical Trials
- Phase 0
- 0
- Phase 1
- 0
- Phase 2
- 1
- Phase 3
- 4
- Phase 4
- 0
- Mechanism of Action
Identification
- Summary
Butoconazole is an imidazole antifungal used to treat vulvovaginal candidiasis.
- Brand Names
- Gynazole-1
- Generic Name
- Butoconazole
- DrugBank Accession Number
- DB00639
- Background
Butoconazole is an imidazole antifungal used in gynecology.
- Type
- Small Molecule
- Groups
- Approved
- Structure
- Weight
- Average: 411.776
Monoisotopic: 410.017802365 - Chemical Formula
- C19H17Cl3N2S
- Synonyms
- 1-[4-(4-Chloro-phenyl)-2-(2,6-dichloro-phenylsulfanyl)-butyl]-1H-imidazole
- Butoconazol
- Butoconazole
- Butoconazolum
- External IDs
- RS 35887
- RS 35887-00-10-3
- RS 35887-10-3
Pharmacology
- Indication
For the local treatment of vulvovaginal candidiasis (infections caused by Candida)
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
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- Pharmacodynamics
Butoconazole is an imidazole derivative that has fungicidal activity in vitro against Candida spp. and has been demonstrated to be clinically effective against vaginal infections due to Candida albicans. Candida albicans has been identified as the predominant species responsible for vulvovaginal candidasis.
- Mechanism of action
The exact mechanism of the antifungal action of butoconazole is unknown, however, it is presumed to function as other imidazole derivatives via inhibition of steroid synthesis. Imidazoles generally inhibit the conversion of lanosterol to ergosterol via the inhibition of the enzyme cytochrome P450 14α-demethylase, resulting in a change in fungal cell membrane lipid composition. This structural change alters cell permeability and, ultimately, results in the osmotic disruption or growth inhibition of the fungal cell.
Target Actions Organism AErgosterol otherCandida albicans ALanosterol 14-alpha demethylase inhibitorYeast - Absorption
Following vaginal administration of butoconazole nitrate vaginal cream, 2% to 3 women, 1.7% (range 1.3-2.2%) of the dose was absorbed on average.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Oral, rat: LD50 = >1720 mg/kg.
- 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.Not Available
- 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.
- Product Ingredients
Ingredient UNII CAS InChI Key Butoconazole nitrate 4805237NP5 64872-77-1 ZHPWRQIPPNZNML-UHFFFAOYSA-N - International/Other Brands
- Femstat (Bayer) / Femstat 3 (Bayer) / Gynazol (Gedeon Richter) / Gynazole (OM) / Gynofort (Gedeon Richter) / Gynomyk (Will) / Inulead (Fuji Yakuhin) / Mycelex-3 (Bayer) / Volusol (Farmindustria)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Gynazole-1 Cream 20 mg/1g Vaginal Physicians Total Care, Inc. 2003-06-30 2008-06-30 US Gynazole-1 Cream 20 mg/1g Vaginal Ther Rx Corporation 2009-11-23 2011-06-30 US Gynazole.1 Cream 2 % Vaginal Ferring Pharmaceuticals 2004-04-20 2014-01-15 Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Gynazole 1 Cream 100 mg/5g Vaginal AMAG Pharmaceuticals, Inc. 2012-12-27 2016-10-01 US Gynazole 1 Cream 100 mg/5g Vaginal Padagis Israel Pharmaceuticals Ltd 2015-04-29 Not applicable US
Categories
- ATC Codes
- G01AF20 — Combinations of imidazole derivatives
- G01AF — Imidazole derivatives
- G01A — ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
- G01 — GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phenylbutylamines. These are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Phenylbutylamines
- Direct Parent
- Phenylbutylamines
- Alternative Parents
- Thiophenol ethers / Dichlorobenzenes / Alkylarylthioethers / N-substituted imidazoles / Aryl chlorides / Heteroaromatic compounds / Sulfenyl compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds show 2 more
- Substituents
- 1,3-dichlorobenzene / Alkylarylthioether / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Aryl thioether / Azacycle / Azole / Chlorobenzene / Halobenzene show 15 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- conazole antifungal drug, aryl sulfide, imidazoles, imidazole antifungal drug, dichlorobenzene, monochlorobenzenes (CHEBI:3240)
- Affected organisms
- Fungi, yeast and protozoans
Chemical Identifiers
- UNII
- 0Q771797PH
- CAS number
- 64872-76-0
- InChI Key
- SWLMUYACZKCSHZ-UHFFFAOYSA-N
- InChI
- InChI=1S/C19H17Cl3N2S/c20-15-7-4-14(5-8-15)6-9-16(12-24-11-10-23-13-24)25-19-17(21)2-1-3-18(19)22/h1-5,7-8,10-11,13,16H,6,9,12H2
- IUPAC Name
- 1-[4-(4-chlorophenyl)-2-[(2,6-dichlorophenyl)sulfanyl]butyl]-1H-imidazole
- SMILES
- ClC1=CC=C(CCC(CN2C=CN=C2)SC2=C(Cl)C=CC=C2Cl)C=C1
References
- Synthesis Reference
Laszlo Czibula, Laszlo Dobay, Eva Werkne Papp, Judit Nagyne Bagdy, Ferenc Sebok, "High Purity Butoconazole Nitrate with Specified Particle Size and a Process for the Preparation Thereof." U.S. Patent US20080221190, issued September 11, 2008.
US20080221190- General References
- FDA Approved Drug Products: Gynazole-1 (butoconazole nitrate) vaginal cream [Link]
- External Links
- Human Metabolome Database
- HMDB0014777
- KEGG Drug
- D07598
- KEGG Compound
- C08065
- PubChem Compound
- 47472
- PubChem Substance
- 46508016
- ChemSpider
- 43192
- BindingDB
- 79206
- 19884
- ChEBI
- 3240
- ChEMBL
- CHEMBL1295
- Therapeutic Targets Database
- DAP001267
- PharmGKB
- PA164781353
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Butoconazole
- FDA label
- Download (4.11 MB)
- MSDS
- Download (81.6 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Treatment Vulvovaginal Candidiasis 1 somestatus stop reason just information to hide 3 Completed Treatment Vaginal Infections 1 somestatus stop reason just information to hide 3 Completed Treatment Vaginal Inflammation / Vulvovaginitis 1 somestatus stop reason just information to hide 2 Withdrawn Treatment Vulvovaginal Candidiasis 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Roche palo alto llc
- Bayer healthcare llc
- Kv pharmaceutical co
- Packagers
- A-S Medication Solutions LLC
- Bayer Healthcare
- KV Pharmaceutical Co.
- Pharmedix
- Physicians Total Care Inc.
- Ther-Rx Corp.
- Dosage Forms
Form Route Strength Cream Vaginal 100 mg/5g Cream Vaginal 20 mg/1g Cream Vaginal 2 % - Prices
Unit description Cost Unit Gynazole-1 cream 10.89USD g Femstat 3 cream 0.96USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5266329 No 1993-11-30 2010-11-30 US US5993856 No 1999-11-30 2017-11-17 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) ~159°C with decomposition (nitrate salt) Not Available water solubility Nitrate salt: 0.26 mg/ml (practically insoluble) Not Available logP 6.7 Not Available - Predicted Properties
Property Value Source Water Solubility 0.000818 mg/mL ALOGPS logP 6.7 ALOGPS logP 6.55 Chemaxon logS -5.7 ALOGPS pKa (Strongest Basic) 6.51 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 17.82 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 108.99 m3·mol-1 Chemaxon Polarizability 41.01 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9258 Blood Brain Barrier + 0.9716 Caco-2 permeable + 0.6035 P-glycoprotein substrate Non-substrate 0.6398 P-glycoprotein inhibitor I Non-inhibitor 0.6239 P-glycoprotein inhibitor II Inhibitor 0.6822 Renal organic cation transporter Inhibitor 0.7157 CYP450 2C9 substrate Non-substrate 0.7714 CYP450 2D6 substrate Non-substrate 0.8601 CYP450 3A4 substrate Non-substrate 0.6941 CYP450 1A2 substrate Inhibitor 0.934 CYP450 2C9 inhibitor Inhibitor 0.8949 CYP450 2D6 inhibitor Inhibitor 0.8932 CYP450 2C19 inhibitor Inhibitor 0.8994 CYP450 3A4 inhibitor Inhibitor 0.8365 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.9896 Ames test Non AMES toxic 0.7381 Carcinogenicity Non-carcinogens 0.9223 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.0919 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.792 hERG inhibition (predictor II) Inhibitor 0.8263
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0059-6921000000-df9fbb2ed1919d5db32d Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-01q9-0093500000-e8e375492e39f40c30e7 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0a6r-0610900000-eab9dc101ca2b69c1caa Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-03di-0217900000-af425ca7db93cf54bd79 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0059-8920100000-70d1ccd1228d1eacaebd Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0cfr-0914000000-f2ccd916f346103340e1 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-003r-9710100000-22a479b25362ba81cf80 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 184.5623835 predictedDarkChem Lite v0.1.0 [M-H]- 181.65535 predictedDeepCCS 1.0 (2019) [M+H]+ 185.3313835 predictedDarkChem Lite v0.1.0 [M+H]+ 184.01335 predictedDeepCCS 1.0 (2019) [M+Na]+ 185.1349835 predictedDarkChem Lite v0.1.0 [M+Na]+ 190.66496 predictedDeepCCS 1.0 (2019)
Targets
References
- Pfaller MA, Riley J, Koerner T: Effects of terconazole and other azole antifungal agents on the sterol and carbohydrate composition of Candida albicans. Diagn Microbiol Infect Dis. 1990 Jan-Feb;13(1):31-5. [Article]
- Kind
- Protein
- Organism
- Yeast
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Sterol 14alpha-demethylase that plays a critical role in the third module of ergosterol biosynthesis pathway, being ergosterol the major sterol component in fungal membranes that participates in a variety of functions (PubMed:10393548, PubMed:28258218, PubMed:8647850, PubMed:9559662). The third module or late pathway involves the ergosterol synthesis itself through consecutive reactions that mainly occur in the endoplasmic reticulum (ER) membrane (By similarity). In filamentous fungi, during the initial step of this module, lanosterol (lanosta-8,24-dien-3beta-ol) can be metabolized to eburicol (By similarity). Sterol 14alpha-demethylase catalyzes the three-step oxidative removal of the 14alpha-methyl group (C-32) of both these sterols in the form of formate, and converts eburicol and lanosterol to 14-demethyleburicol (4,4,24-trimethylergosta-8,14,24(28)-trienol) and 4,4-dimethyl-5alpha-cholesta-8,14,24-trien-3beta-ol, respectively, which are further metabolized by other enzymes in the pathway to ergosterol (PubMed:10393548, PubMed:28258218, PubMed:8647850, PubMed:9559662). Can also use substrates not intrinsic to fungi, such as 24,25-dihydrolanosterol (DHL), producing 4,4-dimethyl-8,14-cholestadien-3-beta-ol, but at lower rates than the endogenous substrates (By similarity).
- Specific Function
- heme binding
- Gene Name
- ERG11
- Uniprot ID
- P10613
- Uniprot Name
- Lanosterol 14-alpha demethylase
- Molecular Weight
- 60674.965 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Drug created at June 13, 2005 13:24 / Updated at November 06, 2024 20:00