Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C52H88N10O15 |
Molecular Weight | 1093.3131 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 16 / 16 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
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@]3([H])[C@@H](O)CCN3C(=O)[C@@]([H])(NC(=O)[C@@]([H])(NC2=O)[C@H](O)[C@@H](O)C4=CC=C(O)C=C4)[C@H](O)CCN)NC(=O)CCCCCCCC[C@@H](C)C[C@@H](C)CC)[C@@H](C)O
InChI
InChIKey=JYIKNQVWKBUSNH-WVDDFWQHSA-N
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
Caspofungin is an echinocandin antifungal drug, which is approved and is sold under the brand worldwide name cancidas. Caspofungin inhibits the synthesis of beta (1,3)-D-glucan, an essential component of the cell wall of susceptible Aspergillus species and Candida species. Beta (1,3)-D-glucan is not present in mammalian cells. Cancidas is indicated for the treatment of candidemia and the following candida infections: intra-abdominal abscesses, peritonitis, and pleural space infections in adult and pediatric patients. Also is indicated for the treatment of esophageal candidiasis in adult and pediatric patients and for the treatment of invasive aspergillosis in adult and pediatric patients, but has not been studied as initial therapy for invasive aspergillosis.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20930076
Curator's Comment: The ability to penetrate the blood-CSF/blood-brain barrier is poor as a consequence of their high molecular mass
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2364673 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16162025 |
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Target ID: CHEMBL2364674 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16162025 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | CANCIDAS Approved UseCANCIDAS® is indicated in adults and pediatric patients (3 months and older) for: Empirical therapy for presumed fungal infections in febrile, neutropenic patients Treatment of candidemia and the following Candida infections: intra-abdominal abscesses, peritonitis and pleural space infections. CANCIDAS has not been studied in endocarditis, osteomyelitis, and meningitis due to Candida. Treatment of esophageal candidiasis [see Clinical Studies (14.3) Launch Date2001 |
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Curative | CANCIDAS Approved UseCANCIDAS® is indicated in adults and pediatric patients (3 months and older) for: Empirical therapy for presumed fungal infections in febrile, neutropenic patients Treatment of candidemia and the following Candida infections: intra-abdominal abscesses, peritonitis and pleural space infections. CANCIDAS has not been studied in endocarditis, osteomyelitis, and meningitis due to Candida. Treatment of esophageal candidiasis [see Clinical Studies (14.3) Launch Date2001 |
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Curative | CANCIDAS Approved UseCANCIDAS® is indicated in adults and pediatric patients (3 months and older) for: Empirical therapy for presumed fungal infections in febrile, neutropenic patients Treatment of candidemia and the following Candida infections: intra-abdominal abscesses, peritonitis and pleural space infections. CANCIDAS has not been studied in endocarditis, osteomyelitis, and meningitis due to Candida. Treatment of esophageal candidiasis [see Clinical Studies (14.3) Launch Date2001 |
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Curative | CANCIDAS Approved UseCANCIDAS® is indicated in adults and pediatric patients (3 months and older) for: Empirical therapy for presumed fungal infections in febrile, neutropenic patients Treatment of candidemia and the following Candida infections: intra-abdominal abscesses, peritonitis and pleural space infections. CANCIDAS has not been studied in endocarditis, osteomyelitis, and meningitis due to Candida. Treatment of esophageal candidiasis [see Clinical Studies (14.3) Launch Date2001 |
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Curative | CANCIDAS Approved UseCANCIDAS® is indicated in adults and pediatric patients (3 months and older) for: Empirical therapy for presumed fungal infections in febrile, neutropenic patients Treatment of candidemia and the following Candida infections: intra-abdominal abscesses, peritonitis and pleural space infections. CANCIDAS has not been studied in endocarditis, osteomyelitis, and meningitis due to Candida. Treatment of esophageal candidiasis [see Clinical Studies (14.3) Launch Date2001 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
8.65 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25139840 |
50 mg 1 times / day steady-state, intravenous dose: 50 mg route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
CASPOFUNGIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
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7.51 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25139840 |
50 mg 1 times / day multiple, intravenous dose: 50 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
CASPOFUNGIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
107.2 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25139840 |
50 mg 1 times / day steady-state, intravenous dose: 50 mg route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
CASPOFUNGIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
88.7 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25139840 |
50 mg 1 times / day multiple, intravenous dose: 50 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
CASPOFUNGIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
18.49 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25139840 |
50 mg 1 times / day steady-state, intravenous dose: 50 mg route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
CASPOFUNGIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
15.67 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25139840 |
50 mg 1 times / day multiple, intravenous dose: 50 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
CASPOFUNGIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3% |
CASPOFUNGIN plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
113 mg 1 times / day multiple, intravenous (starting) Overdose Dose: 113 mg, 1 times / day Route: intravenous Route: multiple Dose: 113 mg, 1 times / day Sources: |
healthy, 16 years n = 1 Health Status: healthy Age Group: 16 years Population Size: 1 Sources: |
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50 mg/m2 1 times / day multiple, intravenous (starting) Recommended Dose: 50 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 50 mg/m2, 1 times / day Sources: |
unhealthy, 2-11 years n = 171 Health Status: unhealthy Age Group: 2-11 years Population Size: 171 Sources: |
Disc. AE: Hypotension, Rash... AEs leading to discontinuation/dose reduction: Hypotension (1 patient) Sources: Rash (1 patient) |
70 mg single, intravenous (starting) Dose: 70 mg Route: intravenous Route: single Dose: 70 mg Sources: |
unhealthy, 58 years n = 1 Health Status: unhealthy Age Group: 58 years Sex: M Population Size: 1 Sources: |
Other AEs: Kounis syndrome... |
70 mg single, intravenous (starting) Dose: 70 mg Route: intravenous Route: single Dose: 70 mg Sources: |
unhealthy, 86 years n = 1 Health Status: unhealthy Age Group: 86 years Sex: M Population Size: 1 Sources: |
Disc. AE: Toxic epidermal necrolysis... AEs leading to discontinuation/dose reduction: Toxic epidermal necrolysis (severe, 1 patient) Sources: |
250 mg single, intravenous Highest studied dose Dose: 250 mg Route: intravenous Route: single Dose: 250 mg Sources: |
healthy, adult n = 6 Health Status: healthy Age Group: adult Population Size: 6 Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Hypotension | 1 patient Disc. AE |
50 mg/m2 1 times / day multiple, intravenous (starting) Recommended Dose: 50 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 50 mg/m2, 1 times / day Sources: |
unhealthy, 2-11 years n = 171 Health Status: unhealthy Age Group: 2-11 years Population Size: 171 Sources: |
Rash | 1 patient Disc. AE |
50 mg/m2 1 times / day multiple, intravenous (starting) Recommended Dose: 50 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 50 mg/m2, 1 times / day Sources: |
unhealthy, 2-11 years n = 171 Health Status: unhealthy Age Group: 2-11 years Population Size: 171 Sources: |
Kounis syndrome | grade 5, 1 patient | 70 mg single, intravenous (starting) Dose: 70 mg Route: intravenous Route: single Dose: 70 mg Sources: |
unhealthy, 58 years n = 1 Health Status: unhealthy Age Group: 58 years Sex: M Population Size: 1 Sources: |
Toxic epidermal necrolysis | severe, 1 patient Disc. AE |
70 mg single, intravenous (starting) Dose: 70 mg Route: intravenous Route: single Dose: 70 mg Sources: |
unhealthy, 86 years n = 1 Health Status: unhealthy Age Group: 86 years Sex: M Population Size: 1 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.pmda.go.jp/drugs/2012/P201200014/170050000_22400AMX00036_I100_1.pdf#page=15 Page: (PMDA_I100) 15-16 |
likely | |||
Sources: https://www.pmda.go.jp/drugs/2012/P201200014/170050000_22400AMX00036_I100_1.pdf#page=23 Page: (PMDA_I100) 23 |
no | |||
Sources: https://www.pmda.go.jp/drugs/2012/P201200014/170050000_22400AMX00036_I100_1.pdf#page=16 Page: (PMDA_I100) 16 |
no | |||
Sources: https://www.pmda.go.jp/drugs/2012/P201200014/170050000_22400AMX00036_I100_1.pdf#page=15 Page: (PMDA_I100) 15 |
no |
PubMed
Title | Date | PubMed |
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Comment: caspofungin acetate for treatment of invasive fungal infections. | 2003 Apr |
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Effects of amphotericin B and caspofungin on histamine expression. | 2003 Aug |
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Comment: caspofungin acetate for treatment of invasive fungal infections. | 2003 Dec |
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Caspofungin acetate for treatment of invasive fungal infections. | 2003 Jan |
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Successful treatment of Candida krusei infection with caspofungin acetate: a new antifungal agent. | 2003 May |
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Aspergillus nidulans RhoA is involved in polar growth, branching, and cell wall synthesis. | 2004 Jan |
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Gateways to clinical trials. | 2004 Mar |
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Gateways to clinical trials. | 2005 Jan-Feb |
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Gateways to clinical trials. | 2005 Nov |
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Comparison of galactomannan detection, PCR-enzyme-linked immunosorbent assay, and real-time PCR for diagnosis of invasive aspergillosis in a neutropenic rat model and effect of caspofungin acetate. | 2005 Nov |
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Gateways to clinical trials. | 2006 Jan-Feb |
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Voriconazole in the management of nosocomial invasive fungal infections. | 2006 Jun |
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Comparison of antifungal treatments for murine fusariosis. | 2006 Nov |
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Comparison of echinocandin antifungals. | 2007 Mar |
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Gateways to clinical trials. | 2007 Oct |
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[A retrospective study of amphotericin B treatment for invasive fungal infection]. | 2007 Sep |
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Visual compatibility of caspofungin acetate with commonly used drugs during simulated Y-site delivery. | 2008 Mar 1 |
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Genomic analysis of the basal lineage fungus Rhizopus oryzae reveals a whole-genome duplication. | 2009 Jul |
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Gateways to clinical trials. | 2009 Jun |
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Gateways to clinical trials. | 2009 Nov |
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Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis. | 2015 May 18 |
Sample Use Guides
Administer CANCIDAS (caspofungin acetate) by slow intravenous (IV) infusion over approximately 1 hour. Do not administer CANCIDAS by IV bolus administration.
Recommended Dosage in Adult Patients [18 years of age and older] The dosage and duration of CANCIDAS treatment for each indication are as follows: Empirical Therapy for Presumed Fungal Infections in Febrile Neutropenic Patients Administer a single 70-mg loading dose on Day 1, followed by 50 mg once daily thereafter. Duration of treatment should be based on the patient’s clinical response. Continue empirical therapy until resolution of neutropenia. In general, treat patients found to have a fungal infection for a minimum of 14 days after the last positive culture and continue treatment for at least 7 days after both neutropenia and clinical symptoms are resolved. If the 50-mg dose is well tolerated but does not provide an adequate clinical response, the daily dose can be increased to 70 mg. Candidemia and Other Candida Infections: administer a single 70-mg loading dose on Day 1, followed by 50 mg once daily thereafter. Duration of treatment should be dictated by the patient’s clinical and microbiological response. In general, continue antifungal therapy for at least 14 days after the last positive culture. Patients with neutropenia who remain persistently neutropenic may warrant a longer course of therapy pending resolution of the neutropenia.
Esophageal Candidiasis: the dose is 50 mg once daily for 7 to 14 days after symptom resolution. A 70-mg loading dose has not been studied for this indication. Because of the risk of relapse of oropharyngeal candidiasis in patients with HIV infections, suppressive oral therapy could be considered. Invasive Aspergillosis: administer a single 70-mg loading dose on Day 1, followed by 50 mg once daily thereafter. Duration of treatment should be based upon the severity of the patient’s underlying disease, recovery from immunosuppression, and clinical response.
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17785281
It was evaluated the susceptibility of 27 clinical isolates of Pythium insidiosum to caspofungin in vitro. Three reading criteria for MICs were adopted: MIC0, MIC1 and MIC2 (100%, 90% and 50% growth inhibition, respectively). Of the isolates 51.8% had an MIC0 of 64 mg/L, 88.8% of isolates had an MIC1 between 8 and 64 mg/L and 62.9% of isolates had a minimum fungicidal concentration of 64 mg/L. The results showed that caspofungin had limited fungistatic activity against P. insidiosum.
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NCI_THESAURUS |
C514
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N0000175507
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WHO-ATC |
J02AX04
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NDF-RT |
N0000175508
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WHO-VATC |
QJ02AX04
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LIVERTOX |
156
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DTXSID30873204
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7476
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SUB16405MIG
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162808-62-0
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F0XDI6ZL63
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DB00520
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CASPOFUNGIN
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m3159
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C28910
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CHEMBL499808
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140108
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Caspofungin
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C105417
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F0XDI6ZL63
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100000089518
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474180
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2977
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16119814
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7778
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ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)
SALT/SOLVATE (PARENT)