Ibrexafungerp

CAT: 0804-HY-107126-01Size: 1 mgDry Ice: NoHazardous: No

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CAT#:0804-HY-107126-01Size:1 mg

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Description

Ibrexafungerp (MK 3118) is an orally active β-1,3-glucan synthesis inhibitor, with potential antifungal activity. Ibrexafungerp can be used for research of Candida and Aspergillus infections[1].

CAS Number

1207753-03-4

Product Name Alternative

MK 3118; SCY-078

UNSPSC

12352005

Hazard Statement

H302, H312, H332

Target

Fungal

Type

Reference compound

Related Pathways

Anti-infection

Applications

COVID-19-immunoregulation

Field of Research

Infection

Assay Protocol

https://www.medchemexpress.com/ibrexafungerp.html

Purity

99.83

Solubility

DMSO : 100 mg/mL (ultrasonic)

Smiles

C[C@@]12[C@@](CC3)([H])[C@@](C[C@](N4C(C5=CC=NC=C5)=NC=N4)([H])[C@@H]1OC[C@](C)(N)C(C)(C)C)(COC2)C([C@@]3([H])[C@]6(CC[C@]7(C)[C@H](C)C(C)C)C)=CC[C@]6([C@@H]7C(O)=O)C

Molecular Formula

C44H67N5O4

Molecular Weight

730.03

Precautions

H302, H312, H332

References & Citations

[1]James M Apgar, et al. Ibrexafungerp: An orally active β-1,3-glucan synthesis inhibitor. Bioorg Med Chem Lett. 2021 Jan 15;32:127661. |[2]Mahmoud Ghannoum, et al. Ibrexafungerp: A Novel Oral Triterpenoid Antifungal in Development for the Treatment of Candida auris Infections. Antibiotics (Basel) . 2020 Aug 25;9 (9) :539. |[3]Stephen A Wring, et al. Preclinical Pharmacokinetics and Pharmacodynamic Target of SCY-078, a First-in-Class Orally Active Antifungal Glucan Synthesis Inhibitor, in Murine Models of Disseminated Candidiasis. Antimicrob Agents Chemother. 2017 Mar 24;61 (4) :e02068-16. |[4]Ghannoum M, et al. Efficacy of Ibrexafungerp (SCY-078) against Candida auris in an In Vivo Guinea Pig Cutaneous Infection Model. Antimicrob Agents Chemother. 2020 Sep 21;64 (10) :e00854-20. |[5]Arendrup MC, et al. In Vitro Activity of Ibrexafungerp (SCY-078) against Candida auris Isolates as Determined by EUCAST Methodology and Comparison with Activity against C. albicans and C. glabrata and with the Activities of Six Comparator Agents. Antimicrob Agents Chemother. 2020 Feb 21;64 (3) :e02136-19.

Shipping Conditions

Room Temperature

Storage Conditions

-20°C, 3 years; 4°C, 2 years (Powder)

Scientific Category

Reference compound1

Clinical Information

Launched

Chemical Information

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. It was developed out of a need to treat fungal infections that may have become resistant to echinocandins or azole antifungals. Ibrexafungerp is orally bioavailable compared to the echinocandins [caspofungin], [micafungin], and [anidulafungin]; which can only be administered parenterally. 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. Ibrexafungerp was granted FDA approval on 1 June 2021.

CAS Number	1207753-03-4
PubChem CID	46871657
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-1,2,4-triazol-1-yl)-17-oxapentacyclo[13.3.3.01,14.02,11.05,10]henicos-2-ene-6-carboxylic acid
Molecular Formula	C44H67N5O4
Molecular Weight	730.0
XLogP	5.8
Topological Polar Surface Area	125
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	9
Heavy Atom Count	53
Formal Charge	0
Complexity	1430

SMILES

C[C@H](C(C)C)[C@]1(CC[C@@]2([C@H]3CC[C@H]4[C@]5(COC[C@]4(C3=CC[C@]2([C@@H]1C(=O)O)C)C[C@H]([C@@H]5OC[C@@](C)(C(C)(C)C)N)N6C(=NC=N6)C7=CC=NC=C7)C)C)C

InChI

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

InChIKey

BODYFEUFKHPRCK-ZCZMVWJSSA-N

Chemical Structure

2D Structure

CAS: 1207753-03-4

CID: 46871657

Formula: C44H67N5O4

MW: 730.0

Interactive 3D Structure

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View on PubChem Raw 3D data

Computed Properties

Property	Value
Molecular Weight	730.0
XLogP3	5.8
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	9
Exact Mass	729.51930564
Monoisotopic Mass	729.51930564
Topological Polar Surface Area	125 Å²
Heavy Atom Count	53
Formal Charge	0
Complexity	1430
Isotope Atom Count	0
Defined Atom Stereocenter Count	12
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	1
Compound Is Canonicalized	Yes

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Ibrexafungerp

Chemical Information

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