MICAFUNGIN SODIUM DIHYDRATE

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+].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=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

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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 10	Inhibitor 8,504		0.208 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Esophageal candidiasis 9	Curative		Approved 8,583	MYCAMINE
Candida infections in patients undergoing hematopoietic stem cell transplantation 3	Preventing		Approved 8,583	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 1,946	inhibitor 2,438	inhibitor 2,507	inhibitor 2,217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1,741 CYP3A 227 CYP2C19 2,057 CYP2E1 1,060	P-gp 2,052 CYP1A2 1,197 CYP2B6 776 CYP2C 16 CYP1A1 389 NTCP 22 OATP1B1/3 11 BSEP 63 BCRP 697 MRP3 58 arylsulfatase 3

Drug as perpetrator

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Target	Modality	Activity
P-gp 1,932	inhibitor 4,027	no
CYP2C19 2,141	inhibitor 4,027	yes [Inhibition 50 uM]
CYP2C9 2,497	inhibitor 4,027	yes [Inhibition 50 uM]
CYP2D6 2,546	inhibitor 4,027	yes [Inhibition 50 uM]
CYP2E1 1,146	inhibitor 4,027	yes [Inhibition 50 uM]

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Drug as victim

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Target	Modality	Activity
P-gp 2,052	substrate 4,014	inconclusive
arylsulfatase 3	substrate 4,014	likely
BCRP 697	substrate 4,014	yes
BSEP 63	substrate 4,014	yes
CYP1A1 389	substrate 4,014	yes

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2,263	inhibitor 2,237

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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
In vitro activities of a new lipopeptide antifungal agent, FK463, against a variety of clinically important fungi.	2000 Jan	10602723
Efficacy of FK463, a (1,3)-beta-D-glucan synthase inhibitor, in disseminated azole-resistant candida albicans infection in mice.	2000 Jun	10817741
Efficacy of FK463, a new lipopeptide antifungal agent, in mouse models of pulmonary aspergillosis.	2000 Mar	10681328
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

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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.

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Name

Type

Language

MICAFUNGIN SODIUM DIHYDRATE

Common Name

English

MICAFUNGIN SODIUM HYDRATE

Preferred 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

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Code System

Code

Type

Description

PUBCHEM

131666059

PRIMARY

CAS

2054923-12-3

PRIMARY

SMS_ID

300000023932

PRIMARY

FDA UNII

R8QS8RE925

PRIMARY

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PARENT (SALT/SOLVATE)


					R10H71BSWG

MICAFUNGIN

SUBSTANCE RECORD


					R8QS8RE925

MICAFUNGIN SODIUM DIHYDRATE

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