IBREXAFUNGERP

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C44H67N5O4
Molecular Weight	730.0339
Optical Activity	UNSPECIFIED
Defined Stereocenters	12 / 12
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

[H][C@]12CC[C@@]3([H])[C@@]4(C)COC[C@@]3(C[C@H]([C@@H]4OC[C@](C)(N)C(C)(C)C)N5N=CN=C5C6=CC=NC=C6)C1=CC[C@@]7(C)[C@H](C(O)=O)[C@](C)(CC[C@]27C)[C@H](C)C(C)C

InChI

InChIKey=BODYFEUFKHPRCK-ZCZMVWJSSA-N

InChI=1S/C44H67N5O4/c1-27(2)28(3)39(7)18-19-41(9)30-12-13-33-40(8)23-52-25-44(33,31(30)14-17-42(41,10)34(39)37(50)51)22-32(35(40)53-24-43(11,45)38(4,5)6)49-36(47-26-48-49)29-15-20-46-21-16-29/h14-16,20-21,26-28,30,32-35H,12-13,17-19,22-25,45H2,1-11H3,(H,50,51)/t28-,30+,32-,33+,34-,35+,39-,40-,41-,42+,43+,44+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C44H67N5O4
Molecular Weight	730.0339
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	12 / 12
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

MK-3118 is an orally active inhibitor of fungal β-(1,3)-glucan synthase patented by Merck Sharp & Dohme Corp for the treatment of fungal infections. MK-3118 demonstrated enhanced efficacy for most C. albicans and C. glabrata ER isolates relative to caspofungin. MK-3118 showed no or poor activity against Mucoromycotina and Fusarium spp. However, MK-3118 was highly active against Paecilomyces variotii and was the only compound displaying some activity against notoriously pan-resistant Scedosporium prolificans.

Originator

Approval Year

PubMed

Title	Date	PubMed
No data available in table

Patents

Substance Class	Chemical
Record UNII	A92JFM5XNU
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

IBREXAFUNGERP

Official Name

English

SCY-078

Code

English

IBREXAFUNGERP [USAN]

Common Name

English

Ibrexafungerp [WHO-DD]

Common Name

English

(1S,4AR,6AS,7R,8R,10AR,10BR,12AR,14R,15R)-15-((2R)- 2-AMINO-2,3,3-TRIMETHYLBUTOXY)-1,6A,8,10A-TETRAMETHYL-8- ((2R)-3-METHYLBUTAN-2-YL)-14-(5-(PYRIDIN-4-YL)-1H-1,2,4- TRIAZOL-1-YL)-1,6,6A,7,8,9,10,10A,10B,11,12,12A-DODECAHYDRO-2H,4H-1,4A-PROPANOPHENANTHRO

Systematic Name

English

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Classification Tree

Code System

Code

Designated

FDA ORPHAN DRUG

519616

Designated

FDA ORPHAN DRUG

531716

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Code System

Code

Type

Description

DAILYMED

A92JFM5XNU

PRIMARY

INN

10597

PRIMARY

DRUG BANK

DB12471

PRIMARY

RXCUI

2560213

PRIMARY

USAN

GH-40

PRIMARY

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Related Record

Type

Details


					8K89NB4OML

CANDIDA GLABRATA

TARGET ORGANISM->INHIBITOR

Amount:


					76HJ8T68WO

IBREXAFUNGERP PHOSPHATE

SALT/SOLVATE -> PARENT

Amount:


					138TJ2U1SD

ISSATCHENKIA ORIENTALIS WHOLE

TARGET ORGANISM->INHIBITOR

Amount:


					4D7G21HDBC

CANDIDA ALBICANS

TARGET ORGANISM->INHIBITOR

Amount:


					M4NU2SDX3E

IBREXAFUNGERP CITRATE

SALT/SOLVATE -> PARENT

Amount:

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Related Record

Type

Details


					A92JFM5XNU

IBREXAFUNGERP

ACTIVE MOIETY

Comments:

MK-3118, a glucan synthase inhibitor derived from enfumafungin, and comparator agents were tested against 71 Aspergillus spp., including itraconazole-resistant strains (MIC, 4 .MU.g/ml), using CLSI and EUCAST reference broth microdilution methods. The CLSI 90% minimum effective concentration (MEC90)/MIC90 values (.MU.g/ml) for MK-3118, amphotericin B, and caspofungin, respectively, were as follows: 0.12, 2, and 0.03 for Aspergillus flavus species complex (SC) 0.25, 2, and 0.06 for Aspergillus fumigatus SC; 0.12, 2, and 0.06 for Aspergillus terreus SC and 0.06, 1, and 0.03 for Aspergillus niger SC. Essential agreement between the values found by CLSI and EUCAST (+/-2 log2 dilution steps) was 94.3%. MK-3118 was determined to be a potent agent regardless of the in vitro method applied, with excellent activity against contemporary wild-type and itraconazole-resistant strains of Aspergillus spp.

Amount:

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