Rilzabrutinib | CAS#1575596-29-0 | BTK inhibitor

MedKoo Cat#: 462574 | Name: Rilzabrutinib

Description:

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

Rilzabrutinib, also known as PRN1008, is a reversible covalent, selective and oral active inhibitor of Bruton’s Tyrosine Kinase (BTK).

Chemical Structure

Rilzabrutinib

CAS#1575596-29-0

Theoretical Analysis

MedKoo Cat#: 462574

Name: Rilzabrutinib

CAS#: 1575596-29-0

Chemical Formula: C36H40FN9O3

Exact Mass: 665.3238

Molecular Weight: 665.77

Elemental Analysis: C, 64.95; H, 6.06; F, 2.85; N, 18.93; O, 7.21

Price and Availability

Size	Price	Availability
25mg	USD 550.00	2 Weeks
50mg	USD 950.00	2 Weeks
100mg	USD 1,650.00	2 Weeks
1g	USD 4,850.00	2 Weeks

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Related CAS #

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Synonym

PRN1008; PRN 1008; PRN-1008; Rilzabrutinib;

IUPAC/Chemical Name

(R,E)-2-(3-(4-amino-3-(2-fluoro-4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carbonyl)-4-methyl-4-(4-(oxetan-3-yl)piperazin-1-yl)pent-2-enenitrile

InChi Key

LCFFREMLXLZNHE-GBOLQPHISA-N

InChi Code

InChI=1S/C36H40FN9O3/c1-36(2,45-15-13-43(14-16-45)26-21-48-22-26)18-24(19-38)35(47)44-12-6-7-25(20-44)46-34-31(33(39)40-23-41-34)32(42-46)29-11-10-28(17-30(29)37)49-27-8-4-3-5-9-27/h3-5,8-11,17-18,23,25-26H,6-7,12-16,20-22H2,1-2H3,(H2,39,40,41)/b24-18+/t25-/m1/s1

SMILES Code

NC1=C2C(C3=C(C=C(OC4=CC=CC=C4)C=C3)F)=NN([C@H]5CN(CCC5)C(/C(C#N)=C/C(C)(N6CCN(C7COC7)CC6)C)=O)C2=NC=N1

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 and ethanol

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO and ethanol

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Rilzabrutinib has an an IC50 of 1.3 nM.

In vitro activity:

Rilzabrutinib inhibited Btk-dependent pathways of platelet aggregation upon GPVI, VWF/GPIb, and FcγRIIA activation. It is less potent than remibrutinib but still has antiplatelet activity. Reference: Front Cardiovasc Med. 2021 Sep 24;8:749022. https://pubmed.ncbi.nlm.nih.gov/34631841/

In vivo activity:

PRN1008 monotherapy may have some beneficial effects in some cases of canine pemphigus foliaceus. All four dogs showed reduction in lesions and a decrease in their canine Pemphigus Disease Activity Index score during the first two weeks of rilzabrutinib treatment. Three dogs continued to improve and sustained near complete remission by 20 weeks. Reference: Vet Dermatol. 2020 Oct;31(5):410-e110. https://pubmed.ncbi.nlm.nih.gov/32803903/

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	150.20
	Ethanol	100.0	150.20

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 665.77 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. Duan R, Goldmann L, Brandl R, Spannagl M, Weber C, Siess W, von Hundelshausen P. Effects of the Btk-Inhibitors Remibrutinib (LOU064) and Rilzabrutinib (PRN1008) With Varying Btk Selectivity Over Tec on Platelet Aggregation and in vitro Bleeding Time. Front Cardiovasc Med. 2021 Sep 24;8:749022. doi: 10.3389/fcvm.2021.749022. PMID: 34631841; PMCID: PMC8498029. 2. Goodale EC, White SD, Bizikova P, Borjesson D, Murrell DF, Bisconte A, Francesco M, Hill RJ, Masjedizadeh M, Nunn P, Gourlay SG, Jordan TJM, Emery CB, Outerbridge CA. Open trial of Bruton's tyrosine kinase inhibitor (PRN1008) in the treatment of canine pemphigus foliaceus. Vet Dermatol. 2020 Oct;31(5):410-e110. doi: 10.1111/vde.12878. Epub 2020 Aug 17. PMID: 32803903. 3. Smith PF, Krishnarajah J, Nunn PA, Hill RJ, Karr D, Tam D, Masjedizadeh M, Funk JO, Gourlay SG. A phase I trial of PRN1008, a novel reversible covalent inhibitor of Bruton's tyrosine kinase, in healthy volunteers. Br J Clin Pharmacol. 2017 Nov;83(11):2367-2376. doi: 10.1111/bcp.13351. Epub 2017 Aug 1. PMID: 28636208; PMCID: PMC5651318.

In vitro protocol:

In vivo protocol:

1. Goodale EC, White SD, Bizikova P, Borjesson D, Murrell DF, Bisconte A, Francesco M, Hill RJ, Masjedizadeh M, Nunn P, Gourlay SG, Jordan TJM, Emery CB, Outerbridge CA. Open trial of Bruton's tyrosine kinase inhibitor (PRN1008) in the treatment of canine pemphigus foliaceus. Vet Dermatol. 2020 Oct;31(5):410-e110. doi: 10.1111/vde.12878. Epub 2020 Aug 17. PMID: 32803903. 2. Smith PF, Krishnarajah J, Nunn PA, Hill RJ, Karr D, Tam D, Masjedizadeh M, Funk JO, Gourlay SG. A phase I trial of PRN1008, a novel reversible covalent inhibitor of Bruton's tyrosine kinase, in healthy volunteers. Br J Clin Pharmacol. 2017 Nov;83(11):2367-2376. doi: 10.1111/bcp.13351. Epub 2017 Aug 1. PMID: 28636208; PMCID: PMC5651318.

1: Smith PF, Krishnarajah J, Nunn PA, et al. A phase I trial of PRN1008, a novel reversible covalent inhibitor of Bruton's tyrosine kinase, in healthy volunteers. Br J Clin Pharmacol. 2017;83(11):2367-2376. doi:10.1111/bcp.13351 2: Hill RJ, Bradshaw JM, Bisconte A, Tam D, Owens TD, Brameld KA, Smith PF, Funk JO, Goldstein DM, Nunn PA. Preclinical Characterization of PRN1008, a Novel Reversible Covalent Inhibitor of BTK that Shows Efficacy in a RAT Model of Collagen-Induced Arthritis. Annals of the Rheumatic Diseases 2015; 74(Suppl 2): 216.