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

Details

Stereochemistry ABSOLUTE
Molecular Formula C56H71N9O23S
Molecular Weight 1270.274
Optical Activity UNSPECIFIED
Defined Stereocenters 15 / 15
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MICAFUNGIN

SMILES

[H][C@@]12C[C@@H](O)CN1C(=O)[C@@]([H])(NC(=O)[C@H](C[C@@H](O)[C@@H](O)NC(=O)[C@]3([H])[C@@H](O)[C@@H](C)CN3C(=O)[C@@]([H])(NC(=O)[C@@]([H])(NC2=O)[C@H](O)[C@@H](O)C4=CC(OS(O)(=O)=O)=C(O)C=C4)[C@H](O)CC(N)=O)NC(=O)C5=CC=C(C=C5)C6=NOC(=C6)C7=CC=C(OCCCCC)C=C7)[C@@H](C)O

InChI

InChIKey=PIEUQSKUWLMALL-YABMTYFHSA-N
InChI=1S/C56H71N9O23S/c1-4-5-6-17-86-32-14-11-28(12-15-32)39-21-33(63-87-39)27-7-9-29(10-8-27)49(75)58-34-20-38(70)52(78)62-54(80)45-46(72)25(2)23-65(45)56(82)43(37(69)22-41(57)71)60-53(79)44(48(74)47(73)30-13-16-36(68)40(18-30)88-89(83,84)85)61-51(77)35-19-31(67)24-64(35)55(81)42(26(3)66)59-50(34)76/h7-16,18,21,25-26,31,34-35,37-38,42-48,52,66-70,72-74,78H,4-6,17,19-20,22-24H2,1-3H3,(H2,57,71)(H,58,75)(H,59,76)(H,60,79)(H,61,77)(H,62,80)(H,83,84,85)/t25-,26+,31+,34-,35-,37+,38+,42-,43-,44-,45-,46-,47-,48-,52+/m0/s1

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including: https://www.drugs.com/ppa/micafungin.html | https://en.wikipedia.org/wiki/Micafungin

Micafungin (trade name Mycamine) is an echinocandin antifungal drug. Micafungin, the active ingredient in Mycamine, inhibits the synthesis of 1,3-β-D-glucan, an essential component of fungal cell walls, which is not present in mammalian cells. Micafungin is indicated for the treatment of candidemia, acute disseminated candidiasis, Candida peritonitis, abscesses and esophageal candidiasis. Possible histamine-mediated symptoms have been reported with Mycamine, including rash, pruritus, facial swelling and vasodilatation.

CNS Activity

Curator's Comment: Micafungin was present in low levels at brain tissue, indicating limited penetration into central nervous system (CNS) tissue. https://www.ncbi.nlm.nih.gov/pubmed/19933794

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.208 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
MYCAMINE

Approved Use

Mycamine® is indicated in adult and pediatric patients 4 months and older for: Mycamine is an echinocandin indicated in adult and pediatric patients 4 months and older for: •Treatment of Patients with Candidemia, Acute Disseminated Candidiasis, Candida Peritonitis and Abscesses (1.1) •Treatment of Patients with Esophageal Candidiasis (1.2) •Prophylaxis of Candida Infections in Patients Undergoing Hematopoietic Stem Cell Transplantation (1.3) 1.1 Treatment of Patients with Candidemia, Acute Disseminated Candidiasis, Candida Peritonitis and Abscesses [see Clinical Studies (14.1)

Launch Date

1.11093114E12
Preventing
MYCAMINE

Approved Use

Mycamine® is indicated in adult and pediatric patients 4 months and older for: Mycamine is an echinocandin indicated in adult and pediatric patients 4 months and older for: •Treatment of Patients with Candidemia, Acute Disseminated Candidiasis, Candida Peritonitis and Abscesses (1.1) •Treatment of Patients with Esophageal Candidiasis (1.2) •Prophylaxis of Candida Infections in Patients Undergoing Hematopoietic Stem Cell Transplantation (1.3) 1.1 Treatment of Patients with Candidemia, Acute Disseminated Candidiasis, Candida Peritonitis and Abscesses [see Clinical Studies (14.1)

Launch Date

1.11093114E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
16.4 μg/mL
150 mg 1 times / day multiple, intravenous
dose: 150 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
MICAFUNGIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
60.8 μg/mL
8 mg/kg bw 1 times / day multiple, intravenous
dose: 8 mg/kg bw
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
MICAFUNGIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
10.1 μg/mL
100 mg 1 times / day steady-state, intravenous
dose: 100 mg
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered:
MICAFUNGIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
167 μg × h/mL
150 mg 1 times / day multiple, intravenous
dose: 150 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
MICAFUNGIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
663 μg × h/mL
8 mg/kg bw 1 times / day multiple, intravenous
dose: 8 mg/kg bw
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
MICAFUNGIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
97 μg × h/mL
100 mg 1 times / day steady-state, intravenous
dose: 100 mg
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered:
MICAFUNGIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
15.2 h
150 mg 1 times / day multiple, intravenous
dose: 150 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
MICAFUNGIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
17.2 h
8 mg/kg bw 1 times / day multiple, intravenous
dose: 8 mg/kg bw
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
MICAFUNGIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
13.4 h
100 mg 1 times / day steady-state, intravenous
dose: 100 mg
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered:
MICAFUNGIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
1%
100 mg 1 times / day steady-state, intravenous
dose: 100 mg
route of administration: Intravenous
experiment type: STEADY-STATE
co-administered:
MICAFUNGIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
8 mg/kg 1 times / day multiple, intravenous
Highest studied dose
Dose: 8 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 8 mg/kg, 1 times / day
Sources: Page: p.48
unhealthy, 19 - 62
n = 8
Health Status: unhealthy
Condition: Haematopoietic stem cell transplantation
Age Group: 19 - 62
Sex: M+F
Population Size: 8
Sources: Page: p.48
200 mg single, intravenous
Highest studied dose
Dose: 200 mg
Route: intravenous
Route: single
Dose: 200 mg
Co-administed with::
prednisolone, iv, single(20 mg)
Sources: Page: p.1, p.4
healthy
Health Status: healthy
Condition: Candidiasis
Sources: Page: p.1, p.4
Disc. AE: Intravascular hemolysis...
AEs leading to
discontinuation/dose reduction:
Intravascular hemolysis (acute)
Sources: Page: p.1, p.4
16 mg/kg single, intravenous
Overdose
Dose: 16 mg/kg
Route: intravenous
Route: single
Dose: 16 mg/kg
Sources: Page: p.9
unhealthy
150 mg 1 times / day multiple, intravenous
Recommended
Dose: 150 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 150 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Oesophageal candidiasis
Sources: Page: p.1
Disc. AE: Anaphylaxis, Anaphylactoid reaction...
AEs leading to
discontinuation/dose reduction:
Anaphylaxis
Anaphylactoid reaction
Sources: Page: p.1
150 mg 1 times / day multiple, intravenous
Recommended
Dose: 150 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 150 mg, 1 times / day
Sources: Page: p.1, p.4
unhealthy
Health Status: unhealthy
Condition: Oesophageal candidiasis
Sources: Page: p.1, p.4
Disc. AE: Hemolysis, Hemolytic anemia...
AEs leading to
discontinuation/dose reduction:
Hemolysis (significant)
Hemolytic anemia
Abnormal liver function tests
Hepatic impairment
Hepatitis
Hepatic failure
Blood urea increased
Creatinine increased
Renal impairment
Renal failure (acute)
Sources: Page: p.1, p.4
150 mg 1 times / day multiple, intravenous
Recommended
Dose: 150 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 150 mg, 1 times / day
Sources: Page: p.5
unhealthy
Disc. AE: Exfoliative conditions, Stevens-Johnson syndrome...
AEs leading to
discontinuation/dose reduction:
Exfoliative conditions
Stevens-Johnson syndrome
Toxic epidermal necrolysis
Rash
Sources: Page: p.5
150 mg 1 times / day multiple, intravenous
Recommended
Dose: 150 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 150 mg, 1 times / day
Sources: Page: p.8
unhealthy
Disc. AE: Hepatic and hepatobiliary disorders, Hepatic and hepatobiliary disorders...
AEs leading to
discontinuation/dose reduction:
Hepatic and hepatobiliary disorders (1.1%)
Hepatic and hepatobiliary disorders (serious, 0.4%)
Sources: Page: p.8
AEs

AEs

AESignificanceDosePopulation
Intravascular hemolysis acute
Disc. AE
200 mg single, intravenous
Highest studied dose
Dose: 200 mg
Route: intravenous
Route: single
Dose: 200 mg
Co-administed with::
prednisolone, iv, single(20 mg)
Sources: Page: p.1, p.4
healthy
Health Status: healthy
Condition: Candidiasis
Sources: Page: p.1, p.4
Anaphylactoid reaction Disc. AE
150 mg 1 times / day multiple, intravenous
Recommended
Dose: 150 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 150 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Oesophageal candidiasis
Sources: Page: p.1
Anaphylaxis Disc. AE
150 mg 1 times / day multiple, intravenous
Recommended
Dose: 150 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 150 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Oesophageal candidiasis
Sources: Page: p.1
Abnormal liver function tests Disc. AE
150 mg 1 times / day multiple, intravenous
Recommended
Dose: 150 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 150 mg, 1 times / day
Sources: Page: p.1, p.4
unhealthy
Health Status: unhealthy
Condition: Oesophageal candidiasis
Sources: Page: p.1, p.4
Blood urea increased Disc. AE
150 mg 1 times / day multiple, intravenous
Recommended
Dose: 150 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 150 mg, 1 times / day
Sources: Page: p.1, p.4
unhealthy
Health Status: unhealthy
Condition: Oesophageal candidiasis
Sources: Page: p.1, p.4
Creatinine increased Disc. AE
150 mg 1 times / day multiple, intravenous
Recommended
Dose: 150 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 150 mg, 1 times / day
Sources: Page: p.1, p.4
unhealthy
Health Status: unhealthy
Condition: Oesophageal candidiasis
Sources: Page: p.1, p.4
Hemolytic anemia Disc. AE
150 mg 1 times / day multiple, intravenous
Recommended
Dose: 150 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 150 mg, 1 times / day
Sources: Page: p.1, p.4
unhealthy
Health Status: unhealthy
Condition: Oesophageal candidiasis
Sources: Page: p.1, p.4
Hepatic failure Disc. AE
150 mg 1 times / day multiple, intravenous
Recommended
Dose: 150 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 150 mg, 1 times / day
Sources: Page: p.1, p.4
unhealthy
Health Status: unhealthy
Condition: Oesophageal candidiasis
Sources: Page: p.1, p.4
Hepatic impairment Disc. AE
150 mg 1 times / day multiple, intravenous
Recommended
Dose: 150 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 150 mg, 1 times / day
Sources: Page: p.1, p.4
unhealthy
Health Status: unhealthy
Condition: Oesophageal candidiasis
Sources: Page: p.1, p.4
Hepatitis Disc. AE
150 mg 1 times / day multiple, intravenous
Recommended
Dose: 150 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 150 mg, 1 times / day
Sources: Page: p.1, p.4
unhealthy
Health Status: unhealthy
Condition: Oesophageal candidiasis
Sources: Page: p.1, p.4
Renal impairment Disc. AE
150 mg 1 times / day multiple, intravenous
Recommended
Dose: 150 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 150 mg, 1 times / day
Sources: Page: p.1, p.4
unhealthy
Health Status: unhealthy
Condition: Oesophageal candidiasis
Sources: Page: p.1, p.4
Renal failure acute
Disc. AE
150 mg 1 times / day multiple, intravenous
Recommended
Dose: 150 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 150 mg, 1 times / day
Sources: Page: p.1, p.4
unhealthy
Health Status: unhealthy
Condition: Oesophageal candidiasis
Sources: Page: p.1, p.4
Hemolysis significant
Disc. AE
150 mg 1 times / day multiple, intravenous
Recommended
Dose: 150 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 150 mg, 1 times / day
Sources: Page: p.1, p.4
unhealthy
Health Status: unhealthy
Condition: Oesophageal candidiasis
Sources: Page: p.1, p.4
Exfoliative conditions Disc. AE
150 mg 1 times / day multiple, intravenous
Recommended
Dose: 150 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 150 mg, 1 times / day
Sources: Page: p.5
unhealthy
Rash Disc. AE
150 mg 1 times / day multiple, intravenous
Recommended
Dose: 150 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 150 mg, 1 times / day
Sources: Page: p.5
unhealthy
Stevens-Johnson syndrome Disc. AE
150 mg 1 times / day multiple, intravenous
Recommended
Dose: 150 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 150 mg, 1 times / day
Sources: Page: p.5
unhealthy
Toxic epidermal necrolysis Disc. AE
150 mg 1 times / day multiple, intravenous
Recommended
Dose: 150 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 150 mg, 1 times / day
Sources: Page: p.5
unhealthy
Hepatic and hepatobiliary disorders 1.1%
Disc. AE
150 mg 1 times / day multiple, intravenous
Recommended
Dose: 150 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 150 mg, 1 times / day
Sources: Page: p.8
unhealthy
Hepatic and hepatobiliary disorders serious, 0.4%
Disc. AE
150 mg 1 times / day multiple, intravenous
Recommended
Dose: 150 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 150 mg, 1 times / day
Sources: Page: p.8
unhealthy
Overview

Overview

Drug as perpetrator​Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Efficacy of FK463, a new lipopeptide antifungal agent, in mouse models of pulmonary aspergillosis.
2000 Mar
Prophylactic effect of FK463, a novel antifungal lipopeptide, against Pneumocystis carinii infection in mice.
2000 Sep
Antifungals: what's in the pipeline.
2001 Oct
In vitro interactions of micafungin with other antifungal drugs against clinical isolates of four species of Cryptococcus.
2005 Jul
Micafungin sodium, the second of the echinocandin class of antifungals: theory and practice.
2006 Aug
Determination of MICs of aminocandin for Candida spp. and filamentous fungi.
2006 Dec
Echinocandins in the management of invasive fungal infections, part 1.
2006 Sep 15
Echinocandins: A ray of hope in antifungal drug therapy.
2010 Feb
Multilaboratory testing of two-drug combinations of antifungals against Candida albicans, Candida glabrata, and Candida parapsilosis.
2011 Apr
In vitro activity of E1210, a novel antifungal, against clinically important yeasts and molds.
2011 Oct
In vitro antifungal susceptibility of clinically relevant species belonging to Aspergillus section Flavi.
2013 Apr
Patents

Sample Use Guides

Esophageal Candidiasis - 150 mg per day Prophylaxis of Candida Infections in HSCT Recipients - 50 mg per day
Route of Administration: Intravenous
The IC50 value of FK463 for mannan inhibition was over 100 ug/ml.
Name Type Language
MICAFUNGIN
EMA EPAR   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
MICAFUNGIN [JAN]
Common Name English
MICAFUNGIN [MI]
Common Name English
Micafungin [WHO-DD]
Common Name English
PNEUMOCANDIN A0, 1-((4R,5R)-4,5-DIHYDROXY-N(SUP 2)-(4-(5-(4-(PENTYLOXY)PHENYL)-3-ISOXAZOLYL)BENZOYL)-L-ORNITHINE)-4-((4S)-4-HYDROXY-4-(4-HYDROXY-3-(SULFOOXY)PHENYL)-L-THREONINE)-
Common Name English
MICAFUNGIN [EMA EPAR]
Common Name English
MICAFUNGIN [VANDF]
Common Name English
micafungin [INN]
Common Name English
Classification Tree Code System Code
LIVERTOX 634
Created by admin on Thu Jul 06 21:53:07 UTC 2023 , Edited by admin on Thu Jul 06 21:53:07 UTC 2023
WHO-ATC J02AX05
Created by admin on Thu Jul 06 21:53:07 UTC 2023 , Edited by admin on Thu Jul 06 21:53:07 UTC 2023
NDF-RT N0000175508
Created by admin on Thu Jul 06 21:53:07 UTC 2023 , Edited by admin on Thu Jul 06 21:53:07 UTC 2023
WHO-VATC QJ02AX05
Created by admin on Thu Jul 06 21:53:07 UTC 2023 , Edited by admin on Thu Jul 06 21:53:07 UTC 2023
NCI_THESAURUS C514
Created by admin on Thu Jul 06 21:53:07 UTC 2023 , Edited by admin on Thu Jul 06 21:53:07 UTC 2023
NDF-RT N0000175508
Created by admin on Thu Jul 06 21:53:07 UTC 2023 , Edited by admin on Thu Jul 06 21:53:07 UTC 2023
NDF-RT N0000175507
Created by admin on Thu Jul 06 21:53:07 UTC 2023 , Edited by admin on Thu Jul 06 21:53:07 UTC 2023
Code System Code Type Description
DAILYMED
R10H71BSWG
Created by admin on Thu Jul 06 21:53:07 UTC 2023 , Edited by admin on Thu Jul 06 21:53:07 UTC 2023
PRIMARY
MESH
C121905
Created by admin on Thu Jul 06 21:53:07 UTC 2023 , Edited by admin on Thu Jul 06 21:53:07 UTC 2023
PRIMARY
SMS_ID
100000091615
Created by admin on Thu Jul 06 21:53:07 UTC 2023 , Edited by admin on Thu Jul 06 21:53:07 UTC 2023
PRIMARY
ChEMBL
CHEMBL457547
Created by admin on Thu Jul 06 21:53:07 UTC 2023 , Edited by admin on Thu Jul 06 21:53:07 UTC 2023
PRIMARY
CAS
235114-32-6
Created by admin on Thu Jul 06 21:53:07 UTC 2023 , Edited by admin on Thu Jul 06 21:53:07 UTC 2023
PRIMARY
DRUG CENTRAL
1798
Created by admin on Thu Jul 06 21:53:07 UTC 2023 , Edited by admin on Thu Jul 06 21:53:07 UTC 2023
PRIMARY
CHEBI
600520
Created by admin on Thu Jul 06 21:53:07 UTC 2023 , Edited by admin on Thu Jul 06 21:53:07 UTC 2023
PRIMARY
MERCK INDEX
M7524
Created by admin on Thu Jul 06 21:53:07 UTC 2023 , Edited by admin on Thu Jul 06 21:53:07 UTC 2023
PRIMARY Merck Index
INN
8069
Created by admin on Thu Jul 06 21:53:07 UTC 2023 , Edited by admin on Thu Jul 06 21:53:07 UTC 2023
PRIMARY
RXCUI
325887
Created by admin on Thu Jul 06 21:53:07 UTC 2023 , Edited by admin on Thu Jul 06 21:53:07 UTC 2023
PRIMARY RxNorm
DRUG BANK
DB01141
Created by admin on Thu Jul 06 21:53:07 UTC 2023 , Edited by admin on Thu Jul 06 21:53:07 UTC 2023
PRIMARY
EPA CompTox
DTXSID90873341
Created by admin on Thu Jul 06 21:53:07 UTC 2023 , Edited by admin on Thu Jul 06 21:53:07 UTC 2023
PRIMARY
NCI_THESAURUS
C1850
Created by admin on Thu Jul 06 21:53:07 UTC 2023 , Edited by admin on Thu Jul 06 21:53:07 UTC 2023
PRIMARY
FDA UNII
R10H71BSWG
Created by admin on Thu Jul 06 21:53:07 UTC 2023 , Edited by admin on Thu Jul 06 21:53:07 UTC 2023
PRIMARY
PUBCHEM
477468
Created by admin on Thu Jul 06 21:53:07 UTC 2023 , Edited by admin on Thu Jul 06 21:53:07 UTC 2023
PRIMARY
WIKIPEDIA
MICAFUNGIN
Created by admin on Thu Jul 06 21:53:07 UTC 2023 , Edited by admin on Thu Jul 06 21:53:07 UTC 2023
PRIMARY
EVMPD
SUB16444MIG
Created by admin on Thu Jul 06 21:53:07 UTC 2023 , Edited by admin on Thu Jul 06 21:53:07 UTC 2023
PRIMARY