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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
Structure of IBREXAFUNGERP

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
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

2021
470
PubMed

PubMed

TitleDatePubMed
Patents

Patents

20100113439
3
8188085
3
WO2010019204
3
Substance Class Chemical
Created
by admin
on Sat Dec 16 07:57:37 GMT 2023
Edited
by admin
on Sat Dec 16 07:57:37 GMT 2023
Record UNII
A92JFM5XNU
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
IBREXAFUNGERP
USAN   INN  
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
MK-3118
Code English
MK3118
Code English
MK-3118 FREE BASE
Code English
4H-1,4A-PROPANO-2H-PHENANTHRO(1,2-C)PYRAN-7-CARBOXYLIC ACID, 15-((2R)-2-AMINO-2,3,3-TRIMETHYLBUTOXY)-8-((1R)-1,2-DIMETHYLPROPYL)-1,6,6A,7,8,9,10,10A,10B,11,12,12A-DODECAHYDRO-1,6A,8,10A-TETRAMETHYL-14-(5-(4-PYRIDINYL)-1H-1,2,4-TRIAZOL-1-YL)-, (1S,4AR,6AS
Systematic Name English
ibrexafungerp [INN]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 519616
Created by admin on Sat Dec 16 07:57:37 GMT 2023 , Edited by admin on Sat Dec 16 07:57:37 GMT 2023
FDA ORPHAN DRUG 531716
Created by admin on Sat Dec 16 07:57:37 GMT 2023 , Edited by admin on Sat Dec 16 07:57:37 GMT 2023
Code System Code Type Description
DAILYMED
A92JFM5XNU
Created by admin on Sat Dec 16 07:57:37 GMT 2023 , Edited by admin on Sat Dec 16 07:57:37 GMT 2023
PRIMARY
INN
10597
Created by admin on Sat Dec 16 07:57:37 GMT 2023 , Edited by admin on Sat Dec 16 07:57:37 GMT 2023
PRIMARY
DRUG BANK
DB12471
Created by admin on Sat Dec 16 07:57:37 GMT 2023 , Edited by admin on Sat Dec 16 07:57:37 GMT 2023
PRIMARY
RXCUI
2560213
Created by admin on Sat Dec 16 07:57:37 GMT 2023 , Edited by admin on Sat Dec 16 07:57:37 GMT 2023
PRIMARY
USAN
GH-40
Created by admin on Sat Dec 16 07:57:37 GMT 2023 , Edited by admin on Sat Dec 16 07:57:37 GMT 2023
PRIMARY
FDA UNII
A92JFM5XNU
Created by admin on Sat Dec 16 07:57:37 GMT 2023 , Edited by admin on Sat Dec 16 07:57:37 GMT 2023
PRIMARY
NCI_THESAURUS
C162185
Created by admin on Sat Dec 16 07:57:37 GMT 2023 , Edited by admin on Sat Dec 16 07:57:37 GMT 2023
PRIMARY
EPA CompTox
DTXSID901336871
Created by admin on Sat Dec 16 07:57:37 GMT 2023 , Edited by admin on Sat Dec 16 07:57:37 GMT 2023
PRIMARY
PUBCHEM
46871657
Created by admin on Sat Dec 16 07:57:37 GMT 2023 , Edited by admin on Sat Dec 16 07:57:37 GMT 2023
PRIMARY
SMS_ID
100000177832
Created by admin on Sat Dec 16 07:57:37 GMT 2023 , Edited by admin on Sat Dec 16 07:57:37 GMT 2023
PRIMARY
CAS
1207753-03-4
Created by admin on Sat Dec 16 07:57:37 GMT 2023 , Edited by admin on Sat Dec 16 07:57:37 GMT 2023
PRIMARY
Related Record Type Details
CANDIDA GLABRATA
TARGET ORGANISM->INHIBITOR
Structure of IBREXAFUNGERP PHOSPHATE
SALT/SOLVATE -> PARENT
ISSATCHENKIA ORIENTALIS WHOLE
TARGET ORGANISM->INHIBITOR
CANDIDA ALBICANS
TARGET ORGANISM->INHIBITOR
Structure of IBREXAFUNGERP CITRATE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of IBREXAFUNGERP
ACTIVE MOIETY
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.
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