Caspofungin

• Catalog No.: DB00520
• CAS Number: 179463-17-3
• M. F.: C52H88N10O15
• M. W.: 1093.31312

SYNONYMS

• IUPAC name: N-[(3S,6S,9S,11R,15S,18S,20R,21S,24S,25S)-3-[(1R)-3-amino-1-hydroxypropyl]-21-[(2-aminoethyl)amino]-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-hexaazatricyclo[22.3.0.0^{9,13}]heptacosan-18-yl]-10,12-dimethyltetradecanamide
• IUPAC Traditional name: caspofungin
• Brand Name: Cancidas
• Synonyms: Caspofungin acetate; Capsofungin

DATABASE IDS

• PubChem SID: 46508288
• CAS Number: 179463-17-3
• PubChem CID: 2826718

PROPERTIES

• Hydrophobicity(logP): 0

DETAILS

Description (English)

• Drug Groups: approved
• Description: Caspofungin (brand name Cancidas worldwide) is an antifungal drug, the first of a new class termed the echinocandins from Merck & Co., Inc. It shows activity against infections with Aspergillus and Candida, and works by inhibiting β(1,3)-D-Glucan of the fungal cell wall. Caspofungin is administered intravenously.
• Indication: For the treatment of esophageal candidiasis and invasive aspergillosis in patients who are refractory to or intolerant of other therapies.
• Pharmacology: Caspofungin is an antifungal drug, and belongs to a new class termed the echinocandins. It is used to treat Aspergillus and Candida infection, and works by inhibiting cell wall synthesis. Antifungals in the echinocandin class inhibit the synthesis of glucan in the cell wall, probably via the enzyme 1,3-beta glucan synthase. There is a potential for resistance development to occur, however in vitro resistance development to Caspofungin by Aspergillus species has not been studied.
• Toxicity: Side effects include rash, swelling, and nausea (rare)
• Affected Organisms: Aspergillis, Candida and other fungi
• Biotransformation: Metabolized slowly by hydrolysis and N-acetylation
• Absorption: 92% tissue distribution within 36-48 hours after intravenous infusion
• Half Life: 9-11 hours
• Protein Binding: 97%
• Elimination: After single intravenous administration of [3H] caspofungin acetate, excretion of caspofungin and its metabolites in humans was 35% of dose in feces and 41% of dose in urine.
• Clearance: * 12 mL/min [After single IV administration]
• References: Letscher-Bru, Valérie, and Raoul Herbrecht. 2003. Caspofungin: the first representative of a new antifungal class. Journal of Antimicrobial Chemotherapy 51, no. 3 (March 1): 513 -521. "doi:10.1093/jac/dkg117":http://dx.doi.org/10.1093/jac/dkg117.; Sucher AJ, Chahine EB, Balcer HE: Echinocandins: the newest class of antifungals. Ann Pharmacother. 2009 Oct;43(10):1647-57. Epub 2009 Sep 1. [Pubmed] ; Morrison VA: Caspofungin: an overview. Expert Rev Anti Infect Ther. 2005 Oct;3(5):697-705. [Pubmed] ; McCormack PL, Perry CM: Caspofungin: a review of its use in the treatment of fungal infections. Drugs. 2005;65(14):2049-68. [Pubmed] ; Morris MI, Villmann M: Echinocandins in the management of invasive fungal infections, part 1. Am J Health Syst Pharm. 2006 Sep 15;63(18):1693-703. [Pubmed] ; Morris MI, Villmann M: Echinocandins in the management of invasive fungal infections, Part 2. Am J Health Syst Pharm. 2006 Oct 1;63(19):1813-20. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• Morrison VA: Caspofungin: an overview. Expert Rev Anti Infect Ther. 2005 Oct;3(5):697-705. Pubmed
• McCormack PL, Perry CM: Caspofungin: a review of its use in the treatment of fungal infections. Drugs. 2005;65(14):2049-68. Pubmed
• Morris MI, Villmann M: Echinocandins in the management of invasive fungal infections, part 1. Am J Health Syst Pharm. 2006 Sep 15;63(18):1693-703. Pubmed
• Morris MI, Villmann M: Echinocandins in the management of invasive fungal infections, Part 2. Am J Health Syst Pharm. 2006 Oct 1;63(19):1813-20. Pubmed
• Letscher-Bru, Valérie, and Raoul Herbrecht. 2003. Caspofungin: the first representative of a new antifungal class. Journal of Antimicrobial Chemotherapy 51, no. 3 (March 1): 513 -521. "doi:10.1093/jac/dkg117":http://dx.doi.org/10.1093/jac/dkg117.
• Sucher AJ, Chahine EB, Balcer HE: Echinocandins: the newest class of antifungals. Ann Pharmacother. 2009 Oct;43(10):1647-57. Epub 2009 Sep 1. Pubmed