AZD5991 sodium | CAS#2143010-83-5 | MCL-1 inhibitor

MedKoo Cat#: 126163 | Name: AZD5991 sodium

Description:

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

AZD5991 is a potent and selective Mcl-1 inhibitor for treatment of hematologic cancers. AZD5991 is a rationally designed macrocycle with sub-nanomolar affinity for Mcl-1. AZD5991 is an inhibitor of induced myeloid leukemia cell differentiation protein (myeloid cell leukemia-1; Mcl-1; Bcl2-L-3), with potential pro-apoptotic and antineoplastic activities. Upon administration, AZD5991 binds to Mcl-1, thereby preventing the binding of Mcl-1 to and inactivation of certain pro-apoptotic proteins, and promoting apoptosis of cells overexpressing Mcl-1.

Chemical Structure

AZD5991 sodium

CAS#2143061-85-0 (sodium)

Theoretical Analysis

MedKoo Cat#: 126163

Name: AZD5991 sodium

CAS#: 2143061-85-0 (sodium)

Chemical Formula: C35H33ClN5NaO3S2

Exact Mass: 0.0000

Molecular Weight: 694.24

Elemental Analysis: C, 60.55; H, 4.79; Cl, 5.11; N, 10.09; Na, 3.31; O, 6.91; S, 9.24

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

2143061-81-6 (free acid) 2143061-85-0 (sodium) 2143061-82-7 2143010-83-5

Synonym

AZD5991; AZD 5991; AZD-5991; AZD-5991 Racemate

IUPAC/Chemical Name

sodium (Z)-16-chloro-11,21,25,61-tetramethyl-11H,21H,61H-10-oxa-4,8-dithia-1(7,3)-indola-2(4,3),6(3,5)-dipyrazola-9(3,1)-naphthalenacyclotridecaphane-12-carboxylate

InChi Key

VAIMBJAMKYIIRT-UHFFFAOYSA-M

InChi Code

InChI=1S/C35H34ClN5O3S2.Na/c1-20-31-29(38-40(20)3)19-45-17-22-15-23(41(4)37-22)18-46-24-14-21-8-5-6-9-25(21)30(16-24)44-13-7-10-26-27-11-12-28(36)32(31)33(27)39(2)34(26)35(42)43;/h5-6,8-9,11-12,14-16H,7,10,13,17-19H2,1-4H3,(H,42,43);/q;+1/p-1

SMILES Code

O=C([O-])C1=C2CCCOC3=CC(SCC4=CC(CSCC5=NN(C(C)=C5C6=C(C=CC2=C6N1C)Cl)C)=NN4C)=CC7=CC=CC=C37.[Na+]

Appearance

To be determined

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 694.24 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

1: Desai P, Lonial S, Cashen A, Kamdar M, Flinn I, O'Brien S, Garcia JS, Korde N, Moslehi J, Wey M, Cheung P, Sharma S, Olabode D, Chen H, Ali Syed F, Liu M, Saeh J, Andrade-Campos M, Kadia TM, Blachly JS. A Phase 1 First-in-Human Study of the MCL-1 Inhibitor AZD5991 in Patients with Relapsed/Refractory Hematologic Malignancies. Clin Cancer Res. 2024 Nov 1;30(21):4844-4855. doi: 10.1158/1078-0432.CCR-24-0028. PMID: 39167622; PMCID: PMC11528199. 2: White MJ, Cheatham L, Wen S, Scarfe G, Cidado J, Reimer C, Hariparsad N, Jones RDO, Drew L, McGinnity DF, Vasalou C. A PKPD Case Study: Achieving Clinically Relevant Exposures of AZD5991 in Oncology Mouse Models. AAPS J. 2023 Jun 28;25(4):66. doi: 10.1208/s12248-023-00836-z. PMID: 37380821. 3: Zhang H, Nakauchi Y, Köhnke T, Stafford M, Bottomly D, Thomas R, Wilmot B, McWeeney SK, Majeti R, Tyner JW. Integrated analysis of patient samples identifies biomarkers for venetoclax efficacy and combination strategies in acute myeloid leukemia. Nat Cancer. 2020 Aug;1(8):826-839. doi: 10.1038/s43018-020-0103-x. Epub 2020 Aug 18. PMID: 33123685; PMCID: PMC7591155. 4: Liu S, Qiao X, Wu S, Gai Y, Su Y, Edwards H, Wang Y, Lin H, Taub JW, Wang G, Ge Y. c-Myc plays a critical role in the antileukemic activity of the Mcl-1-selective inhibitor AZD5991 in acute myeloid leukemia. Apoptosis. 2022 Dec;27(11-12):913-928. doi: 10.1007/s10495-022-01756-7. Epub 2022 Aug 9. PMID: 35943677. 5: Yang W, Cook S, Wu D. Pre-clinical Formulation Development of an in situ Meglumine Salt of AZD5991: A Novel Macrocyclic Mcl-1 Inhibitor. Pharm Res. 2023 Apr;40(4):977-988. doi: 10.1007/s11095-023-03503-2. Epub 2023 Apr 3. PMID: 37012536. 6: Wang Y, Wang D, Wang Y, Yang H, Wang G, Wu S. Synergistic activity and mechanism of cytarabine and MCL-1 inhibitor AZD5991 against acute myeloid leukemia. Neoplasma. 2023 Apr;70(2):287-293. doi: 10.4149/neo_2023_221217N1185. Epub 2023 Feb 23. PMID: 36812234. 7: Tron AE, Belmonte MA, Adam A, Aquila BM, Boise LH, Chiarparin E, Cidado J, Embrey KJ, Gangl E, Gibbons FD, Gregory GP, Hargreaves D, Hendricks JA, Johannes JW, Johnstone RW, Kazmirski SL, Kettle JG, Lamb ML, Matulis SM, Nooka AK, Packer MJ, Peng B, Rawlins PB, Robbins DW, Schuller AG, Su N, Yang W, Ye Q, Zheng X, Secrist JP, Clark EA, Wilson DM, Fawell SE, Hird AW. Discovery of Mcl-1-specific inhibitor AZD5991 and preclinical activity in multiple myeloma and acute myeloid leukemia. Nat Commun. 2018 Dec 17;9(1):5341. doi: 10.1038/s41467-018-07551-w. PMID: 30559424; PMCID: PMC6297231. 8: Li Y, Lee HH, Jiang VC, Che Y, McIntosh J, Jordan A, Vargas J, Zhang T, Yan F, Simmons ME, Wang W, Nie L, Yao Y, Jain P, Wang M, Liu Y. Potentiation of apoptosis in drug-resistant mantle cell lymphoma cells by MCL-1 inhibitor involves downregulation of inhibitor of apoptosis proteins. Cell Death Dis. 2023 Nov 2;14(11):714. doi: 10.1038/s41419-023-06233-w. PMID: 37919300; PMCID: PMC10622549. 9: Goliaei A, Woods HA, Tron AE, Belmonte MA, Secrist JP, Ferguson D, Drew L, Fretland AJ, Aldridge BB, Gibbons FD. Multiscale Model Identifies Improved Schedule for Treatment of Acute Myeloid Leukemia In Vitro With the Mcl-1 Inhibitor AZD5991. CPT Pharmacometrics Syst Pharmacol. 2020 Oct;9(10):561-570. doi: 10.1002/psp4.12552. Epub 2020 Sep 17. PMID: 32860732; PMCID: PMC7577016. 10: Balazs AYS, Carbajo RJ, Davies NL, Dong Y, Hird AW, Johannes JW, Lamb ML, McCoull W, Raubo P, Robb GR, Packer MJ, Chiarparin E. Correction to "Free Ligand 1D NMR Conformational Signatures To Enhance Structure Based Drug Design of a Mcl-1 Inhibitor (AZD5991) and Other Synthetic Macrocycles". J Med Chem. 2021 Mar 11;64(5):2849. doi: 10.1021/acs.jmedchem.1c00273. Epub 2021 Mar 1. Erratum for: J Med Chem. 2019 Nov 14;62(21):9418-9437. doi: 10.1021/acs.jmedchem.9b00716. PMID: 33646774.