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

[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

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 7 Target ID: CHEMBL2364673 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2005/21506,21754lbl.pdf	Inhibitor 8297		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 8429	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
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 8429	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

C_max

Value	Dose	Analyte	Population
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
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

AUC

Value	Dose	Analyte	Population
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
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

T_1/2

Value	Dose	Analyte	Population
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
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

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 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: https://pubmed.ncbi.nlm.nih.gov/16715107 Page: p.48	Sources: https://pubmed.ncbi.nlm.nih.gov/16715107 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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021506s011s012lbl.pdf Page: p.1, p.4	healthy Health Status: healthy Condition: Candidiasis Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021506s011s012lbl.pdf Page: p.1, p.4	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 Page: p.1, p.4
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 Page: p.9	unhealthy Health Status: unhealthy Condition: Candidiasis Sources: https://www.ema.europa.eu/en/documents/product-information/mycamine-epar-product-information_en.pdf Page: p.9	Sources: https://www.ema.europa.eu/en/documents/product-information/mycamine-epar-product-information_en.pdf Page: p.9
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 Page: p.1	unhealthy Health Status: unhealthy Condition: Oesophageal candidiasis Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021506s011s012lbl.pdf Page: p.1	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 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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021506s011s012lbl.pdf Page: p.1, p.4	unhealthy Health Status: unhealthy Condition: Oesophageal candidiasis Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021506s011s012lbl.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021506s011s012lbl.pdf 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: https://www.ema.europa.eu/en/documents/product-information/mycamine-epar-product-information_en.pdf Page: p.5	unhealthy Health Status: unhealthy Condition: Candidiasis Sources: https://www.ema.europa.eu/en/documents/product-information/mycamine-epar-product-information_en.pdf Page: p.5	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 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: https://www.ema.europa.eu/en/documents/product-information/mycamine-epar-product-information_en.pdf Page: p.8	unhealthy Health Status: unhealthy Condition: Candidiasis Sources: https://www.ema.europa.eu/en/documents/product-information/mycamine-epar-product-information_en.pdf Page: p.8	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 Page: p.8

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737	inhibitor 1767	inhibitor 1852	inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1461 CYP3A 214 CYP2C19 1478 CYP2E1 882	P-gp 1537 CYP1A2 1054 CYP2B6 664 CYP2C 11 CYP1A1 349 NTCP 17 OATP1B1/3 11 BSEP 52 BCRP 561 MRP3 50 arylsulfatase 3

Drug as perpetrator

Target	Modality	Activity
P-gp 1650	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/21-506_Mycamine_biopharmr.pdf Page: 77.0	no
CYP2C19 1553	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/21-506_Mycamine_biopharmr.pdf Page: 75.0	yes [Inhibition 50 uM]
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/21-506_Mycamine_biopharmr.pdf Page: 75.0	yes [Inhibition 50 uM]
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/21-506_Mycamine_biopharmr.pdf Page: 75.0	yes [Inhibition 50 uM]
CYP2E1 970	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/21-506_Mycamine_biopharmr.pdf Page: 75.0	yes [Inhibition 50 uM]
CYP3A 298	inhibitor 3277 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 1537	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/21-506_Mycamine_biopharmr.pdf Page: 78.0	inconclusive
arylsulfatase 3	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/21-506_Mycamine_biopharmr.pdf Page: 76.0	likely
BCRP 561	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/21449041/	yes
BSEP 52	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/21449041/	yes
CYP1A1 349	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/21-506_Mycamine_biopharmr.pdf Page: 56.0	yes
CYP1A2 1054	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/21-506_Mycamine_biopharmr.pdf Page: 56.0	yes
CYP2B6 664	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/21-506_Mycamine_biopharmr.pdf Page: 56.0	yes
CYP2C 11	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/21-506_Mycamine_biopharmr.pdf Page: 56.0	yes
CYP3A4 1737	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2005/21-506_Mycamine_biopharmr.pdf Page: 56.0	yes
MRP3 50	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/21449041/	yes
NTCP 17	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/21449041/	yes
OATP1B1/3 11	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/21449041/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 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
In vitro activities of a new lipopeptide antifungal agent, FK463, against a variety of clinically important fungi.	2000 Jan	10602723
Efficacy of FK463, a new lipopeptide antifungal agent, in mouse models of disseminated candidiasis and aspergillosis.	2000 Mar	10681327
In vitro antifungal activity of FK463, a new water-soluble echinocandin-like lipopeptide.	2000 Sep	10980180
Efficacy of micafungin alone or in combination against systemic murine aspergillosis.	2003 Apr	12654692
Micafungin: pharmacology, experimental therapeutics and clinical applications.	2005 Apr	15882123
Micafungin: a new echinocandin.	2006 Apr 15	16575738
Micafungin sodium, the second of the echinocandin class of antifungals: theory and practice.	2006 Aug	17661660
Determination of MICs of aminocandin for Candida spp. and filamentous fungi.	2006 Dec	17021057
Echinocandins in the management of invasive fungal infections, Part 2.	2006 Oct 1	16990627
In vitro and in vivo antifungal activities of T-2307, a novel arylamidine.	2008 Apr	18227186
Efficacy of SPK-843, a novel polyene antifungal, in comparison with amphotericin B, liposomal amphotericin B, and micafungin against murine pulmonary aspergillosis.	2008 May	18299412
Review of the pharmacology and clinical studies of micafungin.	2009 Dec 29	20054447
Echinocandins: the newest class of antifungals.	2009 Oct	19724014
Echinocandins: A ray of hope in antifungal drug therapy.	2010 Feb	20606829
Isavuconazole: a comprehensive review of spectrum of activity of a new triazole.	2010 Nov	20524153
Multilaboratory testing of two-drug combinations of antifungals against Candida albicans, Candida glabrata, and Candida parapsilosis.	2011 Apr	21282457
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	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 Nov	21900519
Antifungal susceptibilities of Aspergillus fumigatus clinical isolates obtained in Nagasaki, Japan.	2012 Jan	22024829

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 `Sat Dec 16 16:23:28 UTC 2023` Edited by `admin` on `Sat Dec 16 16:23:28 UTC 2023`
Record UNII	R10H71BSWG
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

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 [EMA EPAR]

Common Name

English

MICAFUNGIN [VANDF]

Common Name

English

micafungin [INN]

Common Name

English

Classification Tree Code System Code

LIVERTOX

634