Caspofungin
Systematic (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
Identifiers
CAS number	179463-17-3
ATC code	J02AX04
PubChem	468682
DrugBank	APRD00199
Chemical data
Formula	C52H88N10O15
Mol. mass	1093.31 g/mol
Pharmacokinetic data
Bioavailability	100% (i.v.-use only)
Protein binding	97%
Metabolism	?
Half life	9-11 hours
Excretion	?
Therapeutic considerations
Licence data	EU US Image File history File links Size of this preview: 508 × 599 pixelsFull resolution (1191 × 1404 pixel, file size: 32 KB, MIME type: image/png) Chemical structure of caspofungin created with ChemDraw. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A section of the Anatomical Therapeutic Chemical Classification System. ... PubChem is a database of chemical molecules. ... The DrugBank database available at the University of Alberta is a unique bioinformatics and cheminformatics resource that combines detailed drug (i. ... A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... For other uses, see Carbon (disambiguation). ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, symbol, number nitrogen, N, 7 Chemical series nonmetals Group, period, block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... General Name, symbol, number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, period, block 16, 2, p Appearance colorless (gas) pale blue (liquid) Standard atomic weight 15. ... The molecular mass (abbreviated Mr) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... A drugs efficacy may be affected by the degree to which it binds to the proteins within blood plasma. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... The biological half-life of a substance is the time required for half of that substance to be removed from an organism by either a physical or a chemical process. ... The kidneys are important excretory organs in vertebrates. ... The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ...
Pregnancy cat.	C The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ...
Legal status	℞ Prescription only The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ...
Routes	IV

Caspofungin (INN^[1]) (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. In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body. ... IV may refer to: The Roman number for four — meaning one (I) less than five (V). ... An International Nonproprietary Name (INN) is the official non-proprietary or generic name given to a pharmaceutical substance, as designated by the World Health Organization. ... Something antifungal kills or inhibits the growth of fungus. ... Echinocandins are antifungal drugs that inhibit the synthesis of glucan in the cell wall, probably via the enzyme 1,3-β glucan synthase. ... Merck & Co. ... Species Aspergillus caesiellus Aspergillus candidus Aspergillus carneus Aspergillus clavatus Aspergillus deflectus Aspergillus flavus Aspergillus fumigatus Aspergillus glaucus Aspergillus nidulans Aspergillus niger Aspergillus ochraceus Aspergillus oryzae Aspergillus parasiticus Aspergillus penicilloides Aspergillus restrictus Aspergillus sojae Aspergillus sydowi Aspergillus terreus Aspergillus ustus Aspergillus versicolor Aspergillus is a genus of around 200 filamentous fungi... Species C. albicans C. dubliniensis C. glabrata C. guilliermondii C. kefyr C. krusei C. lusitaniae C. milleri C. oleophila C. parapsilosis C. tropicalis C. utilis Candida is a genus of yeasts. ... Plant cells separated by transparent cell walls. ... An intravenous drip in a hospital Intravenous therapy or IV therapy is the administration of liquid substances directly into a vein. ...

Indications

Caspofungin acetate for injection was originally approved by both the FDA, in the US, and the EMEA, in Europe, in 2001. Its currently approved therapeutic indications by both organisms include the empirical therapy of presumed fungal infections in febrile, neutropenic adult patients and the treatment of invasive aspergillosis in adult patients whose disease is refractory to, or who are intolerant of, other antifungal agents (i.e., conventional or lipid formulations of amphotericin B and/or itraconazole). Additionally, the FDA approval includes indication for the treatment of candidemia and some specific Candida infections (intra-abdominal abscesses, peritonitis, pleural cavity infections and oesophagitis) and the EMEA approval includes indication for the treatment of general invasive candidiasis in adult patients. The United States Food and Drug Administration is the government agency responsible for regulating food, dietary supplements, drugs, cosmetics, medical devices, biologics and blood products in the United States. ... EMEA can mean: Europe, the Middle East and Africa European Medicines Agency This is a disambiguation page — a navigational aid which lists other pages that might otherwise share the same title. ... Amphotericin B (Fungilin®, Fungizone®, Abelcet®, AmBisome®, Fungisome®, Amphocil®, Amphotec®) is a polyene antimycotic drug, used intravenously in systemic fungal infections. ... Itraconazole (marketed as Sporanox® by Janssen Pharmaceutica) is a triazole antifungal agent that is prescribed to patients with fungal infections. ... Fungemia (also known as Candidemia, Candedemia, and Invasive Candidiasis) is the presence of fungi or yeasts in the blood. ... The lungs are surrounded by two membranes, the pleurae. ...

Clinical Efficacy

36% of patients refractory to other therapies responded well to caspofungin therapy, while even 70% of patients intolerant to other therapies were classified as responders. Direct comparative studies to other drugs in the treatment of invasive aspergillosis have so far not been undertaken.

Contraindications

Known hypersensitivity to caspofungin acetate or any other ingredient contained in the formulation

Warnings

• Hepatic Effects

The concomitant use of caspofungin and cyclosporine in healthy volunteers led to a more frequent increase of liver enzymes (ALT=SGPT and AST=SGOT) than noted with cyclosporine alone. Combination treatment is only indicated, if the potential benefit for the patient outweighs the potential risk.

Dosage reduction in patients with moderately impaired liver function is recommended. No clinical data exists regarding the use of caspofungin in patients with severely impaired liver function.

• Sensitivity Reactions

Reactions due to histamine release (rash, facial swelling, pruritus, sensation of warmth and one case of anaphylaxis) have been seen. Those reactions should be carefully watched for.

• Drug Resistance

In a few patients with infections caused by C. albicans mutants with reduced sensitivity to caspofungin have been noticed. Currently there is no data regarding development of resistance in other fungi than C. albicans.

Pregnancy and lactation

Caspofungin has in animal studies been shown to have embroyotoxic properties and therefore has been assigned to class C. It should only be given to pregnant women, if the benefit to the mother clearly outweighs the potenial risk to the unborn.

The drug is found in the milk of lactating rats; it is not known, whether this effect can be seen in women, too. Lactating women should be treated cautiously.

Geriatric patients

Ordinarily, no dose adjustments are necessary.

Pediatric patients

There is no sufficient clinical experience to judge the safety and efficacy in patients younger than 18 years of age.

Side-effects

Compared to amphotericin B, caspofungin seems to have a relatively low incidence of side-effects. In clinical studies and post-marketing reports the side-effects seen in 1% or more of the patients were as follows:

• Gastrointestinal system : nausea, vomiting, abdominal pain, and diarrhea
• Central nervous system : headache
• Whole body : fever, phlebitis or thrombophlebitis, complications at intravenous cannulation site (e.g. induration), unspecified pain, flu-like-syndrome, myalgia, chills, and paresthesia
• Respiratory : dyspnea
• Renal : increased plasma creatinine
• Hematological : anemia
• Electrolytes : hypokalemia
• Liver : increased liver enzymes (asymptomatic)
• Hypersensitivity : rash, facial edema, pruritus
• Others : tachycardia

Additionally, infrequent cases of symptomatic liver damage, peripheral edema and swelling, and hypercalcemia have been seen. One case of anaphylaxis (severe allergic reaction) has also been noted. For the Physics term GUT, please refer to Grand unification theory The gastrointestinal or digestive tract, also referred to as the GI tract or the alimentary canal or the gut, is the system of organs within multicellular animals which takes in food, digests it to extract energy and nutrients, and... For other uses, see Nausea (disambiguation). ... Emesis redirects here. ... Abdominal pain can be one of the symptoms associated with transient disorders or serious disease. ... Types 5-7 on the Bristol Stool Chart are often associated with diarrhea Diarrhea (in American English) or diarrhoea (in British English) is a condition in which the sufferer has frequent watery, loose bowel movements (from the Greek word διάρροια; literally meaning through-flowing). Acute infectious diarrhea is a common cause... A diagram showing the CNS: 1. ... A headache (cephalalgia in medical terminology) is a condition of pain in the head; sometimes neck or upper back pain may also be interpreted as a headache. ... This article needs additional references or sources for verification. ... Phlebitis is an inflammation of a vein, usually in the legs. ... An intravenous drip in a hospital Intravenous therapy or IV therapy is the administration of liquid substances directly into a vein. ... Paresthesia or paraesthesia (in British English) is a sensation of tingling, pricking, or numbness of a persons skin with no apparent long-term physical effect, more generally known as the feeling of pins and needles or of a limb being asleep (but not directly related to the phenomenon of... Respiration can refer to: Cellular respiration, which is the use of oxygen in the metabolism of organic molecules. ... Dyspnea (R06. ... Kidneys viewed from behind with spine removed The kidneys are bean-shaped excretory organs in vertebrates. ... Creatinine is a breakdown product of creatine phosphate in muscle, and is usually produced at a fairly constant rate by the body (depending on muscle mass). ... Red blood cells (erythrocytes) are present in the blood and help carry oxygen to the rest of the cells in the body Blood is a circulating tissue composed of fluid plasma and cells (red blood cells, white blood cells, platelets). ... This article discusses the medical condition. ... An electrolyte is a substance containing free ions that behaves as an electrically conductive medium. ... Hypokalemia is a potentially fatal condition in which the body fails to retain sufficient potassium to maintain health. ... For the bird, see Liver bird. ... Liver function tests (LFTs or LFs), are groups of clinical biochemistry laboratory blood assays designed to give a doctor or other health professional information about the state of a patients liver. ... Hypersensitivity refers to undesirable (damaging, discomfort-producing and sometimes fatal) reactions produced by the normal immune system. ... An itch (Latin: pruritus) is a sensation felt on an area of skin that makes a person or animal want to scratch it. ... This article or section does not cite any references or sources. ... Hypercalcaemia is an elevated calcium level in the blood. ... Anaphylaxis is an acute systemic (multi-system) and severe Type I Hypersensitivity allergic reaction in humans and other mammals. ...

Resistance

Resistance in Candida albicans has been described but is currently still rare. The mechanism is probably a point mutation in the 1→3-β-D-glucan synthase gene.^[2] Binomial name Candida albicans (C.P. Robin) Berkhout 1923 Synonyms Candida stellatoidea [1] Candida albicans is a diploid asexual fungus (a form of yeast), and a causal agent of opportunistic oral and vaginal infections in humans. ...

Drug interactions

• Cyclosporine : see under Hepatic Effects
• Tacrolimus : potential pharmacokinetic interactions
• Other systemic antimycotic agents : with amphotericin B, itraconazole and mycophenolate no interactions have been seen
• Inducers of drug clearance (e.g. carbamazepine, phenytoin, rifampin, dexamethason) : consider 70mg i.v. as maintenance dose instead of 50mg

Duration of treatment

The mean duration of therapy in previous studies was 34 days. Some patients were even healed by a 1-day treatment. However, a few patients were treated for as long as 162 days and tolerated the drug well, indicating that longtime use may be indicated and tolerated favourably in complicated cases of aspergillosis. Generally, the duration of treatment is dictated by the severity of the disease, the clinical response and the improvement of immunecompetence in immunecompromised patients.

Dosage

An initial dose of 70 mg by i.v.-infusion is given followed by 50 mg i.v. daily. If no response is seen or if inducers of caspofungin clearance (see above) are coadministered the daily dose may be increased to 70 mg i.v. An infusion should take approximately 1 hour.

Dosage forms

• Cancidas® 50mg for i.v.-infusion (manufacturer Merck)
• Cancidas® 70mg for i.v.-infusion (manufacturer Merck)
• Brand names in countries other than the US may vary.

External references

• AHFS Database
• CDC on Aspergillosis
• Swiss pharma-compendium on Caspofungin
• Cancidas.com
• FDA on Cancidas
• EMEA on Cancidas

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References