케토코나졸

케토코나졸
케토코나졸 구조식 이미지
카스 번호:
65277-42-1
한글명:
케토코나졸
동의어(한글):
케토코나졸;케토코나졸(KETOCONAZOLE)
상품명:
Ketoconazole
동의어(영문):
ketoconazol;Extina;nizoral;Xolegel;KETOKONAZOL;KETOCONZOLE;CIS-1-ACETYL-4-(4-((2-(2 4-DICHLOROPHENY L)-2-(1H-IMIDAZOL-1-YLMETHYL)-1 3-DIOXOL AN-4-YL)METHOXY);Nizral;R-41400;kw-1414
CBNumber:
CB9146879
분자식:
C26H28Cl2N4O4
포뮬러 무게:
531.43
MOL 파일:
65277-42-1.mol

케토코나졸 속성

녹는점
148-152 °C
끓는 점
753.4±60.0 °C(Predicted)
밀도
1.4046 (rough estimate)
굴절률
-10.5 ° (C=0.4, CHCl3)
인화점
9℃
저장 조건
2-8°C
용해도
메탄올: 용해성50mg/mL
산도 계수 (pKa)
pKa 3.25/6.22(H2O,t =25,I=0.025) (Uncertain)
물리적 상태
회백색 고체
색상
흰색에서 밝은 노란색
optical activity
[α]20/D -1 to 1°, c = 4 in methanol
수용성
DMSO, 에탄올, 클로로포름, 물 및 메탄올에 용해됩니다.
Merck
14,5302
BCS Class
2
안정성
제공된 대로 구매일로부터 2년 동안 안정적입니다. DMSO 또는 에탄올 용액은 -20°C에서 최대 3개월 동안 보관할 수 있습니다.
InChIKey
XMAYWYJOQHXEEK-OZXSUGGESA-N
LogP
4.350
CAS 데이터베이스
65277-42-1(CAS DataBase Reference)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 T,N,F
위험 카페고리 넘버 25-36/37/38-23/24/25-50/53-48/22-60-39/23/24/25-11
안전지침서 36-45-36/37/39-26-61-60-53-36/37-16-7
유엔번호(UN No.) UN 2811 6.1/PG 3
WGK 독일 3
RTECS 번호 TK7912300
위험 등급 6.1(b)
포장분류 III
HS 번호 29349990
유해 물질 데이터 65277-42-1(Hazardous Substances Data)
독성 LD50 in mice, rats, guinea pigs, dogs (mg/kg): 44, 86, 28, 49 i.v.; 702, 227, 202, 780 orally (Heel)
기존화학 물질 KE-00116
그림문자(GHS): GHS hazard pictogramsGHS hazard pictogramsGHS hazard pictograms
신호 어: Danger
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H301 삼키면 유독함 급성 독성 물질 - 경구 구분 3 위험 GHS hazard pictograms P264, P270, P301+P310, P321, P330,P405, P501
H373 장기간 또는 반복 노출되면 장기(또는, 영향을 받은 알려진 모든 장기를 명시)에 손상을 일으킬 수 있음 특정 표적장기 독성 - 반복 노출 구분 2 경고 P260, P314, P501
H410 장기적 영향에 의해 수생생물에 매우 유독함 수생 환경유해성 물질 - 만성 구분 1 경고 GHS hazard pictograms P273, P391, P501
예방조치문구:
P201 사용 전 취급 설명서를 확보하시오.
P202 모든 안전 조치 문구를 읽고 이해하기 전에는 취급하지 마시오.
P260 분진·흄·가스·미스트·증기·...·스프레이를 흡입하지 마시오.
P264 취급 후에는 손을 철저히 씻으시오.
P264 취급 후에는 손을 철저히 씻으시오.
P273 환경으로 배출하지 마시오.
P301+P310 삼켰다면 즉시 의료기관(의사)의 진찰을 받으시오.
NFPA 704
0
2 0

케토코나졸 MSDS


cis-1-Acetyl-4-(4-((2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazine

케토코나졸 C화학적 특성, 용도, 생산

개요

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.

화학적 성질

White or almost white powder.

용도

Ketoconazole is used to treat candidiasis, chronic mucocutaneous candidiasis, oral thrush, candiduria, blastomycosis, coccidioidomycosis, histoplasmosis, chromomycosis, and paracoccidioidomycosis. Ketoconazole is an antifungal agent.

Indications

Ketoconazole (Nizoral) is approved for treating dermatophyte infections unresponsive to griseofulvin and for patients unable to tolerate that drug. It 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.

World Health Organization (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.

원료

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.

일반 설명

Ketoconazole is an imidazole antifungal agent administered through topical or oral means. It is used for the treatment of chronic mucocutaneous candidiasis, fungal infections of the gastro-intestinal tract, dermatophyte infections, systemic infections, and fungal infections in immuno-compromised patients.

Pharmaceutical Applications

A synthetic dioxolane imidazole available for oral and topical use.

생물학적 활성

Antifungal agent; potent inhibitor of cytochrome P450c17.

Mechanism of action

Ketoconazole has little effect on Aspergillus or Cryptococcus. Ketoconazole is highly dependent on low stomach pH for absorption, and antacids or drugs that raise stomach pH will lower the bioavailability of ketoconazole. As with other azoles, it is extensively metabolized by microsomal enzymes. All the metabolites are inactive. Evidence that CYP3A4 plays a significant role in metabolism of ketoconazole is that coadministration of CYP3A4 inducers, such as phenytoin, carbamazepine, and rifampin, can cause as much as a 50% reduction in levels of ketoconazole.

Pharmacokinetics

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

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.

부작용

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.

신진 대사

Ketoconazole is extensively degraded by the liver, and very little active drug is excreted in either the urine or bile; the dose need not be modified for renal insufficiency. Adverse reactions to topical ketoconazole are very rare.

주의 사항

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.

케토코나졸 준비 용품 및 원자재

원자재

준비 용품


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