MICAFUNGIN

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 Search

SMILES

CCCCCOC1=CC=C(C=C1)C2=CC(=NO2)C3=CC=C(C=C3)C(=O)N[C@H]4C[C@@H](O)[C@@H](O)NC(=O)[C@@H]5[C@@H](O)[C@@H](C)CN5C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]6C[C@@H](O)CN6C(=O)[C@@H](NC4=O)[C@@H](C)O)[C@H](O)[C@@H](O)C7=CC(OS(O)(=O)=O)=C(O)C=C7)[C@H](O)CC(N)=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

Molecular Formula	C56H71N9O23S
Molecular Weight	1270.274
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	15 / 15
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19933794
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
1,3-beta-glucan synthase 10 Target ID: CHEMBL2364673 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2005/21506,21754lbl.pdf	Inhibitor 8504		0.208 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Esophageal candidiasis 9 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2005/21506,21754lbl.pdf	Curative		Approved 8583	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
Candida infections in patients undergoing hematopoietic stem cell transplantation 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2005/21506,21754lbl.pdf	Preventing		Approved 8583	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

C_max

Value	Dose	Analyte	Population
10.1 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021506s011s012lbl.pdf	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
16.4 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021506s011s012lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021506s011s012lbl.pdf	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

AUC

Value	Dose	Analyte	Population
97 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021506s011s012lbl.pdf	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
167 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021506s011s012lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021506s011s012lbl.pdf	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

T_1/2

Value	Dose	Analyte	Population
13.4 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021506s011s012lbl.pdf	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
15.2 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021506s011s012lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021506s011s012lbl.pdf	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
1% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021506s011s012lbl.pdf	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

Dose	Population	Adverse 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: https://pubmed.ncbi.nlm.nih.gov/16715107	unhealthy, 19 - 62 Health Status: unhealthy Age Group: 19 - 62 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/16715107	Sources: https://pubmed.ncbi.nlm.nih.gov/16715107
200 mg single, intravenous Highest studied dose Dose: 200 mg Route: intravenous Route: single Dose: 200 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021506s011s012lbl.pdf	healthy Health Status: healthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021506s011s012lbl.pdf	Disc. AE: Intravascular hemolysis... AEs leading to discontinuation/dose reduction: Intravascular hemolysis (acute) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021506s011s012lbl.pdf
16 mg/kg single, intravenous Overdose Dose: 16 mg/kg Route: intravenous Route: single Dose: 16 mg/kg Sources: https://www.ema.europa.eu/en/documents/product-information/mycamine-epar-product-information_en.pdf	unhealthy Health Status: unhealthy Sources: https://www.ema.europa.eu/en/documents/product-information/mycamine-epar-product-information_en.pdf	Sources: https://www.ema.europa.eu/en/documents/product-information/mycamine-epar-product-information_en.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021506s011s012lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021506s011s012lbl.pdf	Disc. AE: Anaphylaxis, Anaphylactoid reaction... AEs leading to discontinuation/dose reduction: Anaphylaxis Anaphylactoid reaction Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021506s011s012lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021506s011s012lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021506s011s012lbl.pdf	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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021506s011s012lbl.pdf
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: https://www.ema.europa.eu/en/documents/product-information/mycamine-epar-product-information_en.pdf	unhealthy Health Status: unhealthy Sources: https://www.ema.europa.eu/en/documents/product-information/mycamine-epar-product-information_en.pdf	Disc. AE: Exfoliative conditions, Stevens-Johnson syndrome... AEs leading to discontinuation/dose reduction: Exfoliative conditions Stevens-Johnson syndrome Toxic epidermal necrolysis Rash Sources: https://www.ema.europa.eu/en/documents/product-information/mycamine-epar-product-information_en.pdf
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: https://www.ema.europa.eu/en/documents/product-information/mycamine-epar-product-information_en.pdf	unhealthy Health Status: unhealthy Sources: https://www.ema.europa.eu/en/documents/product-information/mycamine-epar-product-information_en.pdf	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: https://www.ema.europa.eu/en/documents/product-information/mycamine-epar-product-information_en.pdf

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1741 CYP3A 227 CYP2C19 2057 CYP2E1 1060	P-gp 2052 CYP1A2 1197 CYP2B6 776 CYP2C 16 CYP1A1 389 NTCP 22 OATP1B1/3 11 BSEP 63 BCRP 697 MRP3 58 arylsulfatase 3

Drug as perpetrator

Target	Modality	Activity
P-gp 1932	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/21-506_Mycamine_biopharmr.pdf Page: 77.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/21-506_Mycamine_biopharmr.pdf Page: 75.0	yes [Inhibition 50 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/21-506_Mycamine_biopharmr.pdf Page: 75.0	yes [Inhibition 50 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/21-506_Mycamine_biopharmr.pdf Page: 75.0	yes [Inhibition 50 uM]
CYP2E1 1146	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/21-506_Mycamine_biopharmr.pdf Page: 75.0	yes [Inhibition 50 uM]
CYP3A 317	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/21-506_Mycamine_biopharmr.pdf Page: 75.0	yes [Inhibition 50 uM]

Drug as victim

Target	Modality	Activity
P-gp 2052	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/21-506_Mycamine_biopharmr.pdf Page: 78.0	inconclusive
arylsulfatase 3	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/21-506_Mycamine_biopharmr.pdf Page: 76.0	likely
BCRP 697	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21449041/	yes
BSEP 63	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21449041/	yes
CYP1A1 389	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/21-506_Mycamine_biopharmr.pdf Page: 56.0	yes
CYP1A2 1197	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/21-506_Mycamine_biopharmr.pdf Page: 56.0	yes
CYP2B6 776	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/21-506_Mycamine_biopharmr.pdf Page: 56.0	yes
CYP2C 16	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/21-506_Mycamine_biopharmr.pdf Page: 56.0	yes
CYP3A4 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/21-506_Mycamine_biopharmr.pdf Page: 56.0	yes
MRP3 58	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21449041/	yes
NTCP 22	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21449041/	yes
OATP1B1/3 11	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/21449041/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/21-506_Mycamine_pharmr.pdf Page: 24, 25

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:600520	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:600520
ChemicalBook	CB71471028	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB71471028

PubMed

Title	Date	PubMed
Comparative in vitro fungicidal activity of echinocandins against Candida albicans in peritoneal dialysis fluids.	2013-11	23551835
Amphotericin B- and voriconazole-echinocandin combinations against Aspergillus spp.: Effect of serum on inhibitory and fungicidal interactions.	2013-10	23856768
KB425796-A, a novel antifungal antibiotic produced by Paenibacillus sp. 530603.	2013-08	23778117
Identification of ten KB425796-A congeners from Paenibacillus sp. 530603 using an antifungal assay against Aspergillus fumigatus in combination with micafungin.	2013-08	23778114
Synergistic antifungal activity of KB425796-C in combination with micafungin against Aspergillus fumigatus and its efficacy in murine infection models.	2013-08	23756682
In vitro antifungal susceptibility of clinically relevant species belonging to Aspergillus section Flavi.	2013-04	23335742
Identification and characterization of the echinocandin B biosynthetic gene cluster from Emericella rugulosa NRRL 11440.	2012-10-10	22998630
Antifungal susceptibilities of Aspergillus fumigatus clinical isolates obtained in Nagasaki, Japan.	2012-01	22024829
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.	2011-12	21937186
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.	2011-11	21900519
In vitro activity of E1210, a novel antifungal, against clinically important yeasts and molds.	2011-10	21825291
Multilaboratory testing of two-drug combinations of antifungals against Candida albicans, Candida glabrata, and Candida parapsilosis.	2011-04	21282457
Isavuconazole: a comprehensive review of spectrum of activity of a new triazole.	2010-11	20524153
Echinocandins: A ray of hope in antifungal drug therapy.	2010-02	20606829
Review of the pharmacology and clinical studies of micafungin.	2009-12-29	20054447
Echinocandins: the newest class of antifungals.	2009-10	19724014
Efficacy of SPK-843, a novel polyene antifungal, in comparison with amphotericin B, liposomal amphotericin B, and micafungin against murine pulmonary aspergillosis.	2008-05	18299412
In vitro and in vivo antifungal activities of T-2307, a novel arylamidine.	2008-04	18227186
The echinocandin micafungin: a review of the pharmacology, spectrum of activity, clinical efficacy and safety.	2007-06	17516879
Role of micafungin in the antifungal armamentarium.	2007	17504145
Determination of MICs of aminocandin for Candida spp. and filamentous fungi.	2006-12	17021057
Echinocandins in the management of invasive fungal infections, Part 2.	2006-10-01	16990627
Echinocandins in the management of invasive fungal infections, part 1.	2006-09-15	16960253
Micafungin sodium, the second of the echinocandin class of antifungals: theory and practice.	2006-08	17661660
Emerging echinocandins for treatment of invasive fungal infections.	2006-05	16634699
Micafungin: a new echinocandin.	2006-04-15	16575738
In vitro interactions of micafungin with other antifungal drugs against clinical isolates of four species of Cryptococcus.	2005-07	15980382
Micafungin: pharmacology, experimental therapeutics and clinical applications.	2005-04	15882123
Efficacy of micafungin alone or in combination against systemic murine aspergillosis.	2003-04	12654692
In vitro activity of micafungin (FK-463) against Candida spp.: microdilution, time-kill, and postantifungal-effect studies.	2002-12	12435687
Antifungals: what's in the pipeline.	2001-10	11587930
In vitro antifungal activity of a novel lipopeptide antifungal agent, FK463, against various fungal pathogens.	2000-10	11132964
In vitro antifungal activity of FK463, a new water-soluble echinocandin-like lipopeptide.	2000-09	10980180
Prophylactic effect of FK463, a novel antifungal lipopeptide, against Pneumocystis carinii infection in mice.	2000-09	10952565
Efficacy of FK463, a (1,3)-beta-D-glucan synthase inhibitor, in disseminated azole-resistant candida albicans infection in mice.	2000-06	10817741
Efficacy of FK463, a new lipopeptide antifungal agent, in mouse models of pulmonary aspergillosis.	2000-03	10681328
Efficacy of FK463, a new lipopeptide antifungal agent, in mouse models of disseminated candidiasis and aspergillosis.	2000-03	10681327
In vitro activities of a new lipopeptide antifungal agent, FK463, against a variety of clinically important fungi.	2000-01	10602723

Patents

Sample Use Guides

In Vivo Use Guide

Esophageal Candidiasis - 150 mg per day Prophylaxis of Candida Infections in HSCT Recipients - 50 mg per day

Route of Administration: Intravenous

In Vitro Use Guide

The IC50 value of FK463 for mannan inhibition was over 100 ug/ml.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 07:48:20 GMT 2025` Edited by `admin` on `Wed Apr 02 07:48:20 GMT 2025`
Record UNII	R10H71BSWG
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

MICAFUNGIN [EMA EPAR]

Preferred Name

English

MICAFUNGIN

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 [VANDF]

Common Name

English

micafungin [INN]

Common Name

English

Classification Tree Code System Code

LIVERTOX

634