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Showing drug card for Caspofungin (DB00520)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-06-23 18:08:16
Primary Accession Number DB00520
Secondary Accession Number
  • APRD00199
Name Caspofungin
Drug Type
  • Approved
  • Small Molecule
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.
Synonyms
  1. Capsofungin
  2. Caspofungin acetate
Brand Names
  1. Cancidas
Brand Mixtures Not Available
Chemical IUPAC 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
Chemical Formula C52H88N10O15
Chemical Structure Structure
CAS Registry Number 179463-17-3
InChI Identifier InChI=1/C52H88N10O15/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/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)/t28?,29?,30-,33-,34+,35+,36-,37+,38-,40+,41+,42+,43+,44+,45+,46+/m1/s1/f/h56-60H
InChI Key JYIKNQVWKBUSNH-FUOOKJLVDM
KEGG Drug Not Available
KEGG Compound Not Available
PubChem Compound 468682 Link Image
PubChem Substance 622847 Link Image
ChEBI ID Not Available
PharmGKB ID Not Available
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 02244266 Link Image
RxList Link http://www.rxlist.com/cgi/generic/caspofungin.htm Link Image
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Caspofungin Link Image
FDA Label
Material Safety Data Sheet (MSDS) Not Available
Synthesis Reference Not Available
Average Molecular Weight 1093.3131
Monoisotopic Molecular Weight 1092.6431
State Solid
Melting Point Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 3.67e-01 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity
Predicted LogP 0.17 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -3.47 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES CC[C@@H](C)C[C@H](C)CCCCCCCCC(=O)N[C@H]1C[C@@H](O)[C@@H](NCCN)NC(=O)[C@@H]2[C@@H](O)CCN2C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]2C[C@@H](O)CN2C(=O)[C@@H](NC1=O)[C@@H](C)O)[C@H](O)[C@@H](O)C1=CC=C(O)C=C1)[C@H](O)CCN
Canonical SMILES CCC(C)CC(C)CCCCCCCCC(=O)NC1CC(O)C(NCCN)NC(=O)C2C(O)CCN2C(=O)C(NC(=O)C(NC(=O)C2CC(O)CN2C(=O)C(NC1=O)C(C)O)C(O)C(O)C1=CC=C(O)C=C1)C(O)CCN
Drug Category
  • Antifungal Agents
  • Antifungals
ATC Codes
AHFS Codes
  • 08:14.16
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.
Mechanism of Action Caspofungin inhibits the synthesis of b (1,3)-D-glucan, an essential component of the cell wall of Aspergillus species and Candida species. b (1,3)-D-glucan is not present in mammalian cells. The primary target is beta-(1,3)-glucan synthase.
Absorption 92% tissue distribution within 36-48 hours after intravenous infusion
Toxicity Side effects include rash, swelling, and nausea (rare)
Protein Binding 97%
Biotransformation Metabolized slowly by hydrolysis and N-acetylation
Half Life 9-11 hours
Dosage Forms
Form Route
Powder, for solution Intravenous
Patient Information Not Available
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions Not Available
Food Interactions Not Available
Pathways Not Available
General References
  1. Drugs.com Link Image
  2. Wikipedia Link Image
  3. RxList Link Image
Organisms Affected
  • Aspergillis, Candida and other fungi
Targets
  1. Beta-1,3-glucan synthase
Drug Target 1 [top]
Target 1 ID 351
Target 1 Name Beta-1,3-glucan synthase
Target 1 Synonyms
  1. EC 2.4.1.34
Target 1 Gene Name Not Available
Target 1 Protein Sequence >Beta-1,3-glucan synthase 
DANQDNYLEECLKIRSVLAEFEELTTDNVSPYTPGIATEAETPVAILGAREYIFSENVGV
LGDVAASKEQTFGTLFARTLAQIGGKLHYGHPDFLNGIFMTTRGGISKAQKGLHLNEDIY
AG
Target 1 Number of Residues 124
Target 1 Molecular Weight 13224
Target 1 Theoretical pI 4.43
Target 1 GO Classification
Function
catalytic activity
transferase activity
transferase activity, transferring glycosyl groups
UDP-glycosyltransferase activity
UDP-glucosyltransferase activity
1,3-beta-glucan synthase activity
Process
physiological process
metabolism
macromolecule metabolism
carbohydrate metabolism
polysaccharide metabolism
cellular polysaccharide metabolism
glucan metabolism
beta-glucan metabolism
beta-1,3 glucan metabolism
beta-1,3 glucan biosynthesis
Component
cell
membrane
protein complex
1,3-beta-glucan synthase complex
Target 1 General Function Involved in 1,3-beta-glucan synthase activity
Target 1 Specific Function Not Available
Target 1 Pathways
Name SMPDB Link KEGG Link
Starch and sucrose metabolism SMP00058 Link Image map00500 Link Image
Target 1 Reactions
  • UDP-glucose + (1,3-beta-D-glucosyl)n = UDP + (1,3-beta-D-glucosyl)n+1
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • None
Target 1 Essentiality Essential
Target 1 GenBank ID Protein 42716259 Link Image
Target 1 UniProtKB/Swiss-Prot ID Q5DRK6 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name Q5DRK6_ASPNG Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location Not Available
Target 1 Gene Sequence >365 bp 
GACGCGAATCAGGATAACTACCTGGAGGAGTGTCTCAAGATCCGTAGCGTTCTGGCTGAG
TTCGAAGAACTTACCACCGACAATGTCTCGCCCTACACTCCTGGTATTGCCACCGAAGCT
GAGACCCCAGTCGCCATTCTCGGTGCTCGTGAATACATTTTCTCTGAGAATGTTGGTGTT
CTTGGTGACGTTGCTGCCAGTAAGGAACAGACGTTCGGTACCCTGTTTGCTCGTACCCTT
GCGCAGATTGGTGGAAAGCTGCATTATGGTCACCCTGATTTCCTAAACGGTATCTTCATG
ACGACGCGTGGTGGTATCTCCAAGGCTCAGAAGGGTCTCCACCTGAATGAAGACATCTAC
GCCGG
Target 1 GenBank Gene ID
Target 1 GeneCard ID Not Available
Target 1 GenAtlas ID Not Available
Target 1 HGNC ID Not Available
Target 1 Chromosome Location Not Available
Target 1 Locus Not Available
Target 1 SNPs Not Available
Target 1 General References Not Available
Target 1 Drug References
  1. Del Poeta M, Cruz MC, Cardenas ME, Perfect JR, Heitman J: Synergistic antifungal activities of bafilomycin A(1), fluconazole, and the pneumocandin MK-0991/caspofungin acetate (L-743,873) with calcineurin inhibitors FK506 and L-685,818 against Cryptococcus neoformans. Antimicrob Agents Chemother. 2000 Mar;44(3):739-46. [PubMed Link Image]
  2. Liu TT, Lee RE, Barker KS, Lee RE, Wei L, Homayouni R, Rogers PD: Genome-wide expression profiling of the response to azole, polyene, echinocandin, and pyrimidine antifungal agents in Candida albicans. Antimicrob Agents Chemother. 2005 Jun;49(6):2226-36. [PubMed Link Image]
  3. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed Link Image]
  4. Argimon S, Galello F, Pereyra E, Rossi S, Moreno S: Mucor rouxii Rho1 protein; characterization and possible role in polarized growth. Antonie Van Leeuwenhoek. 2007 Apr;91(3):237-51. Epub 2006 Nov 2. [PubMed Link Image]
  5. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.