Caspofungin

Structural formula
General
Non-proprietary name	Caspofungin
other names	1 - [(4 R , 5 S ) -5 - [(2-aminoethyl) amino] - N 2- (10,12-dimethyl-1-oxotetradecyl) -4-hydroxy- L- ornithine] -5 - [( 3 R ) -3-hydroxy- L- ornithine] pneumocandin B 0 ; (4 R , 5 S ) -5 - ((2-aminoethyl) amino) - N 2 - (10,12-dimethyltetradecanoyl) -4-hydroxy- L -ornithyl- L -threonyl- trans -4-hydroxy- L - prolyl- ( S ) -4-hydroxy-4- ( p -hydroxyphenyl) - L -threonyl- threo -3-hydroxy- L -ornithyl- trans -3-hydroxy- L -proline-cyclic- (6 → 1) - peptide;
Molecular formula	C 52 H 88 N 10 O 15 (caspofungin) ; C 52 H 88 N 10 O 15 2C 2 H 4 O 2 (caspofungin diacetate) ;
External identifiers / databases
PubChem	2826718
DrugBank	DB00520
Wikidata	Q420875
Drug information
ATC code	J02 AX04
Drug class	Antifungal , Echinocandin
Mechanism of action	Inhibition of β (1,3) - D -glucan synthase
properties
Molar mass	1093.31 g · mol -1 (Caspofungin) ; 1213.42 g · mol -1 (· caspofungin diacetate) ;
solubility	slightly soluble in water and in methanol, less soluble in ethanol (caspofungin diacetate)
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Caspofungin is an antifungal from the echinocandins group and is used in the treatment of fungal infections. It is marketed by MSD under the name Cancidas .

chemistry

Caspofungin is a semi-synthetic lipopeptide compound ( Echinocandin ) whose starting substance is Pneumocandin B ₀ . This is obtained from the fungus Glarea lozoyensis .

pharmacology

Mechanism of action

Mushrooms have from chitin and other polysaccharides existing cell wall . One building block of this cell wall is β (1,3) - D -glucan. Caspofungin inhibits the enzyme β (1,3) - D -glucan synthase, which is responsible for the structure of this cell wall component in fungi. Human cells do not have such a cell wall and therefore also no β (1,3) - D -glucan synthase.

Germ spectrum

Aspergillus spp., Candida spp., Histoplasma capsulatum , Coccidioides immitis

Ineffective at

Cryptococcus neoformans , Fusarium sp., Scedoporium , Trichosporon spp., Family of the Zygomycetes

Absorption and distribution in the body (pharmacokinetics)

Caspofungin is not absorbed in the intestine . It can therefore only be given intravenously . It is 96% bound to plasma proteins. The breakdown of the substance takes place mainly in the liver . 35% of it is excreted in the faeces and around 41% through the kidneys . The biological half-life is 9–11 hours.

Application areas (indications)

Treatment of invasive candida infections in adult or pediatric patients.
Treatment of invasive aspergillosis in adult or pediatric patients who are unresponsive or intolerant to therapy with amphotericin B , lipid formulations of amphotericin B and / or itraconazole . Failure to respond is defined as progression of the infection or if there is no improvement after at least 7 days of antifungal therapy at therapeutic doses.
Empirical therapy for suspected fungal infections (such as Candida or Aspergillus) in adult or pediatric patients with fever and neutropenia .

Contraindications (contraindications)

Hypersensitivity to caspofungin or any other ingredient.

Adverse effects (side effects)

Fever , chills
inflammatory reactions at the infusion site ( phlebitis )
Abdominal pain , nausea , vomiting
Rash, itching , sweating
Anemia ( anemia )
a headache

Drug interactions

Concurrent administration of cyclosporine increased the concentration of cyclosporine. Caspofungin remained unchanged.
When tacrolimus was administered at the same time , its minimum plasma concentration decreased.
In a few patients, the AUC of caspofungin decreased with simultaneous use of
- Efavirenz
- Nevirapine
- Rifampicin
- Dexamethasone
- Phenytoin
- Carbamazepine

literature

Technical information: CANCIDAS ^® (as of September 2011)

Web links

Individual evidence

↑ Maryadele J. O'Neil et al. (Ed.): The Merck Index. An Encyclopedia of Chemicals, Drugs, and Biologicals. 14th edition. Merck & Co., Inc., Whitehouse Station NJ 2006, ISBN 0-911910-13-1 , pp. 308-309.
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ Red List, as of August 2009.
↑ AM comp. d. Switzerland, as of August 2009.
↑ AGES-PharmMed, as of August 2009.

[MERCK_Index-1] Maryadele J. O'Neil et al. (Ed.): The Merck Index. An Encyclopedia of Chemicals, Drugs, and Biologicals. 14th edition. Merck & Co., Inc., Whitehouse Station NJ 2006, ISBN 0-911910-13-1 , pp. 308-309.

[NV-2] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[3] Red List, as of August 2009.

[4] AM comp. d. Switzerland, as of August 2009.

[5] AGES-PharmMed, as of August 2009.