U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C52H88N10O15.2C2H4O2
Molecular Weight 1213.417
Optical Activity UNSPECIFIED
Defined Stereocenters 16 / 16
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CASPOFUNGIN ACETATE

SMILES

CC(O)=O.CC(O)=O.[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=OGUJBRYAAJYXQP-IJFZAWIJSA-N
InChI=1S/C52H88N10O15.2C2H4O2/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;2*1-2(3)4/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);2*1H3,(H,3,4)/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
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
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
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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
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
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 (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:
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)
Rash (1 patient)
Sources:
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...
Other AEs:
Kounis syndrome (grade 5, 1 patient)
Sources:
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

AEs

AESignificanceDosePopulation
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

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
Moisture assay of an antifungal by near-infrared diffuse reflectance spectroscopy.
2002 Apr 1
Caspofungin: an echinocandin antifungal agent.
2002 Mar
An advanced double column-switching technique (LC-LC) for liquid chromatography/electrospray ionisation tandem mass spectrometry for fully automated analysis of caspofungin.
2004
Aspergillus nidulans RhoA is involved in polar growth, branching, and cell wall synthesis.
2004 Jan
Gateways to clinical trials.
2004 Oct
Gateways to clinical trials.
2005 Dec
Gateways to clinical trials.
2005 Jan-Feb
Gateways to clinical trials.
2005 Jul-Aug
Gateways to clinical trials.
2005 May
Candida glabrata prosthetic valve endocarditis treated successfully with fluconazole plus caspofungin without surgery: a case report and literature review.
2005 Nov
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
Gateways to clinical trials.
2005 Oct
Limitations of caspofungin in the treatment of obstructive pyonephrosis due to Candida glabrata infection.
2006 Aug 8
Gateways to clinical trials.
2006 Jan-Feb
Gateways to clinical trials.
2006 Jul-Aug
Gateways to clinical trials.
2006 May
Comparison of antifungal treatments for murine fusariosis.
2006 Nov
Gateways to Clinical Trials.
2008 Nov
Acute refractory hyperkalaemia and fatal cardiac arrest related to administration of liposomal amphotericin B.
2008 Nov
Gateways to clinical trials.
2008 Sep
Treatment for multiple Aspergillus spondylitis including a hip joint.
2009 Dec
Genomic analysis of the basal lineage fungus Rhizopus oryzae reveals a whole-genome duplication.
2009 Jul
Gateways to clinical trials.
2009 Jun
Gateways to clinical trials.
2009 Nov
Echinocandins: A ray of hope in antifungal drug therapy.
2010 Feb
Gateways to clinical trials.
2010 Jun
Recent advances in the treatment of mucormycosis.
2010 Nov
Evaluating retinal toxicity of intravitreal caspofungin in the mouse eye.
2010 Nov
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.
2015 May 18
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
CASPOFUNGIN ACETATE
JAN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN  
Official Name English
CASPOFUNGIN ACETATE [VANDF]
Common Name English
CANCIDAS
Brand Name English
CASPOFUNGIN ACETATE [MART.]
Common Name English
Caspofungin acetate [WHO-DD]
Common Name English
1-((4R,5S)-5-((2-AMINOETHYL)AMINO)-N(SUP 2)-(10,12-DIMETHYL-1-OXOTETRADECYL)-4-HYDROXY-L-ORNITHINE)-5-((3R)-3-HYDROXY-L-ORNITHINE)PNEUMOCANDIN B(SUB 0), DIACETATE (SALT)
Common Name English
MK-0991
Code English
CASPOFUNGIN DIACETATE
Common Name English
CASPOFUNGIN ACETATE [USAN]
Common Name English
CASPOFUNGIN ACETATE [MI]
Common Name English
CASPOFUNGIN ACETATE [JAN]
Common Name English
CASPOFUNGIN ACETATE [ORANGE BOOK]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C514
Created by admin on Fri Dec 15 16:09:54 GMT 2023 , Edited by admin on Fri Dec 15 16:09:54 GMT 2023
Code System Code Type Description
RXCUI
282363
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PRIMARY RxNorm
MERCK INDEX
m3159
Created by admin on Fri Dec 15 16:09:54 GMT 2023 , Edited by admin on Fri Dec 15 16:09:54 GMT 2023
PRIMARY Merck Index
DAILYMED
VUW370O5QE
Created by admin on Fri Dec 15 16:09:54 GMT 2023 , Edited by admin on Fri Dec 15 16:09:54 GMT 2023
PRIMARY
SMS_ID
100000089286
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PRIMARY
NCI_THESAURUS
C1724
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PRIMARY
DRUG BANK
DBSALT000020
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PRIMARY
CHEBI
59900
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PRIMARY
USAN
KK-07
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PRIMARY
EVMPD
SUB12476MIG
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PRIMARY
FDA UNII
VUW370O5QE
Created by admin on Fri Dec 15 16:09:54 GMT 2023 , Edited by admin on Fri Dec 15 16:09:54 GMT 2023
PRIMARY
EPA CompTox
DTXSID60904590
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PRIMARY
PUBCHEM
16119813
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PRIMARY
ChEMBL
CHEMBL499808
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PRIMARY
CAS
179463-17-3
Created by admin on Fri Dec 15 16:09:54 GMT 2023 , Edited by admin on Fri Dec 15 16:09:54 GMT 2023
PRIMARY