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Caspofungin Acetate

CAS# 179463-17-3

Caspofungin Acetate

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Chemical structure

Caspofungin Acetate

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Chemical Properties of Caspofungin Acetate

Cas No. 179463-17-3 SDF Download SDF
PubChem ID 6850808 Appearance Powder
Formula C56H96N10O19 M.Wt 1213.42
Type of Compound N/A Storage Desiccate at -20°C
Synonyms L 743872; L 743873; MK 0991
Solubility H2O : ≥ 100 mg/mL (82.41 mM)
DMSO : ≥ 83.3 mg/mL (68.65 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name acetic acid;N-[(3S,6S,9S,11R,15S,18S,20R,21S,24S,25S)-21-(2-aminoethylamino)-3-[(1R)-3-amino-1-hydroxypropyl]-6-[(1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-11,20,25-trihydroxy-15-[(1R)-1-hydroxyethyl]-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexazatricyclo[22.3.0.09,13]heptacosan-18-yl]-10,12-dimethyltetradecanamide
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
Standard InChIKey OGUJBRYAAJYXQP-LLXMLGLCSA-N
Standard InChI InChI=1S/C52H88N10O15.2C2H4O2/c1-5-28(2)24-29(3)12-10-8-6-7-9-11-13-39(69)56-34-26-38(68)46(55-22-21-54)60-50(75)43-37(67)19-23-61(43)52(77)41(36(66)18-20-53)58-49(74)42(45(71)44(70)31-14-16-32(64)17-15-31)59-48(73)35-25-33(65)27-62(35)51(76)40(30(4)63)57-47(34)72;2*1-2(3)4/h14-17,28-30,33-38,40-46,55,63-68,70-71H,5-13,18-27,53-54H2,1-4H3,(H,56,69)(H,57,72)(H,58,74)(H,59,73)(H,60,75);2*1H3,(H,3,4)/t28?,29?,30-,33-,34+,35+,36-,37+,38-,40+,41+,42+,43+,44+,45+,46+;;/m1../s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Caspofungin Acetate

DescriptionCaspofungin (Acetate) is an antifungal drug, and noncompetitively inhibits 1,3-β-d glucan synthase activity.In Vivo:Mice injected with caspofungin at vitreal concentrations from 0.41 to 4.1 μM do not have significant alterations in their ERG waveforms, and their retinas have no detectable morphologic changes or loss of cells. At the vitreal concentration of 41 μM, caspofungin reduces the amplitudes of the a-waves, b-waves, and scotopic threshold responses of the ERG and also produces a decrease in the number of cells in the ganglion cell layer[1]. Caspofungin (8 mg/kg) or amphotericin B at 1 mg/kg given i.p. once daily for 7 days beginning at 30 h after infection resulted in 100% survival through day 28 relative to vehicle control treatment, which results in 100% mortality by day 11 after infectious challenge. Caspofungin reduces recovery of viable Candida from kidney and brain tissues compared to vehicle control treatment on day 5, when control burden peaked. Caspofungin-treated mice dosed with 2 mg/kg or greater have significantly lower brain burden than amphotericin-B-treated mice at day 5. Amphotericin B and caspofungin treatment reduce kidney fungal burden by 1.7 log CFU/g and 2.46 to 3.64 log CFU/g, respectively[2].

References:
[1]. Mojumder DK, et al. Evaluating retinal toxicity of intravitreal caspofungin in the mouse eye. Invest Ophthalmol Vis Sci. 2010 Nov;51(11):5796-803. [2]. Flattery, Amy M. et al. Efficacy of caspofungin in a juvenile mouse model of central nervous system candidiasis. Antimicrobial Agents and Chemotherapy (2011), 55(7), 3491-3497.

Protocol

Animal Administration [2]
Antifungal therapy is initiated at 30 h after infectious challenge and is given by intraperitoneal (i.p.) injection once daily for 7 days. Mice are treated with caspofungin at 1, 2, 4, or 8 mg/kg/day, amphotericin B at 1 mg/kg/day, or vehicle control (sterile distilled water). Efficacy in this model is assessed in 3 ways: by monitoring survival in a group of 10 animals in each treatment group, by monitoring Candida burden in kidney and brain tissues in a second set of treated animals, and by histologically evaluating the kidneys and brains in a third set of treated animals. Mice are euthanized by CO2 inhalation, and tissues for both culture and histology are sampled at 30 h (vehicle-treated control only) and at days 5 (24 h after 4th dose), 8 (24 h after last dose), 14, 21 (caspofungin-treated only), and 28 after challenge.

References:
[1]. Mojumder DK, et al. Evaluating retinal toxicity of intravitreal caspofungin in the mouse eye. Invest Ophthalmol Vis Sci. 2010 Nov;51(11):5796-803. [2]. Flattery, Amy M. et al. Efficacy of caspofungin in a juvenile mouse model of central nervous system candidiasis. Antimicrobial Agents and Chemotherapy (2011), 55(7), 3491-3497.

Caspofungin Acetate Dilution Calculator

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Preparing Stock Solutions of Caspofungin Acetate

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 0.8241 mL 4.1206 mL 8.2412 mL 16.4823 mL 20.6029 mL
5 mM 0.1648 mL 0.8241 mL 1.6482 mL 3.2965 mL 4.1206 mL
10 mM 0.0824 mL 0.4121 mL 0.8241 mL 1.6482 mL 2.0603 mL
50 mM 0.0165 mL 0.0824 mL 0.1648 mL 0.3296 mL 0.4121 mL
100 mM 0.0082 mL 0.0412 mL 0.0824 mL 0.1648 mL 0.206 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Caspofungin Acetate

Caspofungin (Cancidas; L 743872; L 743873; MK 0991) is an antifungal drug.

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References on Caspofungin Acetate

Comedication of caspofungin acetate and cyclosporine A after allogeneic haematopoietic stem cell transplantation leads to negligible hepatotoxicity.[Pubmed:18471157]

Mycoses. 2008;51 Suppl 1:19-24.

Infections and adverse drug reactions both contribute substantially to mortality after allogeneic stem cell transplantation. It is therefore crucial to the transplant physician to develop an optimal anti-infective strategy, i.e. one which is highly effective and shows few side effects. Caspofungin Acetate, the founding member of the echinocandins, is widely used against invasive fungal infections. We retrospectively assessed the hepatotoxicity of Caspofungin Acetate when administered with cyclosporine A. We reviewed the medical charts of 20 recipients of an allogeneic transplant. In detail, the median value of alanine amino transferase before, during and after administration of Caspofungin Acetate was 0.39 [standard error of the mean (SEM) 0.65], 0.77 (17) and 0.56 (0.77) micromol l(-1). The maximal value was 4-, 104- and 3.3-fold the upper normal level. The median value of aspartate amino transferase was 0.28 (SEM 0.45), 0.71 (26.26) and 0.60 (0.84) micromol l(-1). The maximal value before, during and after the administration of Caspofungin Acetate was 3.6-, 203- and 5.3-fold the upper normal level. The median value of gamma glutamyl transferase before, during and after administration of Caspofungin Acetate was 1.27 (SEM 1.78), 2.33 (3.41) and 1.77 (4.32) micromol l(-1). The maximal value was 1.38-, 2.53- and 1.93-fold the upper normal level. The median value of alkaline phosphatase before, during and after administration of Caspofungin Acetate was 1.11 (SEM 0.4), 1.97 (2.30) and 1.66 (5.48) micromol l(-1). The maximal value was 0.88-, 4.2- and 8.42-fold the upper normal level, respectively. The median value of total bilirubin before, during and after administration of Caspofungin Acetate was 23 (SEM 19.69), 38 (55.41) and 20 (67.23) micromol l(-1). The maximal value was 4.18-, 14.18- and 17.88-fold the upper normal level. Taken together, the elevations observed fell after the discontinuation of Caspofungin Acetate. This report is in accordance with published data. As expected, we did not find any evidence pointing to an increase in nephrotoxicity by Caspofungin Acetate.

Successful treatment of liver aspergilloma by caspofungin acetate first-line therapy in a non-immunocompromised patient.[Pubmed:23109838]

Int J Mol Sci. 2012;13(9):11063-70.

Aspergillosis remains to be a life-threatening complication in immunocompromised patients. However, Aspergillus infection can be observed in non-immunocompromised individuals in rare cases. We report a case of liver aspergilloma in a chronic aplastic anemia patient under relatively intact immune status. Therapeutic strategy for this rare condition was extensively discussed and Caspofungin Acetate single agent first-line therapy was applied after careful consideration. Encouraging clinical and radiologic improvements were achieved in response to the antifungal salvage. Our long-term follow-up study also revealed a favorable prognosis. Based on this experience, we suggest Caspofungin Acetate as first-line therapy for treatment plans of liver aspergilloma.

Compatibility of caspofungin acetate injection with other drugs simulated y-site coadministration.[Pubmed:23969719]

Int J Pharm Compd. 2008 May-Jun;12(3):276-8.

The physical compatibility of Caspofungin Acetate injection with selected other drugs during simulated Y-site coadministration was evaluated by visual observation and turbidity measurement. Five-milliliter samples of Caspofungin Acetate 0.7 mg/mL in 0.9% sodium chloride injection were combined with 5 mL of 67 other drugs including antineoplastics,analgesics, anti-infectives, and supportive care drugs, undiluted or diluted in 0.9% sodium chloride injection or 5% dextrose injection, and with a parenteral nutrition admixture. Visual examinations were performed with the unaided eye in normal laboratory fluorescent light and with a Tyndall beam (high-intensity monodirectional light beam) to enhance visualization of small particles and low-level turbidity. The turbidity of each sample was measured as well. The sample mixtures were evaluated immediately and at 1 and 4 hours after preparation. Nineteen of the drugs tested and the parenteral nutrition admixture were incompatible with Caspofungin Acetate 0.7 mg/mL during the 4-hour observation period. The remaining drugs were compatible for at least 4 hours. Gross precipitation or turbidity changes visible in normal diffuse room light with the unaided eye occurred with 18 drugs and with the parenteral nutrition admixture. Microprecipitation of particulates not visible with the unaided eye occurred with cytarabine. The measured turbidity of the Caspofungin Acetate control solutions and the compatible test samples remained essentially unchanged throughout the observation period. In combination with Caspofungin Acetate, 48 drugs and a parenteral nutrition admixture were considered to be physically compatible. In contrast, 19 drugs with the parenteral nutrition admixture exhibited frank precipitation or microparticulate formation within 4 hours and should not be simultaneously administered via Y-site with Caspofungin Acetate.

Engineering of Glarea lozoyensis for exclusive production of the pneumocandin B0 precursor of the antifungal drug caspofungin acetate.[Pubmed:25527531]

Appl Environ Microbiol. 2015 Mar;81(5):1550-8.

Pneumocandins produced by the fungus Glarea lozoyensis are acylated cyclic hexapeptides of the echinocandin family. Pneumocandin B0 is the starting molecule for the first semisynthetic echinocandin antifungal drug, Caspofungin Acetate. In the wild-type strain, pneumocandin B0 is a minor fermentation product, and its industrial production was achieved by a combination of extensive mutation and medium optimization. The pneumocandin biosynthetic gene cluster was previously elucidated by a whole-genome sequencing approach. Knowledge of the biosynthetic cluster suggested an alternative way to produce exclusively pneumocandin B0. Disruption of GLOXY4, encoding a nonheme, alpha-ketoglutarate-dependent oxygenase, confirmed its involvement in l-leucine cyclization to form 4S-methyl-l-proline. The absence of 4S-methyl-l-proline abolishes pneumocandin A0 production, and 3S-hydroxyl-l-proline occupies the hexapeptide core's position 6, resulting in exclusive production of pneumocandin B0. Retrospective analysis of the GLOXY4 gene in a previously isolated pneumocandin B0-exclusive mutant (ATCC 74030) indicated that chemical mutagenesis disrupted the GLOXY4 gene function by introducing two amino acid mutations in GLOXY4. This one-step genetic manipulation can rationally engineer a high-yield production strain.

Description

Caspofungin Acetate (MK-0991 Acetate) is an antifungal drug, and noncompetitively inhibits 1,3-β-d glucan synthase activity.

Keywords:

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