Ibrexafungerp citrate|CAS 1965291-08-0|DC Chemicals

Cas No.:	1965291-08-0
Chemical Name:	Ibrexafungerp citrate
Synonyms:	Ibrexafungerp citrate;M4NU2SDX3E;Ibrexafungerp citrate (USAN);Ibrexafungerp citrate [USAN];D11545
SMILES:	O1C[C@@]2(C)[C@H]([C@@H](C[C@]3(C1)C1=CC[C@@]4(C)[C@H](C(=O)O)[C@@](C)([C@H](C)C(C)C)CC[C@]4(C)[C@H]1CC[C@H]32)N1C(C2C=CN=CC=2)=NC=N1)OC[C@@](C)(C(C)(C)C)N.OC(C(=O)O)(CC(=O)O)CC(=O)O
Formula:	C₅₀H₇₅N₅O₁₁
M.Wt:	922.157414674759
Purity:	>97%
Sotrage:	2 years -20°C Powder, 2 weeks 4°C in DMSO, 6 months -80°C in DMSO
Publication:	1: Sucher AJ, Thai A, Tran C, Mantena N, Noronha A, Chahine EB. Ibrexafungerp: A new triterpenoid antifungal. Am J Health Syst Pharm. 2022 Sep 9:zxac256. doi: 10.1093/ajhp/zxac256. Epub ahead of print. PMID: 36083109. 2: Grant LM, Orenstein R. Treatment of Recurrent Vulvovaginal Candidiasis With Ibrexafungerp. J Investig Med High Impact Case Rep. 2022 Jan- Dec;10:23247096221123144. doi: 10.1177/23247096221123144. PMID: 36059275; PMCID: PMC9445446. 3: Díaz-García J, Gómez A, Machado M, Alcalá L, Reigadas E, Sánchez-Carrillo C, Pérez-Ayala A, Gómez-García De La Pedrosa E, González-Romo F, Cuétara MS, García-Esteban C, Quiles-Melero I, Zurita ND, Muñoz-Algarra M, Durán-Valle MT, Sánchez-García A, Muñoz P, Escribano P, Guinea J; CANDIMAD Study Group. Blood and intra-abdominal Candida spp. from a multicentre study conducted in Madrid using EUCAST: emergence of fluconazole resistance in Candida parapsilosis, low echinocandin resistance and absence of Candida auris. J Antimicrob Chemother. 2022 Aug 29:dkac288. doi: 10.1093/jac/dkac288. Epub ahead of print. PMID: 36031723. 4: Wiederhold NP. Pharmacodynamics, Mechanisms of Action and Resistance, and Spectrum of Activity of New Antifungal Agents. J Fungi (Basel). 2022 Aug 16;8(8):857. doi: 10.3390/jof8080857. PMID: 36012845; PMCID: PMC9410397. 5: Oteseconazole (Vivjoa) for recurrent vulvovaginal candidiasis. Med Lett Drugs Ther. 2022 Aug 8;64(1656):124-126. PMID: 35921077. 6: Díaz-García J, Gómez A, Alcalá L, Reigadas E, Sánchez-Carrillo C, Pérez-Ayala A, Gómez-García de la Pedrosa E, González-Romo F, Merino-Amador P, Cuétara MS, García-Esteban C, Quiles-Melero I, Zurita ND, Muñoz-Algarra M, Sánchez-Romero I, Durán-Valle MT, Sánchez-García A, Alcoceba E, Muñoz P, Escribano P, Guinea J; CANDIMAD study group. Evidence of Fluconazole-Resistant Candida parapsilosis Genotypes Spreading across Hospitals Located in Madrid, Spain and Harboring the Y132F ERG11p Substitution. Antimicrob Agents Chemother. 2022 Aug 16;66(8):e0071022. doi: 10.1128/aac.00710-22. Epub 2022 Jul 19. PMID: 35852369; PMCID: PMC9380585. 7: Logan A, Wolfe A, Williamson JC. Antifungal Resistance and the Role of New Therapeutic Agents. Curr Infect Dis Rep. 2022;24(9):105-116. doi: 10.1007/s11908-022-00782-5. Epub 2022 Jul 5. PMID: 35812838; PMCID: PMC9255453. 8: Hoenigl M, Sprute R, Arastehfar A, Perfect JR, Lass-Flörl C, Bellmann R, Prattes J, Thompson GR 3rd, Wiederhold NP, Al Obaidi MM, Willinger B, Arendrup MC, Koehler P, Oliverio M, Egger M, Schwartz IS, Cornely OA, Pappas PG, Krause R. Invasive candidiasis: investigational drugs in the clinical development pipeline and mechanisms of action. Expert Opin Investig Drugs. 2022 Aug;31(8):795-812. doi: 10.1080/13543784.2022.2086120. Epub 2022 Jun 15. PMID: 35657026; PMCID: PMC9339492. 9: Quindós G, Miranda-Cadena K, San-Millán R, Borroto-Esoda K, Cantón E, Linares-Sicilia MJ, Hamprecht A, Montesinos I, Tortorano AM, Prigitano A, Vidal- García M, Marcos-Arias C, Guridi A, Sanchez-Reus F, Machuca-Bárcena J, Rodríguez-Iglesias MA, Martín-Mazuelos E, Castro-Méndez C, López-Soria L, Ruiz- Gaitán A, Fernandez-Rivero M, Lorenzo D, Capilla J, Rezusta A, Pemán J, Guarro J, Pereira J, Pais C, Romeo O, Ezpeleta G, Jauregizar N, Angulo D, Eraso E. In Vitro Antifungal Activity of Ibrexafungerp (SCY-078) Against Contemporary Blood Isolates From Medically Relevant Species of Candida: A European Study. Front Cell Infect Microbiol. 2022 May 16;12:906563. doi: 10.3389/fcimb.2022.906563. PMID: 35651755; PMCID: PMC9149255. 10: Daraskevicius J, Petraitis V, Davainis L, Zucenka A. The Feasibility of Ibrexafungerp for the Treatment of Fungal Infections in Patients with Hematological Malignancies. J Fungi (Basel). 2022 Apr 23;8(5):440. doi: 10.3390/jof8050440. PMID: 35628696; PMCID: PMC9144376.

Description:

Ibrexafungerp citrate is a triterpenoid antifungal. Similarly to echinocandins, it inhibits the synthesis of 1,3-β-d-glucan. However, it binds to a different site on the enzyme than echinocandins, resulting in limited cross-resistance. Ibrexafungerp exerts concentration-dependent fungicidal activity against Candida species and retains in vitro activity against most fluconazole-resistant strains.

References:

1: Sucher AJ, Thai A, Tran C, Mantena N, Noronha A, Chahine EB. Ibrexafungerp: A new triterpenoid antifungal. Am J Health Syst Pharm. 2022 Sep 9:zxac256. doi: 10.1093/ajhp/zxac256. Epub ahead of print. PMID: 36083109. 2: Grant LM, Orenstein R. Treatment of Recurrent Vulvovaginal Candidiasis With Ibrexafungerp. J Investig Med High Impact Case Rep. 2022 Jan- Dec;10:23247096221123144. doi: 10.1177/23247096221123144. PMID: 36059275; PMCID: PMC9445446. 3: Díaz-García J, Gómez A, Machado M, Alcalá L, Reigadas E, Sánchez-Carrillo C, Pérez-Ayala A, Gómez-García De La Pedrosa E, González-Romo F, Cuétara MS, García-Esteban C, Quiles-Melero I, Zurita ND, Muñoz-Algarra M, Durán-Valle MT, Sánchez-García A, Muñoz P, Escribano P, Guinea J; CANDIMAD Study Group. Blood and intra-abdominal Candida spp. from a multicentre study conducted in Madrid using EUCAST: emergence of fluconazole resistance in Candida parapsilosis, low echinocandin resistance and absence of Candida auris. J Antimicrob Chemother. 2022 Aug 29:dkac288. doi: 10.1093/jac/dkac288. Epub ahead of print. PMID: 36031723. 4: Wiederhold NP. Pharmacodynamics, Mechanisms of Action and Resistance, and Spectrum of Activity of New Antifungal Agents. J Fungi (Basel). 2022 Aug 16;8(8):857. doi: 10.3390/jof8080857. PMID: 36012845; PMCID: PMC9410397. 5: Oteseconazole (Vivjoa) for recurrent vulvovaginal candidiasis. Med Lett Drugs Ther. 2022 Aug 8;64(1656):124-126. PMID: 35921077. 6: Díaz-García J, Gómez A, Alcalá L, Reigadas E, Sánchez-Carrillo C, Pérez-Ayala A, Gómez-García de la Pedrosa E, González-Romo F, Merino-Amador P, Cuétara MS, García-Esteban C, Quiles-Melero I, Zurita ND, Muñoz-Algarra M, Sánchez-Romero I, Durán-Valle MT, Sánchez-García A, Alcoceba E, Muñoz P, Escribano P, Guinea J; CANDIMAD study group. Evidence of Fluconazole-Resistant Candida parapsilosis Genotypes Spreading across Hospitals Located in Madrid, Spain and Harboring the Y132F ERG11p Substitution. Antimicrob Agents Chemother. 2022 Aug 16;66(8):e0071022. doi: 10.1128/aac.00710-22. Epub 2022 Jul 19. PMID: 35852369; PMCID: PMC9380585. 7: Logan A, Wolfe A, Williamson JC. Antifungal Resistance and the Role of New Therapeutic Agents. Curr Infect Dis Rep. 2022;24(9):105-116. doi: 10.1007/s11908-022-00782-5. Epub 2022 Jul 5. PMID: 35812838; PMCID: PMC9255453. 8: Hoenigl M, Sprute R, Arastehfar A, Perfect JR, Lass-Flörl C, Bellmann R, Prattes J, Thompson GR 3rd, Wiederhold NP, Al Obaidi MM, Willinger B, Arendrup MC, Koehler P, Oliverio M, Egger M, Schwartz IS, Cornely OA, Pappas PG, Krause R. Invasive candidiasis: investigational drugs in the clinical development pipeline and mechanisms of action. Expert Opin Investig Drugs. 2022 Aug;31(8):795-812. doi: 10.1080/13543784.2022.2086120. Epub 2022 Jun 15. PMID: 35657026; PMCID: PMC9339492. 9: Quindós G, Miranda-Cadena K, San-Millán R, Borroto-Esoda K, Cantón E, Linares-Sicilia MJ, Hamprecht A, Montesinos I, Tortorano AM, Prigitano A, Vidal- García M, Marcos-Arias C, Guridi A, Sanchez-Reus F, Machuca-Bárcena J, Rodríguez-Iglesias MA, Martín-Mazuelos E, Castro-Méndez C, López-Soria L, Ruiz- Gaitán A, Fernandez-Rivero M, Lorenzo D, Capilla J, Rezusta A, Pemán J, Guarro J, Pereira J, Pais C, Romeo O, Ezpeleta G, Jauregizar N, Angulo D, Eraso E. In Vitro Antifungal Activity of Ibrexafungerp (SCY-078) Against Contemporary Blood Isolates From Medically Relevant Species of Candida: A European Study. Front Cell Infect Microbiol. 2022 May 16;12:906563. doi: 10.3389/fcimb.2022.906563. PMID: 35651755; PMCID: PMC9149255. 10: Daraskevicius J, Petraitis V, Davainis L, Zucenka A. The Feasibility of Ibrexafungerp for the Treatment of Fungal Infections in Patients with Hematological Malignancies. J Fungi (Basel). 2022 Apr 23;8(5):440. doi: 10.3390/jof8050440. PMID: 35628696; PMCID: PMC9144376.

MSDS

COA

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2018-0101

Cat. No.	Product name	Field of application
DC46180	Aureobasidin A(Basifungin)	Aureobasidin A (Basifungin), a cyclic depsipetide, is an antifungal antibiotic. Aureobasidin A (Basifungin) A is an inhibitor of the inositolphosphorylceramide synthase AUR1.
DC45537	FR179642	FR179642 is a key intermediate in the synthesis of the echinocandin antifungal Micafungin. FR179642 is the cyclic peptide nucleus of the echinocandin-like antifungal lipopeptide FR901379.
DC44113	Ibrexafungerp citrate	Ibrexafungerp citrate is a triterpenoid antifungal. Similarly to echinocandins, it inhibits the synthesis of 1,3-β-d-glucan. However, it binds to a different site on the enzyme than echinocandins, resulting in limited cross-resistance. Ibrexafungerp exerts concentration-dependent fungicidal activity against Candida species and retains in vitro activity against most fluconazole-resistant strains.
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DC28240	Alexidine dihydrochloride	Alexidine dihydrochloride is an anticancer agent that targets a mitochondrial tyrosine phosphatase, PTPMT1, in mammalian cells and causes mitochondrial apoptosis. Alexidine dihydrochloride has antifungal and antibiofilm activity against a diverse range of fungal pathogens.
DC28220	Rezafungin	Rezafungin (Biafungin) is a next-generation, broad-spectrum, and long-lasting echinocandin. Rezafungin shows potent antifungal activity against Candida spp., Aspergillus spp., and Pneumocystis spp..