トルナフタート
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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2015/06/08 10:32:00」(JST)
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Tolnaftate
|
Systematic (IUPAC) name |
O-2-naphthyl methyl(3-methylphenyl)thiocarbamate |
Clinical data |
Trade names |
Tinactin |
AHFS/Drugs.com |
monograph |
MedlinePlus |
a682617 |
Legal status
|
|
Identifiers |
CAS Registry Number
|
2398-96-1 Y |
ATC code
|
D01AE18 |
PubChem |
CID: 5510 |
DrugBank |
DB00525 Y |
ChemSpider |
5309 Y |
UNII |
06KB629TKV Y |
KEGG |
D00381 Y |
ChEBI |
CHEBI:9620 N |
ChEMBL |
CHEMBL83668 Y |
Chemical data |
Formula |
C19H17NOS |
Molecular mass
|
307.41 g/mol |
SMILES
- S=C(Oc2ccc1c(cccc1)c2)N(c3cc(ccc3)C)C
|
InChI
-
InChI=1S/C19H17NOS/c1-14-6-5-9-17(12-14)20(2)19(22)21-18-11-10-15-7-3-4-8-16(15)13-18/h3-13H,1-2H3 Y
Key:FUSNMLFNXJSCDI-UHFFFAOYSA-N Y
|
Physical data |
Melting point |
110 to 111.5 °C (230.0 to 232.7 °F) |
N (what is this?) (verify) |
Tolnaftate is a synthetic thiocarbamate used as an anti-fungal agent that may be sold without medical prescription in most jurisdictions. It is supplied as a cream, powder, spray, and liquid aerosol. Tolnaftate is used to treat fungal conditions such as jock itch, athlete's foot and ringworm. It is sold under several brand names, including Absorbine, Aftate, Genaspor, Lamisil AF, Mycil (Reckitt Benckiser), NP 27, Odor Eaters (Combe Incorporated), Scholl, Tinactin (Bayer), Tinaderm, and Ting.
Contents
- 1 Synthesis
- 2 Mechanism
- 3 Uses
- 4 References
- 5 External links
Synthesis
Tolnaftatesynthesis:
U.S. Patent 3,334,126 GB 697897 FR 1337797 [1]
Equimolar amounts of 2-naphthol and thiophosgene are combined to make a monosubstituted product of thiophosgene.
The synthesis of tolnaftate is a three-step process first involving 2-napthol with a base, to deprotonate the acidic phenol hydrogen. NaH, NaNH2 are commonly used. Other common bases may also be used with the same effect. Treatment of N-methyl-m-toluidine with CS2 and CH3Br results in a thiocarbamate intermediate that reacts with the negatively charged oxygen on the deprotonated 2-napthol, displacing the -SCH3 group and forming the final product.
Mechanism
Although the exact mechanism of action is not entirely known, it is believed to inhibit squalene epoxidase,[2] an important enzyme in the biosynthetic pathway of ergosterol (a key component of the fungal membrane) in a similar way to allylamines.[3]
Uses
Tolnaftate has been found to be generally slightly less effective than azoles when used to treat tinea pedis (athlete's foot). It is, however, useful when dealing with ringworm, especially when passed from pets to humans.[4]
References
- ^ Noguchi, T.; Hashimoto, Y.; Miyazaki, K.; Kaji, A.; J. Pharm. Soc. Japan 1968, 88, 335
- ^ Ryder NS, Frank I, Dupont MC (May 1986). "Ergosterol biosynthesis inhibition by the thiocarbamate antifungal agents tolnaftate and tolciclate". Antimicrob. Agents Chemother. 29 (5): 858–60. doi:10.1128/aac.29.5.858. PMC 284167. PMID 3524433.
- ^ "antifung". Retrieved 2008-07-09.
- ^ Crawford F, Hart R, Bell-Syer S, Torgerson D, Young P, Russell I. Topical treatments for fungal infections of the skin and nails of the foot (Cochrane Review). In: The Cochrane Library, Issue 1, 2003. Oxford: Update Software.
External links
- Medline's entry for tolnaftate
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 |
|
|
|
UpToDate Contents
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English Journal
- Characterization of iprodione resistance in Botrytis cinerea from strawberry and blackberry.
- Grabke A, Fernández-Ortuño D, Amiri A, Li X, Peres NA, Smith P, Schnabel G.
- Phytopathology.Phytopathology.2014 Apr;104(4):396-402. doi: 10.1094/PHYTO-06-13-0156-R.
- Gray mold, caused by the fungal pathogen Botrytis cinerea, is one of the most destructive diseases of strawberry. Control of the disease in commercial fields is largely dependent on the application of fungicides, including the dicarboximide iprodione. Single-spore isolates were collected from strawb
- PMID 24156554
- Studying the penetration of fatty acids into human skin by ex vivo TOF-SIMS imaging.
- Kezutyte T1, Desbenoit N, Brunelle A, Briedis V.
- Biointerphases.Biointerphases.2013 Dec;8(1):3. doi: 10.1186/1559-4106-8-3. Epub 2013 Feb 6.
- Fatty acids classified as chemical penetration enhancers (CPEs) might cause the fluidization and perturbation of stratum corneum (SC) lipid matrix. The penetration of oleic, linoleic, lauric and capric acids into human skin was studied by time-of-flight secondary ion mass spectrometry (TOF-SIMS) ima
- PMID 24706116
- Detailed study of precipitation of a poorly water soluble test compound using methodologies as in activity and solubility screening - mixing and automation effects.
- Gillespie C1, Kennedy AR, Edwards D, Dowden L, Daublain P, Halling P.
- Combinatorial chemistry & high throughput screening.Comb Chem High Throughput Screen.2013 Sep;16(8):636-43.
- Storage of pharmaceutical discovery compounds dissolved in dimethylsulfoxide (DMSO) is commonplace within industry. Often, the DMSO stock solution is added to an aqueous system (e.g. in bioassay or kinetic solubility testing)- since most test compounds are hydrophobic, precipitation could occur. Lit
- PMID 23713459
Japanese Journal
- 抗真菌薬はアトピー性皮膚炎患者T細胞のIL‐4,IL‐5産生を抑制する
- 神田 奈緒子
- 日本医真菌学会雑誌 45(3), 137-142, 2004
- アトピー性皮膚炎患者の治療に抗真菌薬が有効であることが報告されている.アトピー性皮膚炎患者および健常者の末梢血T細胞の抗CD3,CD28抗体刺激によるTh1,Th2サイトカイン産生に対する抗真菌薬の作用について検討した.抗CD3,CD28抗体で刺激したT細胞のIL-4,IL-5の放出量はアトピー性皮膚炎患者では健常者と比較して高かった.アゾール系抗真菌薬ケトコナゾール,イトラコナゾール,ミコナゾー …
- NAID 130003672089
- モルモット足白癬モデルにおけるTolnaftate外用剤の治療効果
- 山口 英世,内田 勝久,田中 崇,山口 智彦
- The Japanese journal of antibiotics 54(6), 323-330, 2001-06-25
- NAID 10006802141
- 抗菌活性を有する 2-アニリノ-4-フェニルチアゾールの合成およびそのステロール生合成阻害活性
- 汲田 泉,野田 薫
- 日本農薬学会誌 26(2), 136-142, 2001-05-20
- 我々は先に, T.mentagrophytesやB.cinereraに対して高い抗菌活性を示すと同時に, それに対応した強いスクワレンエポキシダーゼ阻害活性を示す3-(2, 6-ジクロルフェニル)-5-フェニルアミノ-1, 2, 4-チアジアゾール類を見出した.スクワレンエポキシダーゼ阻害剤は二つの疎水性ドメインと, それらをつなぐスペーサーからなるというNussbaumerらのモデルを参考にして …
- NAID 110001713237
Related Links
- Tolnaftate is a synthetic thiocarbamate used as an anti-fungal agent that may be sold without medical prescription in most jurisdictions. It is supplied as a cream, powder, spray, and liquid aerosol. Tolnaftate is used to treat fungal conditions ...
- Tolnaftate comes as a cream, liquid, powder, gel, spray powder, and spray liquid for application to the skin. Tolnaftate usually is applied twice a day. Follow the directions on the package or on your prescription label carefully, and ask your ...
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