ABBV-744
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MedKoo CAT#: 206981

CAS#: 2138861-99-9

Description: ABBV-744 is a BDII-selective BET bromodomain inhibitor that is being investigated to treat AML and metastic castration-resistant prostate cancer.


Chemical Structure

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ABBV-744
CAS# 2138861-99-9

Theoretical Analysis

MedKoo Cat#: 206981
Name: ABBV-744
CAS#: 2138861-99-9
Chemical Formula: C28H30FN3O4
Exact Mass: 491.222
Molecular Weight: 491.5634
Elemental Analysis: C, 68.42; H, 6.15; F, 3.86; N, 8.55; O, 13.02

Price and Availability

Size Price Availability Quantity
10.0mg USD 190.0 Same Day
25.0mg USD 350.0 Same Day
50.0mg USD 550.0 Same Day
100.0mg USD 950.0 Same Day
200.0mg USD 1450.0 Same Day
500.0mg USD 2650.0 Same Day
1.0g USD 3850.0 Same Day
2.0g USD 6450.0 Same Day
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Synonym: ABBV-744; ABBV 744; ABBV744.

IUPAC/Chemical Name: N-ethyl-4-(2-(4-fluoro-2,6-dimethylphenoxy)-5-(2-hydroxypropan-2-yl)phenyl)-6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridine-2-carboxamide

InChi Key: OEDSFMUSNZDJFD-UHFFFAOYSA-N

InChi Code: InChI=1S/C28H30FN3O4/c1-7-30-26(33)22-13-20-21(14-32(6)27(34)24(20)31-22)19-12-17(28(4,5)35)8-9-23(19)36-25-15(2)10-18(29)11-16(25)3/h8-14,31,35H,7H2,1-6H3,(H,30,33)

SMILES Code: O=C(C(N1)=CC(C(C2=CC(C(C)(O)C)=CC=C2OC3=C(C)C=C(F)C=C3C)=CN4C)=C1C4=O)NCC

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: >2 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

Biological target: ABBV-744 is a highly BDII-selective BET bromodomain inhibitor.
In vitro activity: Compound 46 (ABBV744) was tested for binding against the first and second bromodomains of BRD2, BRD3, and BRDt in the TR-FRET binding assay and displayed similarly potent and selective binding to that observed with BRD4 (Table 9). Whereas potent dual-bromodomain BET inhibitors such as 5 show potent antiproliferative effects against a wide range of cancer cell lines,46 shows substantially higher relative potency against cell lines derived from prostate cancer and AML, implying that BD1 inhibition is not required to inhibit proliferation in a subset of cancer indications. Reference: J Med Chem. 2020 May 28;63(10):5585-5623. https://pubmed.ncbi.nlm.nih.gov/32324999/
In vivo activity: In a mouse xenograft model using LNCaP cells, treatment with 4.7 mg kg−1 ABBV-744 (1/16 of the maximum tolerated dose (MTD)) caused a delay in tumour growth that was equivalent to ABBV-075 treatment at the MTD dose of 1 mg kg−1 (Fig. 4a). Comparing efficacious exposure levels of ABBV-744 in LNCaP tumour-bearing mice (4.7 mg kg−1; area under the curve, 1.1 μg h ml−1) and MTD (75 mg kg−1; area under the curve, 13.1 μg h ml−1) demonstrated that ABBV-744 was able to produce significant antitumour activity at 1/12 of the highest tolerable exposure of ABBV-744 (Extended Data Fig. 8a). The activity exhibited by ABBV-744 at 1/16 of the MTD of ABBV-744 was superior to the activities achieved using JQ1 and iBET at their respective MTDs or, in the case of RVX-208, at the highest feasible dose in this model (Extended Data Fig. 8b, c). Similarly, ABBV-744 at 1/16 MTD also displayed equivalent or better antitumour activity compared with ABBV-075 at MTD in the enzalutamide-resistant MDA-PCa-2b xenograft model (Fig. 4b). Reference: Nature. 2020 Feb;578(7794):306-310. https://pubmed.ncbi.nlm.nih.gov/31969702/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 33.57 68.29
DMSO:PBS (pH 7.2) (1:3) 0.25 0.51
DMF 30.0 61.03

Preparing Stock Solutions

The following data is based on the product molecular weight 491.5634 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.

Recalculate based on batch purity %
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. Fakhar Z, Khan S, AlOmar SY, Alkhuriji A, Ahmad A. ABBV-744 as a potential inhibitor of SARS-CoV-2 main protease enzyme against COVID-19. Sci Rep. 2021 Jan 8;11(1):234. doi: 10.1038/s41598-020-79918-3. PMID: 33420186; PMCID: PMC7794216. 2. Sheppard GS, Wang L, Fidanze SD, Hasvold LA, Liu D, Pratt JK, Park CH, Longenecker K, Qiu W, Torrent M, Kovar PJ, Bui M, Faivre E, Huang X, Lin X, Wilcox D, Zhang L, Shen Y, Albert DH, Magoc TJ, Rajaraman G, Kati WM, McDaniel KF. Discovery of N-Ethyl-4-[2-(4-fluoro-2,6-dimethyl-phenoxy)-5-(1-hydroxy-1-methyl-ethyl)phenyl]-6-methyl-7-oxo-1H-pyrrolo[2,3-c]pyridine-2-carboxamide (ABBV-744), a BET Bromodomain Inhibitor with Selectivity for the Second Bromodomain. J Med Chem. 2020 May 28;63(10):5585-5623. doi: 10.1021/acs.jmedchem.0c00628. Epub 2020 May 7. PMID: 32324999. 3. Sheppard GS, Wang L, Fidanze SD, Hasvold LA, Liu D, Pratt JK, Park CH, Longenecker K, Qiu W, Torrent M, Kovar PJ, Bui M, Faivre E, Huang X, Lin X, Wilcox D, Zhang L, Shen Y, Albert DH, Magoc TJ, Rajaraman G, Kati WM, McDaniel KF. Discovery of N-Ethyl-4-[2-(4-fluoro-2,6-dimethyl-phenoxy)-5-(1-hydroxy-1-methyl-ethyl)phenyl]-6-methyl-7-oxo-1H-pyrrolo[2,3-c]pyridine-2-carboxamide (ABBV-744), a BET Bromodomain Inhibitor with Selectivity for the Second Bromodomain. J Med Chem. 2020 May 28;63(10):5585-5623. doi: 10.1021/acs.jmedchem.0c00628. Epub 2020 May 7. PMID: 32324999. 4. Faivre EJ, McDaniel KF, Albert DH, Mantena SR, Plotnik JP, Wilcox D, Zhang L, Bui MH, Sheppard GS, Wang L, Sehgal V, Lin X, Huang X, Lu X, Uziel T, Hessler P, Lam LT, Bellin RJ, Mehta G, Fidanze S, Pratt JK, Liu D, Hasvold LA, Sun C, Panchal SC, Nicolette JJ, Fossey SL, Park CH, Longenecker K, Bigelow L, Torrent M, Rosenberg SH, Kati WM, Shen Y. Selective inhibition of the BD2 bromodomain of BET proteins in prostate cancer. Nature. 2020 Feb;578(7794):306-310. doi: 10.1038/s41586-020-1930-8. Epub 2020 Jan 22. PMID: 31969702.
In vitro protocol: 1. Fakhar Z, Khan S, AlOmar SY, Alkhuriji A, Ahmad A. ABBV-744 as a potential inhibitor of SARS-CoV-2 main protease enzyme against COVID-19. Sci Rep. 2021 Jan 8;11(1):234. doi: 10.1038/s41598-020-79918-3. PMID: 33420186; PMCID: PMC7794216. 2. Sheppard GS, Wang L, Fidanze SD, Hasvold LA, Liu D, Pratt JK, Park CH, Longenecker K, Qiu W, Torrent M, Kovar PJ, Bui M, Faivre E, Huang X, Lin X, Wilcox D, Zhang L, Shen Y, Albert DH, Magoc TJ, Rajaraman G, Kati WM, McDaniel KF. Discovery of N-Ethyl-4-[2-(4-fluoro-2,6-dimethyl-phenoxy)-5-(1-hydroxy-1-methyl-ethyl)phenyl]-6-methyl-7-oxo-1H-pyrrolo[2,3-c]pyridine-2-carboxamide (ABBV-744), a BET Bromodomain Inhibitor with Selectivity for the Second Bromodomain. J Med Chem. 2020 May 28;63(10):5585-5623. doi: 10.1021/acs.jmedchem.0c00628. Epub 2020 May 7. PMID: 32324999.
In vivo protocol: 1. Sheppard GS, Wang L, Fidanze SD, Hasvold LA, Liu D, Pratt JK, Park CH, Longenecker K, Qiu W, Torrent M, Kovar PJ, Bui M, Faivre E, Huang X, Lin X, Wilcox D, Zhang L, Shen Y, Albert DH, Magoc TJ, Rajaraman G, Kati WM, McDaniel KF. Discovery of N-Ethyl-4-[2-(4-fluoro-2,6-dimethyl-phenoxy)-5-(1-hydroxy-1-methyl-ethyl)phenyl]-6-methyl-7-oxo-1H-pyrrolo[2,3-c]pyridine-2-carboxamide (ABBV-744), a BET Bromodomain Inhibitor with Selectivity for the Second Bromodomain. J Med Chem. 2020 May 28;63(10):5585-5623. doi: 10.1021/acs.jmedchem.0c00628. Epub 2020 May 7. PMID: 32324999. 2. Faivre EJ, McDaniel KF, Albert DH, Mantena SR, Plotnik JP, Wilcox D, Zhang L, Bui MH, Sheppard GS, Wang L, Sehgal V, Lin X, Huang X, Lu X, Uziel T, Hessler P, Lam LT, Bellin RJ, Mehta G, Fidanze S, Pratt JK, Liu D, Hasvold LA, Sun C, Panchal SC, Nicolette JJ, Fossey SL, Park CH, Longenecker K, Bigelow L, Torrent M, Rosenberg SH, Kati WM, Shen Y. Selective inhibition of the BD2 bromodomain of BET proteins in prostate cancer. Nature. 2020 Feb;578(7794):306-310. doi: 10.1038/s41586-020-1930-8. Epub 2020 Jan 22. PMID: 31969702.

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ABBV-744

10.0mg / USD 190.0