U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C44H67N5O4.C6H8O7
Molecular Weight 922.1593
Optical Activity UNSPECIFIED
Defined Stereocenters 12 / 12
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IBREXAFUNGERP CITRATE

SMILES

CC(C)[C@@]([H])(C)[C@@]1(C)CC[C@]2(C)[C@@]3([H])CC[C@@]4([H])[C@@]5(C)COC[C@@]4(C[C@]([H])([C@]5([H])OC[C@@](C)(C(C)(C)C)N)n6c(-c7ccncc7)ncn6)C3=CC[C@@]2(C)[C@]1([H])C(=O)O.C(C(=O)O)C(CC(=O)O)(C(=O)O)O

InChI

InChIKey=WKIRTJACGBEXBZ-FQGZCCSZSA-N
InChI=1S/C44H67N5O4.C6H8O7/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;7-3(8)1-6(13,5(11)12)2-4(9)10/h14-16,20-21,26-28,30,32-35H,12-13,17-19,22-25,45H2,1-11H3,(H,50,51);13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/t28-,30+,32-,33+,34-,35+,39-,40-,41-,42+,43+,44+;/m1./s1

HIDE SMILES / InChI

Molecular Formula C6H8O7
Molecular Weight 192.1238
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C44H67N5O4
Molecular Weight 730.0355
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 12 / 12
E/Z Centers 0
Optical Activity UNSPECIFIED

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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Antifungal activities of SCY-078 (MK-3118) and standard antifungal agents against clinical non-Aspergillus mold isolates.
2015 Jul
Patents
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:24:14 UTC 2021
Edited
by admin
on Fri Jun 25 21:24:14 UTC 2021
Record UNII
M4NU2SDX3E
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
IBREXAFUNGERP CITRATE
USAN  
Official Name 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 CITRATE [USAN]
Common Name English
SCY-078 CITRATE
Code English
BREXAFEMME
Brand 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
Code System Code Type Description
PUBCHEM
137552087
Created by admin on Fri Jun 25 21:24:14 UTC 2021 , Edited by admin on Fri Jun 25 21:24:14 UTC 2021
PRIMARY
NCI_THESAURUS
C174692
Created by admin on Fri Jun 25 21:24:14 UTC 2021 , Edited by admin on Fri Jun 25 21:24:14 UTC 2021
PRIMARY
CAS
1965291-08-0
Created by admin on Fri Jun 25 21:24:14 UTC 2021 , Edited by admin on Fri Jun 25 21:24:14 UTC 2021
PRIMARY
FDA UNII
M4NU2SDX3E
Created by admin on Fri Jun 25 21:24:14 UTC 2021 , Edited by admin on Fri Jun 25 21:24:14 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY