Identification

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

Caspofungin (brand name Cancidas worldwide) is an antifungal drug, the first of a new class termed the echinocandins from Merck & Co., Inc. It shows activity against infections with Aspergillus and Candida, and works by inhibiting β(1,3)-D-Glucan of the fungal cell wall. Caspofungin is administered intravenously.

Structure
Thumb
Synonyms
  • (4R,5S)-5-((2-Aminoethyl)amino)-N(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
  • 1-[(4R,5S)-5-[(2-Aminoethyl)amino]-N(2)-(10,12-dimethyl-1-oxotetradecyl)-4-hydroxy-L-ornithine]-5-[(3R)-3-hydroxy-L-ornithine]-pneumocandin b0
Product Ingredients
IngredientUNIICASInChI Key
Caspofungin acetateVUW370O5QE179463-17-3OGUJBRYAAJYXQP-LLXMLGLCSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CancidasPowder, for solution50 mgIntravenousMerck Ltd.2001-08-23Not applicableCanada
CancidasInjection, powder, for solution50 mgIntravenousMerck Sharp & Dohme Limited2001-10-24Not applicableEu
CancidasInjection, powder, lyophilized, for solution7 mg/mLIntravenousMerck Sharp & Dohme Limited2001-01-26Not applicableUs
CancidasInjection, powder, lyophilized, for solution5 mg/mLIntravenousMerck Sharp & Dohme Limited2001-01-26Not applicableUs
CancidasPowder, for solution70 mgIntravenousMerck Ltd.2001-10-23Not applicableCanada
CancidasInjection, powder, for solution70 mgIntravenousMerck Sharp & Dohme Limited2001-10-24Not applicableEu
Caspofungin AcetateInjection, powder, lyophilized, for solution7 mg/mLIntravenousFresenius Kabi2016-12-30Not applicableUs
Caspofungin AcetateInjection, powder, lyophilized, for solution5 mg/mLIntravenousFresenius Kabi2016-12-30Not applicableUs
Caspofungin Acetate for InjectionPowder, for solution50 mgIntravenousMylan PharmaceuticalsNot applicableNot applicableCanada
Caspofungin Acetate for InjectionPowder, for solution70 mgIntravenousSandoz Canada IncorporatedNot applicableNot applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Caspofungin AcetateInjection, powder, lyophilized, for solution50 mg/10.8mLIntravenousAthenex Pharmaceutical Division, Llc.2017-10-04Not applicableUs
Caspofungin AcetateInjection, powder, lyophilized, for solution7 mg/mLIntravenousGland Pharma Limited2017-10-29Not applicableUs
Caspofungin acetateInjection, powder, for solution5 mg/mLIntravenousMylan Institutional2017-09-29Not applicableUs
Caspofungin AcetateInjection, powder, lyophilized, for solution7 mg/mLIntravenousAlvogen, Inc.2017-12-01Not applicableUs
Caspofungin AcetateInjection, powder, lyophilized, for solution5 mg/mLIntravenousGland Pharma Limited2017-10-29Not applicableUs
Caspofungin AcetateInjection, powder, lyophilized, for solution70 mg/10.8mLIntravenousAthenex Pharmaceutical Division, Llc.2017-10-04Not applicableUs
Caspofungin AcetateInjection, powder, lyophilized, for solution5 mg/mLIntravenousAlvogen, Inc.2017-12-01Not applicableUs
Caspofungin acetateInjection, powder, for solution7 mg/mLIntravenousMylan Institutional2017-09-29Not applicableUs
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)
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
DrugInteractionDrug group
AfatinibThe serum concentration of Afatinib can be increased when it is combined with Caspofungin.Approved
AgmatineThe therapeutic efficacy of Caspofungin can be increased when used in combination with Agmatine.Experimental, Investigational
AmiodaroneThe therapeutic efficacy of Caspofungin can be increased when used in combination with Amiodarone.Approved, Investigational
AmlodipineThe therapeutic efficacy of Caspofungin can be increased when used in combination with Amlodipine.Approved
Amphotericin BThe therapeutic efficacy of Amphotericin B can be decreased when used in combination with Caspofungin.Approved, Investigational
AmrinoneThe therapeutic efficacy of Caspofungin can be increased when used in combination with Amrinone.Approved
AranidipineThe therapeutic efficacy of Caspofungin can be increased when used in combination with Aranidipine.Approved, Investigational
AsunaprevirThe serum concentration of Asunaprevir can be increased when it is combined with Caspofungin.Approved, Investigational, Withdrawn
AtorvastatinThe risk or severity of adverse effects can be increased when Caspofungin is combined with Atorvastatin.Approved
AzelnidipineThe therapeutic efficacy of Caspofungin can be increased when used in combination with Azelnidipine.Approved, Investigational
AzimilideThe therapeutic efficacy of Caspofungin can be increased when used in combination with Azimilide.Investigational
BarnidipineThe therapeutic efficacy of Caspofungin can be increased when used in combination with Barnidipine.Approved
BencyclaneThe therapeutic efficacy of Caspofungin can be increased when used in combination with Bencyclane.Experimental
BenidipineThe therapeutic efficacy of Caspofungin can be increased when used in combination with Benidipine.Approved, Investigational
BepridilThe therapeutic efficacy of Caspofungin can be increased when used in combination with Bepridil.Approved, Withdrawn
BioallethrinThe therapeutic efficacy of Caspofungin can be increased when used in combination with Bioallethrin.Approved, Experimental
BosutinibThe serum concentration of Bosutinib can be increased when it is combined with Caspofungin.Approved
Brentuximab vedotinThe serum concentration of Brentuximab vedotin can be increased when it is combined with Caspofungin.Approved, Investigational
BromocriptineThe risk or severity of adverse effects can be increased when Bromocriptine is combined with Caspofungin.Approved, Investigational
BuspironeThe metabolism of Buspirone can be decreased when combined with Caspofungin.Approved, Investigational
BusulfanThe serum concentration of Busulfan can be increased when it is combined with Caspofungin.Approved, Investigational
CabergolineThe risk or severity of adverse effects can be increased when Cabergoline is combined with Caspofungin.Approved
CarbamazepineThe serum concentration of Caspofungin can be decreased when it is combined with Carbamazepine.Approved, Investigational
CarboxyamidotriazoleThe therapeutic efficacy of Caspofungin can be increased when used in combination with Carboxyamidotriazole.Investigational
CaroverineThe therapeutic efficacy of Caspofungin can be increased when used in combination with Caroverine.Experimental
CerivastatinThe serum concentration of Cerivastatin can be increased when it is combined with Caspofungin.Approved, Withdrawn
CilnidipineThe therapeutic efficacy of Caspofungin can be increased when used in combination with Cilnidipine.Approved, Investigational
CinnarizineThe therapeutic efficacy of Caspofungin can be increased when used in combination with Cinnarizine.Approved, Investigational
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Caspofungin.Approved, Investigational, Withdrawn
ClevidipineThe therapeutic efficacy of Caspofungin can be increased when used in combination with Clevidipine.Approved, Investigational
ColchicineThe serum concentration of Colchicine can be increased when it is combined with Caspofungin.Approved
CyclandelateThe therapeutic efficacy of Caspofungin can be increased when used in combination with Cyclandelate.Approved
CyclosporineThe risk or severity of adverse effects can be increased when Cyclosporine is combined with Caspofungin.Approved, Investigational, Vet Approved
Dabigatran etexilateThe serum concentration of the active metabolites of Dabigatran etexilate can be increased when Dabigatran etexilate is used in combination with Caspofungin.Approved
DarodipineThe therapeutic efficacy of Caspofungin can be increased when used in combination with Darodipine.Experimental
DexamethasoneThe serum concentration of Caspofungin can be decreased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
DidanosineDidanosine can cause a decrease in the absorption of Caspofungin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
DihydroergocornineThe risk or severity of adverse effects can be increased when Dihydroergocornine is combined with Caspofungin.Approved
DihydroergocristineThe risk or severity of adverse effects can be increased when Dihydroergocristine is combined with Caspofungin.Approved, Experimental
DihydroergocryptineThe risk or severity of adverse effects can be increased when Dihydroergocryptine is combined with Caspofungin.Experimental
DihydroergotamineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Caspofungin.Approved, Investigational
DiltiazemThe therapeutic efficacy of Caspofungin can be increased when used in combination with Diltiazem.Approved, Investigational
DocetaxelThe metabolism of Docetaxel can be decreased when combined with Caspofungin.Approved, Investigational
DofetilideThe serum concentration of Dofetilide can be increased when it is combined with Caspofungin.Approved, Investigational
DotarizineThe therapeutic efficacy of Caspofungin can be increased when used in combination with Dotarizine.Investigational
DoxorubicinThe serum concentration of Doxorubicin can be increased when it is combined with Caspofungin.Approved, Investigational
EdoxabanThe serum concentration of Edoxaban can be increased when it is combined with Caspofungin.Approved
EfavirenzThe serum concentration of Caspofungin can be decreased when it is combined with Efavirenz.Approved, Investigational
EfonidipineThe therapeutic efficacy of Caspofungin can be increased when used in combination with Efonidipine.Approved, Investigational
EperisoneThe therapeutic efficacy of Caspofungin can be increased when used in combination with Eperisone.Approved, Investigational
ErgonovineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Caspofungin.Approved
ErgotamineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Caspofungin.Approved
EthosuximideThe therapeutic efficacy of Caspofungin can be increased when used in combination with Ethosuximide.Approved
EtravirineThe serum concentration of Etravirine can be increased when it is combined with Caspofungin.Approved
EverolimusThe serum concentration of Everolimus can be increased when it is combined with Caspofungin.Approved
FelodipineThe therapeutic efficacy of Caspofungin can be increased when used in combination with Felodipine.Approved, Investigational
FendilineThe therapeutic efficacy of Caspofungin can be increased when used in combination with Fendiline.Withdrawn
Fish oilThe therapeutic efficacy of Caspofungin can be increased when used in combination with Fish oil.Approved, Nutraceutical
FlunarizineThe therapeutic efficacy of Caspofungin can be increased when used in combination with Flunarizine.Approved
FluspirileneThe therapeutic efficacy of Caspofungin can be increased when used in combination with Fluspirilene.Approved, Investigational
FluvastatinThe serum concentration of Fluvastatin can be increased when it is combined with Caspofungin.Approved
FosphenytoinThe serum concentration of Caspofungin can be decreased when it is combined with Fosphenytoin.Approved, Investigational
GabapentinThe therapeutic efficacy of Caspofungin can be increased when used in combination with Gabapentin.Approved, Investigational
GallopamilThe therapeutic efficacy of Caspofungin can be increased when used in combination with Gallopamil.Investigational
IbrutinibThe serum concentration of Ibrutinib can be increased when it is combined with Caspofungin.Approved
IsradipineThe therapeutic efficacy of Caspofungin can be increased when used in combination with Isradipine.Approved, Investigational
LacidipineThe therapeutic efficacy of Caspofungin can be increased when used in combination with Lacidipine.Approved, Investigational
LamotrigineThe therapeutic efficacy of Caspofungin can be increased when used in combination with Lamotrigine.Approved, Investigational
LedipasvirThe serum concentration of Ledipasvir can be increased when it is combined with Caspofungin.Approved
LercanidipineThe therapeutic efficacy of Caspofungin can be increased when used in combination with Lercanidipine.Approved, Investigational
LevetiracetamThe therapeutic efficacy of Caspofungin can be increased when used in combination with Levetiracetam.Approved, Investigational
LidoflazineThe therapeutic efficacy of Caspofungin can be increased when used in combination with Lidoflazine.Experimental
LisurideThe risk or severity of adverse effects can be increased when Lisuride is combined with Caspofungin.Approved, Investigational
LoperamideThe therapeutic efficacy of Caspofungin can be increased when used in combination with Loperamide.Approved
LosartanThe metabolism of Losartan can be decreased when combined with Caspofungin.Approved
LovastatinThe serum concentration of Lovastatin can be increased when it is combined with Caspofungin.Approved, Investigational
Lysergic Acid DiethylamideThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Caspofungin.Illicit, Investigational, Withdrawn
Magnesium sulfateThe therapeutic efficacy of Caspofungin can be increased when used in combination with Magnesium sulfate.Approved, Investigational, Vet Approved
ManidipineThe therapeutic efficacy of Caspofungin can be increased when used in combination with Manidipine.Approved, Investigational
MentholThe therapeutic efficacy of Caspofungin can be increased when used in combination with Menthol.Approved
MetergolineThe risk or severity of adverse effects can be increased when Metergoline is combined with Caspofungin.Experimental
MethsuximideThe therapeutic efficacy of Caspofungin can be increased when used in combination with Methsuximide.Approved
MethylergometrineThe risk or severity of adverse effects can be increased when Methylergometrine is combined with Caspofungin.Approved
MethysergideThe risk or severity of adverse effects can be increased when Methysergide is combined with Caspofungin.Approved
MevastatinThe serum concentration of Mevastatin can be increased when it is combined with Caspofungin.Experimental
MibefradilThe therapeutic efficacy of Caspofungin can be increased when used in combination with Mibefradil.Investigational, Withdrawn
NaftopidilThe therapeutic efficacy of Caspofungin can be increased when used in combination with Naftopidil.Investigational
NaloxegolThe serum concentration of Naloxegol can be increased when it is combined with Caspofungin.Approved
NevirapineThe serum concentration of Caspofungin can be decreased when it is combined with Nevirapine.Approved
NicardipineThe therapeutic efficacy of Caspofungin can be increased when used in combination with Nicardipine.Approved, Investigational
NicergolineThe risk or severity of adverse effects can be increased when Nicergoline is combined with Caspofungin.Approved, Investigational
NifedipineThe therapeutic efficacy of Caspofungin can be increased when used in combination with Nifedipine.Approved
NiguldipineThe therapeutic efficacy of Caspofungin can be increased when used in combination with Niguldipine.Experimental
NiludipineThe therapeutic efficacy of Caspofungin can be increased when used in combination with Niludipine.Experimental
NilvadipineThe therapeutic efficacy of Caspofungin can be increased when used in combination with Nilvadipine.Approved, Investigational
NimesulideThe therapeutic efficacy of Caspofungin can be increased when used in combination with Nimesulide.Approved, Investigational, Withdrawn
NimodipineThe therapeutic efficacy of Caspofungin can be increased when used in combination with Nimodipine.Approved, Investigational
NintedanibThe serum concentration of Nintedanib can be increased when it is combined with Caspofungin.Approved
NisoldipineThe therapeutic efficacy of Caspofungin can be increased when used in combination with Nisoldipine.Approved
NitrendipineThe therapeutic efficacy of Caspofungin can be increased when used in combination with Nitrendipine.Approved, Investigational
NylidrinThe therapeutic efficacy of Caspofungin can be increased when used in combination with Nylidrin.Approved
OtiloniumThe therapeutic efficacy of Caspofungin can be increased when used in combination with Otilonium.Experimental, Investigational
PazopanibThe serum concentration of Pazopanib can be increased when it is combined with Caspofungin.Approved
PergolideThe risk or severity of adverse effects can be increased when Pergolide is combined with Caspofungin.Approved, Investigational, Vet Approved, Withdrawn
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Caspofungin.Approved, Vet Approved
PinaveriumThe therapeutic efficacy of Caspofungin can be increased when used in combination with Pinaverium.Approved
PitavastatinThe serum concentration of Pitavastatin can be increased when it is combined with Caspofungin.Approved
PravastatinThe serum concentration of Pravastatin can be increased when it is combined with Caspofungin.Approved
PrenylamineThe therapeutic efficacy of Caspofungin can be increased when used in combination with Prenylamine.Withdrawn
ProgesteroneThe absorption of Progesterone can be decreased when combined with Caspofungin.Approved, Vet Approved
PrucaloprideThe serum concentration of Prucalopride can be increased when it is combined with Caspofungin.Approved
QuinidineThe serum concentration of Quinidine can be increased when it is combined with Caspofungin.Approved, Investigational
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Caspofungin.Approved, Investigational
RifabutinThe serum concentration of Rifabutin can be increased when it is combined with Caspofungin.Approved, Investigational
RifampicinThe serum concentration of Caspofungin can be decreased when it is combined with Rifampicin.Approved
RifapentineThe serum concentration of Rifapentine can be increased when it is combined with Caspofungin.Approved, Investigational
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Caspofungin.Approved, Investigational
RilpivirineThe serum concentration of Rilpivirine can be increased when it is combined with Caspofungin.Approved
RosuvastatinThe serum concentration of Rosuvastatin can be increased when it is combined with Caspofungin.Approved
SeletracetamThe therapeutic efficacy of Caspofungin can be increased when used in combination with Seletracetam.Investigational
SilodosinThe serum concentration of Silodosin can be increased when it is combined with Caspofungin.Approved
SimvastatinThe serum concentration of Simvastatin can be increased when it is combined with Caspofungin.Approved
SolifenacinThe metabolism of Solifenacin can be decreased when combined with Caspofungin.Approved
SucralfateSucralfate can cause a decrease in the absorption of Caspofungin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
SunitinibThe metabolism of Sunitinib can be decreased when combined with Caspofungin.Approved, Investigational
TacrolimusThe serum concentration of Tacrolimus can be decreased when it is combined with Caspofungin.Approved, Investigational
TergurideThe risk or severity of adverse effects can be increased when Terguride is combined with Caspofungin.Experimental
TerodilineThe therapeutic efficacy of Caspofungin can be increased when used in combination with Terodiline.Experimental
TetrahydropalmatineThe therapeutic efficacy of Caspofungin can be increased when used in combination with Tetrahydropalmatine.Investigational
Tolfenamic AcidThe therapeutic efficacy of Caspofungin can be increased when used in combination with Tolfenamic Acid.Approved, Investigational
TolvaptanThe serum concentration of Tolvaptan can be increased when it is combined with Caspofungin.Approved
TopotecanThe serum concentration of Topotecan can be increased when it is combined with Caspofungin.Approved, Investigational
TranilastThe therapeutic efficacy of Caspofungin can be increased when used in combination with Tranilast.Approved, Investigational
TrimebutineThe therapeutic efficacy of Caspofungin can be increased when used in combination with Trimebutine.Approved
TrimethadioneThe therapeutic efficacy of Caspofungin can be increased when used in combination with Trimethadione.Approved
VerapamilThe therapeutic efficacy of Caspofungin can be increased when used in combination with Verapamil.Approved
VincristineThe excretion of Vincristine can be decreased when combined with Caspofungin.Approved, Investigational
VinpocetineThe therapeutic efficacy of Caspofungin can be increased when used in combination with Vinpocetine.Investigational
WIN 55212-2The therapeutic efficacy of Caspofungin can be increased when used in combination with WIN 55212-2.Experimental
ZiconotideThe therapeutic efficacy of Caspofungin can be increased when used in combination with Ziconotide.Approved
ZolpidemThe serum concentration of Zolpidem can be increased when it is combined with Caspofungin.Approved
ZonisamideThe therapeutic efficacy of Caspofungin can be increased when used in combination with Zonisamide.Approved, Investigational
Food Interactions
Not Available

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
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 AvailableInfection NOS1
1, 2WithdrawnPreventionLeukemia Acute Myeloid Leukemia (AML) / Pulmonary Aspergillosis - Invasive1
2CompletedPreventionInfections, Fungal1
2CompletedPreventionIntra-abdominal Perforation1
2CompletedPreventionInvasive Pulmonary Aspergillosis1
2CompletedSupportive CareCancers1
2CompletedTreatmentAspergillosis / Candidiasis, Invasive / Esophageal Candidiasis1
2CompletedTreatmentAspergillosis / Candidiasis infection1
2CompletedTreatmentFevers / Neutropenias1
2CompletedTreatmentFungus Diseases / Hematopoietic Stem Cell Transplantation (HSCT)1
2CompletedTreatmentInfections, Fungal1
2CompletedTreatmentInvasive Aspergillosis1
2CompletedTreatmentCandidiasis infection1
2RecruitingTreatmentCandidemia / Candidiasis, Invasive / Fungaemia / Infections, Fungal / Mycoses1
2TerminatedSupportive CareInfection NOS / Unspecified Adult Solid Tumor, Protocol Specific1
2TerminatedTreatmentCandidiasis, Invasive2
2Unknown StatusPreventionFungaemia / Mycoses1
2Unknown StatusPreventionInfections, Fungal / Transplantation, Liver1
2, 3CompletedTreatmentThermal Injury1
3Active Not RecruitingSupportive CareAdult Acute Megakaryoblastic Leukemia (M7) / Adult Acute Minimally Differentiated Myeloid Leukemia (M0) / Adult Acute Monoblastic Leukemia (M5a) / 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;q22) / Adult Acute Myeloid Leukemia With T(16;16)(p13;q22) / Adult Acute Myeloid Leukemia With T(8;21)(q22;q22) / Adult Acute Myelomonocytic Leukemia (M4) / Adult Erythroleukemia (M6a) / Adult Pure Erythroid Leukemia (M6b) / Childhood Acute Erythroleukemia (M6) / Childhood Acute Megakaryocytic Leukemia (M7) / Childhood Acute Minimally Differentiated Myeloid Leukemia (M0) / Childhood Acute Monoblastic Leukemia (M5a) / 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 Myelomonocytic Leukemia (M4) / Infections, Fungal / Neutropenias / Recurrent Adult Acute Myeloid Leukemia / Recurrent Childhood Acute Myeloid Leukemia / Secondary Acute Myeloid Leukemia / Untreated Adult Acute Myeloid Leukemia / Untreated Childhood Acute Myeloid Leukemia and Other Myeloid Malignancies1
3Active Not RecruitingSupportive CareHematopoietic/Lymphoid Cancer / Infections, Fungal1
3Active Not RecruitingSupportive CareInfections, Fungal / Leukemias / Myelodysplastic Syndromes1
3CompletedPreventionMycoses / Transplantation, Liver1
3CompletedSupportive CareCancers1
3CompletedTreatmentCandidemia / Candidiasis, Invasive / Mycoses1
3CompletedTreatmentCandidemia / Candidiasis infection1
3CompletedTreatmentCandidiasis, Invasive1
3CompletedTreatmentInfections, Fungal3
3CompletedTreatmentOral Candidiasis1
3CompletedTreatmentCandidiasis infection1
3TerminatedPreventionCandidiasis infection1
4CompletedNot AvailableAspergillosis / Candidiasis infection1
4CompletedNot AvailableBMI >30 kg/m2 / Infections, Fungal1
4CompletedOtherBacterial Infections and Mycoses / Liver Diseases1
4CompletedPreventionCandidiasis, Invasive1
4CompletedTreatmentCandidemia1
4CompletedTreatmentCritically Ill / Suspected Invasive Candidiasis1
4CompletedTreatmentInvasive Aspergillosis1
4CompletedTreatmentNeoplasms, Hematologic1
4Unknown StatusTreatmentChronic Obstructive Pulmonary Disease (COPD) / Invasive Pulmonary Aspergillosis1
Not AvailableActive Not RecruitingNot AvailableSystemic Fungal Infections1
Not AvailableCompletedNot AvailableInvasive Fungal Infections1
Not AvailableCompletedSupportive CareFever, Sweats, and Hot Flashes / Infection NOS / Leukemias / Malignant Lymphomas / Neuroblastomas / Neutropenias / Renal Cancers / Sarcomas1
Not AvailableEnrolling by InvitationTreatmentInvasive Fungal Infections1
Not AvailableNot Yet RecruitingNot AvailableCritical Illness / Infections, Fungal / Shock, Septic1
Not AvailableRecruitingTreatmentPneumonia, Pneumocystis1
Not AvailableRecruitingTreatmentShock1

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
Powder, for solutionIntravenous50 mg
Powder, for solutionIntravenous70 mg
Injection, powder, for solutionIntravenous5 mg/mL
Injection, powder, for solutionIntravenous7 mg/mL
Injection, powder, lyophilized, for solutionIntravenous5 mg/mL
Injection, powder, lyophilized, for solutionIntravenous50 mg/10.8mL
Injection, powder, lyophilized, for solutionIntravenous7 mg/mL
Injection, powder, lyophilized, for solutionIntravenous70 mg/10.8mL
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)
US5378804No1993-03-162013-03-16Us
CA2251928No2003-06-172017-04-15Canada
CA2118757No2002-05-142014-03-10Canada
US6136783Yes1997-09-282017-09-28Us
US5952300Yes1997-09-282017-09-28Us
US5514650Yes1995-07-262015-07-26Us
US9636407No2012-12-212032-12-21Us

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
Human
Pharmacological action
Unknown
Actions
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
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
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
Human
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]
Kind
Protein
Organism
Human
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
Human
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
Human
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 July 13, 2018 01:00