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

Details

Stereochemistry ABSOLUTE
Molecular Formula C56H70N9O23S.Na
Molecular Weight 1292.256
Optical Activity UNSPECIFIED
Defined Stereocenters 15 / 15
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MICAFUNGIN SODIUM

SMILES

[Na+].[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=KOOAFHGJVIVFMZ-WZPXRXMFSA-M
InChI=1S/C56H71N9O23S.Na/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);/q;+1/p-1/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

2005
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

2005
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
In vitro antifungal activity of a novel lipopeptide antifungal agent, FK463, against various fungal pathogens.
2000 Oct
In vitro antifungal activity of FK463, a new water-soluble echinocandin-like lipopeptide.
2000 Sep
Antifungals: what's in the pipeline.
2001 Oct
In vitro activity of micafungin (FK-463) against Candida spp.: microdilution, time-kill, and postantifungal-effect studies.
2002 Dec
Efficacy of micafungin alone or in combination against systemic murine aspergillosis.
2003 Apr
Micafungin: pharmacology, experimental therapeutics and clinical applications.
2005 Apr
In vitro interactions of micafungin with other antifungal drugs against clinical isolates of four species of Cryptococcus.
2005 Jul
Micafungin: a new echinocandin.
2006 Apr 15
Emerging echinocandins for treatment of invasive fungal infections.
2006 May
Echinocandins in the management of invasive fungal infections, part 1.
2006 Sep 15
Echinocandins: A ray of hope in antifungal drug therapy.
2010 Feb
Isavuconazole: a comprehensive review of spectrum of activity of a new triazole.
2010 Nov
Multilaboratory testing of two-drug combinations of antifungals against Candida albicans, Candida glabrata, and Candida parapsilosis.
2011 Apr
Triazole and echinocandin MIC distributions with epidemiological cutoff values for differentiation of wild-type strains from non-wild-type strains of six uncommon species of Candida.
2011 Nov
Identification and characterization of the echinocandin B biosynthetic gene cluster from Emericella rugulosa NRRL 11440.
2012 Oct 10
In vitro antifungal susceptibility of clinically relevant species belonging to Aspergillus section Flavi.
2013 Apr
KB425796-A, a novel antifungal antibiotic produced by Paenibacillus sp. 530603.
2013 Aug
Identification of ten KB425796-A congeners from Paenibacillus sp. 530603 using an antifungal assay against Aspergillus fumigatus in combination with micafungin.
2013 Aug
Synergistic antifungal activity of KB425796-C in combination with micafungin against Aspergillus fumigatus and its efficacy in murine infection models.
2013 Aug
Comparative in vitro fungicidal activity of echinocandins against Candida albicans in peritoneal dialysis fluids.
2013 Nov
Amphotericin B- and voriconazole-echinocandin combinations against Aspergillus spp.: Effect of serum on inhibitory and fungicidal interactions.
2013 Oct
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 SODIUM
JAN   MART.   ORANGE BOOK   USAN   WHO-DD  
USAN  
Official Name English
Micafungin sodium [WHO-DD]
Common Name English
MICAFUNGIN NA
VANDF  
Common Name English
FK463
Code English
FUNGUARD
Brand Name English
MYCAMINE
Brand Name English
MICAFUNGIN NA [VANDF]
Common Name English
MICAFUNGIN SODIUM SALT [MI]
Common Name English
MICAFUNGIN SODIUM [ORANGE BOOK]
Common Name English
MICAFUNGIN SODIUM [JAN]
Common Name English
MICAFUNGIN SODIUM [USAN]
Common Name English
FK-463
Code English
MICAFUNGIN SODIUM [MART.]
Common Name English
MICAFUNGIN SODIUM SALT
MI  
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C514
Created by admin on Fri Dec 15 15:37:46 GMT 2023 , Edited by admin on Fri Dec 15 15:37:46 GMT 2023
Code System Code Type Description
DAILYMED
IS1UP79R56
Created by admin on Fri Dec 15 15:37:46 GMT 2023 , Edited by admin on Fri Dec 15 15:37:46 GMT 2023
PRIMARY
DRUG BANK
DBSALT001165
Created by admin on Fri Dec 15 15:37:46 GMT 2023 , Edited by admin on Fri Dec 15 15:37:46 GMT 2023
PRIMARY
MERCK INDEX
m7524
Created by admin on Fri Dec 15 15:37:46 GMT 2023 , Edited by admin on Fri Dec 15 15:37:46 GMT 2023
PRIMARY Merck Index
RXCUI
487070
Created by admin on Fri Dec 15 15:37:46 GMT 2023 , Edited by admin on Fri Dec 15 15:37:46 GMT 2023
PRIMARY RxNorm
FDA UNII
IS1UP79R56
Created by admin on Fri Dec 15 15:37:46 GMT 2023 , Edited by admin on Fri Dec 15 15:37:46 GMT 2023
PRIMARY
ChEMBL
CHEMBL457547
Created by admin on Fri Dec 15 15:37:46 GMT 2023 , Edited by admin on Fri Dec 15 15:37:46 GMT 2023
PRIMARY
SMS_ID
100000089575
Created by admin on Fri Dec 15 15:37:46 GMT 2023 , Edited by admin on Fri Dec 15 15:37:46 GMT 2023
PRIMARY
EVMPD
SUB20666
Created by admin on Fri Dec 15 15:37:46 GMT 2023 , Edited by admin on Fri Dec 15 15:37:46 GMT 2023
PRIMARY
CHEBI
600520
Created by admin on Fri Dec 15 15:37:46 GMT 2023 , Edited by admin on Fri Dec 15 15:37:46 GMT 2023
PRIMARY
PUBCHEM
23666118
Created by admin on Fri Dec 15 15:37:46 GMT 2023 , Edited by admin on Fri Dec 15 15:37:46 GMT 2023
PRIMARY
CAS
208538-73-2
Created by admin on Fri Dec 15 15:37:46 GMT 2023 , Edited by admin on Fri Dec 15 15:37:46 GMT 2023
PRIMARY
RS_ITEM_NUM
1443384
Created by admin on Fri Dec 15 15:37:46 GMT 2023 , Edited by admin on Fri Dec 15 15:37:46 GMT 2023
PRIMARY
NCI_THESAURUS
C66145
Created by admin on Fri Dec 15 15:37:46 GMT 2023 , Edited by admin on Fri Dec 15 15:37:46 GMT 2023
PRIMARY
USAN
PP-74
Created by admin on Fri Dec 15 15:37:46 GMT 2023 , Edited by admin on Fri Dec 15 15:37:46 GMT 2023
PRIMARY