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Details

Stereochemistry ABSOLUTE
Molecular Formula C52H88N10O15
Molecular Weight 1093.3152
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(=N[C@@]1([H])C[C@]([H])([C@@]([H])(NCCN)N=C([C@]2([H])[C@]([H])(CCN2C(=O)[C@]([H])([C@@]([H])(CCN)O)N=C([C@]([H])([C@@]([H])([C@]([H])(c3ccc(cc3)O)O)O)N=C([C@]4([H])C[C@]([H])(CN4C(=O)[C@]([H])([C@@]([H])(C)O)N=C1O)O)O)O)O)O)O)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

HIDE SMILES / InChI

Molecular Formula C52H88N10O15
Molecular Weight 1093.3152
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 16 / 16
E/Z Centers 0
Optical Activity UNSPECIFIED

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

9.8046719E11
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

9.8046719E11
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

9.8046719E11
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

9.8046719E11
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

9.8046719E11
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
Effects of amphotericin B and caspofungin on histamine expression.
2003 Aug
Gateways to clinical trials.
2003 Dec
Comment: caspofungin acetate for treatment of invasive fungal infections.
2003 Dec
Microbial natural products as a source of antifungals.
2003 Jan
Gateways to clinical trials.
2003 Jan-Feb
Successful treatment of Candida krusei infection with caspofungin acetate: a new antifungal agent.
2003 May
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 Jul-Aug
Gateways to clinical trials.
2004 Jun
Gateways to clinical trials.
2004 Mar
Analysis of beta-1,3-glucan assembly in Saccharomyces cerevisiae using a synthetic interaction network and altered sensitivity to caspofungin.
2004 May
Caspofungin versus liposomal amphotericin B for empirical antifungal therapy in patients with persistent fever and neutropenia.
2004 Sep 30
Gateways to clinical trials.
2005 Dec
Gateways to clinical trials.
2005 Jan-Feb
Gateways to clinical trials.
2005 Jun
Gateways to clinical trials.
2005 Mar
Gateways to clinical trials.
2005 May
Fatal Blastoschizomyces capitatus sepsis in a neutropenic patient with acute myeloid leukemia: first documented case from Greece.
2005 May
Gateways to clinical trials.
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
Limitations of caspofungin in the treatment of obstructive pyonephrosis due to Candida glabrata infection.
2006 Aug 8
Gateways to clinical trials.
2006 Jan-Feb
FsFKS1, the 1,3-beta-glucan synthase from the caspofungin-resistant fungus Fusarium solani.
2006 Jul
Gateways to clinical trials.
2006 Jul-Aug
Voriconazole in the management of nosocomial invasive fungal infections.
2006 Jun
Gateways to clinical trials.
2006 May
Comparison of antifungal treatments for murine fusariosis.
2006 Nov
Gateways to clinical trials.
2006 Oct
Gateways to clinical trials.
2006 Sep
Antimicrobial susceptibility of Fusarium, Aspergillus, and other filamentous fungi isolated from keratitis.
2007 Jun
Comparison of echinocandin antifungals.
2007 Mar
Gateways to clinical trials.
2007 Oct
[A retrospective study of amphotericin B treatment for invasive fungal infection].
2007 Sep
Comedication of caspofungin acetate and cyclosporine A after allogeneic haematopoietic stem cell transplantation leads to negligible hepatotoxicity.
2008
Gateways to clinical trials. July-August 2008.
2008 Jul-Aug
Visual compatibility of caspofungin acetate with commonly used drugs during simulated Y-site delivery.
2008 Mar 1
Gateways to Clinical Trials.
2008 Nov
Acute refractory hyperkalaemia and fatal cardiac arrest related to administration of liposomal amphotericin B.
2008 Nov
[Tolerance of caspofungin in intensive care unit: a prospective study].
2008 Oct
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.
Substance Class Chemical
Created
by admin
on Sat Jun 26 09:58:38 UTC 2021
Edited
by admin
on Sat Jun 26 09:58:38 UTC 2021
Record UNII
F0XDI6ZL63
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CASPOFUNGIN
EMA EPAR   HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
CASPOFUNGIN [WHO-DD]
Common 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-743,872
Code English
L-743872
Code 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 Sat Jun 26 09:58:39 UTC 2021 , Edited by admin on Sat Jun 26 09:58:39 UTC 2021
NDF-RT N0000175507
Created by admin on Sat Jun 26 09:58:39 UTC 2021 , Edited by admin on Sat Jun 26 09:58:39 UTC 2021
WHO-ATC J02AX04
Created by admin on Sat Jun 26 09:58:39 UTC 2021 , Edited by admin on Sat Jun 26 09:58:39 UTC 2021
NDF-RT N0000175508
Created by admin on Sat Jun 26 09:58:39 UTC 2021 , Edited by admin on Sat Jun 26 09:58:39 UTC 2021
WHO-VATC QJ02AX04
Created by admin on Sat Jun 26 09:58:39 UTC 2021 , Edited by admin on Sat Jun 26 09:58:39 UTC 2021
NDF-RT N0000175508
Created by admin on Sat Jun 26 09:58:39 UTC 2021 , Edited by admin on Sat Jun 26 09:58:39 UTC 2021
LIVERTOX 156
Created by admin on Sat Jun 26 09:58:39 UTC 2021 , Edited by admin on Sat Jun 26 09:58:39 UTC 2021
Code System Code Type Description
HSDB
7476
Created by admin on Sat Jun 26 09:58:39 UTC 2021 , Edited by admin on Sat Jun 26 09:58:39 UTC 2021
PRIMARY
EVMPD
SUB16405MIG
Created by admin on Sat Jun 26 09:58:39 UTC 2021 , Edited by admin on Sat Jun 26 09:58:39 UTC 2021
PRIMARY
CAS
162808-62-0
Created by admin on Sat Jun 26 09:58:39 UTC 2021 , Edited by admin on Sat Jun 26 09:58:39 UTC 2021
PRIMARY
DRUG BANK
DB00520
Created by admin on Sat Jun 26 09:58:39 UTC 2021 , Edited by admin on Sat Jun 26 09:58:39 UTC 2021
PRIMARY
WIKIPEDIA
CASPOFUNGIN
Created by admin on Sat Jun 26 09:58:39 UTC 2021 , Edited by admin on Sat Jun 26 09:58:39 UTC 2021
PRIMARY
MERCK INDEX
M3159
Created by admin on Sat Jun 26 09:58:39 UTC 2021 , Edited by admin on Sat Jun 26 09:58:39 UTC 2021
PRIMARY Merck Index
NCI_THESAURUS
C28910
Created by admin on Sat Jun 26 09:58:39 UTC 2021 , Edited by admin on Sat Jun 26 09:58:39 UTC 2021
PRIMARY
ChEMBL
CHEMBL499808
Created by admin on Sat Jun 26 09:58:39 UTC 2021 , Edited by admin on Sat Jun 26 09:58:39 UTC 2021
PRIMARY
RXCUI
140108
Created by admin on Sat Jun 26 09:58:39 UTC 2021 , Edited by admin on Sat Jun 26 09:58:39 UTC 2021
PRIMARY RxNorm
LACTMED
Caspofungin
Created by admin on Sat Jun 26 09:58:39 UTC 2021 , Edited by admin on Sat Jun 26 09:58:39 UTC 2021
PRIMARY
MESH
C105417
Created by admin on Sat Jun 26 09:58:39 UTC 2021 , Edited by admin on Sat Jun 26 09:58:39 UTC 2021
PRIMARY
FDA UNII
F0XDI6ZL63
Created by admin on Sat Jun 26 09:58:39 UTC 2021 , Edited by admin on Sat Jun 26 09:58:39 UTC 2021
PRIMARY
DRUG CENTRAL
2977
Created by admin on Sat Jun 26 09:58:39 UTC 2021 , Edited by admin on Sat Jun 26 09:58:39 UTC 2021
PRIMARY
PUBCHEM
16119814
Created by admin on Sat Jun 26 09:58:39 UTC 2021 , Edited by admin on Sat Jun 26 09:58:39 UTC 2021
PRIMARY
INN
7778
Created by admin on Sat Jun 26 09:58:39 UTC 2021 , Edited by admin on Sat Jun 26 09:58:39 UTC 2021
PRIMARY
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