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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

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C56H70N9O23S
Molecular Weight 1269.267
Charge -1
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 15 / 15
E/Z Centers 0
Optical Activity UNSPECIFIED

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
Micafungin: a new echinocandin.
2006 Apr 15
Echinocandins: the newest class of antifungals.
2009 Oct
In vitro activity of isavuconazole against 208 Aspergillus flavus isolates in comparison with 7 other antifungal agents: assessment according to the methodology of the European Committee on Antimicrobial Susceptibility Testing.
2011 Dec
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:37:46 GMT 2023
Edited
by admin
on Fri Dec 15 15:37:46 GMT 2023
Record UNII
IS1UP79R56
Record Status Validated (UNII)
Record Version
  • Download
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
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