Ibrexafungerp

Ibrexafungerp
Names
Pronunciation/aɪˌbrɛksəˈfʌndʒɜːrp/
eye-BREKS-ə-FUN-jurp
Trade namesBrexafemme
Other namesSCY-078
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
Clinical data
Drug classAntifungal
Main usesVaginal yeast infection[1]
Side effectsDiarrhea, nausea, abdominal pain, dizziness[1]
InteractionsCYP3A inhibitors[1]
WHO AWaReUnlinkedWikibase error: ⧼unlinkedwikibase-error-statements-entity-not-set⧽
Pregnancy
category
  • Contraindicated[1]
Routes of
use		By mouth, intravenous
Typical dose300 mg BID x 1 day[1]
External links
AHFS/Drugs.comMonograph
Legal
License data
Legal status
Pharmacokinetics
Protein binding>99%[1]
MetabolismHydroxylation (CYP3A4) then conjugation (glucuronidation, sulfation)[1]
Elimination half-life20 hours[1]
Chemical and physical data
FormulaC44H67N5O4
Molar mass730.051 g·mol−1
3D model (JSmol)
SMILES
  • CC(C)[C@@H](C)[C@@]1(C)CC[C@]2(C)[C@H]3CC[C@H]4[C@@]5(C)COC[C@@]4(C[C@@H](n4ncnc4-c4ccncc4)[C@@H]5OC[C@](C)(N)C(C)(C)C)C3=CC[C@@]2(C)[C@@H]1C(=O)O
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
  • Key:BODYFEUFKHPRCK-ZCZMVWJSSA-N

Ibrexafungerp, sold under the brand name Brexafemme, is an antifungal medication used to treat vaginal yeast infection.[1] It may be used in females after the start of menstruation.[1] It is taken by mouth.[1]

Common side effects include diarrhea, nausea, abdominal pain, and dizziness.[1] Use in pregnancy may harm the baby.[1] It is a triterpenoid antifungal and acts via blocking glucan synthase, which prevents formation of the fungal cell wall.[1]

Ibrexafungerp was approved for medical use in the United States in 2021.[1] It is not approved in Europe or the United Kingdom as of 2022.[2] In the United States a course of treatment costs about 500 USD as of 2022.[3]

Medical uses

Ibrexafungerp is indicated for the treatment of adult and postmenarchal pediatric females with vulvovaginal candidiasis (VVC).[1]

Dosage

It is taken at a dose of 300 mg twice for a single day.[1]

Pharmacology

An estimated 75% of women will have at least one episode of VVC and 40 to 45% will have two or more episodes in their lifetime.[4]

Pharmacodynamics

Ibrexafungerp is a triterpenoid antifungal agent.[1] It acts via inhibition of the enzyme glucan synthase, which is involved in the formation of 1,3-β-D-glucan—an essential component of the fungal cell wall.[1] The compound has concentration-dependent fungicidal activity against Candida species.[1]

Pharmacokinetics

Ibrexafungerp has a time to maximal concentrations of 4 to 6 hours.[1] It is metabolized by hydroxylation via CYP3A4 and subsequently by glucuronidation and sulfation.[1] The medication has an elimination half-life of approximately 20 hours.[1]

History

Ibrexafungerp is the first triterpenoid antifungal to be FDA approved.[1] It is the first, and so far only, non-azole oral antifungal to be FDA approved for the treatment of vaginal yeast infections.[5]

Research

Ibrexafungerp is undergoing trials for an intravenous formulation for the treatment of various fungal diseases, including fungal infections caused primarily by Candida (including C. auris) and Aspergillus species. It has demonstrated broad-spectrum antifungal activity against multidrug-resistant pathogens, including azole- and echinocandin-resistant strains.[6]

References

  1. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 "Brexafemme- ibrexafungerp tablet, film coated". DailyMed. Archived from the original on 12 September 2021. Retrieved 12 September 2021.
  2. ↑ "Ibrexafungerp". SPS - Specialist Pharmacy Service. 2 August 2018. Archived from the original on 8 December 2021. Retrieved 29 October 2022.
  3. ↑ "Ibrexafungerp". Archived from the original on 29 October 2022. Retrieved 29 October 2022.
  4. ↑ "Vulvovaginal Candidiasis - STI Treatment Guidelines". www.cdc.gov. 2021-07-22. Archived from the original on 14 September 2022. Retrieved 2022-04-06.
  5. ↑ "Scynexis Announces FDA Approval of Brexafemme (ibrexafungerp tablets) as the First and Only Oral Non-Azole Treatment for Vaginal Yeast Infections". Scynexis, Inc. (Press release). 2 June 2021. Archived from the original on 31 December 2021. Retrieved 2 June 2021.
  6. ↑ "SCYNEXIS Announces Successful Completion of Phase 1 Trial Evaluating Intravenous (IV) Formulation of Ibrexafungerp". www.scynexis.com. Scynexis inc. 9 November 2021. Archived from the original on 20 October 2022. Retrieved 20 October 2022.

Further reading

External sites:
Identifiers:
  • Clinical trial number NCT03734991 for "Efficacy and Safety of Oral Ibrexafungerp (SCY-078) vs. Placebo in Subjects With Acute Vulvovaginal Candidiasis (VANISH 303)" at ClinicalTrials.gov
  • Clinical trial number NCT03987620 for "Efficacy and Safety of Oral Ibrexafungerp (SCY-078) vs. Placebo in Subjects With Acute Vulvovaginal Candidiasis (Vanish 306)" at ClinicalTrials.gov
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