チオコナゾール
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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2015/10/16 23:03:49」(JST)
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Tioconazole
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Systematic (IUPAC) name |
(RS)-1-[2-[(2-Chloro-3-thienyl)methoxy]-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole
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Clinical data |
Trade names |
Vagistat-1 |
AHFS/Drugs.com |
monograph |
Legal status |
|
Routes of
administration |
Topical |
Identifiers |
CAS Registry Number |
65899-73-2 Y |
ATC code |
D01AC07 G01AF08 |
PubChem |
CID: 5482 |
DrugBank |
DB01007 N |
ChemSpider |
5282 N |
UNII |
S57Y5X1117 N |
KEGG |
D00890 Y |
ChEBI |
CHEBI:9604 N |
ChEMBL |
CHEMBL1200438 N |
Synonyms |
Thioconazole |
Chemical data |
Formula |
C16H13Cl3N2OS |
Molecular mass |
387.711 g/mol |
N (what is this?) (verify) |
Tioconazole is an antifungal medication of the imidazole class used to treat infections caused by a fungus or yeast. It is marketed under the brand names Trosyd and Gyno-Trosyd (Pfizer). Tioconazole ointments serve to treat women's vaginal yeast infections.[1] They are available in one day doses, as opposed to the 7-day treatments more common in use in the past.
Tioconazole topical (skin) preparations are also available for ringworm, jock itch, athlete's foot, and tinea versicolor or "sun fungus".
Contents
- 1 Side effects
- 2 Synthesis
- 3 See also
- 4 References
Side effects
Side effects (for the women's formulas) may include temporary burning/irritation of the vaginal area, moderate drowsiness, headache similar to a sinus headache, hives, and upper respiratory infection.[citation needed] These side effects may be only temporary, and do not normally interfere with the patient's comfort enough to outweigh the end result.
Synthesis
Antimycotic imidazole derivative.
Tiaconazole synthesis:
[2]
A displacement reaction between 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol and 2-chloro-3-(chloromethyl)thiophene is performed.
See also
References
- ^ Tioconazole, Mayo Clinic
- ^ G. E. Gymer, BE 841309 ; idem, U.S. Patent 4,062,966 (1976, 1977 both to Pfizer).
- ^ Godefroi, E. F.; Heeres, J.; Van Cutsem, J.; Janssen, P. A. J. (1969). "Preparation and antimycotic properties of derivatives of 1-phenethylimidazole". Journal of Medicinal Chemistry 12 (5): 784. doi:10.1021/jm00305a014.
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Wikimedia Commons has media related to Tioconazole. |
Antifungals (D01 and J02)
|
|
Wall/
membrane |
Ergosterol
inhibitors |
Azoles
(lanosterol 14
alpha-demethylase inhibitors) |
Imidazoles |
- Topical: bifonazole
- butoconazole
- chlormidazole
- clotrimazole#
- croconazole
- econazole
- fenticonazole
- ketoconazole
- isoconazole
- miconazole#
- neticonazole
- omoconazole
- oxiconazole
- sertaconazole
- sulconazole
- tioconazole
|
|
Triazoles |
- Topical: (fluconazole#, fosfluconazole
- terconazole)
- Systemic: (fluconazole
- hexaconazole
- isavuconazole
- itraconazole
- posaconazole
- voriconazole)
|
|
Thiazoles |
|
|
|
Polyene antimycotics
(ergosterol binding) |
- Topical: (hamycin
- natamycin
- nystatin#)
Systemic: (amphotericin B#, hamycin)
|
|
Allylamines
(squalene monooxygenase
inhibitors) |
- Topical: (amorolfine
- butenafine
- naftifine
- terbinafine)
Systemic: terbinafine
|
|
|
β-glucan synthase
inhibitors |
- echinocandins (anidulafungin
- caspofungin
- micafungin)
|
|
|
Intracellular |
Pyrimidine analogues/
thymidylate synthase inhibitors |
|
|
Mitotic inhibitors |
|
|
Aminoacyl tRNA synthetase inhibitors |
|
|
|
Others |
- bromochlorosalicylanilide
- methylrosaniline
- tribromometacresol
- undecylenic acid
- polynoxylin
- chlorophetanol
- chlorphenesin
- ticlatone
- sulbentine
- ethylparaben
- haloprogin
- salicylic acid
- selenium disulfide#
- ciclopirox
- amorolfine
- dimazole
- tolnaftate
- tolciclate
- sodium thiosulfate#
- Whitfield's ointment#
- potassium iodide#
- taurolidine
- tea tree oil
- citronella oil
- lemon grass
- orange oil
- patchouli
- lemon myrtle
- PCP: pentamidine
- dapsone
- atovaquone
|
|
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
Index of fungal disease
|
|
Description |
|
|
Disease |
|
|
Treatment |
|
|
|
Gynecological anti-infectives and antiseptics (G01)
|
|
Antibiotics |
- Candicidin
- Chloramphenicol
- Hachimycin
- Oxytetracycline
- Carfecillin
- Mepartricin
- Clindamycin
- Pentamycin
|
|
Arsenic compounds |
|
|
Quinoline derivatives |
- Diiodohydroxyquinoline
- Clioquinol
- Chlorquinaldol
- Dequalinium
- Broxyquinoline
- Oxyquinoline
|
|
Organic acids |
- Lactic acid
- Acetic acid
- Ascorbic acid
|
|
Sulfonamides |
|
|
Antifungals |
Imidazoles |
- Metronidazole
- Clotrimazole
- Miconazole
- Econazole
- Ornidazole
- Isoconazole
- Tioconazole
- Ketoconazole
- Fenticonazole
- Azanidazole
- Propenidazole
- Butoconazole
- Omoconazole
- Oxiconazole
- Flutrimazole
|
|
Triazoles |
|
|
Polyenes |
- Nystatin
- Natamycin
- Amphotericin B
|
|
Other |
- Ciclopirox
- Methylrosaniline
|
|
|
Other |
- Clodantoin
- Inosine
- Policresulen
- Nifuratel
- Furazolidone
- Povidone-iodine
- Protiofate
- Lactobacillus fermentum
- Copper usnate
|
|
Index of reproductive medicine
|
|
Description |
- Anatomy
- Physiology
- Development
- sex determination and differentiation
|
|
Disease |
- Infections
- Congenital
- Neoplasms and cancer
- male
- female
- gonadal
- germ cell
- Other
- Symptoms and signs
|
|
Treatment |
- Procedures
- Drugs
- benign prostatic hypertrophy
- erectile dysfunction and premature ejaculation
- sexual dysfunction
- infection
- hormones
- androgens
- estrogens
- progestogens
- GnRH
- prolactin
- Assisted reproduction
- Birth control
|
|
|
UpToDate Contents
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English Journal
- Use of isothermal microcalorimetry to quantify the influence of glucose and antifungals on the growth of Candida albicans in urine.
- Wernli L, Bonkat G, Gasser TC, Bachmann A, Braissant O.Author information Department of Urology, University Hospital Basel, Basel, Switzerland.AbstractAIMS: Urinary tract infection (UTI) caused by Candida spp. is an increasing problem in clinical practice. Risk factors include diabetes mellitus, extremes of age, urinary tract abnormalities and indwelling catheters. Here, we determined the applicability of isothermal microcalorimetry (IMC) for the detection and antifungal drug susceptibility testing of Candida albicans in artificial urine.
- Journal of applied microbiology.J Appl Microbiol.2013 Nov;115(5):1186-93. doi: 10.1111/jam.12306. Epub 2013 Aug 8.
- AIMS: Urinary tract infection (UTI) caused by Candida spp. is an increasing problem in clinical practice. Risk factors include diabetes mellitus, extremes of age, urinary tract abnormalities and indwelling catheters. Here, we determined the applicability of isothermal microcalorimetry (IMC) for the
- PMID 23865534
- Candida glabrata drug:H+ antiporter CgQdr2 confers imidazole drug resistance, being activated by transcription factor CgPdr1.
- Costa C, Pires C, Cabrito TR, Renaudin A, Ohno M, Chibana H, Sá-Correia I, Teixeira MC.Author information Department of Bioengineering, Instituto Superior Técnico, Technical University of Lisbon, Lisbon, Portugal.AbstractThe widespread emergence of antifungal drug resistance poses a severe clinical problem. Though predicted to play a role in this phenomenon, the drug:H(+) antiporters (DHA) of the major facilitator superfamily have largely escaped characterization in pathogenic yeasts. This work describes the first DHA from the pathogenic yeast Candida glabrata reported to be involved in antifungal drug resistance, the C. glabrata QDR2 (CgQDR2) gene (ORF CAGL0G08624g). The expression of CgQDR2 in C. glabrata was found to confer resistance to the antifungal drugs miconazole, tioconazole, clotrimazole, and ketoconazole. By use of a green fluorescent protein (GFP) fusion, the CgQdr2 protein was found to be targeted to the plasma membrane in C. glabrata. In agreement with these observations, CgQDR2 expression was found to decrease the intracellular accumulation of radiolabeled clotrimazole in C. glabrata and to play a role in the extrusion of this antifungal from preloaded cells. Interestingly, the functional heterologous expression of CgQDR2 in the model yeast Saccharomyces cerevisiae further confirmed the role of this gene as a multidrug resistance determinant: its expression was able to complement the susceptibility phenotype exhibited by its S. cerevisiae homologue, QDR2, in the presence of imidazoles and of the antimalarial and antiarrhythmic drug quinidine. In contrast to the findings reported for Qdr2, CgQdr2 expression does not contribute to the ability of yeast to grow under K(+)-limiting conditions. Interestingly, CgQDR2 transcript levels were seen to be upregulated in C. glabrata cells challenged with clotrimazole or quinidine. This upregulation was found to depend directly on the transcription factor CgPdr1, the major regulator of multidrug resistance in this pathogenic yeast, which has also been found to be a determinant of quinidine and clotrimazole resistance in C. glabrata.
- Antimicrobial agents and chemotherapy.Antimicrob Agents Chemother.2013 Jul;57(7):3159-67. doi: 10.1128/AAC.00811-12. Epub 2013 Apr 29.
- The widespread emergence of antifungal drug resistance poses a severe clinical problem. Though predicted to play a role in this phenomenon, the drug:H(+) antiporters (DHA) of the major facilitator superfamily have largely escaped characterization in pathogenic yeasts. This work describes the first D
- PMID 23629708
- Separation of selected imidazole enantiomers using dual cyclodextrin system in micellar electrokinetic chromatography.
- Wan Ibrahim WA, Abd Wahib SM, Hermawan D, Sanagi MM, Aboul-Enein HY.Author information Separation Science and Technology Group (SepSTec), Department of Chemistry, Faculty of Science, Universiti Teknologi Malaysia, UTM Johor Bahru, Johor, Malaysia. wanaini@kimia.fs.utm.myAbstractCyclodextrin-modified micellar electrokinetic chromatography (CD-MEKC) method was developed for simultaneous enantioseparation of three imidazole drugs namely tioconazole, isoconazole and fenticonazole. Three easily available and inexpensive cyclodextrins namely 2-hydroxypropyl-β-cyclodextrin (HP-β-CD), 2-hydroxypropyl-γ-cyclodextrin (HP-γ-CD) and heptakis(2,6-di-O-methyl)-β-cyclodextrin (DM-β-CD) were evaluated to discriminate the six stereoisomers of the drugs. However, none of the three CDs gave a complete enantioseparation of the drugs. Effective enantioseparation of tioconazole, isoconazole and fenticonazole was achieved using a combination of 35 mM HP-γ-CD and 10 mM DM-β-CD as chiral selectors. The best separation using both HP-γ-CD and DM-β-CD (35 mM:10 mM) as chiral selectors were accomplished in background electrolyte (BGE) containing 35 mM phosphate buffer (pH 7.0), 50 mM sodium dodecyl sulfate (SDS) and 15% (v/v) acetonitrile at 27 kV and 30 °C with all peaks resolved in less than 15 min with resolutions, Rs 1.90-27.22 and peak efficiencies, N > 180 000. The developed method was linear over the concentration range of 25-200 mg l(-1) (r(2) > 0.998) and the detection limits (S/N = 3) of the three imidazole drugs were found to be 2.7-7.7 mg l(-1). The CD-MEKC method was successfully applied to the determination of the three imidazole drugs in spiked human urine sample and commercial cream formulation of tioconazole and isoconazole with good recovery (93.6-106.2%) and good RSDs ranging from 2.30-6.8%.
- Chirality.Chirality.2013 Jun;25(6):328-35. doi: 10.1002/chir.22156.
- Cyclodextrin-modified micellar electrokinetic chromatography (CD-MEKC) method was developed for simultaneous enantioseparation of three imidazole drugs namely tioconazole, isoconazole and fenticonazole. Three easily available and inexpensive cyclodextrins namely 2-hydroxypropyl-β-cyclodextrin (HP-�
- PMID 23716264
Japanese Journal
- Difference in Percutaneous Absorption and Intracutaneous Distribution in Guinea Pigs among Topical Antifungal Drugs : Tioconazole Solution, Tioconazole Cream, Miconazole Nitrate Solution and Bifonazole Solution(Biopharmacy)
- Sobue Satoshi,Sekiguchi Kaneo
- Biological & pharmaceutical bulletin 27(9), 1428-1432, 2004-09-01
- … Tioconazole (TCZ) is an imidazole antifungal agent with broad spectrum activity. …
- NAID 110003608988
- Open access capillary electrophoresis A walk up capillary electrophoresis service for the synthetic chemist
- SHARMA-SINGH Gorkhn,BROWN David A.,PULLEN Frank S.,WRIGHT Adrian G.
- Journal of chromatography. A : including electrophoresis and other separation methods 888(1), 219-227, 2000-08-04
- NAID 10013185921
- 松田 哲男,堀 嘉昭,松本 忠彦
- 西日本皮膚科 58(1), 138-143, 1996
- … Tioconazoleの1%含有液剤であるSTR液の手·足白癬, 体部白癬および股部白癬に対する有効性, 安全性ならびに有用性を検討するため, 九州大学医学部皮膚科とその関連施設による研究班を結成し, 臨床試験を実施した。 …
- NAID 130004474161
Related Links
- Tioconazole is an antifungal medication of the imidazole class used to treat infections caused by a fungus or yeast. It is marketed under the brand names Trosyd and Gyno-Trosyd (Pfizer). Tioconazole ointments serve to treat women's vaginal ...
- Consumer information about the medication TIOCONAZOLE - VAGINAL (Vagistat -1), includes side effects, drug interactions, recommended dosages, and storage information. Read more about the prescription drug TIOCONAZOLE - VAGINAL.