Caspofungin
Identification
- Summary
Caspofungin is an echinocandin used to treat a variety of fungal infections.
- Brand Names
- Cancidas
- Generic Name
- Caspofungin
- DrugBank Accession Number
- DB00520
- Background
Caspofungin (brand name Cancidas worldwide) is an antifungal drug and the first member of a new drug class called the echinocandins, as coined by Merck & Co., Inc. It is typically administered intravenously. It shows activity against infections with Aspergillus and Candida, and works by inhibiting β(1,3)-D-Glucan of the fungal cell wall.
- Type
- Small Molecule
- Groups
- Approved
- Structure
- Weight
- Average: 1093.331
Monoisotopic: 1092.643062174 - Chemical Formula
- C52H88N10O15
- Synonyms
- (4R,5S)-5-((2-Aminoethyl)amino)-N(sup 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
- Caspofungin
- Caspofungina
- External IDs
- L 743,872
- L 743872
- MK 0991
Pharmacology
- Indication
For the treatment of esophageal candidiasis and invasive aspergillosis in patients who are refractory to or intolerant of other therapies.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Candidemia •••••••••••• Treatment of Esophageal candidiasis •••••••••••• Treatment of Fungal infections •••••••••••• Treatment of Invasive aspergillosis •••••••••••• •••••••••• •• •• •••••••••• •• ••••• ••••••••• Treatment of Oropharyngeal candidiasis ••• ••••• - Contraindications & Blackbox Warnings
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- Pharmacodynamics
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 beta-(1,3)-D-glucan, an essential component of the cell wall of Aspergillus species and Candida species. beta-(1,3)-D-glucan is not present in mammalian cells. The primary target is beta-(1,3)-glucan synthase.
Target Actions Organism A1,3-beta-glucan synthase component FKS1 inhibitorAspergillus niger (strain CBS 513.88 / FGSC A1513) - Absorption
92% tissue distribution within 36-48 hours after intravenous infusion
- Volume of distribution
Not Available
- Protein binding
97%
- Metabolism
Metabolized slowly by hydrolysis and N-acetylation
- Route of 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.
- Half-life
9-11 hours
- Clearance
- 12 mL/min [After single IV administration]
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Side effects include rash, swelling, and nausea (rare)
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcenocoumarol The therapeutic efficacy of Acenocoumarol can be increased when used in combination with Caspofungin. Acetylcysteine The excretion of Caspofungin can be decreased when combined with Acetylcysteine. Acyclovir The excretion of Acyclovir can be decreased when combined with Caspofungin. Adefovir dipivoxil The excretion of Adefovir dipivoxil can be decreased when combined with Caspofungin. Ambrisentan The excretion of Ambrisentan can be decreased when combined with Caspofungin. - Food Interactions
- No interactions found.
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Caspofungin acetate VUW370O5QE 179463-17-3 OGUJBRYAAJYXQP-IJFZAWIJSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Cancidas Injection, powder, lyophilized, for solution 7 mg/1mL Intravenous Merck Sharp & Dohme Llc 2001-01-26 Not applicable US Cancidas Injection, powder, lyophilized, for solution 5 mg/1mL Intravenous Merck Sharp & Dohme Llc 2001-01-26 Not applicable US Cancidas Powder, for solution 70 mg / vial Intravenous Merck Ltd. 2001-10-23 Not applicable Canada Cancidas Injection, powder, for solution 50 mg Intravenous Merck Sharp & Dohme B.V. 2016-09-08 Not applicable EU Cancidas Powder, for solution 50 mg / vial Intravenous Merck Ltd. 2001-08-23 Not applicable Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Caspofungin Acetate Injection, powder, lyophilized, for solution 7 mg/1mL Intravenous Fosun Pharma USA Inc. 2019-04-02 Not applicable US Caspofungin Acetate Injection, powder, lyophilized, for solution 5 mg/1mL Intravenous Almaject, Inc. 2020-03-31 Not applicable US Caspofungin Acetate Injection, powder, lyophilized, for solution 5 mg/1mL Intravenous Fosun Pharma USA Inc. 2019-04-02 Not applicable US Caspofungin Acetate Injection, powder, lyophilized, for solution 7 mg/1mL Intravenous Alvogen Inc. 2017-12-01 2021-10-01 US Caspofungin Acetate Injection, powder, lyophilized, for solution 5 mg/1mL Intravenous Sandoz Inc 2018-09-04 Not applicable US
Categories
- ATC Codes
- J02AX04 — Caspofungin
- Drug Categories
- Amino Acids, Peptides, and Proteins
- Anti-Infective Agents
- Antifungal Agents
- Antiinfectives for Systemic Use
- Antimycotics for Systemic Use
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
- Cytochrome P-450 Enzyme Inhibitors
- Echinocandin Antifungal
- Echinocandins
- Enzyme Inhibitors
- Lipids
- Lipopeptides
- OAT1/SLC22A6 inhibitors
- OATP1B1/SLCO1B1 Inhibitors
- OATP1B1/SLCO1B1 Substrates
- OATP1B3 substrates
- P-glycoprotein inhibitors
- Peptides
- Peptides, Cyclic
- Classification
- Not classified
- Affected organisms
- Aspergillis, Candida and other fungi
Chemical Identifiers
- UNII
- F0XDI6ZL63
- CAS number
- 162808-62-0
- InChI Key
- JYIKNQVWKBUSNH-WVDDFWQHSA-N
- InChI
- InChI=1S/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-/m0/s1
- IUPAC Name
- (10R,12S)-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
- SMILES
- [H][C@@]12C[C@@H](O)CN1C(=O)[C@@H](NC(=O)[C@]([H])(C[C@@H](O)[C@@H](NCCN)NC(=O)[C@@H]1[C@@H](O)CCN1C(=O)[C@@H](NC(=O)[C@@H](NC2=O)[C@H](O)[C@@H](O)C1=CC=C(O)C=C1)[C@H](O)CCN)NC(=O)CCCCCCCC[C@@H](C)C[C@@H](C)CC)[C@@H](C)O
References
- Synthesis Reference
Johannes Ludescher, Ingolf Macher, Ole Storm, Stephan Bertel, "Process and Intermediates for the Synthesis of Caspofungin." U.S. Patent US20080319162, issued December 25, 2008.
US20080319162- General References
- Sucher AJ, Chahine EB, Balcer HE: Echinocandins: the newest class of antifungals. Ann Pharmacother. 2009 Oct;43(10):1647-57. doi: 10.1345/aph.1M237. Epub 2009 Sep 1. [Article]
- Morrison VA: Caspofungin: an overview. Expert Rev Anti Infect Ther. 2005 Oct;3(5):697-705. [Article]
- McCormack PL, Perry CM: Caspofungin: a review of its use in the treatment of fungal infections. Drugs. 2005;65(14):2049-68. [Article]
- 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. [Article]
- 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. [Article]
- External Links
- KEGG Drug
- D07626
- PubChem Compound
- 3035406
- PubChem Substance
- 46508288
- ChemSpider
- 17277006
- 140108
- ChEBI
- 474180
- ChEMBL
- CHEMBL499808
- Therapeutic Targets Database
- DAP000547
- PharmGKB
- PA164743013
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Caspofungin
- FDA label
- Download (87.9 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Not Available Fungal Infections / Obesity 1 4 Completed Other Bacterial Infections and Mycoses / Liver Disease 1 4 Completed Prevention Invasive Candidiasis 1 4 Completed Treatment Candidemia 1 4 Completed Treatment Critically Ill Patients / Suspected Invasive Candidiasis 1
Pharmacoeconomics
- Manufacturers
- Merck and co inc
- Packagers
- Cardinal Health
- Merck & Co.
- Oso Biopharmaceuticals Manufacturing LLC
- Dosage Forms
Form Route Strength Injection, powder, lyophilized, for solution Intravenous Solution Intravenous 70.000 mg Injection Intravenous Injection, powder, for solution Intravenous; Parenteral 50 MG Injection, powder, for solution Intravenous; Parenteral 70 MG Injection, powder, lyophilized, for solution Not applicable 1 kg/1kg Powder, for solution Intravenous 50 mg / vial Powder, for solution Intravenous 50 MG Powder, for solution Intravenous 70 mg / vial Injection, powder, for solution Intravenous 70 mg/vial Injection, solution, concentrate Intravenous 50 mg Injection, solution, concentrate Intravenous 70 mg Injection, solution Intravenous 50 mg Injection, solution Intravenous 70 mg Injection Intravenous 50 mg Injection Intravenous 70 mg Injection, powder, lyophilized, for solution Intravenous 50.00 mg Injection, powder, lyophilized, for solution Intravenous 70.00 mg Injection Intravenous 5 mg/1mL Injection Intravenous 7 mg/1mL Injection, powder, for solution Intravenous 5 mg/1mL Injection, powder, for solution Intravenous 7 mg/1mL Injection, powder, lyophilized, for solution Intravenous 5 mg/1mL Injection, powder, lyophilized, for solution Intravenous 50 mg/10.8mL Injection, powder, lyophilized, for solution Intravenous 7 mg/1mL Injection, powder, lyophilized, for solution Intravenous 70 mg/10.8mL Injection, powder, for solution 50 MG Injection, powder, for solution 70 MG Injection, powder, for solution Intravenous Injection, powder, for solution Parenteral 50 MG Injection, powder, for solution Parenteral 70 MG Injection, powder, for solution Injection, powder, for solution Intravenous 50 mg/vial Solution Intravenous 60.60 mg Injection, powder, for solution Intravenous 55.49 mg Injection, powder, for solution Intravenous 77.69 mg Solution Intravenous 50.00 mg Injection, powder, lyophilized, for solution Intravenous 50 mg Injection, powder, lyophilized, for solution Intravenous 70 mg Solution Intravenous 50.000 mg Injection, powder, for solution Intravenous 50 MG Injection, powder, for solution Intravenous 70 MG Injection, powder, for solution Parenteral Powder 50 MG Powder 70 mg Solution Intravenous 55.493 mg - Prices
Unit description Cost Unit Cancidas iv 70 mg vial 421.06USD vial Cancidas iv 50 mg vial 405.25USD vial DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5378804 No 1995-01-03 2013-03-16 US CA2251928 No 2003-06-17 2017-04-15 Canada CA2118757 No 2002-05-14 2014-03-10 Canada US6136783 Yes 2000-10-24 2017-09-28 US US5952300 Yes 1999-09-14 2017-09-28 US US5514650 Yes 1996-05-07 2015-07-26 US US9636407 No 2017-05-02 2032-12-21 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP 0 Not Available - Predicted Properties
Property Value Source Water Solubility 0.367 mg/mL ALOGPS logP 0.17 ALOGPS logP -4.8 Chemaxon logS -3.5 ALOGPS pKa (Strongest Acidic) 8.75 Chemaxon pKa (Strongest Basic) 9.76 Chemaxon Physiological Charge 2 Chemaxon Hydrogen Acceptor Count 18 Chemaxon Hydrogen Donor Count 16 Chemaxon Polar Surface Area 412.03 Å2 Chemaxon Rotatable Bond Count 23 Chemaxon Refractivity 278.78 m3·mol-1 Chemaxon Polarizability 117.66 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.7566 Blood Brain Barrier - 0.96 Caco-2 permeable - 0.8091 P-glycoprotein substrate Substrate 0.8694 P-glycoprotein inhibitor I Non-inhibitor 0.9653 P-glycoprotein inhibitor II Non-inhibitor 0.9174 Renal organic cation transporter Non-inhibitor 0.9379 CYP450 2C9 substrate Non-substrate 0.831 CYP450 2D6 substrate Non-substrate 0.8166 CYP450 3A4 substrate Non-substrate 0.51 CYP450 1A2 substrate Non-inhibitor 0.9389 CYP450 2C9 inhibitor Non-inhibitor 0.9161 CYP450 2D6 inhibitor Non-inhibitor 0.8904 CYP450 2C19 inhibitor Non-inhibitor 0.875 CYP450 3A4 inhibitor Non-inhibitor 0.9682 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9781 Ames test Non AMES toxic 0.7398 Carcinogenicity Non-carcinogens 0.8315 Biodegradation Not ready biodegradable 0.9683 Rat acute toxicity 2.9344 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9637 hERG inhibition (predictor II) Non-inhibitor 0.716
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Not Available
Targets
- Kind
- Protein
- Organism
- Aspergillus niger (strain CBS 513.88 / FGSC A1513)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- 1,3-beta-d-glucan synthase activity
- Specific Function
- Catalytic subunit of the 1,3-beta-glucan synthase. Synthesizes 1,3-beta-glucan, a major structural component of the cell wall. Involved in cell wall synthesis, maintenance and cell wall remodeling ...
- Gene Name
- fksA
- Uniprot ID
- A2QLK4
- Uniprot Name
- 1,3-beta-glucan synthase component FKS1
- Molecular Weight
- 216972.8 Da
References
- Sucher AJ, Chahine EB, Balcer HE: Echinocandins: the newest class of antifungals. Ann Pharmacother. 2009 Oct;43(10):1647-57. doi: 10.1345/aph.1M237. Epub 2009 Sep 1. [Article]
- Morrison VA: Caspofungin: an overview. Expert Rev Anti Infect Ther. 2005 Oct;3(5):697-705. [Article]
- McCormack PL, Perry CM: Caspofungin: a review of its use in the treatment of fungal infections. Drugs. 2005;65(14):2049-68. [Article]
- 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. [Article]
- 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. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- Curator comments
- There is conflicting evidence in the literature regarding this enzyme action. The EMA label does not consider Caspofungin a CYP3A4 inhibitor, however another resource considers it an inhibitor.
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Secondary active organic cation transmembrane transporter activity
- Specific Function
- Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnico...
- Gene Name
- SLC22A1
- Uniprot ID
- O15245
- Uniprot Name
- Solute carrier family 22 member 1
- Molecular Weight
- 61153.345 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- Sandhu P, Lee W, Xu X, Leake BF, Yamazaki M, Stone JA, Lin JH, Pearson PG, Kim RB: Hepatic uptake of the novel antifungal agent caspofungin. Drug Metab Dispos. 2005 May;33(5):676-82. Epub 2005 Feb 16. [Article]
- Lempers VJ, van den Heuvel JJ, Russel FG, Aarnoutse RE, Burger DM, Bruggemann RJ, Koenderink JB: Inhibitory Potential of Antifungal Drugs on ATP-Binding Cassette Transporters P-Glycoprotein, MRP1 to MRP5, BCRP, and BSEP. Antimicrob Agents Chemother. 2016 May 23;60(6):3372-9. doi: 10.1128/AAC.02931-15. Print 2016 Jun. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
- Gene Name
- SLC22A6
- Uniprot ID
- Q4U2R8
- Uniprot Name
- Solute carrier family 22 member 6
- Molecular Weight
- 61815.78 Da
References
- Sandhu P, Lee W, Xu X, Leake BF, Yamazaki M, Stone JA, Lin JH, Pearson PG, Kim RB: Hepatic uptake of the novel antifungal agent caspofungin. Drug Metab Dispos. 2005 May;33(5):676-82. Epub 2005 Feb 16. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
- Gene Name
- SLCO1B1
- Uniprot ID
- Q9Y6L6
- Uniprot Name
- Solute carrier organic anion transporter family member 1B1
- Molecular Weight
- 76447.99 Da
References
- Sandhu P, Lee W, Xu X, Leake BF, Yamazaki M, Stone JA, Lin JH, Pearson PG, Kim RB: Hepatic uptake of the novel antifungal agent caspofungin. Drug Metab Dispos. 2005 May;33(5):676-82. Epub 2005 Feb 16. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent uptake of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotre...
- Gene Name
- SLCO1B3
- Uniprot ID
- Q9NPD5
- Uniprot Name
- Solute carrier organic anion transporter family member 1B3
- Molecular Weight
- 77402.175 Da
References
- Sandhu P, Lee W, Xu X, Leake BF, Yamazaki M, Stone JA, Lin JH, Pearson PG, Kim RB: Hepatic uptake of the novel antifungal agent caspofungin. Drug Metab Dispos. 2005 May;33(5):676-82. Epub 2005 Feb 16. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:54