Ketoconazole
- CAS No.
- 65277-42-1
- Chemical Name:
- Ketoconazole
- Synonyms
- 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
- Molecular Formula:
- C26H28Cl2N4O4
- Molecular Weight:
- 531.43
- MOL File:
- 65277-42-1.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/8/21 22:41:43
| Melting point | 148-152 °C |
|---|---|
| Boiling point | 753.4±60.0 °C(Predicted) |
| Density | 1.4046 (rough estimate) |
| refractive index | -10.5 ° (C=0.4, CHCl3) |
| Flash point | 9℃ |
| storage temp. | 2-8°C |
| solubility | methanol: soluble50mg/mL |
| pka | pKa 3.25/6.22(H2O,t =25,I=0.025) (Uncertain) |
| form | Off-white solid |
| color | white to light yellow |
| optical activity | [α]20/D -1 to 1°, c = 4 in methanol |
| Water Solubility | Soluble in DMSO, ethanol, chloroform, water, and methanol. |
| Merck | 14,5302 |
| BCS Class | 2 |
| Stability | Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months. |
| InChIKey | XMAYWYJOQHXEEK-OZXSUGGESA-N |
| LogP | 4.350 |
| CAS DataBase Reference | 65277-42-1(CAS DataBase Reference) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |    GHS06,GHS08,GHS09 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Danger | |||||||||
| Hazard statements | H301-H360F-H373-H410 | |||||||||
| Precautionary statements | P201-P202-P260-P264-P273-P301+P310 | |||||||||
| Hazard Codes | T,N,F | |||||||||
| Risk Statements | 25-36/37/38-23/24/25-50/53-48/22-60-39/23/24/25-11 | |||||||||
| Safety Statements | 36-45-36/37/39-26-61-60-53-36/37-16-7 | |||||||||
| RIDADR | UN 2811 6.1/PG 3 | |||||||||
| WGK Germany | 3 | |||||||||
| RTECS | TK7912300 | |||||||||
| HazardClass | 6.1(b) | |||||||||
| PackingGroup | III | |||||||||
| HS Code | 29349990 | |||||||||
| Toxicity | LD50 in mice, rats, guinea pigs, dogs (mg/kg): 44, 86, 28, 49 i.v.; 702, 227, 202, 780 orally (Heel) | |||||||||
| NFPA 704 |
|
Ketoconazole price More Price(8)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | UC280 | Ketoconazole | 65277-42-1 | 5MG | ₹25915.05 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | UC280 | Ketoconazole | 65277-42-1 | 10MG | ₹46612.45 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | PHR1385 | Ketoconazole Pharmaceutical Secondary Standard; Certified Reference Material | 65277-42-1 | 1G | ₹7664.1 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | K1003 | Ketoconazole 99.0-101.0% (EP, titration) | 65277-42-1 | 100MG | ₹18326.73 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | K-004 | Ketoconazole solution 2.0?mg/mL in methanol, ampule of 1?mL, certified reference material, Cerilliant? | 65277-42-1 | 1ML | ₹18952.5 | 2022-06-14 | Buy |
Ketoconazole Chemical Properties,Uses,Production
Description
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.
Chemical Properties
White or almost white powder.
Uses
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.
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.
General Description
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.
Biological Activity
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.
Side effects
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.
Metabolism
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.
Precautions
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 Preparation Products And Raw materials
Raw materials
1of2
chevron_rightPreparation Products
| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| Jigs Chemical ltd | +919099003427 | Gujarat, India | 239 | 58 | Inquiry |
| THE MOLECULEZ | +91-7506703683 +91-7506703683 | Maharashtra, India | 79 | 58 | Inquiry |
| PRODIGIOUS LIFE SCIENCES | +91-9177472555 +91-9177472555 | Hyderabad, India | 236 | 58 | Inquiry |
| STELLENCE PHARMSCIENCE PVT TLD | +91-9820778787 +91-9820778787 | Bangalore, India | 25 | 58 | Inquiry |
| SNECOFRi Pvt Ltd | +91-9032850129 +91-9032850129 | Telangana, India | 404 | 58 | Inquiry |
| Shiv pharma chem | +91-9974421207 +91-9974421207 | Gujarat, India | 52 | 58 | Inquiry |
| Gonane Pharma | +91-9819380043 +91-9819380043 | NaviMumbai, India | 192 | 58 | Inquiry |
| Shree HariKrishna Pharmaceuticals | +91-9925611910 +91-9925611910 | Gujarat, India | 16 | 58 | Inquiry |
| CNS CHEMICALS | +91-9381957258 +91-9381957258 | Telangana, India | 354 | 58 | Inquiry |
| Piramal Pharma Solutions | +919892735994 | Maharashtra, India | 48 | 58 | Inquiry |
| Supplier | Advantage |
|---|---|
| Jigs Chemical ltd | 58 |
| THE MOLECULEZ | 58 |
| PRODIGIOUS LIFE SCIENCES | 58 |
| STELLENCE PHARMSCIENCE PVT TLD | 58 |
| SNECOFRi Pvt Ltd | 58 |
| Shiv pharma chem | 58 |
| Gonane Pharma | 58 |
| Shree HariKrishna Pharmaceuticals | 58 |
| CNS CHEMICALS | 58 |
| Piramal Pharma Solutions | 58 |
Related articles
- What is ketoconazole used to treat?
- Ketoconazole is a imidazole antimycotic ketoconazole used to treat systemic therapy of dermatomycoses, blastomycosis, coccidio....
- Mar 16，2024
- Safety of Ketoconazole
- Ketoconazole is an imidazole fungicidal agent with a very broad spectrum of activity against many fungal species that is used ....
- Jul 4，2022
65277-42-1(Ketoconazole)Related Search:
1of4
chevron_right