Details of the Drug

General Information of Drug (ID: DMGQIPT)

Drug Name
Caspofungin
Synonyms
CASPO; Cancidas; Capsofungin; Caspofungin [INN]; M991; Cancidas (TM); Cancidas (TN); Caspofungin (INN); MK-0991; L-743,872; [1(R)-hydroxyethyl]-1,4,7,13,16,22-hexaazatricyclo[22.3.0.0(9,13)]heptacosane-2,5,8,14,17,23-hexaone diacetate; Pneumocandin B0, 1-[(4R,5S)-5-[(2-aminoethyl)amino]-N2-(10,12-dimethyl-1-oxotetradecyl)-4-hydroxy-L-ornithine]-5-[(3R)-3-hydroxy-L-ornithine]-(9CI); (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; (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
Indication
Disease Entry ICD 11 Status REF
Candidiasis 1F23 Approved [1]
Fungal infection 1F29-1F2F Approved [2]
Mycoses 1F2Z Approved [1]
Mycosis fungoides 2B01 Approved [1]
Candidemia 1F23.3Y Investigative [1]
Esophageal candidiasis N.A. Investigative [1]
⏷ Show the Full List of Indication(s)
Therapeutic Class
Antifungal Agents
Drug Type
Small molecular drug
Structure
3D MOL is unavailable 2D MOL
#Ro5 Violations (Lipinski): 4 Molecular Weight (mw) 1093.3
Logarithm of the Partition Coefficient (xlogp) 0.3
Rotatable Bond Count (rotbonds) 23
Hydrogen Bond Donor Count (hbonddonor) 16
Hydrogen Bond Acceptor Count (hbondacc) 18
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [3]
Clearance
The drug present in the plasma can be removed from the body at the rate of 0.14 mL/min/kg [4]
Elimination
1.4% of drug is excreted from urine in the unchanged form [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 9 - 11 hours [4]
Metabolism
The drug is metabolized via the hydrolysis and N-acetylation []
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.9146 micromolar/kg/day [5]
Unbound Fraction
The unbound fraction of drug in plasma is 0.035% [4]
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.13 L/kg [4]
Chemical Identifiers
Formula
C52H88N10O15
IUPAC Name
N-[(3S,6S,9S,11R,15S,18S,20R,21S,24S,25S)-21-(2-aminoethylamino)-3-[(1R)-3-amino-1-hydroxypropyl]-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-hexazatricyclo[22.3.0.09,13]heptacosan-18-yl]-10,12-dimethyltetradecanamide
Canonical SMILES
CCC(C)CC(C)CCCCCCCCC(=O)N[C@H]1C[C@H]([C@H](NC(=O)[C@@H]2[C@H](CCN2C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@@H](NC1=O)[C@@H](C)O)O)[C@@H]([C@H](C4=CC=C(C=C4)O)O)O)[C@@H](CCN)O)O)NCCN)O
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
InChIKey
JYIKNQVWKBUSNH-OGZDCFRISA-N
Cross-matching ID
PubChem CID
2826718
ChEBI ID
CHEBI:474180
CAS Number
162808-62-0
DrugBank ID
DB00520
TTD ID
D00ZCN
VARIDT ID
DR00493
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Fungal 1,3-beta-glucan synthase (Fung GSC2) TT0SFXH FKS2_YEAST Modulator [6]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Organic anion transporting polypeptide 1B1 (SLCO1B1) DT3D8F0 SO1B1_HUMAN Substrate [7]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Caspofungin (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Remdesivir DMBFZ6L Moderate Increased risk of hepatotoxicity by the combination of Caspofungin and Remdesivir. 1D6YCoronavirus Disease 2019 [1D6YCoronavirus Disease 2019] [8]
Ivosidenib DM8S6T7 Moderate Increased metabolism of Caspofungin caused by Ivosidenib mediated induction of CYP450 enzyme. Acute myeloid leukaemia [2A60] [9]
Arn-509 DMT81LZ Moderate Increased metabolism of Caspofungin caused by Arn-509 mediated induction of CYP450 enzyme. Acute myeloid leukaemia [2A60] [9]
Mitotane DMU1GX0 Moderate Increased metabolism of Caspofungin caused by Mitotane mediated induction of CYP450 enzyme. Adrenal cancer [2D11] [9]
Bedaquiline DM3906J Moderate Increased risk of hepatotoxicity by the combination of Caspofungin and Bedaquiline. Antimicrobial drug resistance [MG50-MG52] [10]
Methylphenobarbital DMDSWAG Moderate Increased metabolism of Caspofungin caused by Methylphenobarbital mediated induction of CYP450 enzyme. Anxiety disorder [6B00-6B0Z] [11]
Pexidartinib DMS2J0Z Major Increased risk of hepatotoxicity by the combination of Caspofungin and Pexidartinib. Bone/articular cartilage neoplasm [2F7B] [12]
Lumacaftor DMCLWDJ Moderate Increased metabolism of Caspofungin caused by Lumacaftor mediated induction of CYP450 enzyme. Cystic fibrosis [CA25] [11]
Primidone DM0WX6I Moderate Increased metabolism of Caspofungin caused by Primidone mediated induction of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [9]
Felbamate DM1V5ZS Moderate Increased metabolism of Caspofungin caused by Felbamate mediated induction of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [9]
Oxcarbazepine DM5PU6O Moderate Increased metabolism of Caspofungin caused by Oxcarbazepine mediated induction of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [9]
Cenobamate DM8KLU9 Moderate Increased metabolism of Caspofungin caused by Cenobamate mediated induction of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [9]
Fosphenytoin DMOX3LB Major Increased metabolism of Caspofungin caused by Fosphenytoin mediated induction of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [9]
Rufinamide DMWE60C Moderate Increased metabolism of Caspofungin caused by Rufinamide mediated induction of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [13]
Phenobarbital DMXZOCG Moderate Increased metabolism of Caspofungin caused by Phenobarbital mediated induction of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [9]
Carbamazepine DMZOLBI Major Increased metabolism of Caspofungin caused by Carbamazepine mediated induction of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [9]
Cannabidiol DM0659E Moderate Increased risk of hepatotoxicity by the combination of Caspofungin and Cannabidiol. Epileptic encephalopathy [8A62] [13]
Rifampin DMA8J1G Major Increased metabolism of Caspofungin caused by Rifampin mediated induction of CYP450 enzyme. HIV-infected patients with tuberculosis [1B10-1B14] [14]
Rifapentine DMCHV4I Moderate Increased metabolism of Caspofungin caused by Rifapentine mediated induction of CYP450 enzyme. HIV-infected patients with tuberculosis [1B10-1B14] [9]
Brentuximab vedotin DMWLC57 Moderate Increased risk of hepatotoxicity by the combination of Caspofungin and Brentuximab vedotin. Hodgkin lymphoma [2B30] [15]
Efavirenz DMC0GSJ Major Increased metabolism of Caspofungin caused by Efavirenz mediated induction of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [9]
Etravirine DMGV8QU Moderate Increased metabolism of Caspofungin caused by Etravirine mediated induction of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [9]
Mipomersen DMGSRN1 Major Increased risk of hepatotoxicity by the combination of Caspofungin and Mipomersen. Hyper-lipoproteinaemia [5C80] [16]
Teriflunomide DMQ2FKJ Major Increased risk of hepatotoxicity by the combination of Caspofungin and Teriflunomide. Hyper-lipoproteinaemia [5C80] [17]
BMS-201038 DMQTAGO Major Increased risk of hepatotoxicity by the combination of Caspofungin and BMS-201038. Hyper-lipoproteinaemia [5C80] [18]
Amobarbital DM0GQ8N Moderate Increased metabolism of Caspofungin caused by Amobarbital mediated induction of CYP450 enzyme. Insomnia [7A00-7A0Z] [9]
Methotrexate DM2TEOL Moderate Increased risk of hepatotoxicity by the combination of Caspofungin and Methotrexate. Leukaemia [2A60-2B33] [13]
PF-06463922 DMKM7EW Moderate Increased metabolism of Caspofungin caused by PF-06463922 mediated induction of CYP450 enzyme. Lung cancer [2C25] [9]
Calaspargase pegol DMQZBXI Moderate Increased risk of hepatotoxicity by the combination of Caspofungin and Calaspargase pegol. Malignant haematopoietic neoplasm [2B33] [19]
Idelalisib DM602WT Moderate Increased risk of hepatotoxicity by the combination of Caspofungin and Idelalisib. Mature B-cell leukaemia [2A82] [20]
Clofarabine DMCVJ86 Moderate Increased risk of hepatotoxicity by the combination of Caspofungin and Clofarabine. Mature B-cell lymphoma [2A85] [21]
Vemurafenib DM62UG5 Moderate Increased metabolism of Caspofungin caused by Vemurafenib mediated induction of CYP450 enzyme. Melanoma [2C30] [9]
Dabrafenib DMX6OE3 Moderate Increased metabolism of Caspofungin caused by Dabrafenib mediated induction of CYP450 enzyme. Melanoma [2C30] [9]
Rifabutin DM1YBHK Moderate Increased metabolism of Caspofungin caused by Rifabutin mediated induction of CYP450 enzyme. Mycobacterium infection [1B10-1B21] [9]
Modafinil DMYILBE Minor Increased metabolism of Caspofungin caused by Modafinil mediated induction of CYP450 enzyme. Narcolepsy [7A20] [22]
Enzalutamide DMGL19D Moderate Increased metabolism of Caspofungin caused by Enzalutamide mediated induction of CYP450 enzyme. Prostate cancer [2C82] [9]
Bosentan DMIOGBU Moderate Increased metabolism of Caspofungin caused by Bosentan mediated induction of CYP450 enzyme. Pulmonary hypertension [BB01] [9]
Dexamethasone DMMWZET Major Increased metabolism of Caspofungin caused by Dexamethasone mediated induction of CYP450 enzyme. Rheumatoid arthritis [FA20] [9]
Nafcillin DMN9RPO Moderate Increased metabolism of Caspofungin caused by Nafcillin mediated induction of CYP450 enzyme. Rheumatoid arthritis [FA20] [9]
Leflunomide DMR8ONJ Major Increased risk of hepatotoxicity by the combination of Caspofungin and Leflunomide. Rheumatoid arthritis [FA20] [17]
Trabectedin DMG3Y89 Moderate Increased risk of hepatotoxicity by the combination of Caspofungin and Trabectedin. Solid tumour/cancer [2A00-2F9Z] [13]
Armodafinil DMGB035 Minor Increased metabolism of Caspofungin caused by Armodafinil mediated induction of CYP450 enzyme. Solid tumour/cancer [2A00-2F9Z] [22]
Naltrexone DMUL45H Moderate Increased risk of hepatotoxicity by the combination of Caspofungin and Naltrexone. Substance abuse [6C40] [23]
Elagolix DMB2C0E Moderate Increased metabolism of Caspofungin caused by Elagolix mediated induction of CYP450 enzyme. Uterine fibroid [2E86] [9]
⏷ Show the Full List of 44 DDI Information of This Drug

References

1 Caspofungin FDA Label
2 Echinocandins: pharmacokinetic and therapeutic issues. Curr Med Res Opin. 2009 Jul;25(7):1741-50.
3 BDDCS applied to over 900 drugs
4 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
6 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
7 Organic anion transporting polypeptide 1B1: a genetically polymorphic transporter of major importance for hepatic drug uptake. Pharmacol Rev. 2011 Mar;63(1):157-81.
8 Cerner Multum, Inc. "Australian Product Information.".
9 Product Information. Cancidas (caspofungin) Merck & Co, Inc, West Point, PA.
10 Product Information. Sirturo (bedaquiline). Janssen Pharmaceuticals, Titusville, NJ.
11 Patel S, Robinson R, Burk M "Hypertensive crisis associated with St. John's Wort." Am J Med 112 (2002): 507-8. [PMID: 11959071]
12 Product Information. Turalio (pexidartinib). Daiichi Sankyo, Inc., Parsippany, NJ.
13 Cerner Multum, Inc. "UK Summary of Product Characteristics.".
14 Product Information. Cancidas (caspofungin) Merck &amp Co, Inc, West Point, PA.
15 Product Information. Adcetris (brentuximab vedotin). Seattle Genetics Inc, Bothell, WA.
16 Product Information. Kynamro (mipomersen). Genzyme Corporation, Cambridge, MA.
17 Canadian Pharmacists Association.
18 Product Information. Juxtapid (lomitapide). Aegerion Pharmaceuticals Inc, Cambridge, MA.
19 Al-Nawakil C, Willems L, Mauprivez C, et.al "Successful treatment of l-asparaginase-induced severe acute hepatotoxicity using mitochondrial cofactors." Leuk Lymphoma 55 (2014): 1670-4. [PMID: 24090500]
20 Product Information. Zydelig (idelalisib). Gilead Sciences, Foster City, CA.
21 Product Information. Clolar (clofarabine). sanofi-aventis, Bridgewater, NJ.
22 Doherty MM, Charman WN "The mucosa of the small intestine: how clinically relevant as an organ of drug metabolism?" Clin Pharmacokinet 41 (2002): 235-53. [PMID: 11978143]
23 Product Information. ReVia (naltrexone). DuPont Pharmaceuticals, Wilmington, DE.