Ketoconazol Produkt Beschreibung

Ketoconazole Struktur
65277-42-1
  • CAS-Nr.65277-42-1
  • Bezeichnung:Ketoconazol
  • Englisch Name:Ketoconazole
  • Synonyma:Ketoconazol
    Nizral;nizoral;kw-1414;R-41400;Fitonal;ketoderm;fungoral;Brizoral;Onofin K;fungarest
  • CBNumber:CB9146879
  • Summenformel:C26H28Cl2N4O4
  • Molgewicht:531.43
  • MOL-Datei:65277-42-1.mol
Ketoconazol physikalisch-chemischer Eigenschaften
  • Schmelzpunkt: :146°C
  • Siedepunkt: :753.4±60.0 °C(Predicted)
  • Dichte :1.4046 (rough estimate)
  • Brechungsindex :-10.5 ° (C=0.4, CHCl3)
  • Flammpunkt: :9℃
  • storage temp.  :2-8°C
  • Löslichkeit :methanol: soluble50mg/mL
  • pka :pKa 3.25/6.22(H2O,t =25,I=0.025) (Uncertain)
  • Aggregatzustand :Off-white solid
  • Farbe :white to light yellow
  • Optische Aktivität :[α]20/D -1 to 1°, c = 4 in methanol
  • Wasserlöslichkeit :Soluble in DMSO, ethanol, chloroform, water, and methanol.
  • Merck  :14,5302
  • InChIKey :XMAYWYJOQHXEEK-OZXSUGGESA-N
  • CAS Datenbank :65277-42-1(CAS DataBase Reference)
Sicherheit

Ketoconazole Chemische Eigenschaften,Einsatz,Produktion Methoden

  • R-Sätze Betriebsanweisung: R25:Giftig beim Verschlucken.
    R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
    R23/24/25:Giftig beim Einatmen, Verschlucken und Berührung mit der Haut.
  • S-Sätze Betriebsanweisung: S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
    S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
    S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
    S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
  • Chemische Eigenschaften White or almost white powder.
  • Verwenden Inhibits cytochrome P-450 dependent steps in the biosynthesis of steroid hormones in vivo. Antimetastatic and antineoplastic activity. Orally active 5-lipoxygenase and thromboxane synthase inhibitor
  • Verwenden antifungal, PXR/SRC1 & CAR/SRC1 inhibitor
  • Verwenden For the treatment of the following systemic fungal infections: candidiasis, chronic mucocutaneous candidiasis, oral thrush, candiduria, blastomycosis, coccidioidomycosis, histoplasmosis, chromomycosis, and paracoccidioidomycosis.
  • Verwenden An inhibitor of CYP proteins, thromboxane synthetase, and 5-LO
  • Indications Ketoconazole (Nizoral) is approved for treating dermatophyte infections unresponsive to griseofulvin and for patients unable to tolerate that drug. A single oral dose is also effective for the treatment of pityriasis versicolor. Other effective drugs that are less hepatotoxic may be preferred, however.
  • Indications Ketoconazole (Nizoral) is a broad-spectrum antifungal agent that in very high doses inhibits several steps in the biosynthesis of both adrenal and gonadal steroids. While the normal antifungal dose is 200 mg/day, testosterone biosynthesis in both the adrenal and testis is completely abolished by doses of 800 to 1,600 mg/day. This drug is used most commonly for large virilizing adrenal tumors that cannot be surgically removed.
  • Indications Ketoconazole (Nizoral), an orally effective broadspectrum antifungal agent, blocks hydroxylating enzyme systems by interacting with cytochrome P450 at the heme iron site to inhibit steroid and/or androgen synthesis in adrenals, gonads, liver, and kidney. The most sensitive site of action appears to be the C17-20 lyase reaction involved in the formation of sex steroids. This explains the greater suppressibility of testosterone production than with cortisol. Cholesterol side-chain cleavage and 11β/18-hydroxylase are secondary sites of inhibition.
  • Trademarks Ketozole (Taro); Nizoral (Janssen); Nizoral (McNeil);Cerozalol;Cetonax;Fetonal;Fungarol;Fungo-hubber;Ketocidin;Ketoisdin;Ketonan;Ketoral;Micoral;Micotek;Micoticum;Nizcrem;Nizoral 2% shampoo;Nizoral 20% cream;Nizovules;Nizshampoo;Oromycosal;Oronazol;Panfungol;Rofenid;Spike;Unidox.
  • Weltgesundheitsorganisation (WHO) Ketoconazole, an imidazole antifungal agent, was introduced in 1978 for the topical and systemic treatment of a wide variety of fungal infections. Its use by mouth has been associated with hepatotoxicity, including cases of hepatitis, which have usually been reversible on discontinuation of the drug, but some fatalities have also occurred. Ketoconazole is widely marketed.
  • Antimicrobial activity The spectrum includes dermatophytes, some dimorphic fungi and Candida spp.
  • Acquired resistance Resistance has been documented in patients treated for chronic mucocutaneous candidosis and AIDS patients with oropharyngeal or esophageal candidosis. Some fluconazoleresistant C. albicans and C. glabrata are cross-resistant to ketoconazole.
  • Pharmazeutische Anwendungen A synthetic dioxolane imidazole available for oral and topical use.
  • Biologische Aktivität Antifungal agent; potent inhibitor of cytochrome P450c17.
  • Pharmakokinetik Oral absorption: Variable
    Cmax 400 mg oral: c. 5–6 mg/L after 2 h
    Plasma half-life: 6–10 h
    Volume of distribution: 0.36 L/kg
    Plasma protein binding: >95%
    It is erratically absorbed after oral administration. Absorption is favored by an acid pH. Food delays absorption, but does not significantly reduce the peak serum concentration. Absorption is reduced if it is given with compounds that reduce gastric acid secretion. Penetration into CSF is generally poor and unreliable, although effective concentrations have been recorded with high doses in some cases of active meningitis. It is extensively metabolized by the liver, and the metabolites are excreted in the bile. Less than 1% of an oral dose is excreted unchanged in the urine.
  • Clinical Use Mucosal candidosis
    Pityriasis versicolor
    Seborrheic dermatitis
    Non-life-threatening forms of blastomycosis, coccidioidomycosis, histoplasmosis and paracoccidioidomycosis
  • Clinical Use Ketoconazole can be used as palliative treatment for Cushing’s syndrome in patients undergoing surgery or receiving pituitary radiation and in those for whom more definitive treatment is still contemplated. Because surgical treatment is not always well tolerated by elderly patients, ketoconazole 200 to 1,000 mg/day can be a valuable alternative for the control of hypercortisolism. Common side effects include pruritus, liver dysfunction, and gastrointestinal symptoms.
  • Clinical Use Ketoconazole remains useful in the treatment of cutaneous and mucous membrane dermatophyte and yeast infections, but it has been replaced by the newer triazoles in the treatment of most serious Candida infections and disseminated mycoses. Ketoconazole is usually effective in the treatment of thrush, but fluconazole is superior to ketoconazole for refractory thrush. Widespread dermatophyte infections on skin surfaces can be treated easily with oral ketoconazole when the use of topical antifungal agents would be impractical. Treatment of vulvovaginal candidiasis with topical imidazoles is less expensive.
  • Nebenwirkungen Because of its effectiveness in blocking C17-20 lyase activities, ketoconazole does not enhance existing hirsutism associated with metyrapone. On the other hand, the antiandrogenic effects of ketoconazole may prove disconcerting to male patients.
  • Nebenwirkungen Unwanted effects include nausea, vomiting, abdominal pain, headache, rashes, urticaria and pruritus. Transient abnormalities of liver enzymes, interference with testosterone synthesis (leading to gynecomastia, alopecia and oligospermia) and rare fatal hepatic damage have been reported.
  • Nebenwirkungen Nausea, vomiting, and anorexia occur commonly with ketoconazole, especially when high doses are prescribed. Epigastric distress can be reduced by taking ketoconazole with food. Pruritis and/or allergic dermatitis occurs in 10% of patients. Liver enzyme elevations during therapy are not unusual and are usually reversible. Severe ketoconazole-associated hepatitis is rare.
    At high doses, ketoconazole causes a clinically significant reduction in testosterone synthesis and blocks the adrenal response to corticotropin. Gynecomastia, impotence, reduced sperm counts, and diminished libido can occur in men, and prolonged drug use can result in irregular menses in women. These hormonal effects have led to the use of ketoconazole as a potential adjunctive treatment for prostatic carcinoma.
  • Veterinary Drugs and Treatments Because of its comparative lack of toxicity when compared to amphotericin B, oral administration, and relatively good efficacy, ketoconazole has been used to treat several fungal infections in dogs, cats, and other small species. Ketoconazole is often employed with amphotericin B to enhance the efficacy of ketoconazole, and by reducing the dose of amphotericin B, decreasing its risk of toxicity. See the Dosage section or Pharmacology section for specifics. Newer antifungal agents (fluconazole, itraconazole) have advantages over ketoconazole, primarily less toxicity and/or enhanced efficacy; however, ketoconazole can be significantly less expensive than the newer agents. Ketoconazole is considered by some to still be the drug of choice for treating histoplasmosis in dogs.
    Use of ketoconazole in cats is controversial and some say it should never be used that species. Ketoconazole is also used clinically for the medical treatment of hyperadrenocorticism in dogs. Ketoconazole appears to be a viable option (although relatively expensive) to mitotane, particularly for palliative therapy in dogs with large, malignant, or invasive tumors where surgery is not an option. Ketoconazole is also used frequently in dogs for stabilization prior to surgery. It is a reversible inhibitor of steroidogenesis, so it is usually not a viable option for long-term treatment.
    Because it interferes with the metabolism of cyclosporine, it has been used to reduce the dosage necessary for cyclosporine in dogs.
  • Vorsichtsmaßnahmen Both rifampin and isoniazid lower plasma ketoconazolelevels, and concomitant administration should be avoided.Phenytoin serum levels should be monitored closelywhen ketoconazole is prescribed.Ketoconazole causes increasesin serum concentrations of warfarin, cyclosporine,and sulfonylureas. Because of its ability to increase serumcyclosporine levels, ketoconazole has been given to cyclosporine-dependent cardiac transplant recipients to reducethe dose of cyclosporine needed and as a cost-savingmeasure.
Ketoconazole Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
Ketoconazol Anbieter Lieferant Produzent Hersteller Vertrieb Händler.
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65277-42-1, Ketoconazole Verwandte Suche:
  • Ketoconazole - CAS 65277-42-1 - Calbiochem
  • ,3-dioxolan-4-yl)methoxy)phenyl)-,cis-
  • fungarest
  • fungoral
  • ketoconazol
  • ketoderm
  • ketoisdin
  • kw-1414
  • nizoral
  • orifungalm
  • panfungol
  • piperazine,1-acetyl-4-(4-((2-(2,4-dichlorophenyl)-2-(1h-imidazol-1-ylmethyl)-1
  • R-41400
  • (+/-)-CIS-1-ACETYL-4-(4-[(2-[2,4-DICHLOROPHENYL]-2-[1H-IMIDAZOL-1-YLMETHYL]-1,3-DIOXOLAN-4-YL)-METHOXY]PHENYL)PIPERAZINE
  • [+/-]-CIS-1-ACETYL-4-[4-([2-(2,4-DICHLOROPHENYL)-2-(1H-IMIDAZOL-1-YLMETHYL)-1,3-DIOXOLAN-4-YL]-METHOXY)-PHENYL]PIPERAZINE
  • CIS-1-ACETYL-4-[4-[[2-(2,4-DICHLOROPHENYL)-2-(1H-IMIDAZOL-1-YLMETHYL)-1,3-DIOXOLAN-4-YL]METHOXY]PHENYL]PIPERAZINE
  • KETOCONAZOLE-D3
  • KETOCANAZOLE
  • KETOCONAZOLE
  • KETOKONAZOL
  • Ketoconazole USP25/EP2002/CP2000
  • KETOCONAZOLE, MM(CRM STANDARD)
  • KETOCONAZOLE, USP STANDARD
  • KETOCONAZOLE, IMP. D (EP): 1-(4-{4-[(RS,SR)-2-(2,4-DICHLOROPHENYL)-2-(1-IMIDAZOLYLMETHYL)-1,3-DIOXOLAN-4-YLMETHOXY]PHENYL}PIPERAZINE MM(CRM STANDARD)
  • KETOCONAZOLE, EP STANDARD
  • KETOCONAZOLE EP USP
  • KETOCONAZOLE EPK(CRM STANDARD)
  • KETOCONAZOLE USP(CRM STANDARD)
  • KETOCONAZOLE(REAGENT / STANDARD GRADE)
  • MICONAZOLE EPM(CRM STANDARD)
  • KetoconazoleUsp24
  • Ketoconazole-Bp/Ep/Usp
  • Ketoconaole
  • Piperazine, 1-acetyl-4-4-(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-ylmethoxyphenyl-, rel-
  • KETOCONAZOLE,USP22(BULK
  • KETOCONAZOLE EP
  • KETOCONAZOLE(RG)
  • Piperazine, 1-acetyl-4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-, rel- (9CI)
  • KETOCONZOLE
  • (+/-)-cis-1-Acetyl-4-[4-[[2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazine
  • Fungarest, Ketoderm
  • Ketokonazole (DMF)
  • 1-[4-[4-[[(2R,4S)-2-(2,4-Dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone
  • Nizral
  • (±)-cis-1-Acetyl-4-(p-((2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazine
  • Fitonal
  • rel-2-(2,4-Dichlorophenyl)-2α*-(1H-imidazole-1-ylmethyl)-4β*-[4-(4-acetylpiperazine-1-yl)phenoxymethyl]-1,3-dioxolane
  • Ketoconazole,(±)-cis-1-Acetyl-4-(4-[(2-[2,4-dichlorophenyl]-2-[1H-imidazol-1-ylmethyl]-1,3-dioxolan-4-yl)-methoxy]phenyl)piperazine
  • Ketoconazole (200 mg)
  • 1-[4-(4-{[(2S,4R)-2-(2,4-dichlorophenyl)-2-(1H-iMidazol-1-ylMethyl)-1,3-dioxolan-4-yl]Methoxy}phenyl)piperazin-1-yl]ethan-1-one
  • Brizoral
  • Ketozoral
  • Onofin K
  • rel-1-[4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-iMidazol-1-ylMethyl)-1,3-dioxolan-4-yl]Methoxy]phenyl]-1-piperazinyl]ethanone
  • Ketoconazole API
  • Ketoconazole/R41400
  • Ketoconazole Capsules
  • Ketoconazole, 98.0%(LC&T