Caspofungin

Title: Caspofungin
CAS Registry Number: 162808-62-0
CAS Name: 1-[(4R,5S)-5-[(2-Aminoethyl)amino]-N2-(10,12-dimethyl-1-oxotetradecyl)-4-hydroxy-L-ornithine]-5-[(3R)-3-hydroxy-L-ornithine]-pneumocandin B0
Molecular Formula: C52H88N10O15
Molecular Weight: 1093.31
Percent Composition: C 57.13%, H 8.11%, N 12.81%, O 21.95%
Literature References: Semisynthetic echinocandin antifungal that inhibits 1,3-b-D-glucan synthase which is required for cell wall synthesis. Prepn: J. M. Balkovec et al., WO 9421677; eidem, US 5378804 (1994, 1995 both to Merck & Co.). HPLC/MS determn in plasma: C. M. Chavez-Eng et al., J. Chromatogr. B 721, 229 (1999). Clinical study vs amphotericin B, q.v. in Candida esophagitis: A. Villanueva et al., Clin. Infect. Dis. 33, 1529 (2001). Review of in vitro antifungal activity, pharmacology and clinical development: A. H. Groll, T. J. Walsh, Expert Opin. Invest. Drugs 10, 1545-1558 (2001); A. Hoang, Am. J. Health-Syst. Pharm. 58, 1206-1214 (2001).
Derivative Type: Acetate
CAS Registry Number: 179463-17-3
Manufacturers' Codes: MK-0991
Trademarks: Cancidas (Merck & Co.)
Molecular Formula: C52H88N10O15.2C2H4O2
Molecular Weight: 1213.42
Percent Composition: C 55.43%, H 7.97%, N 11.54%, O 25.05%
Properties: Hygroscopic white to off-white powder. Freely sol in water, methanol; slightly sol in ethanol.
Therap-Cat: Antifungal.
Keywords: Antifungal (Antibiotics); Echinocandins.
Cassaidine Cassaine Cassamine Castanea Castanospermine

Caspofungin
Caspofungin.svg
Caspofungin ball-and-stick.png
Systematic (IUPAC) name
N-[(3S,6S,9S,11R,15S,18S,20R,21R,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[22.3.0.09,13]heptacosan-18-yl]-10,12-dimethyltetradecanamide
Clinical data
Trade names Cancidas
AHFS/Drugs.com monograph
Licence data EMA:Link, US FDA:link
Pregnancy cat. C
Legal status Prescription only
Routes IV
Pharmacokinetic data
Bioavailability 100% (intravenous use only)
Protein binding 97%
Half-life 9–11 hours
Identifiers
CAS number 179463-17-3 YesY
ATC code J02AX04
PubChem CID 468682
DrugBank DB00520
ChemSpider 13180298 YesY
UNII VUW370O5QE N
ChEMBL CHEMBL499808 N
Chemical data
Formula C52H88N10O15 
Mol. mass 1093.31 g/mol
 N (what is this?)  (verify)

Caspofungin (INN[1]) (brand name Cancidas worldwide) is a lipopeptide antifungal drug from Merck & Co., Inc.. It is a member of a new class of antifungals termed the echinocandins. It works by inhibiting the enzyme (1→3)-β-D-glucan synthase and thereby disturbing the integrity of the fungal cell wall. Caspofungin was the first inhibitor of fungal (1→3)-β-D-glucan synthesis to be approved by the United States Food and Drug Administration.[2] Caspofungin is administered intravenously.