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Details

Stereochemistry ABSOLUTE
Molecular Formula C56H70N9O23S.Na.2H2O
Molecular Weight 1328.287
Optical Activity UNSPECIFIED
Defined Stereocenters 15 / 15
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MICAFUNGIN SODIUM DIHYDRATE

SMILES

O.O.[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=GNIAFSGJOPITOX-AVTCCIINSA-M
InChI=1S/C56H71N9O23S.Na.2H2O/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);;2*1H2/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 H2O
Molecular Weight 18.0153
Charge 0
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

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
In vitro activities of a new lipopeptide antifungal agent, FK463, against a variety of clinically important fungi.
2000 Jan
Efficacy of FK463, a (1,3)-beta-D-glucan synthase inhibitor, in disseminated azole-resistant candida albicans infection in mice.
2000 Jun
Efficacy of FK463, a new lipopeptide antifungal agent, in mouse models of pulmonary aspergillosis.
2000 Mar
Efficacy of FK463, a new lipopeptide antifungal agent, in mouse models of disseminated candidiasis and aspergillosis.
2000 Mar
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
Prophylactic effect of FK463, a novel antifungal lipopeptide, against Pneumocystis carinii infection in mice.
2000 Sep
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
Micafungin: a new echinocandin.
2006 Apr 15
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
Emerging echinocandins for treatment of invasive fungal infections.
2006 May
Echinocandins in the management of invasive fungal infections, Part 2.
2006 Oct 1
Role of micafungin in the antifungal armamentarium.
2007
The echinocandin micafungin: a review of the pharmacology, spectrum of activity, clinical efficacy and safety.
2007 Jun
In vitro and in vivo antifungal activities of T-2307, a novel arylamidine.
2008 Apr
Efficacy of SPK-843, a novel polyene antifungal, in comparison with amphotericin B, liposomal amphotericin B, and micafungin against murine pulmonary aspergillosis.
2008 May
Review of the pharmacology and clinical studies of micafungin.
2009 Dec 29
Echinocandins: the newest class of antifungals.
2009 Oct
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
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
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
Antifungal susceptibilities of Aspergillus fumigatus clinical isolates obtained in Nagasaki, Japan.
2012 Jan
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
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 Sat Dec 16 18:42:14 UTC 2023
Edited
by admin
on Sat Dec 16 18:42:14 UTC 2023
Record UNII
R8QS8RE925
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MICAFUNGIN SODIUM DIHYDRATE
Common Name English
MICAFUNGIN SODIUM HYDRATE
Common Name English
PNEUMOCANDIN A0, 1-((4R,5R)-4,5-DIHYDROXY-N2-(4-(5-(4-(PENTYLOXY)PHENYL)-3-ISOXAZOLYL)BENZOYL)-L-ORNITHINE)-4-((4S)-4-HYDROXY-4-(4-HYDROXY-3-(SULFOOXY)PHENYL)-L-THREONINE)-, SODIUM SALT, HYDRATE (1:1:2)
Systematic Name English
MICAFUNGIN SODIUM HYDRATE [JAN]
Common Name English
Code System Code Type Description
PUBCHEM
131666059
Created by admin on Sat Dec 16 18:42:15 UTC 2023 , Edited by admin on Sat Dec 16 18:42:15 UTC 2023
PRIMARY
CAS
2054923-12-3
Created by admin on Sat Dec 16 18:42:15 UTC 2023 , Edited by admin on Sat Dec 16 18:42:15 UTC 2023
PRIMARY
SMS_ID
300000023932
Created by admin on Sat Dec 16 18:42:15 UTC 2023 , Edited by admin on Sat Dec 16 18:42:15 UTC 2023
PRIMARY
FDA UNII
R8QS8RE925
Created by admin on Sat Dec 16 18:42:15 UTC 2023 , Edited by admin on Sat Dec 16 18:42:15 UTC 2023
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE
PARENT -> SALT/SOLVATE