Caspofungin Acetate
Caspofungin acetate (MK-0991), a new antifungal agent with minimal toxicity, inhibits synthesis of 1,3-β-D-glucan, an essential component of the fungal cell wall [1].
In vitro: Incubation of A. fumigatu with a single dose of caspofungin affected the same proportion of apical and subapical branching cells for up to 72 h.The cells at the active centers for new cell wall synthesis within A. fumigateshyphae are killed when they are exposed to caspofungin [1]. Caspofungin acetate irreversibly inhibited the enzyme 1,3-β-D-glucan synthase, preventing the formation of glucan polymers and disrupting the integrity of the fungal cell wall. The elimination half-life of caspofungin acetate was 9-10 hours [2]. Caspofungin showed activity against Aspergillusspp. as well as a variety of Candidaspp[3]. Growth kinetic studies of caspofungin acetate against Candida albicans and Candida tropicalis isolates showed that caspofungin acetate exhibited fungicidal activity (i.e., a 99% reduction in viability) within 3 to 7 h at concentrations ranging from 0.06 to 1 μg/ml (0.25 to 4 times the MIC) [4]. The minimal inhibitory concentration for 90% inhibition of Candida species by caspofungin acetate were as follows:C. albicans 0.5 μg/mL (range, 0.25-0.5), C. glabrata 1.0 μg/mL (range, 0.25-2.0), C. tropicalis 1.0 μg/mL (range, 0.25-1.0), C. parapsilosis 0.5 μg/mL (range, 0.25-1.0), and C. krusei 2.0 μg/mL (range, 0.5-2.0) [4].
Clinical trials: In a trial of 128 patients with Candida esophagitis, clinical response rates were higher with caspofungin acetate 50 or 70 mg/day (85%) than with amphotericin B 0.5 mg/kg/day (67%) [2].
References:
[1] Bowman J C, Hicks P S, Kurtz M B, et al. The antifungal echinocandincaspofungin acetate kills growing cells of Aspergillus fumigatus in vitro [J]. Antimicrobial agents and chemotherapy, 2002, 46 (9): 3001-3012.
[2] Hoang A. Caspofungin acetate: an antifungal agent [J]. American journal of health-system pharmacy, 2001, 58 (13): 1206-1214.
[3] Pacetti S A, Gelone S P. Caspofungin acetate for treatment of invasive fungal infections [J]. Annals of Pharmacotherapy, 2003, 37 (1): 90-98.
[4] Bartizal K, Gill C J, Abruzzo G K, et al. In vitro preclinical evaluation studies with the echinocandin antifungal MK-0991 (L-743,872) [J]. Antimicrobial Agents and Chemotherapy, 1997, 41 (11): 2326-2332.
| Physical Appearance | A solid |
| Storage | Store at -20°C |
| M.Wt | 1213.42 |
| Cas No. | 179463-17-3 |
| Formula | C56H96N10O19 |
| Solubility | ≥60.67 mg/mL in DMSO; insoluble in EtOH; ≥21.5 mg/mL in H2O |
| Chemical Name | acetic acid compound with (Z)-N-((2R,6S,7Z,9S,11R,12S,13E,14aS,15S,20S,21Z,23S,24Z,25aS)-20-((R)-3-amino-1-hydroxypropyl)-12-((2-aminoethyl)amino)-23-((1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl)-2,8,11,14,15,22,25-heptahydroxy-6-((R)-1-hydroxyethyl)-5 |
| SDF | Download SDF |
| Canonical SMILES | CCC(C)CC(C)CCCCCCCCC(=O)NC1CC(C(NC(=O)C2C(CCN2C(=O)C(NC(=O)C(NC(=O)C3CC(CN3C(=O)C(NC1=O)C(C)O)O)C(C(C4=CC=C(C=C4)O)O)O)C(CCN)O)O)NCCN)O.CC(=O)O.CC(=O)O |
| Shipping Condition | Small Molecules with Blue Ice, Modified Nucleotides with Dry Ice. |
| General tips | We do not recommend long-term storage for the solution, please use it up soon. |
| Cell experiment [1]: | |
|
Cell lines |
Aspergillus fumigates |
|
Preparation method |
The solubility of this compound in DMSO is >10 mM. General tips for obtaining a higher concentration: Please warm the tube at 37°C for 10 minutes and/or shake it in the ultrasonic bath for a while. Stock solution can be stored below -20°C for several months. |
|
Reacting condition |
32 μg/mL for 6 h; or 2 μg/mL for 12 h |
|
Applications |
Caspofungin suppressed the synthesis of cell wall β-1,3-glucan, which triggered a compensatory stimulation of chitin synthesis. Caspofungin induced morphological changes in Aspergillus fumigates. Moreover, Treatment with caspofungin induced ChsG-dependent upregulation of chitin synthesis and the formation of chitin-rich microcolonies in Aspergillus fumigates. |
|
References: 1 Walker, L. A., Lee, K. K., Munro, C. A. and Gow, N. A. (2015) Caspofungin Treatment of Aspergillus fumigatus Results in ChsG-Dependent Upregulation of Chitin Synthesis and the Formation of Chitin-Rich Microcolonies. Antimicrob Agents Chemother. 59, 5932-5941 |
|
Quality Control & MSDS
- View current batch:
Chemical structure
Related Biological Data
