Rezafungin acetate | CAS#1396640-59-7 | β-glucan synthase inhibitor

MedKoo Cat#: 461269 | Name: Rezafungin acetate

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Rezafungin (formerly CD101) is a new β-glucan synthase inhibitor that is chemically related with anidulafungin. Rezafungin is a novel echinocandin (form of antifungal) with enhanced stability and pharmacokinetics that achieves high plasma drug exposure and allows for once weekly dose administration. Rezafungin has been shown comparable to other echinocandins, with activity against Candida spp. and Aspergillus spp. including subsets of echinocandin-resistant Candida auris and azole-resistant Aspergillus isolates.

Chemical Structure

Rezafungin acetate

CAS#1631754-41-0 (acetate)

Theoretical Analysis

MedKoo Cat#: 461269

Name: Rezafungin acetate

CAS#: 1631754-41-0 (acetate)

Chemical Formula: C65H88N8O19

Exact Mass: 0.0000

Molecular Weight: 1285.46

Elemental Analysis: C, 60.73; H, 6.90; N, 8.72; O, 23.65

Price and Availability

Size	Price	Availability
5mg	USD 150.00	Ready to ship
10mg	USD 250.00	Ready to ship
25mg	USD 450.00	Ready to ship
50mg	USD 750.00	Ready to ship
100mg	USD 1,250.00	Ready to ship
200mg	USD 1,950.00	Ready to ship
1g	USD 4,650.00	2 Weeks
2g	USD 6,850.00	2 Weeks

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Related CAS #

1631754-41-0 (acetate) 1396640-59-7 (cation) 1396640-60-0 (TFA) Rezafungin chloride

Synonym

Rezafungin; Biafungin; SP-3025; SP 3025; SP3025; CD101; CD-101; CD 101.

IUPAC/Chemical Name

2-(((2R,9S,11R,12R,14aS,15S,16S,20S,25aS)-23-((1S,2S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl)-2,11,15-trihydroxy-6,20-bis((R)-1-hydroxyethyl)-16-methyl-5,8,14,19,22,25-hexaoxo-9-(4''-(pentyloxy)-[1,1':4',1''-terphenyl]-4-carboxamido)tetracosahydro-1H-dipyrrolo[2,1-c:2',1'-l][1,4,7,10,13,16]hexaazacyclohenicosin-12-yl)oxy)-N,N,N-trimethylethan-1-aminium acetate

InChi Key

MXMWJAPNUIKPGF-DPHATNFGSA-N

InChi Code

InChI=1S/C63H84N8O17.C2H4O2/c1-8-9-10-28-87-45-25-21-40(22-26-45)38-13-11-37(12-14-38)39-15-17-42(18-16-39)56(80)64-46-31-48(76)61(88-29-27-71(5,6)7)68-60(84)52-53(77)34(2)32-70(52)63(86)50(36(4)73)66-59(83)51(55(79)54(78)41-19-23-43(74)24-20-41)67-58(82)47-30-44(75)33-69(47)62(85)49(35(3)72)65-57(46)81;1-2(3)4/h11-26,34-36,44,46-55,61,72-73,75-79H,8-10,27-33H2,1-7H3,(H5-,64,65,66,67,68,74,80,81,82,83,84);1H3,(H,3,4)/t34-,35+,36+,44+,46-,47-,48+,49?,50-,51?,52-,53-,54-,55-,61+;/m0./s1

SMILES Code

CCCCCOC1=CC=C(C2=CC=C(C=C2)C3=CC=C(C=C3)C(N[C@H]4C[C@@H](O)[C@H](NC([C@@H]5[C@@H](O)[C@@H](C)CN5C([C@@H](NC(C(NC([C@@H]6C[C@@H](O)CN6C(C(NC4=O)[C@@H](C)O)=O)=O)[C@H](O)[C@@H](O)C7=CC=C(O)C=C7)=O)[C@@H](C)O)=O)=O)OCC[N+](C)(C)C)=O)C=C1.O=C(C)[O-]

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Rezafungin is considered the first molecule of the new generation of long-acting echinocandins. It has several advantages over the already approved by the Food and Drug Administration (FDA) echinocandins as it has better tissue penetration, better pharmacokinetic/phamacodynamic (PK/PD) pharmacometrics, and a good safety profile. It is much more stable in solution than the older echinocandins, making it more flexible in terms of dosing, storage, and manufacturing. These properties would allow rezafungin to be administered once-weekly (intravenous) and to be potentially administered topically and subcutaneously. In addition, higher dose regimens were tested with no evidence of toxic effect. This will eventually prevent (or reduce) the selection of resistant strains. Rezafungin also has several similarities with older echinocandins as they share the same in vitro behavior (very similar Minimum Inhibitory Concentration required to inhibit the growth of 50% of the isolates (MIC50) and half enzyme maximal inhibitory concentration 50% (IC50)) and spectrum, the same target, and the same mechanisms of resistance. The selection of FKS mutants occurred at similar frequency for rezafungin than for anidulafungin and caspofungin.

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#A23T03K06

QC Data

View QC data: current batch, Lot#A23T03K06

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Rezafungin (formerly CD101) is a β-glucan synthase inhibitor.

In vitro activity:

This study compared killing activities of anidulafungin, caspofungin, micafungin, and rezafungin against 13 isolates representing four C. auris clades (South Asian n = 3; East Asian n = 3; South African n = 3; South American n = 4, of which two were of environmental origin). In 50% serum, rezafungin at ≥1-≥ 8 mg/L produced killing against all four clades. The next generation echinocandin, rezafungin, showed the same or better activity at clinically attainable trough concentration regardless of media, compared with anidulafungin, caspofungin, and micafungin against all four tested C. auris clades. Reference: Microorganisms. 2021 Apr 16;9(4):863. https://pubmed.ncbi.nlm.nih.gov/33923783/

In vivo activity:

Herein, the in vivo effects of rezafungin against Pneumocystis murina pneumonia were evaluated in immunosuppressed mouse models of prophylaxis and treatment using microscopy and qPCR assessments. Rezafungin administered for 4 weeks prevented P. murina from developing infection after rezafungin was discontinued. In the treatment model, immunosuppressed mice with P. murina pneumonia were treated with rezafungin 20 mg/kg 3×/week intraperitoneally for 2, 4, 6 and 8 weeks. Treatment with rezafungin for 8 weeks resulted in elimination of P. murina. Collectively, these studies showed that rezafungin could both prevent infection and eliminate P. murina from the lungs of mice. Reference: J Fungi (Basel). 2021 Sep 11;7(9):747. https://pubmed.ncbi.nlm.nih.gov/34575785/

	Solvent	mg/mL	mM
Solubility
	DMSO	230.0	178.92

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 1,285.46 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Kovács R, Tóth Z, Locke JB, Forgács L, Kardos G, Nagy F, Borman AM, Majoros L. Comparison of In Vitro Killing Activity of Rezafungin, Anidulafungin, Caspofungin, and Micafungin against Four Candida auris Clades in RPMI-1640 in the Absence and Presence of Human Serum. Microorganisms. 2021 Apr 16;9(4):863. doi: 10.3390/microorganisms9040863. PMID: 33923783; PMCID: PMC8073555. 2. Helleberg M, Jørgensen KM, Hare RK, Datcu R, Chowdhary A, Arendrup MC. Rezafungin In Vitro Activity against Contemporary Nordic Clinical Candida Isolates and Candida auris Determined by the EUCAST Reference Method. Antimicrob Agents Chemother. 2020 Mar 24;64(4):e02438-19. doi: 10.1128/AAC.02438-19. PMID: 32015032; PMCID: PMC7179313. 3. Cushion MT, Ashbaugh A. The Long-Acting Echinocandin, Rezafungin, Prevents Pneumocystis Pneumonia and Eliminates Pneumocystis from the Lungs in Prophylaxis and Murine Treatment Models. J Fungi (Basel). 2021 Sep 11;7(9):747. doi: 10.3390/jof7090747. PMID: 34575785; PMCID: PMC8468546. 4. Miesel L, Cushion MT, Ashbaugh A, Lopez SR, Ong V. Efficacy of Rezafungin in Prophylactic Mouse Models of Invasive Candidiasis, Aspergillosis, and Pneumocystis Pneumonia. Antimicrob Agents Chemother. 2021 Feb 17;65(3):e01992-20. doi: 10.1128/AAC.01992-20. PMID: 33318018; PMCID: PMC8092522.

In vitro protocol:

In vivo protocol:

1. Cushion MT, Ashbaugh A. The Long-Acting Echinocandin, Rezafungin, Prevents Pneumocystis Pneumonia and Eliminates Pneumocystis from the Lungs in Prophylaxis and Murine Treatment Models. J Fungi (Basel). 2021 Sep 11;7(9):747. doi: 10.3390/jof7090747. PMID: 34575785; PMCID: PMC8468546. 2. Miesel L, Cushion MT, Ashbaugh A, Lopez SR, Ong V. Efficacy of Rezafungin in Prophylactic Mouse Models of Invasive Candidiasis, Aspergillosis, and Pneumocystis Pneumonia. Antimicrob Agents Chemother. 2021 Feb 17;65(3):e01992-20. doi: 10.1128/AAC.01992-20. PMID: 33318018; PMCID: PMC8092522.

1: Alsowaida YS, Alamer A, Thabit AK, Almulhim AS, Aleissa MM, Kalbasi A, Eljaaly K, Almangour TA, Erstad BL. Echinocandin exposures in obese patients: A scoping review and clinical perspectives. Am J Health Syst Pharm. 2023 Jan 21:zxad021. doi: 10.1093/ajhp/zxad021. Epub ahead of print. PMID: 36680786. 2: Sharma N, Wani SN, Behl T, Singh S, Zahoor I, Sehgal A, Bhatia S, Al-Harrasi A, Aleya L, Bungau S. Focusing COVID-19-associated mucormycosis: a major threat to immunocompromised COVID-19. Environ Sci Pollut Res Int. 2023 Jan;30(4):9164-9183. doi: 10.1007/s11356-022-24032-2. Epub 2022 Dec 1. PMID: 36454526; PMCID: PMC9713750. 3: Thompson GR 3rd, Soriano A, Cornely OA, Kullberg BJ, Kollef M, Vazquez J, Honore PM, Bassetti M, Pullman J, Chayakulkeeree M, Poromanski I, Dignani C, Das AF, Sandison T, Pappas PG; ReSTORE trial investigators. Rezafungin versus caspofungin for treatment of candidaemia and invasive candidiasis (ReSTORE): a multicentre, double-blind, double-dummy, randomised phase 3 trial. Lancet. 2023 Jan 7;401(10370):49-59. doi: 10.1016/S0140-6736(22)02324-8. Epub 2022 Nov 25. PMID: 36442484. 4: Guinea J. Rezafungin and invasive candida infections: a new game changing antifungal? Lancet. 2023 Jan 7;401(10370):3-5. doi: 10.1016/S0140-6736(22)02371-6. Epub 2022 Nov 25. PMID: 36442483. 5: Treviño-Rangel RJ, González GM, Montoya AM, Rojas OC, Elizondo-Zertuche M, Álvarez-Villalobos NA. Recent Antifungal Pipeline Developments against Candida auris: A Systematic Review. J Fungi (Basel). 2022 Oct 28;8(11):1144. doi: 10.3390/jof8111144. PMID: 36354911; PMCID: PMC9695453. 6: Stafylidis C, Diamantopoulos P, Athanasoula E, Solomou E, Anastasopoulou A. Acute Lymphoblastic Leukemia and Invasive Mold Infections: A Challenging Field. J Fungi (Basel). 2022 Oct 26;8(11):1127. doi: 10.3390/jof8111127. PMID: 36354894; PMCID: PMC9696423. 7: Arendrup MC, Arikan-Akdagli S, Castanheira M, Guinea J, Locke JB, Meletiadis J, Zaragoza O. Multicentre validation of a modified EUCAST MIC testing method and development of associated epidemiologic cut-off (ECOFF) values for rezafungin. J Antimicrob Chemother. 2022 Dec 23;78(1):185-195. doi: 10.1093/jac/dkac373. PMID: 36329639. 8: Li H, Cao YB, Yan TH, Jiang YY, Yang F. Aneuploidy underlies paradoxical growth of rezafungin and enables cross-tolerance to echinocandins in Candida albicans. J Infect. 2022 Dec;85(6):702-769. doi: 10.1016/j.jinf.2022.09.028. Epub 2022 Oct 1. PMID: 36191677. 9: Siopi M, Papadopoulos A, Spiliopoulou A, Paliogianni F, Abou-Chakra N, Arendrup MC, Damoulari C, Tsioulos G, Giannitsioti E, Frantzeskaki F, Tsangaris I, Pournaras S, Meletiadis J. Pan-Echinocandin Resistant C. parapsilosis Harboring an F652S Fks1 Alteration in a Patient with Prolonged Echinocandin Therapy. J Fungi (Basel). 2022 Sep 1;8(9):931. doi: 10.3390/jof8090931. PMID: 36135656; PMCID: PMC9502558. 10: 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. 11: Jo J, Tran TT, Beyda ND, Simmons D, Hendrickson JA, Almutairi MS, Alnezary FS, Gonzales-Luna AJ, Septimus EJ, Garey KW. Development of the invasive candidiasis discharge [I Can discharge] model: a mixed methods analysis. Eur J Clin Microbiol Infect Dis. 2022 Oct;41(10):1207-1213. doi: 10.1007/s10096-022-04473-w. Epub 2022 Aug 25. PMID: 36002777; PMCID: PMC9489576. 12: 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. 13: Carvalhaes CG, Rhomberg PR, Pfaller MA, Locke JB, Castanheira M. Evaluation of the Post-Antifungal Effect of Rezafungin and Micafungin against Candida albicans, Candida parapsilosis and Candida glabrata. Mycoses. 2022 Nov;65(11):1040-1044. doi: 10.1111/myc.13490. Epub 2022 Jul 18. PMID: 35778886. 14: Pechacek J, Yakubu I, Vissichelli NC, Bruno D, Morales MK. Successful expanded access use of rezafungin, a novel echinocandin, to eradicate refractory invasive candidiasis in a liver transplant recipient. J Antimicrob Chemother. 2022 Aug 25;77(9):2571-2573. doi: 10.1093/jac/dkac206. PMID: 35770840. 15: Domingos EL, Vilhena RO, Santos JMMF, Fachi MM, Böger B, Adam LM, Tonin FS, Pontarolo R. Comparative efficacy and safety of systemic antifungal agents for candidemia: a systematic review with network meta-analysis and multicriteria acceptability analyses. Int J Antimicrob Agents. 2022 Aug;60(2):106614. doi: 10.1016/j.ijantimicag.2022.106614. Epub 2022 Jun 9. PMID: 35691603. 16: 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. 17: Adeel A, Qu MD, Siddiqui E, Levitz SM, Ellison RT 3rd. Expanded Access Use of Rezafungin for Salvage Therapy of Invasive Candida glabrata Infection: A Case Report. Open Forum Infect Dis. 2021 Aug 28;8(11):ofab431. doi: 10.1093/ofid/ofab431. PMID: 35559122; PMCID: PMC9088506. 18: Khalfe Y, Rosen T. Future Fungal Fighters in Dermatology: Novel Antifungal Drug Pipeline. J Drugs Dermatol. 2022 May 1;21(5):496-501. doi: 10.36849/JDD.6373. PMID: 35533026. 19: Gu K, Ruff D, Key C, Thompson M, Jiang S, Sandison T, Flanagan S. A phase I randomized, double-blind, single subcutaneous dose escalation study to determine the safety, tolerability, and pharmacokinetics of rezafungin in healthy adult subjects. Clin Transl Sci. 2022 Jul;15(7):1592-1598. doi: 10.1111/cts.13286. Epub 2022 May 4. PMID: 35439347; PMCID: PMC9283735. 20: Jaber QZ, Logviniuk D, Yona A, Fridman M. Echinocandins Localized to the Target-Harboring Cell Surface Are Not Degraded but Those Entering the Vacuole Are. ACS Chem Biol. 2022 May 20;17(5):1155-1163. doi: 10.1021/acschembio.2c00060. Epub 2022 Apr 11. PMID: 35404573; PMCID: PMC9127807.