Identification

Name
Caspofungin
Accession Number
DB00520  (APRD00199)
Type
Small Molecule
Groups
Approved
Description

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.

Structure
Thumb
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
Product Ingredients
IngredientUNIICASInChI Key
Caspofungin acetateVUW370O5QE179463-17-3OGUJBRYAAJYXQP-LLXMLGLCSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CancidasInjection, powder, lyophilized, for solution5 mg/1mLIntravenousMerck Sharp & Dohme Corp.2001-01-26Not applicableUs
CancidasInjection, powder, for solution70 mgIntravenousMerck Sharp & Dohme Limited2001-10-24Not applicableEu
CancidasInjection, powder, for solution50 mgIntravenousMerck Sharp & Dohme Limited2001-10-24Not applicableEu
CancidasPowder, for solution70 mgIntravenousMerck Ltd.2001-10-23Not applicableCanada
CancidasPowder, for solution50 mgIntravenousMerck Ltd.2001-08-23Not applicableCanada
CancidasInjection, powder, lyophilized, for solution7 mg/1mLIntravenousMerck Sharp & Dohme Corp.2001-01-26Not applicableUs
Caspofungin AcetateInjection, powder, lyophilized, for solution5 mg/1mLIntravenousFresenius Kabi USA, LLC2016-12-30Not applicableUs
Caspofungin AcetateInjection, powder, lyophilized, for solution7 mg/1mLIntravenousFresenius Kabi USA, LLC2016-12-30Not applicableUs
Caspofungin Acetate for InjectionPowder, for solutionIntravenousMylan PharmaceuticalsNot applicableNot applicableCanada
Caspofungin Acetate for InjectionPowder, for solutionIntravenousMylan PharmaceuticalsNot applicableNot applicableCanada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Caspofungin AcetateInjection, powder, lyophilized, for solution5 mg/1mLIntravenousFosun Pharma USA Inc.2019-04-02Not applicableUs
Caspofungin acetateInjection, powder, for solution5 mg/1mLIntravenousMylan Institutional LLC2017-09-29Not applicableUs
Caspofungin AcetateInjection, powder, lyophilized, for solution7 mg/1mLIntravenousGland Pharma Limited2017-10-29Not applicableUs
Caspofungin AcetateInjection, powder, lyophilized, for solution5 mg/1mLIntravenousGland Pharma Limited2017-10-29Not applicableUs
Caspofungin AcetateInjection, powder, lyophilized, for solution7 mg/1mLIntravenousAlmaject, Inc.2020-03-31Not applicableUs
Caspofungin AcetateInjection, powder, lyophilized, for solution5 mg/1mLIntravenousAlmaject, Inc.2020-03-31Not applicableUs
Caspofungin AcetateInjection7 mg/1mLIntravenousCipla USA Inc.2018-07-12Not applicableUs
Caspofungin AcetateInjection5 mg/1mLIntravenousCipla USA Inc.2018-07-12Not applicableUs
Caspofungin AcetateInjection, powder, lyophilized, for solution7 mg/1mLIntravenousAlvogen Inc.2017-12-01Not applicableUs
Caspofungin AcetateInjection, powder, lyophilized, for solution70 mg/10.8mLIntravenousAthenex Pharmaceutical Division, Llc.2017-10-04Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Categories
UNII
F0XDI6ZL63
CAS number
162808-62-0
Weight
Average: 1093.3131
Monoisotopic: 1092.643062196
Chemical Formula
C52H88N10O15
InChI Key
JYIKNQVWKBUSNH-OGZDCFRISA-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+/m1/s1
IUPAC Name
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[22.3.0.0⁹,¹³]heptacosan-18-yl]-10,12-dimethyltetradecanamide
SMILES
CCC(C)CC(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]2C[C@@H](O)CN2C(=O)[C@@H](NC1=O)[C@@H](C)O)[C@H](O)[C@@H](O)C1=CC=C(O)C=C1)[C@H](O)CCN

Pharmacology

Indication

For the treatment of esophageal candidiasis and invasive aspergillosis in patients who are refractory to or intolerant of other therapies.

Associated Conditions
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.

TargetActionsOrganism
A1,3-beta-glucan synthase component FKS1
inhibitor
Aspergillus niger (strain CBS 513.88 / FGSC A1513)
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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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]
Toxicity

Side effects include rash, swelling, and nausea (rare)

Affected organisms
  • Aspergillis, Candida and other fungi
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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.
DrugInteraction
(R)-warfarinThe therapeutic efficacy of (R)-warfarin can be increased when used in combination with Caspofungin.
(S)-WarfarinThe therapeutic efficacy of (S)-Warfarin can be increased when used in combination with Caspofungin.
4-hydroxycoumarinThe therapeutic efficacy of 4-hydroxycoumarin can be increased when used in combination with Caspofungin.
AcenocoumarolThe therapeutic efficacy of Acenocoumarol can be increased when used in combination with Caspofungin.
AcetylcysteineThe excretion of Caspofungin can be decreased when combined with Acetylcysteine.
AcyclovirThe excretion of Acyclovir can be decreased when combined with Caspofungin.
Adefovir dipivoxilThe excretion of Adefovir dipivoxil can be decreased when combined with Caspofungin.
AlprostadilThe excretion of Alprostadil can be decreased when combined with Caspofungin.
AmbrisentanThe excretion of Ambrisentan can be decreased when combined with Caspofungin.
Aminohippuric acidThe excretion of Caspofungin can be decreased when combined with Aminohippuric acid.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
No interactions found.

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
  1. 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. [PubMed:19724014]
  2. Morrison VA: Caspofungin: an overview. Expert Rev Anti Infect Ther. 2005 Oct;3(5):697-705. [PubMed:16207161]
  3. McCormack PL, Perry CM: Caspofungin: a review of its use in the treatment of fungal infections. Drugs. 2005;65(14):2049-68. [PubMed:16162025]
  4. 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. [PubMed:16960253]
  5. 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. [PubMed:16990627]
External Links
KEGG Drug
D07626
PubChem Compound
3035406
PubChem Substance
46508288
ChemSpider
411774
RxNav
140108
ChEBI
474180
ChEMBL
CHEMBL499808
Therapeutic Targets Database
DAP000547
PharmGKB
PA164743013
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Caspofungin
ATC Codes
J02AX04 — Caspofungin
AHFS Codes
  • 08:14.16 — Echinocandins
FDA label
Download (87.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableInfection1
1, 2WithdrawnPreventionLeukemia Acute Myeloid Leukemia (AML) / Pulmonary Aspergillosis - Invasive1
2CompletedPreventionInfections, Fungal1
2CompletedPreventionIntra-abdominal Perforation1
2CompletedPreventionPulmonary Invasive Aspergillosis1
2CompletedSupportive CareMalignancies1
2CompletedTreatmentAspergillosis1
2CompletedTreatmentAspergillosis / Candidiasis1
2CompletedTreatmentAspergillosis / Candidiasis, Invasive / Esophageal Candidiasis1
2CompletedTreatmentCandidemia / Candidiasis, Invasive / Fungaemia / Infections, Fungal / Mycoses1
2CompletedTreatmentCandidiasis2
2CompletedTreatmentFevers / Neutropenia1
2CompletedTreatmentFungus Diseases / Hematopoietic Stem Cell Transplantation (HSCT)1
2CompletedTreatmentInfections, Fungal1
2CompletedTreatmentInvasive Aspergillosis1
2RecruitingTreatmentAllogeneic Stem Cell Transplantation / Hematopoietic Stem Cell Transplantation (HSCT) / Leukemias1
2RecruitingTreatmentInfections, Fungal1
2TerminatedSupportive CareInfection / Unspecified Adult Solid Tumor, Protocol Specific1
2TerminatedTreatmentCandidiasis, Invasive2
2TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Oral Candidiasis1
2Unknown StatusPreventionFungaemia / Mycoses1
2Unknown StatusPreventionInfections, Fungal / Transplantation, Liver1
2, 3CompletedTreatmentThermal Injury1
3Active Not RecruitingSupportive CareAdult Acute Megakaryoblastic Leukemia / Adult Acute Megakaryoblastic Leukemia (M7) / Adult Acute Minimally Differentiated Myeloid Leukemia (M0) / Adult Acute Monoblastic Leukemia / Adult Acute Monoblastic Leukemia (M5a) / Adult Acute Monocytic Leukemia / Adult Acute Monocytic Leukemia (M5b) / Adult Acute Myeloblastic Leukemia With Maturation (M2) / Adult Acute Myeloblastic Leukemia Without Maturation (M1) / Adult Acute Myeloid Leukemia in Remission / Adult Acute Myeloid Leukemia With 11q23 (MLL) Abnormalities / Adult Acute Myeloid Leukemia With Del(5q) / Adult Acute Myeloid Leukemia With Inv(16)(p13.1q22); CBFB-MYH11 / Adult Acute Myeloid Leukemia With Inv(16)(p13;q22) / Adult Acute Myeloid Leukemia With Maturation / Adult Acute Myeloid Leukemia With Minimal Differentiation / Adult Acute Myeloid Leukemia With t(16;16)(p13.1;q22); CBFB-MYH11 / Adult Acute Myeloid Leukemia With T(16;16)(p13;q22) / Adult Acute Myeloid Leukemia With T(8;21)(q22;q22) / Adult Acute Myeloid Leukemia With t(8;21); (q22; q22.1); RUNX1-RUNX1T1 / Adult Acute Myeloid Leukemia With t(9;11)(p22.3;q23.3); MLLT3-KMT2A / Adult Acute Myeloid Leukemia Without Maturation / Adult Acute Myelomonocytic Leukemia / Adult Acute Myelomonocytic Leukemia (M4) / Adult Erythroleukemia / Adult Erythroleukemia (M6a) / Adult Pure Erythroid Leukemia / Adult Pure Erythroid Leukemia (M6b) / Alkylating Agent-Related Acute Myeloid Leukemia / Childhood Acute Erythroid Leukemia / Childhood Acute Erythroleukemia (M6) / Childhood Acute Megakaryoblastic Leukemia / Childhood Acute Megakaryocytic Leukemia (M7) / Childhood Acute Minimally Differentiated Myeloid Leukemia (M0) / Childhood Acute Monoblastic Leukemia / Childhood Acute Monoblastic Leukemia (M5a) / Childhood Acute Monocytic Leukemia / Childhood Acute Monocytic Leukemia (M5b) / Childhood Acute Myeloblastic Leukemia With Maturation (M2) / Childhood Acute Myeloblastic Leukemia Without Maturation (M1) / Childhood Acute Myeloid Leukemia in Remission / Childhood Acute Myeloid Leukemia With Maturation / Childhood Acute Myeloid Leukemia With Minimal Differentiation / Childhood Acute Myeloid Leukemia Without Maturation / Childhood Acute Myelomonocytic Leukemia / Childhood Acute Myelomonocytic Leukemia (M4) / Infections, Fungal / Leukemia Acute Myeloid Leukemia (AML) / Myeloid Neoplasm / Neutropenia / Recurrent Adult Acute Myeloid Leukemia / Recurrent Childhood Acute Myeloid Leukemia / Secondary Acute Myeloid Leukemia (Secondary AML, sAML) / Untreated Adult Acute Myeloid Leukemia / Untreated Childhood Acute Myeloid Leukemia and Other Myeloid Malignancies / Untreated Childhood Myeloid Neoplasm1
3Active Not RecruitingSupportive CareHematopoietic and Lymphoid Cell Neoplasm / Hematopoietic/Lymphoid Cancer / Infections, Fungal1
3Active Not RecruitingSupportive CareInfections, Fungal / Leukemias / Myelodysplastic Syndromes1
3CompletedPreventionMycoses / Transplantation, Liver1
3CompletedSupportive CareMalignancies1
3CompletedTreatmentCandidemia / Candidiasis1
3CompletedTreatmentCandidemia / Candidiasis, Invasive / Mycoses1
3CompletedTreatmentCandidiasis1
3CompletedTreatmentCandidiasis, Invasive1
3CompletedTreatmentInfections, Fungal4
3CompletedTreatmentOral Candidiasis1
3Not Yet RecruitingTreatmentICU Yeast Intra-abdominal Infection1
3RecruitingTreatmentCandidemia / Infections, Fungal / Invasive Candidiases / Mycoses1
3TerminatedPreventionCandidiasis1
3TerminatedTreatmentCandidiasis / Fungaemia1
3TerminatedTreatmentCandidiasis / Fungaemia / Neutropenia1
4CompletedNot AvailableAspergillosis / Candidiasis1
4CompletedNot AvailableBMI >30 kg/m2 / Infections, Fungal1
4CompletedOtherBacterial Infections and Mycoses / Liver Diseases1
4CompletedPreventionCandidiasis, Invasive1
4CompletedTreatmentCandidemia1
4CompletedTreatmentCritically-ill Patients / Suspected Invasive Candidiasis1
4CompletedTreatmentInvasive Aspergillosis1
4CompletedTreatmentPeritonitis / Shock, Septic1
4RecruitingTreatmentPneumocystis Jirovecii Pneumonia1
4TerminatedTreatmentNeoplasms, Hematologic1
4Unknown StatusTreatmentChronic Obstructive Pulmonary Disease (COPD) / Pulmonary Invasive Aspergillosis1
Not AvailableCompletedNot AvailableIllness, Critical / Infection1
Not AvailableCompletedNot AvailableInvasive Fungal Infections1
Not AvailableCompletedNot AvailableSystemic Fungal Infections1
Not AvailableCompletedSupportive CareFever, Sweats, and Hot Flashes / Infection / Leukemias / Malignant Lymphomas / Neuroblastomas / Neutropenia / Renal Cancers / Sarcomas1
Not AvailableCompletedTreatmentEsophageal Candidiasis / Human Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedTreatmentShock1
Not AvailableEnrolling by InvitationTreatmentInvasive Fungal Infections1
Not AvailableNot Yet RecruitingNot AvailableIllness, Critical / Infections, Fungal / Shock, Septic1
Not AvailableRecruitingTreatmentPneumocystis Jirovecii Pneumonia1
Not AvailableTerminatedTreatmentInvasive Aspergillosis / Invasive Fungal Infections / Invasive Fusariosis1

Pharmacoeconomics

Manufacturers
  • Merck and co inc
Packagers
  • Cardinal Health
  • Merck & Co.
  • Oso Biopharmaceuticals Manufacturing LLC
Dosage forms
FormRouteStrength
Injection, powder, for solutionIntravenous50 mg
Injection, powder, for solutionIntravenous70 mg
Injection, powder, lyophilized, for solutionNot applicable1 kg/1kg
Powder, for solutionIntravenous50 mg
Powder, for solutionIntravenous70 mg
InjectionIntravenous5 mg/1mL
InjectionIntravenous7 mg/1mL
Injection, powder, for solutionIntravenous5 mg/1mL
Injection, powder, for solutionIntravenous7 mg/1mL
Injection, powder, lyophilized, for solutionIntravenous5 mg/1mL
Injection, powder, lyophilized, for solutionIntravenous50 mg/10.8mL
Injection, powder, lyophilized, for solutionIntravenous7 mg/1mL
Injection, powder, lyophilized, for solutionIntravenous70 mg/10.8mL
Powder, for solutionIntravenous
Prices
Unit descriptionCostUnit
Cancidas iv 70 mg vial421.06USD vial
Cancidas iv 50 mg vial405.25USD vial
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5378804No1995-01-032013-03-16Us
CA2251928No2003-06-172017-04-15Canada
CA2118757No2002-05-142014-03-10Canada
US6136783Yes2000-10-242017-09-28Us
US5952300Yes1999-09-142017-09-28Us
US5514650Yes1996-05-072015-07-26Us
US9636407No2017-05-022032-12-21Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP0Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.367 mg/mLALOGPS
logP0.17ALOGPS
logP-4.8ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)8.75ChemAxon
pKa (Strongest Basic)9.76ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count16ChemAxon
Polar Surface Area412.03 Å2ChemAxon
Rotatable Bond Count23ChemAxon
Refractivity278.78 m3·mol-1ChemAxon
Polarizability117.52 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.7566
Blood Brain Barrier-0.96
Caco-2 permeable-0.8091
P-glycoprotein substrateSubstrate0.8694
P-glycoprotein inhibitor INon-inhibitor0.9653
P-glycoprotein inhibitor IINon-inhibitor0.9174
Renal organic cation transporterNon-inhibitor0.9379
CYP450 2C9 substrateNon-substrate0.831
CYP450 2D6 substrateNon-substrate0.8166
CYP450 3A4 substrateNon-substrate0.51
CYP450 1A2 substrateNon-inhibitor0.9389
CYP450 2C9 inhibitorNon-inhibitor0.9161
CYP450 2D6 inhibitorNon-inhibitor0.8904
CYP450 2C19 inhibitorNon-inhibitor0.875
CYP450 3A4 inhibitorNon-inhibitor0.9682
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9781
Ames testNon AMES toxic0.7398
CarcinogenicityNon-carcinogens0.8315
BiodegradationNot ready biodegradable0.9683
Rat acute toxicity2.9344 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9637
hERG inhibition (predictor II)Non-inhibitor0.716
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Oligopeptides
Alternative Parents
Cyclic peptides / Macrolactams / N-acyl-alpha amino acids and derivatives / 1-hydroxy-2-unsubstituted benzenoids / Benzene and substituted derivatives / N-acyl amines / Pyrrolidines / Tertiary carboxylic acid amides / 1,3-aminoalcohols / Secondary alcohols
show 9 more
Substituents
Alpha-oligopeptide / Cyclic alpha peptide / Macrolactam / N-acyl-alpha amino acid or derivatives / Alpha-amino acid or derivatives / 1-hydroxy-2-unsubstituted benzenoid / Phenol / Fatty acyl / Monocyclic benzene moiety / Benzenoid
show 26 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
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
  1. 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. [PubMed:19724014]
  2. Morrison VA: Caspofungin: an overview. Expert Rev Anti Infect Ther. 2005 Oct;3(5):697-705. [PubMed:16207161]
  3. McCormack PL, Perry CM: Caspofungin: a review of its use in the treatment of fungal infections. Drugs. 2005;65(14):2049-68. [PubMed:16162025]
  4. 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. [PubMed:16960253]
  5. 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. [PubMed:16990627]

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
  1. Colburn DE, Giles FJ, Oladovich D, Smith JA: In vitro evaluation of cytochrome P450-mediated drug interactions between cytarabine, idarubicin, itraconazole and caspofungin. Hematology. 2004 Jun;9(3):217-21. doi: 10.1080/10245330410001701585. [PubMed:15204103]
  2. Caspofungin EMA label [Link]

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
  1. 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. [PubMed:15716364]
  2. 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. [PubMed:27001813]
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
  1. 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. [PubMed:15716364]
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
  1. 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. [PubMed:15716364]
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
  1. 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. [PubMed:15716364]

Drug created on June 13, 2005 07:24 / Updated on May 28, 2020 04:03

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