Ibrexafungerp citrateProduct ingredient for Ibrexafungerp

Name

Ibrexafungerp citrate

Drug Entry

Ibrexafungerp

Ibrexafungerp, also known as SCY-078 or MK-3118, is a novel enfumafungin derivative oral triterpene antifungal approved for the treatment of vulvovaginal candidiasis (VVC), also known as a vaginal yeast infection.^1,9 It was developed out of a need to treat fungal infections that may have become resistant to echinocandins or azole antifungals.¹ Ibrexafungerp is orally bioavailable compared to the echinocandins caspofungin, micafungin, and anidulafungin; which can only be administered parenterally.^1,2 Similar to echinocandins, ibrexafungerp targets the fungal β-1,3-glucan synthase, which is not present in humans, limiting the chance of renal or hepatic toxicity.^6,9

Ibrexafungerp was granted FDA approval on 1 June 2021.⁹

See full entry for Ibrexafungerp

Accession Number

DBSALT003185

Structure

Similar Structures

Synonyms

Ibrexafungerp citrate

UNII

M4NU2SDX3E

CAS Number

1965291-08-0

Weight

Average: 922.174
Monoisotopic: 921.546308255

Chemical Formula

C₅₀H₇₅N₅O₁₁

InChI Key

WKIRTJACGBEXBZ-FQGZCCSZSA-N

InChI

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

IUPAC Name

(1R,5S,6R,7R,10R,11R,14R,15S,20R,21R)-21-[(2R)-2-amino-2,3,3-trimethylbutoxy]-5,7,10,15-tetramethyl-7-[(2R)-3-methylbutan-2-yl]-20-[5-(pyridin-4-yl)-1H-1,2,4-triazol-1-yl]-17-oxapentacyclo[13.3.3.0^{1,14}.0^{2,11}.0^{5,10}]henicos-2-ene-6-carboxylic acid; 2-hydroxypropane-1,2,3-tricarboxylic acid

SMILES

OC(=O)CC(O)(CC(O)=O)C(O)=O.[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)N3N=CN=C3C3=CC=NC=C3)C1=CC[C@@]1(C)[C@H](C(O)=O)[C@](C)(CC[C@]21C)[C@H](C)C(C)C

External Links

ChemSpider: 90666318
ChEMBL: CHEMBL4298168

Predicted Properties

Property	Value	Source
Water Solubility	0.000346 mg/mL	ALOGPS
logP	3.28	ALOGPS
logP	4.9	Chemaxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	4.39	Chemaxon
pKa (Strongest Basic)	9.75	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	8	Chemaxon
Hydrogen Donor Count	2	Chemaxon
Polar Surface Area	125.38 Å²	Chemaxon
Rotatable Bond Count	14	Chemaxon
Refractivity	230.85 m³·mol^-1	Chemaxon
Polarizability	84.71 Å³	Chemaxon
Number of Rings	7	Chemaxon
Bioavailability	0	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Ibrexafungerp citrateProduct ingredient for Ibrexafungerp

Structure for Ibrexafungerp citrate (DBSALT003185)