Anidulafungin CAS 166663-25-8
Introduction：Basic information about Anidulafungin CAS 166663-25-8, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Anidulafungin Basic information
| Product Name: | Anidulafungin |
| Synonyms: | Anidulafungin;Echinocandin B, 1-(4R,5R)-4,5-dihydroxy-N2-4-(pentyloxy)1,1:4,1-terphenyl-4-ylcarbonyl-L-ornithine-;Anidulafungin(LY303366);Ecalta;Eraxis;LY 303366;LY 303366, Eraxis;1-[(4R,5R)-4,5-dihydroxy-N2-[[4''-(pentyloxy)[1,1'',1''-terphenyl]-4-yl]carbonyl]-L-ornithine]-echinocandin B |
| CAS: | 166663-25-8 |
| MF: | C58H73N7O17 |
| MW: | 1140.24 |
| EINECS: | 658-060-4 |
| Product Categories: | Inhibitors;Antifungals;API |
| Mol File: | 166663-25-8.mol |
Anidulafungin Chemical Properties
| Melting point | >196°C (subl.) |
| Boiling point | 1477.0±65.0 °C(Predicted) |
| density | 1.47±0.1 g/cm3(Predicted) |
| storage temp. | under inert gas (nitrogen or Argon) at 2-8°C |
| solubility | DMSO (Slightly, Heated), Methanol (Slightly) |
| pka | 9.86±0.26(Predicted) |
| form | Solid |
| color | White to Pale Beige |
| InChIKey | SHVCZGIPSKLHSD-GMFGLMPVSA-N |
Safety Information
| Description | Anidulafungin, a semi-synthetic derivative of echinocandin B, has been developedand launched as an intravenous treatment for serious fungal infections,such as candidemia, Candida-derived peritonitis, intra-abdominal abscesses, andesophageal candidiasis. As a non-competitive inhibitor of 1,3-b-D-glucan synthase,which is responsible for the formation of glucan polymers, anidulafungininterferes with the cell wall synthesis of most pathogenic fungi. This mode ofaction is characteristic of the echinocandin class of antifungals. While the firstmember of this class, cilofungin, was withdrawn due to toxicity associated withthe formulation vehicle, anidulafungin follows the successful introductionof caspofungin and micafungin. Compared to the other echinocandins,anidulafungin appears to be more potent (MIC90 ofr0.25 mg/mL for C.albicans,0.5 mg/mL for C.glabrata, 1 mg/mL for C. krusel and C.tropicalis, 2mg/mL forC.lusitaniae, and 2 mg/mL for Aspergillus spp) and is devoid of significant druginteractions since it is neither an inhibitor nor substrate of the cytochrome P450isoenzymes. The emergence of the echinocandins circumvents the concernregarding the rising resistance to the azole and amphotericin B antifungals; nocross-resistance is expected because the echinocandins work at the cell wallrather than the cell membrane. |
| Originator | Eli Lilly (US) |
| Uses | nucleoside reverse transcriptase inhibitor (NRTI) for HIV treatment in adults |
| Uses | Anidulafungin is a semi-synthetic cyclic lipopeptide belonging to the echinocandin class that was reported in 1995 and commercially developed by Eli Lilly. Anidulafungin inhibits the synthesis of β-(1,3)-D-glucan, an essential component of the cell wall of susceptible fungi and is extensively referenced in the literature with over 400 citations. |
| Definition | ChEBI: A semisynthetic echinocandin anti-fungal drug. It is active against Aspergillus and Candida species and is used for the treatment of invasive candidiasis. |
| Brand name | Eraxis (Vicuron). |
| Antimicrobial activity | It is active against Aspergillus spp., Candida spp. and the cyststage of Pneumocystis jirovecii. Resistance has not yet beenreported. |
| Pharmaceutical Applications | A semisynthetic lipopeptide derived from a fermentationproduct of Aspergillus nidulans. Formulated for intravenousinfusion. |
| Pharmacokinetics | Cmax 100 mg 1-h infusion: c. 9 mg/L end infusion Plasma half-life: 18–27 h Volume of distribution: 0.6 L/kg Plasma protein binding: 84% Blood concentrations increase in proportion to dosage. Thesteady state is achieved on the first day after a loading dose(twice the daily maintenance dose). Distribution Levels in the CSF are negligible. Metabolism and excretion Unlike caspofungin and micafungin, anidulafungin is not metabolized by the liver, but undergoes slow non-enzymatic degradation in the blood to a peptide breakdown product which is enzymatically degraded and excreted in the feces and bile. About 30% of a dose is eliminated in the feces, of which less than 10% is unchanged drug. Less than 1% of a dose is excreted in the urine. No dosage adjustment is required in patients with hepatic or renal impairment. Anidulafungin is not cleared by hemodialysis. |
| Clinical Use | Candidemia and certain invasive forms of candidosis Esophageal candidosis |
| Side effects | Occasional histamine-mediated infusion-related reactions,injection site reactions and transient abnormalities of liverenzymes have been reported. |
| Metabolism | Hepatic metabolism of anidulafungin has not been observed. Anidulafungin is not a clinically relevant substrate, inducer, or inhibitor of cytochrome P450 isoenzymes. Anidulafungin undergoes slow chemical degradation at physiologic temperature and pH to a ring-opened peptide that lacks antifungal activity. The ring-opened product is subsequently converted to peptidic degradants and eliminated mainly through biliary excretion.In a single-dose clinical study, radiolabelled [14C]-anidulafungin (~88 mg) was administered to healthy subjects. Approximately 30% of the administered radioactive dose was eliminated in the faeces over 9 days, of which less than 10% was intact drug. Less than 1% of the administered radioactive dose was excreted in the urine, indicating negligible renal clearance. |
| references | [1] zhanel gg1, karlowsky ja, harding ga, balko tv, zelenitsky sa, friesen m, kabani a, turik m, hoban dj. in vitro activity of a new semisynthetic echinocandin, ly-303366, against systemic isolates of candida species, cryptococcus neoformans, blastomyces dermatitidis, and aspergillus species. antimicrob agents chemother. 1997 apr;41(4):863-5. |
Anidulafungin Preparation Products And Raw materials
| Raw materials | Methyl 4-iodobenzoate |
