CAS Number65277-42-1
Synonyms(2R,4S)-ketoconazole; Brizoral; Ketoconazole; Onofin K; Nizral; Fitonal; MFCD00058579; Fungarest; EINECS 265-667-4; Fungoral; Ketoisdin; PANFUNGOL; Ketoderm; kw-1414; NIZORAL; Orifungal M
Molecular FormulaC26H28Cl2N4O4
Molecular Weight531.43
Purity99.0-101.0 (EP, titration)%
Density1.4±0.1 g/cm3
Boiling Point753.4±60.0 °C at 760 mmHg
Melting Point146°C
Appearancepowder
EINECS265-667-4
Symbol
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| Chemical & Physical Properties | |
|---|---|
| CAS Number | 65277-42-1 |
| Catalog No. | 2A-9011099 |
| Chinese Name | 酮康唑 |
| Synonyms | (2R,4S)-ketoconazole; Brizoral; Ketoconazole; Onofin K; Nizral; Fitonal; MFCD00058579; Fungarest; EINECS 265-667-4; Fungoral; Ketoisdin; PANFUNGOL; Ketoderm; kw-1414; NIZORAL; Orifungal M |
| Molecular Formula | C26H28Cl2N4O4 |
| Molecular Weight | 531.43 |
| Purity | 99.0-101.0 (EP, titration) |
| Density | 1.4±0.1 g/cm3 |
| Boiling Point | 753.4±60.0 °C at 760 mmHg |
| Melting Point | 146°C |
| Appearance | powder |
| Water Solubility | Soluble in: methanol |
| Storage Condition | Store in an airtight container in a cool, dry plac |
| Packaging | III |
| Inventory | 20kg and 10kg |
| Application | Ketoconazole is an imidazole antifungal agent, a classic CYP3A4 inhibitor, and an inhibitor of CYP24A1. |
| EINECS | 265-667-4 |
| HTC | 2933990090 |
| PubChem ID | 24278176 |
| MDL Number | MFCD00058579 |
| SMILES | CC(=O)N1CCN(CC1)c2ccc(OC[C@H]3CO[C@@](Cn4ccnc4)(O3)c5ccc(Cl)cc5Cl)cc2 |
| InChI | 1S/C26H28Cl2N4O4/c1-19(33)31-10-12-32(13-11-31)21-3-5-22(6-4-21)34-15-23-16-35-26(36-23,17-30-9-8-29-18-30)24-7-2-20(27)14-25(24)28/h2-9,14,18,23H,10-13,15-17H2,1H3/t23-,26-/m0/s1 |
| InChI Key | XMAYWYJOQHXEEK-OZXSUGGESA-N |
| NACRES Code | NA.85 |
| UNSPSC | 51101500 |
| Hazard Symbols | 6.1(b) |
| MSDS | msds/11099_1_65277_42_1.pdf |
| Bioactivity | Ketoconazole is an imidazole anti-fungal agent, a CYP3A4 and CYP24A1 inhibitor.Target: CYP3A4 CYP24A1Ketoconazole, an imidazole anti-fungal agent, has often produced features of androgen deficiency including decreased libido, gynecomastia, impotence, oligospermia, and decreased testosterone levels, in men being treated for chronic mycotic infections [1]. Ketoconazole also is a cytochrome P450 inhibitor [2].Ketoconazole (KTZ), on the antischistosomal potential of these quinolines against Schistosoma mansoni infection by evaluating parasitological, histopathological, and biochemical parameters. Mice were classified into 7 groups: uninfected untreated (I), infected untreated (II), infected treated orally with PZQ (1,000 mg/kg) (III), QN (400 mg/kg) (IV), KTZ (10 mg/kg)+QN as group IV (V), HF (400 mg/kg) (VI), and KTZ (as group V)+HF (as group VI) (VII). KTZ plus QN or HF produced more inhibition (P<0.05) in hepatic CYP450 (85.7% and 83.8%) and CYT b5 (75.5% and 73.5%) activities, respectively, than in groups treated with QN or HF alone. This was accompanied with more reduction in female (89.0% and 79.3%), total worms (81.4% and 70.3%), and eggs burden (hepatic; 83.8%, 66.0% and intestinal; 68%, 64.5%), respectively, and encountering the granulomatous reaction to parasite eggs trapped in the liver.[3] CYP24A1 inhibitor enhances antiproliferative effects, increases systemic calcitriol exposure, and promotes the activation of caspase-independent apoptosis pathway.[4] Related Catalog Signaling Pathways >> Metabolic Enzyme/Protease >> Cytochrome P450 Signaling Pathways >> Anti-infection >> Fungal Research Areas >> Infection References [1]. Seif El-Din SH, et al. Effect of ketoconazole, a cytochrome P450 inhibitor, on the efficacy of quinine and halofantrine against Schistosoma mansoni in mice. Korean J Parasitol. 2013 Apr;51(2):165-75. [2]. Eil C. Ketoconazole binds to the human androgen receptor. Horm Metab Res. 1992 Aug;24(8):367-70. [3]. Muindi JR et al. CYP24A1 inhibition enhances the antitumor activity of calcitriol. Endocrinology. 2010 Sep;151(9):4301-12. Chemical & Physical Properties Density 1.4±0.1 g/cm3 Boiling Point 753.4±60.0 °C at 760 mmHg Melting Point 146°C Molecular Formula C26H28Cl2N4O4 Molecular Weight 531.431 Flash Point 409.4±32.9 °C Exact Mass 530.148743 PSA 69.06000 LogP 3.55 Vapour Pressure 0.0±2.5 mmHg at 25°C Index of Refraction 1.642 InChIKey XMAYWYJOQHXEEK-OIDFQQKBSA-N SMILES CC(=O)N1CCN(c2ccc(OCC3COC(Cn4ccnc4)(c4ccc(Cl)cc4Cl)O3)cc2)CC1 |
| Use of | Properties Articles411 Name Ketoconazole Synonym More Synonyms Ketoconazole Biological Activity Related Catalog Signaling Pathways >> Metabolic Enzyme/Protease >> Cytochrome P450 Signaling Pathways >> Anti-infection >> Fungal Research Areas >> Infection References [1]. Seif El-Din SH, et al. Effect of ketoconazole, a cytochrome P450 inhibitor, on the efficacy of quinine and halofantrine against Schistosoma mansoni in mice. Korean J Parasitol. 2013 Apr;51(2):165-75. [2]. Eil C. Ketoconazole binds to the human androgen receptor. Horm Metab Res. 1992 Aug;24(8):367-70. [3]. Muindi JR et al. CYP24A1 inhibition enhances the antitumor activity of calcitriol. Endocrinology. 2010 Sep;151(9):4301-12. Chemical & Physical Properties Exact Mass 530.148743 PSA 69.06000 Index of Refraction 1.642 InChIKey XMAYWYJOQHXEEK-OIDFQQKBSA-N |
| Tax Rebate | 13.0% |
| Supervision | None. MFN tariff: 6.5%. Ordinary tariff: 20.0% |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Dangerous Regulations for land transport: 2811 International Dangerous Regulations for sea transport: 2811 International Dangerous Regulations for air transport: 2811 14.2 United Nations shipping name European Land Transport Dangerous Regulations: TOXIC SOLID, ORGANIC, N.O.S. (Ketoconazole) IMDG Code: TOXIC SOLID, ORGANIC, N.O.S. (Ketoconazole) International air transport hazard regulations: Toxic solid, organic, n.o.s. (Ketoconazole) 14.3 Transport hazard categories European Land Transport Danger Regulations: 6.1 International Maritime Transport Danger Regulations: 6.1 International Air Transport Danger Regulations: 6.1 14.4 Package group European Land Transport Danger Regulations: III International Maritime Transport Danger Regulations: III International Air Transport Danger Regulations: III 14.5 Environmental hazards European Land Transport Dangerous Regulations: Yes International Maritime Transport Dangerous Regulations International Air Transport Dangerous Regulations: No Marine Pollutants (Yes/No): Yes 14.6 Special reminder to users No data available |
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