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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
Structure of CASPOFUNGIN

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]3C[C@@H](O)CN3C(=O)[C@@H](NC1=O)[C@@H](C)O)[C@H](O)[C@@H](O)C4=CC=C(O)C=C4)[C@H](O)CCN

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

HIDE SMILES / InChI
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

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

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
CANCIDAS

Approved Use

CANCIDAS® 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 Date

2001
Curative
CANCIDAS

Approved Use

CANCIDAS® 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 Date

2001
Curative
CANCIDAS

Approved Use

CANCIDAS® 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 Date

2001
Curative
CANCIDAS

Approved Use

CANCIDAS® 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 Date

2001
Curative
CANCIDAS

Approved Use

CANCIDAS® 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 Date

2001
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
7.51 mg/L
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
8.65 mg/L
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
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
88.7 mg × h/L
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
107.2 mg × h/L
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
15.67 h
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
18.49 h
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
3%
CASPOFUNGIN plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
113 mg 1 times / day multiple, intravenous
Overdose
Dose: 113 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 113 mg, 1 times / day
Sources:
healthy, 16 years
Health Status: healthy
Age Group: 16 years
Sources:
50 mg/m2 1 times / day multiple, intravenous
Recommended
Dose: 50 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 50 mg/m2, 1 times / day
Sources:
unhealthy, 2-11 years
Health Status: unhealthy
Age Group: 2-11 years
Sources:
Disc. AE: Hypotension, Rash...
AEs leading to
discontinuation/dose reduction:
Hypotension (1 patient)
Rash (1 patient)
Sources:
70 mg single, intravenous
Dose: 70 mg
Route: intravenous
Route: single
Dose: 70 mg
Sources:
unhealthy, 58 years
Health Status: unhealthy
Age Group: 58 years
Sex: M
Sources:
Other AEs: Kounis syndrome...
Other AEs:
Kounis syndrome (grade 5, 1 patient)
Sources:
70 mg single, intravenous
Dose: 70 mg
Route: intravenous
Route: single
Dose: 70 mg
Sources:
unhealthy, 86 years
Health Status: unhealthy
Age Group: 86 years
Sex: M
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
AEs

AEs

AESignificanceDosePopulation
Hypotension 1 patient
Disc. AE
50 mg/m2 1 times / day multiple, intravenous
Recommended
Dose: 50 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 50 mg/m2, 1 times / day
Sources:
unhealthy, 2-11 years
Health Status: unhealthy
Age Group: 2-11 years
Sources:
Rash 1 patient
Disc. AE
50 mg/m2 1 times / day multiple, intravenous
Recommended
Dose: 50 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 50 mg/m2, 1 times / day
Sources:
unhealthy, 2-11 years
Health Status: unhealthy
Age Group: 2-11 years
Sources:
Kounis syndrome grade 5, 1 patient
70 mg single, intravenous
Dose: 70 mg
Route: intravenous
Route: single
Dose: 70 mg
Sources:
unhealthy, 58 years
Health Status: unhealthy
Age Group: 58 years
Sex: M
Sources:
Toxic epidermal necrolysis severe, 1 patient
Disc. AE
70 mg single, intravenous
Dose: 70 mg
Route: intravenous
Route: single
Dose: 70 mg
Sources:
unhealthy, 86 years
Health Status: unhealthy
Age Group: 86 years
Sex: M
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
likely [IC50 131 uM]
likely [IC50 186 uM]
likely [IC50 213 uM]
likely [IC50 216 uM]
likely [IC50 217 uM]
no [IC50 >100 uM]
no [IC50 >200 uM]
no [IC50 >200 uM]
no [IC50 >200 uM]
no [IC50 >200 uM]
no [IC50 >200 uM]
no [IC50 >200 uM]
weak
weak
yes
yes
Drug as victim
PubMed

PubMed

TitleDatePubMed
Caspofungin acetate: an antifungal agent.
2001 Jul 1
Successful treatment of subcutaneously disseminated aspergillosis with caspofungin acetate in an allogeneic peripheral blood stem cell transplantation patient.
2003 Apr
Gateways to clinical trials.
2003 Jan-Feb
Successful treatment of Candida krusei infection with caspofungin acetate: a new antifungal agent.
2003 May
Gateways to clinical trials.
2004 Jul-Aug
Analysis of beta-1,3-glucan assembly in Saccharomyces cerevisiae using a synthetic interaction network and altered sensitivity to caspofungin.
2004 May
Gateways to clinical trials.
2004 Oct
Gateways to clinical trials.
2005 Jul-Aug
Caspofungin versus amphotericin B for candidemia: a pharmacoeconomic analysis.
2005 Jun
Gateways to clinical trials.
2005 Jun
Gateways to clinical trials.
2005 Oct
Gateways to clinical trials.
2006 Jan-Feb
Comparison of antifungal treatments for murine fusariosis.
2006 Nov
Gateways to clinical trials. July-August 2008.
2008 Jul-Aug
Gateways to clinical trials.
2008 Sep
Recent advances in the treatment of mucormycosis.
2010 Nov
Patents

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
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.
Name Type Language
L-743,872
Preferred Name English
CASPOFUNGIN
EMA EPAR   HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
caspofungin [INN]
Common Name English
CASPOFUNGIN [HSDB]
Common Name English
PNEUMOCANDIN B0, 1-((4R,5S)-5-((2-AMINOETHYL)AMINO)-N2-((10R,12S)-10,12-DIMETHYL-1-OXOTETRADECYL)-4-HYDROXY-L-ORNITHINE)-5-((3R)-3-HYDROXY-L-ORNITHINE)-
Systematic Name English
L-743872
Code English
Caspofungin [WHO-DD]
Common Name English
CASPOFUNGIN [EMA EPAR]
Common Name English
CASPOFUNGIN [MI]
Common Name English
CASPOFUNGIN [VANDF]
Common Name English
(4R,5S)-5-((2-AMINOETHYL)AMINO)-N2-(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 (1->6) DISULFIDE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C514
Created by admin on Mon Mar 31 18:30:33 GMT 2025 , Edited by admin on Mon Mar 31 18:30:33 GMT 2025
NDF-RT N0000175507
Created by admin on Mon Mar 31 18:30:33 GMT 2025 , Edited by admin on Mon Mar 31 18:30:33 GMT 2025
WHO-ATC J02AX04
Created by admin on Mon Mar 31 18:30:33 GMT 2025 , Edited by admin on Mon Mar 31 18:30:33 GMT 2025
NDF-RT N0000175508
Created by admin on Mon Mar 31 18:30:33 GMT 2025 , Edited by admin on Mon Mar 31 18:30:33 GMT 2025
WHO-VATC QJ02AX04
Created by admin on Mon Mar 31 18:30:33 GMT 2025 , Edited by admin on Mon Mar 31 18:30:33 GMT 2025
NDF-RT N0000175508
Created by admin on Mon Mar 31 18:30:33 GMT 2025 , Edited by admin on Mon Mar 31 18:30:33 GMT 2025
LIVERTOX 156
Created by admin on Mon Mar 31 18:30:33 GMT 2025 , Edited by admin on Mon Mar 31 18:30:33 GMT 2025
Code System Code Type Description
EPA CompTox
DTXSID30873204
Created by admin on Mon Mar 31 18:30:33 GMT 2025 , Edited by admin on Mon Mar 31 18:30:33 GMT 2025
PRIMARY
HSDB
7476
Created by admin on Mon Mar 31 18:30:33 GMT 2025 , Edited by admin on Mon Mar 31 18:30:33 GMT 2025
PRIMARY
EVMPD
SUB16405MIG
Created by admin on Mon Mar 31 18:30:33 GMT 2025 , Edited by admin on Mon Mar 31 18:30:33 GMT 2025
PRIMARY
CAS
162808-62-0
Created by admin on Mon Mar 31 18:30:33 GMT 2025 , Edited by admin on Mon Mar 31 18:30:33 GMT 2025
PRIMARY
DAILYMED
F0XDI6ZL63
Created by admin on Mon Mar 31 18:30:33 GMT 2025 , Edited by admin on Mon Mar 31 18:30:33 GMT 2025
PRIMARY
DRUG BANK
DB00520
Created by admin on Mon Mar 31 18:30:33 GMT 2025 , Edited by admin on Mon Mar 31 18:30:33 GMT 2025
PRIMARY
WIKIPEDIA
CASPOFUNGIN
Created by admin on Mon Mar 31 18:30:33 GMT 2025 , Edited by admin on Mon Mar 31 18:30:33 GMT 2025
PRIMARY
MERCK INDEX
m3159
Created by admin on Mon Mar 31 18:30:33 GMT 2025 , Edited by admin on Mon Mar 31 18:30:33 GMT 2025
PRIMARY Merck Index
NCI_THESAURUS
C28910
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PRIMARY
ChEMBL
CHEMBL499808
Created by admin on Mon Mar 31 18:30:33 GMT 2025 , Edited by admin on Mon Mar 31 18:30:33 GMT 2025
PRIMARY
RXCUI
140108
Created by admin on Mon Mar 31 18:30:33 GMT 2025 , Edited by admin on Mon Mar 31 18:30:33 GMT 2025
PRIMARY RxNorm
LACTMED
Caspofungin
Created by admin on Mon Mar 31 18:30:33 GMT 2025 , Edited by admin on Mon Mar 31 18:30:33 GMT 2025
PRIMARY
MESH
C105417
Created by admin on Mon Mar 31 18:30:33 GMT 2025 , Edited by admin on Mon Mar 31 18:30:33 GMT 2025
PRIMARY
FDA UNII
F0XDI6ZL63
Created by admin on Mon Mar 31 18:30:33 GMT 2025 , Edited by admin on Mon Mar 31 18:30:33 GMT 2025
PRIMARY
SMS_ID
100000089518
Created by admin on Mon Mar 31 18:30:33 GMT 2025 , Edited by admin on Mon Mar 31 18:30:33 GMT 2025
PRIMARY
CHEBI
474180
Created by admin on Mon Mar 31 18:30:33 GMT 2025 , Edited by admin on Mon Mar 31 18:30:33 GMT 2025
PRIMARY
DRUG CENTRAL
2977
Created by admin on Mon Mar 31 18:30:33 GMT 2025 , Edited by admin on Mon Mar 31 18:30:33 GMT 2025
PRIMARY
PUBCHEM
16119814
Created by admin on Mon Mar 31 18:30:33 GMT 2025 , Edited by admin on Mon Mar 31 18:30:33 GMT 2025
PRIMARY
INN
7778
Created by admin on Mon Mar 31 18:30:33 GMT 2025 , Edited by admin on Mon Mar 31 18:30:33 GMT 2025
PRIMARY