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

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	MOL RATIO 1 MOL RATIO (average)

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

Description

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	Inhibitor 8,297		0.208 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Esophageal candidiasis 9	Curative		Approved 8,429	MYCAMINE
Candida infections in patients undergoing hematopoietic stem cell transplantation 3	Preventing		Approved 8,429	MYCAMINE

C_max

Value	Dose	Analyte	Population
10.1 μg/mL	100 mg 1 times / day steady-state, intravenous	MICAFUNGIN plasma	Homo sapiens
16.4 μg/mL	150 mg 1 times / day multiple, intravenous	MICAFUNGIN plasma	Homo sapiens
60.8 μg/mL	8 mg/kg bw 1 times / day multiple, intravenous	MICAFUNGIN plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
97 μg × h/mL	100 mg 1 times / day steady-state, intravenous	MICAFUNGIN plasma	Homo sapiens
167 μg × h/mL	150 mg 1 times / day multiple, intravenous	MICAFUNGIN plasma	Homo sapiens
663 μg × h/mL	8 mg/kg bw 1 times / day multiple, intravenous	MICAFUNGIN plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
13.4 h	100 mg 1 times / day steady-state, intravenous	MICAFUNGIN plasma	Homo sapiens
15.2 h	150 mg 1 times / day multiple, intravenous	MICAFUNGIN plasma	Homo sapiens
17.2 h	8 mg/kg bw 1 times / day multiple, intravenous	MICAFUNGIN plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
1%	100 mg 1 times / day steady-state, intravenous		MICAFUNGIN plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
8 mg/kg 1 times / day multiple, intravenous Highest studied dose	unhealthy, 19 - 62
200 mg single, intravenous Highest studied dose	healthy	Disc. AE: Intravascular hemolysis...
16 mg/kg single, intravenous Overdose	unhealthy
150 mg 1 times / day multiple, intravenous Recommended	unhealthy	Disc. AE: Anaphylaxis, Anaphylactoid reaction...
150 mg 1 times / day multiple, intravenous Recommended	unhealthy	Disc. AE: Hemolysis, Hemolytic anemia...

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AEs

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AE	Significance	Dose	Population
Intravascular hemolysis	acute Disc. AE	200 mg single, intravenous Highest studied dose	healthy
Anaphylactoid reaction	Disc. AE	150 mg 1 times / day multiple, intravenous Recommended	unhealthy
Anaphylaxis	Disc. AE	150 mg 1 times / day multiple, intravenous Recommended	unhealthy
Abnormal liver function tests	Disc. AE	150 mg 1 times / day multiple, intravenous Recommended	unhealthy
Blood urea increased	Disc. AE	150 mg 1 times / day multiple, intravenous Recommended	unhealthy

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,737	inhibitor 1,767	inhibitor 1,852	inhibitor 1,612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1,461 CYP3A 214 CYP2C19 1,478 CYP2E1 882	P-gp 1,537 CYP1A2 1,054 CYP2B6 664 CYP2C 11 CYP1A1 349 NTCP 17 OATP1B1/3 11 BSEP 52 BCRP 561 MRP3 50 arylsulfatase 3

Drug as perpetrator

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Target	Modality	Activity
P-gp 1,650	inhibitor 3,277	no
CYP2C19 1,553	inhibitor 3,277	yes [Inhibition 50 uM]
CYP2C9 1,819	inhibitor 3,277	yes [Inhibition 50 uM]
CYP2D6 1,891	inhibitor 3,277	yes [Inhibition 50 uM]
CYP2E1 970	inhibitor 3,277	yes [Inhibition 50 uM]

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Drug as victim

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Target	Modality	Activity
P-gp 1,537	substrate 3,367	inconclusive
arylsulfatase 3	substrate 3,367	likely
BCRP 561	substrate 3,367	yes
BSEP 52	substrate 3,367	yes
CYP1A1 349	substrate 3,367	yes

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1,647	inhibitor 1,626

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Sourcing

Sourcing

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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

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PubMed

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Title	Date	PubMed
Efficacy of FK463, a new lipopeptide antifungal agent, in mouse models of disseminated candidiasis and aspergillosis.	2000 Mar	10681327
In vitro antifungal activity of a novel lipopeptide antifungal agent, FK463, against various fungal pathogens.	2000 Oct	11132964
Antifungals: what's in the pipeline.	2001 Oct	11587930
In vitro activity of micafungin (FK-463) against Candida spp.: microdilution, time-kill, and postantifungal-effect studies.	2002 Dec	12435687
Micafungin: a new echinocandin.	2006 Apr 15	16575738

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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
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

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Classification Tree

Code System

Code

Antifungal

LIVERTOX

634

Other antimycotics for systemic use

WHO-ATC

J02AX05

Lipids

NDF-RT

N0000175508

Other antimycotics for systemic use

WHO-VATC

QJ02AX05

Anti-Infective Agent

NCI_THESAURUS

C514

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Code System

Code

Type

Description

DAILYMED

R10H71BSWG

PRIMARY

MESH

C121905

PRIMARY

SMS_ID

100000091615

PRIMARY

ChEMBL

CHEMBL457547

PRIMARY

CAS

235114-32-6

PRIMARY

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Related Record

Type

Details


					R8QS8RE925

MICAFUNGIN SODIUM DIHYDRATE

SALT/SOLVATE -> PARENT

Amount:


					IS1UP79R56

MICAFUNGIN SODIUM

SALT/SOLVATE -> PARENT


					6D53G0FD0Z

PLASMA PROTEIN FRACTION (HUMAN)

BINDER->LIGAND

Comments:

When detennined in human plasma samples following a single dose of micafungin I00 mg, micafungin binding to plasma protein were approximately 99.8%. Micafungin protein binding in

Interaction Type:

BINDING

Amount:

99.8 % (average)

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Related Record

Type

Details


					EVG3RH3PD5

O-DESULFO METHYL MICAFUNGIN

METABOLITE -> PARENT

Interaction Type:

MINOR


					VP4WA4H3TB

DESPENTYL-(.OMEGA.-1)-HYDROXYPENTYL MICAFUNGIN

METABOLITE -> PARENT


					J95YY85R52

O-DESULFO MICAFUNGIN

METABOLITE -> PARENT

Comments:

Activity Questionable (inactive in http://onlinelibrary.wiley.com/doi/10.1592/phco.27.1.53/epdf). However, not important in theraphy as concentration is low. Mediator: arylsulfatase

Qualification:

PLASMA


					VP4WA4H3TB

DESPENTYL-(.OMEGA.-1)-HYDROXYPENTYL MICAFUNGIN

METABOLITE -> PARENT

Comments:

Probably inactive. Mediator: P450 (CYP) isozymes, but not a major pathway for micafungin metabolism in vivo

Qualification:

PLASMA

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Related Record

Type

Details


					R10H71BSWG

MICAFUNGIN

ACTIVE MOIETY

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Name	Property Type	Amount	Referenced Substance	Defining	Parameters	References
Biological Half-life	PHARMACOKINETIC				Population PHARMACOKINETIC 13.5 hours [5 to 22] (average) For children. Population PHARMACOKINETIC 16 hours [11 to 21] (average) For adults.

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator