BI-2545
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 530982

CAS#: 2162961-71-7

Description: BI-2545 is a highly potent, orally active and selective Autotaxin Inhibitor That Significantly Reduces LPA Levels in Vivo. BI-2545 inhibits ATX in the single-digit nanomolar region and translates into good potency in human whole blood. BI-2545 proved to be stable in human and moderately stable in rat liver microsomes. In vitro, BI-2545 showed high Caco-2 permeability and low efflux. BI-2545 shows an excellent PK/target engagement relationship. It is therefore considered a valuable tool for further in vivo studies.

Chemical Structure

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BI-2545
CAS# 2162961-71-7
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 530982
Name: BI-2545
CAS#: 2162961-71-7
Chemical Formula: C23H19F6N5O3
Exact Mass: 527.14
Molecular Weight: 527.427
Elemental Analysis: C, 52.38; H, 3.63; F, 21.61; N, 13.28; O, 9.10

Price and Availability

Size Price Availability Quantity
5mg USD 280 2 weeks
25mg USD 690 2 weeks
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Synonym: BI-2545; BI 2545; BI2545.

IUPAC/Chemical Name: 3,5-bis(trifluoromethyl)benzyl (1R,5S,6r)-6-((1H-benzo[d][1,2,3]triazole-5-carboxamido)methyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate

InChi Key: ZDOBSAPHUUUOHX-BJWYYQGGSA-N

InChi Code: InChI=1S/C23H19F6N5O3/c24-22(25,26)13-3-11(4-14(6-13)23(27,28)29)10-37-21(36)34-8-16-15(17(16)9-34)7-30-20(35)12-1-2-18-19(5-12)32-33-31-18/h1-6,15-17H,7-10H2,(H,30,35)(H,31,32,33)/t15-,16+,17-

SMILES Code: O=C(N1C[C@]2([H])[C@H](CNC(C3=CC=C(NN=N4)C4=C3)=O)[C@]2([H])C1)OCC5=CC(C(F)(F)F)=CC(C(F)(F)F)=C5

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

More Info: Patients with IPF have elevated levels of lysophosphatidic acid (LPA) in their bronchoalveolar lavage fluid (BALF) and exhaled breath condensate.7,8 LPAs are bioactive lysophospholipids that exert a variety of cellular responses including cell proliferation, cell motility and cell survival through their interaction with six Gprotein-coupled receptors (GPCRs) known as LPAR1

Product Data:
Product Data
Instruction:
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Biological target: BI-2545 is a potent autotaxin (ATX) inhibitor that significantly reduces LPA, with IC50s of 2.2 nM and 3.4 nM for human ATX and rat ATX, respectively.
In vitro activity: In vitro, BI-2545 showed high Caco-2 permeability and low efflux. BI-2545 not only displayed good potency in the LPA and rat whole blood assay but also had favorable ADME properties (see Table 4). Reference: ACS Med Chem Lett. 2017 Nov 8;8(12):1252-1257. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5733304/
In vivo activity: ATX inhibitor BI-2545 is orally available in rodents, devoid of hERG channel inhibition, and shows an excellent PK/target engagement relationship. Low clearance was observed in vivo in rats, and in vivo oral dosing to rats resulted in good oral exposure. Under these conditions, the sum of the plasma LPA species was reduced up to 90% (see Figure 5), demonstrating high and sustained in vivo efficacy in reducing LPAs. Reference: ACS Med Chem Lett. 2017 Nov 8;8(12):1252-1257. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5733304/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 250.0 474.00

Preparing Stock Solutions

The following data is based on the product molecular weight 527.43 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. Kuttruff CA, Ferrara M, Bretschneider T, Hoerer S, Handschuh S, Nosse B, Romig H, Nicklin P, Roth GJ. Discovery of BI-2545: A Novel Autotaxin Inhibitor That Significantly Reduces LPA Levels in Vivo. ACS Med Chem Lett. 2017 Nov 8;8(12):1252-1257. doi: 10.1021/acsmedchemlett.7b00312. PMID: 29259743; PMCID: PMC5733304.
In vitro protocol: 1. Kuttruff CA, Ferrara M, Bretschneider T, Hoerer S, Handschuh S, Nosse B, Romig H, Nicklin P, Roth GJ. Discovery of BI-2545: A Novel Autotaxin Inhibitor That Significantly Reduces LPA Levels in Vivo. ACS Med Chem Lett. 2017 Nov 8;8(12):1252-1257. doi: 10.1021/acsmedchemlett.7b00312. PMID: 29259743; PMCID: PMC5733304.
In vivo protocol: 1. Kuttruff CA, Ferrara M, Bretschneider T, Hoerer S, Handschuh S, Nosse B, Romig H, Nicklin P, Roth GJ. Discovery of BI-2545: A Novel Autotaxin Inhibitor That Significantly Reduces LPA Levels in Vivo. ACS Med Chem Lett. 2017 Nov 8;8(12):1252-1257. doi: 10.1021/acsmedchemlett.7b00312. PMID: 29259743; PMCID: PMC5733304.

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Discovery of BI-2545: A Novel Autotaxin Inhibitor That Significantly Reduces LPA Levels in Vivo
Christian A. Kuttruff, Marco Ferrara, Tom Bretschneider, Stefan Hoerer, Sandra Handschuh, Bernd Nosse, Helmut Romig, Paul Nicklin, and Gerald J. Roth Publication Date (Web): November 8, 2017 (Letter). DOI: 10.1021/acsmedchemlett.7b00312