ビホナゾール、ビフォナゾール
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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2014/12/25 02:37:30」(JST)
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Bifonazole
|
Systematic (IUPAC) name |
(RS)-1-[Phenyl(4-phenylphenyl)methyl]-1H-imidazole |
Clinical data |
AHFS/Drugs.com |
International Drug Names |
Legal status |
|
Routes |
topic |
Identifiers |
CAS number |
60628-96-8 Y |
ATC code |
D01AC10 |
PubChem |
CID 2378 |
DrugBank |
DB04794 |
ChemSpider |
2287 Y |
UNII |
QYJ305Z91O Y |
KEGG |
D01775 Y |
ChEBI |
CHEBI:31286 Y |
ChEMBL |
CHEMBL277535 Y |
Chemical data |
Formula |
C22H18N2 |
Mol. mass |
310.392 g/mol |
SMILES
- n1ccn(c1)C(c3ccc(c2ccccc2)cc3)c4ccccc4
|
InChI
-
InChI=1S/C22H18N2/c1-3-7-18(8-4-1)19-11-13-21(14-12-19)22(24-16-15-23-17-24)20-9-5-2-6-10-20/h1-17,22H Y
Key:OCAPBUJLXMYKEJ-UHFFFAOYSA-N Y
|
Y (what is this?) (verify) |
Bifonazole is an imidazole antifungal drug. Bifonazole is marketed by Bayer under the trade mark Canespor in ointment form.
Mechanism of action
Bifonazole has dual mode of action. It blocks transformation of 24-methylendihydrolanosterol to desmethylsterol in fungi together with inhibition of HMG-CoA. This enables fungicidal properties against dermatophytes and distinguishes bifonazole from other antifungal drugs.
Antifungals (D01 and J02)
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|
Wall/
membrane |
Ergosterol
inhibitors
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Azoles
(lanosterol 14
alpha-demethylase inhibitors)
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Imidazoles
|
- Topical: bifonazole
- butoconazole
- clomidazole
- clotrimazole#, croconazole
- econazole
- fenticonazole
- ketoconazole
- isoconazole
- miconazole#, neticonazole
- omoconazole
- oxiconazole
- sertaconazole
- sulconazole
- tioconazole
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|
Triazoles
|
- Topical: (fluconazole#, fosfluconazole
- terconazole)
- Systemic: (fluconazole
- hexaconazole
- isavuconazole†, itraconazole
- posaconazole
- saperconazole
- voriconazole)
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Thiazoles
|
Topical: (abafungin)
|
|
|
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)
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|
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Intracellular |
Pyrimidine analogues/
thymidylate synthase inhibitors
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|
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Mitotic inhibitors
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|
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Aminoacyl tRNA synthetase inhibitors
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|
|
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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
|
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Androgenics
|
|
Receptor |
|
|
Enzyme
(inhibitors) |
20,22-Desmolase
|
- 22-ABC
- 3,3′-Dimethoxybenzidine
- 3-Methoxybenzidine
- Aminoglutethimide
- Cyanoketone
- Danazol
- Etomidate
- Mitotane
- Trilostane
|
|
17α-Hydroxylase,
17,20-Lyase
|
- 22-ABC
- 22-Oxime
- Abiraterone
- Bifonazole
- Clotrimazole
- Cyanoketone
- Cyproterone acetate
- Danazol
- Econazole
- Galeterone
- Gestrinone
- Isoconazole
- Ketoconazole
- L-39
- Levonorgestrel
- Liarozole
- LY-207,320
- MDL-27,302
- Miconazole
- Mifepristone
- Orteronel
- Pioglitazone
- Rosiglitazone
- Spironolactone
- Stanozolol
- SU-10,603
- TGF-β
- Tioconazole
- Troglitazone
- VN/87-1
- YM116
|
|
3β-HSD (I, II)
|
- 4-MA
- Azastene
- Cyanoketone
- Danazol
- Epostane
- Genistein
- Gestrinone
- Levonorgestrel
- Metyrapone
- Oxymetholone
- Pioglitazone
- Rosiglitazone
- Trilostane
- Troglitazone
|
|
17β-HSD (I-XIV)
|
|
|
5α-Reductase (I, II)
|
- 22-Oxime
- Alfatradiol
- Azelaic acid
- β-Sitosterol
- Bexlosteride
- Dutasteride
- Epitestosterone
- Epristeride
- Finasteride
- gamma-Linolenic acid
- Ganoderic acid
- Izonsteride
- L-39
- Lapisteride
- Polyunsaturated fatty acids (α-linolenic acid, linoleic acid, γ-linolenic acid, oleic acid)
- Saw palmetto
- Turosteride
- Vitamin B6
- Zinc
|
|
Aromatase
|
- 1,4,6-Androstatriene-3,17-dione
- 4-Androstene-3,6,17-trione
- 4-Cyclohexylaniline
- 4-Hydroxytestosterone
- 5α-DHNET
- Abyssinone II
- Aminoglutethimide
- Anastrozole
- Ascorbic acid (Vitamin C)
- Atamestane
- Bifonazole
- CGP-45,688
- CGS-47,645
- Clotrimazole
- DHT
- Difeconazole
- Econazole
- Exemestane
- Fadrozole
- Fenarimol
- Finrozole
- Formestane
- Imazalil
- Isoconazole
- Ketoconazole
- Letrozole
- Liarozole
- MEN-11066
- Miconazole
- Minamestane
- Nimorazole
- NKS01
- ORG-33,201
- Penconazole
- Plomestane
- Prochloraz
- Propioconazole
- Pyridoglutethimide
- Rogletimide
- Rotenone
- Talarozole
- Testolactone
- Tioconazole
- Triadimefon
- Triadimenol
- Troglitazone
- Vorozole
- YM511
- Zinc
Note: 21-Hydroxylase inhibitors may also affect androgen levels as they prevent metabolism of androgen precursors.
|
|
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Other |
Endogenous
|
- Androgens: Dihydrotestosterone
- Testosterone
- Antiandrogens: Epitestosterone
- Precursors: Cholesterol
- 22R-Hydroxycholesterol
- 20α,22R-Dihydroxycholesterol
- Pregnenolone
- 17-Hydroxypregnenolone
- Progesterone
- 17-Hydroxyprogesterone
- Cortodoxone/Deoxycortisol
- DHEA
- Androstenediol
- Androstenedione
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|
Indirect
|
- Estrogens/Antiestrogens (see here)
- GnRH agonists/antagonists (see here)
- Gonadotropins/Antigonadotropins (see here)
- Plasma proteins (SHBG, ABP, Albumin)
- Progestogens/Antiprogestins (see here)
- Prolactin
|
|
Procedures
|
- Adrenalectomy
- Hypophysectomy
- Oophorectomy
- Orchiectomy
|
|
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Estrogenics
|
|
Receptor |
ER (α, β)
|
|
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GPER
|
- Agonists: Estradiol
- Fulvestrant
- G-1
- Genistein
- Quercetin
- Tamoxifen
|
|
|
Enzyme
(inhibitors) |
20,22-Desmolase
|
- 22-ABC
- 3,3′-Dimethoxybenzidine
- 3-Methoxybenzidine
- Aminoglutethimide
- Cyanoketone
- Danazol
- Etomidate
- Mitotane
- Trilostane
|
|
17α-Hydroxylase,
17,20-Lyase
|
- 22-ABC
- 22-Oxime
- Abiraterone
- Bifonazole
- Clotrimazole
- Cyanoketone
- Cyproterone
- Danazol
- Econazole
- Galeterone
- Gestrinone
- Isoconazole
- Ketoconazole
- L-39
- Liarozole
- LY-207,320
- MDL-27,302
- Miconazole
- Mifepristone
- Orteronel
- Pioglitazone
- Rosiglitazone
- Spironolactone
- Stanozolol
- SU-10,603
- TGF-β
- Tioconazole
- Troglitazone
- VN/87-1
- YM116
|
|
3β-HSD
|
- 4-MA
- Azastene
- Cyanoketone
- Danazol
- Epostane
- Genistein
- Gestrinone
- Metyrapone
- Oxymetholone
- Pioglitazone
- Rosiglitazone
- Trilostane
- Troglitazone
|
|
17β-HSD
|
|
|
Aromatase
|
- 1,4,6-Androstatriene-3,17-dione
- 4-Androstene-3,6,17-trione
- 4-Cyclohexylaniline
- 4-Hydroxytestosterone
- 5α-DHNET
- Abyssinone II
- Aminoglutethimide
- Anastrozole
- Ascorbic acid (Vitamin C)
- Atamestane
- Bifonazole
- CGP-45,688
- CGS-47,645
- Clotrimazole
- DHT
- Difeconazole
- Econazole
- Exemestane
- Fadrozole
- Fenarimol
- Finrozole
- Formestane
- Imazalil
- Isoconazole
- Ketoconazole
- Letrozole
- Liarozole
- MEN-11066
- Miconazole
- Minamestane
- Nimorazole
- NKS01
- ORG-33,201
- Penconazole
- Plomestane
- Prochloraz
- Propioconazole
- Pyridoglutethimide
- Rogletimide
- Rotenone
- Talarozole
- Testolactone
- Tioconazole
- Triadimefon
- Triadimenol
- Troglitazone
- Vorozole
- YM511
- Zinc
Note: 5α-reductase and 21-hydroxylase inhibitors may also affect estrogen levels as they prevent metabolism of estrogen steroid precursors.
|
|
|
Other |
Endogenous
|
- Estrogens: 5α-Androstane-3β,17β-diol
- DHEA
- Estetrol
- Estradiol
- Estriol
- Estrone
- Antiestrogens: 2-Hydroxyestrone
- 16-Hydroxyestrone
- Precursors: Cholesterol
- 22R-Hydroxycholesterol
- 20α,22R-Dihydroxycholesterol
- Pregnenolone
- 17-Hydroxypregnenolone
- Progesterone
- 17-Hydroxyprogesterone
- Cortodoxone/Deoxycortisol
- DHEA
- DHEA sulfate
- 16-Hydroxy-DHEA
- 16-Hydroxy-DHEA sulfate
- Androstenediol
- Androstenedione
- 16-Hydroxyandrostenedione
- Testosterone
|
|
Indirect
|
- Androgens/Antiandrogens (see here)
- Calcitriol (a form of Vitamin D)
- GnRH agonists/antagonists (see here)
- Gonadotropins//Antigonadotropins (see here)
- Plasma proteins (SHBG, ABP, Albumin)
- Progestogens/Antiprogestins (see here)
- Prolactin
|
|
Procedures
|
- Adrenalectomy
- Hypophysectomy
- Oophorectomy
- Orchiectomy
|
|
|
Progestogenics
|
|
Receptor |
|
|
Enzyme
(inhibitors) |
20,22-Desmolase
|
- 22-ABC
- 3,3′-Dimethoxybenzidine
- 3-Methoxybenzidine
- Aminoglutethimide
- Cyanoketone
- Danazol
- Etomidate
- Mitotane
- Trilostane
|
|
17α-Hydroxylase,
17,20-Lyase
|
- 22-ABC
- 22-Oxime
- Abiraterone
- Bifonazole
- Clotrimazole
- Cyanoketone
- Cyproterone acetate
- Danazol
- Econazole
- Galeterone
- Isoconazole
- Ketoconazole
- L-39
- Levonorgestrel
- Liarozole
- LY-207,320
- MDL-27,302
- Miconazole
- Mifepristone
- Orteronel
- Pioglitazone
- Rosiglitazone
- Spironolactone
- Stanozolol
- SU-10,603
- TGF-β
- Tioconazole
- Troglitazone
- VN/87-1
- YM116
|
|
3β-HSD
|
- 4-MA
- Azastene
- Cyanoketone
- Danazol
- Epostane
- Genistein
- Gestrinone
- Metyrapone
- Norethisterone
- Oxymetholone
- Pioglitazone
- Rosiglitazone
- Trilostane
- Troglitazone
|
|
21-Hydroxylase
|
- Aminoglutethimide
- Amphenone B
- Bifonazole
- Clotrimazole
- Diazepam
- Econazole
- Genistein
- Isoconazole
- Ketoconazole
- Metyrapone
- Miconazole
- Midazolam
- Tioconazole
|
|
|
Other |
Endogenous
|
- Progestogens: Deoxycorticosterone
- 17-Hydroxyprogesterone
- Progesterone
- Precursors: Cholesterol
- 22R-Hydroxycholesterol
- 20α,22R-Dihydroxycholesterol
- Pregnenolone
- 17-Hydroxypregnenolone
|
|
Indirect
|
- Androgens/Antiandrogens (see here)
- Estrogens/Antiestrogens (see here)
- GnRH agonists/antagonists (see here)
- Gonadotropins/Antigonadotropins (see here)
- Plasma proteins (Transcortin, Albumin)
|
|
Procedures
|
- Adrenalectomy
- Hypophysectomy
- Oophorectomy
- Orchiectomy
|
|
|
UpToDate Contents
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English Journal
- Efficacy of 4 weeks topical bifonazole treatment for onychomycosis after nail ablation with 40% urea: a double-blind, randomized, placebo-controlled multicenter study.
- Tietz HJ, Hay R, Querner S, Delcker A, Kurka P, Merk HF.SourceInstitut für Pilzkrankheiten, Berlin, Germany Infectious Disease Clinic, Dermatology Department, King's College Hospital NHS Trust, London, UK Global R&D, Bayer Consumer Care AG, Basel, Switzerland Department of Dermatology and Allergology, University Clinic RWTH, Aachen, Germany.
- Mycoses.Mycoses.2013 Jul;56(4):414-21. doi: 10.1111/myc.12037. Epub 2013 Apr 16.
- Onychomycosis is a common fungal infection most often affecting the toenails. If untreated, it can cause discomfort sufficient to reduce quality of life. To evaluate efficacy and safety of bifonazole cream vs. placebo in onychomycosis treatment after non-surgical nail ablation with urea paste. Fifty
- PMID 23586591
- Luliconazole for the treatment of interdigital tinea pedis: A double-blind, vehicle-controlled study.
- Jarratt M, Jones T, Kempers S, Rich P, Morton K, Nakamura N, Tavakkol A.SourceDermResearch Inc, Austin, Texas, USA.
- Cutis; cutaneous medicine for the practitioner.Cutis.2013 Apr;91(4):203-10.
- Tinea pedis (TP) typically is treated with topical antifungal agents. Luliconazole, a novel imidazole drug, is shown to be as or more effective in vitro and in vivo than bifonazole, terbinafine, and lanoconazole. Two treatment durations with luliconazole cream 1% were evaluated for treatment of TP.
- PMID 23763082
- The effect of topically applied antimycotic agents on inner ear vestibular and cochlear function.
- Perez R, Nazarian Y, Sohmer H, Sichel JY.SourceDepartment of Otolaryngology and Head and Neck Surgery, Shaare Zedek Medical Center, Hebrew University Medical School, Jerusalem. perezro@zahav.net.il
- The Laryngoscope.Laryngoscope.2013 Apr;123(4):1033-9. doi: 10.1002/lary.23718. Epub 2012 Sep 18.
- OBJECTIVES/HYPOTHESIS: To assess and compare the effect of commonly used topical antimycotic agents and their solvents on the function of the vestibular and cochlear parts of the sand rat's inner ear.STUDY DESIGN: Prospective, controlled, animal study.METHODS: Forty-five fat sand rats were randomly
- PMID 22991276
Japanese Journal
- Sulfonamide-1,2,4-thiadiazole Derivatives as Antifungal and Antibacterial Agents: Synthesis, Biological Evaluation, Lipophilicity, and Conformational Studies
- Camoutsis Charalabos,Geronikaki Athina,Ciric Ana,Soković Marina,Zoumpoulakis Panagiotis,Zervou Maria
- Chemical and Pharmaceutical Bulletin 58(2), 160-167, 2010
- … All compound tested showed significant antifungal activity against all the micromycetes, compared to the commercial fungicide bifonazole. …
- NAID 130000161586
- 加藤 卓朗
- 日本医真菌学会雑誌 = Japanese journal of medical mycology 50(4), 207-212, 2009-10-30
- 皮膚と口腔カンジダ症の診断と治療について解説する.本症は年齢や病変部位により,カンジダ性間擦疹,乳児寄生菌性紅斑,カンジダ性指間びらん,カンジダ性爪囲爪炎,爪カンジダ症,口腔カンジダ症などに分類される.本症の診断は直接鏡検で菌要素を認めることで確定する.主要原因菌の<I>Candida albicans</I> は粘膜の常在菌であるため,培養陽性のみでは診断の根拠にならない …
- NAID 10026094530
- 承認後20年目におけるビホナゾールの足白癬に対する有用性について
- 三井 浩,神田 奈緒子,大西 誉光,中居 賢司,鈴木 拓,渡辺 晋一
- The Japanese journal of antibiotics 62(2), 79-89, 2009-04-25
- NAID 10028254626
Related Links
- Bifonazole is an imidazole antifungal drug. Bifonazole is ... Bifonazole has dual mode of action. It blocks ... of HMG-CoA. This enables fungicidal properties against dermatophytes and distinguishes bifonazole from other antifungal drugs.
- CANESTEN ONCE DAILY. BIFONAZOLE TOPICAL CREAM. Bifonazole cream 1 % (AUST R 63479). Consumer Medicine Information. CANESTEN ONCE DAILY BIFONAZOLE TOPICAL CREAM Published by MIMS/myDr August 2001 1 ...
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