Synonym
BYK191023 Dihydrochloride; BYK-191023 HCl; BYK 191023; BYK191023 2HCl; BYK-191023 2HCl; BYK 191023 2HCl;
IUPAC/Chemical Name
2-[2-(4-Methoxy-2-pyridinyl)ethyl]-1H-imidazo[4,5-b]pyridine dihydrochloride
InChi Key
ZVNITETZYOKESF-UHFFFAOYSA-N
InChi Code
InChI=1S/C14H14N4O.2ClH/c1-19-11-6-8-15-10(9-11)4-5-13-17-12-3-2-7-16-14(12)18-13;;/h2-3,6-9H,4-5H2,1H3,(H,16,17,18);2*1H
SMILES Code
COC1=CC(CCC2=NC3=NC=CC=C3N2)=NC=C1.[H]Cl.[H]Cl
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:
Potent and selective inhibitor of iNOS.
In vitro activity:
BYK191023 irreversibly inactivates murine iNOS in an NADPH- and time-dependent manner, whereas it acts only as a reversible l-arginine-competitive inhibitor in the absence of NADPH or during anaerobic preincubation. Time-dependent irreversible inhibition by BYK191023 could also be demonstrated in intact cells using the RAW macrophage or iNOS-overexpressing human embryonic kidney 293 cell lines.
Reference: Mol Pharmacol. 2008 Apr;73(4):1244-53. https://pubmed.ncbi.nlm.nih.gov/18178668/
In vivo activity:
The present study tested the in vivo potency of BYK191023 [2-[2-(4-methoxy-pyridin-2-yl)-ethyl]-3H-imidazo-[4,5-b]pyridine], a selected member of this inhibitor class, in three different rat models of lipopolysaccharide-induced systemic inflammation. Delayed administration of BYK191023 dose-dependently suppressed the lipopolysaccharide-induced increase in plasma nitrate/nitrite (NO(x)) levels with an ED(50) of 14.9 micromol/kg/h. In a model of systemic hypotension following high-dose lipopolysaccharide challenge, curative administration of BYK191023 at a dose that inhibited 83% of the NO(x) increase completely prevented the gradual decrease in mean arterial blood pressure observed in vehicle-treated control animals. The vasopressor effect was specific for endotoxemic animals since BYK191023 did not affect blood pressure in saline-challenged controls. In addition, in a model of lipopolysaccharide-induced vascular hyporesponsiveness, BYK191023 infusion partially restored normal blood pressure responses to norepinephrine and sodium nitroprusside via an l-arginine competitive mechanism. Taken together, BYK191023 is a member of a novel class of highly isoform-selective iNOS inhibitors with promising in vivo activity suitable for mechanistic studies on the role of selective iNOS inhibition as well as clinical development.
Reference: J Pharmacol Exp Ther. 2006 Apr;317(1):181-7. https://pubmed.ncbi.nlm.nih.gov/16368897/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
32.7 |
100.00 |
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
327.20
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. Tiso M, Strub A, Hesslinger C, Kenney CT, Boer R, Stuehr DJ. BYK191023 (2-[2-(4-methoxy-pyridin-2-yl)-ethyl]-3h-imidazo[4,5-b]pyridine) is an NADPH- and time-dependent irreversible inhibitor of inducible nitric-oxide synthase. Mol Pharmacol. 2008 Apr;73(4):1244-53. doi: 10.1124/mol.107.041319. Epub 2008 Jan 4. PMID: 18178668.
2. Strub A, Ulrich WR, Hesslinger C, Eltze M, Fuchss T, Strassner J, Strand S, Lehner MD, Boer R. The novel imidazopyridine 2-[2-(4-methoxy-pyridin-2-yl)-ethyl]-3H-imidazo[4,5-b]pyridine (BYK191023) is a highly selective inhibitor of the inducible nitric-oxide synthase. Mol Pharmacol. 2006 Jan;69(1):328-37. doi: 10.1124/mol.105.017087. Epub 2005 Oct 13. PMID: 16223957.
3. Lehner MD, Marx D, Boer R, Strub A, Hesslinger C, Eltze M, Ulrich WR, Schwoebel F, Schermuly RT, Barsig J. In vivo characterization of the novel imidazopyridine BYK191023 [2-[2-(4-methoxy-pyridin-2-yl)-ethyl]-3H-imidazo[4,5-b]pyridine], a potent and highly selective inhibitor of inducible nitric-oxide synthase. J Pharmacol Exp Ther. 2006 Apr;317(1):181-7. doi: 10.1124/jpet.105.098673. Epub 2005 Dec 20. PMID: 16368897.
In vitro protocol:
1. Tiso M, Strub A, Hesslinger C, Kenney CT, Boer R, Stuehr DJ. BYK191023 (2-[2-(4-methoxy-pyridin-2-yl)-ethyl]-3h-imidazo[4,5-b]pyridine) is an NADPH- and time-dependent irreversible inhibitor of inducible nitric-oxide synthase. Mol Pharmacol. 2008 Apr;73(4):1244-53. doi: 10.1124/mol.107.041319. Epub 2008 Jan 4. PMID: 18178668.
2. Strub A, Ulrich WR, Hesslinger C, Eltze M, Fuchss T, Strassner J, Strand S, Lehner MD, Boer R. The novel imidazopyridine 2-[2-(4-methoxy-pyridin-2-yl)-ethyl]-3H-imidazo[4,5-b]pyridine (BYK191023) is a highly selective inhibitor of the inducible nitric-oxide synthase. Mol Pharmacol. 2006 Jan;69(1):328-37. doi: 10.1124/mol.105.017087. Epub 2005 Oct 13. PMID: 16223957.
In vivo protocol:
1. Lehner MD, Marx D, Boer R, Strub A, Hesslinger C, Eltze M, Ulrich WR, Schwoebel F, Schermuly RT, Barsig J. In vivo characterization of the novel imidazopyridine BYK191023 [2-[2-(4-methoxy-pyridin-2-yl)-ethyl]-3H-imidazo[4,5-b]pyridine], a potent and highly selective inhibitor of inducible nitric-oxide synthase. J Pharmacol Exp Ther. 2006 Apr;317(1):181-7. doi: 10.1124/jpet.105.098673. Epub 2005 Dec 20. PMID: 16368897.
2. Strub A, Ulrich WR, Hesslinger C, Eltze M, Fuchss T, Strassner J, Strand S, Lehner MD, Boer R. The novel imidazopyridine 2-[2-(4-methoxy-pyridin-2-yl)-ethyl]-3H-imidazo[4,5-b]pyridine (BYK191023) is a highly selective inhibitor of the inducible nitric-oxide synthase. Mol Pharmacol. 2006 Jan;69(1):328-37. doi: 10.1124/mol.105.017087. Epub 2005 Oct 13. PMID: 16223957.
1: Stahl W, Matejovic M, Radermacher P. Inhibition of nitric oxide synthase during sepsis: revival because of isoform selectivity? Shock. 2010 Sep;34(3):321-2. doi: 10.1097/SHK.0b013e3181d758b5. PubMed PMID: 20601934.
2: Su F, Huang H, Akieda K, Occhipinti G, Donadello K, Piagnerelli M, De Backer D, Vincent JL. Effects of a selective iNOS inhibitor versus norepinephrine in the treatment of septic shock. Shock. 2010 Sep;34(3):243-9. doi: 10.1097/SHK.0b013e3181d75967. PubMed PMID: 20160666.
3: Tiso M, Strub A, Hesslinger C, Kenney CT, Boer R, Stuehr DJ. BYK191023 (2-[2-(4-methoxy-pyridin-2-yl)-ethyl]-3h-imidazo[4,5-b]pyridine) is an NADPH- and time-dependent irreversible inhibitor of inducible nitric-oxide synthase. Mol Pharmacol. 2008 Apr;73(4):1244-53. doi: 10.1124/mol.107.041319. Epub 2008 Jan 4. PubMed PMID: 18178668.
4: Lehner MD, Marx D, Boer R, Strub A, Hesslinger C, Eltze M, Ulrich WR, Schwoebel F, Schermuly RT, Barsig J. In vivo characterization of the novel imidazopyridine BYK191023 [2-[2-(4-methoxy-pyridin-2-yl)-ethyl]-3H-imidazo[4,5-b]pyridine], a potent and highly selective inhibitor of inducible nitric-oxide synthase. J Pharmacol Exp Ther. 2006 Apr;317(1):181-7. Epub 2005 Dec 20. PubMed PMID: 16368897.
5: Strub A, Ulrich WR, Hesslinger C, Eltze M, Fuchss T, Strassner J, Strand S, Lehner MD, Boer R. The novel imidazopyridine 2-[2-(4-methoxy-pyridin-2-yl)-ethyl]-3H-imidazo[4,5-b]pyridine (BYK191023) is a highly selective inhibitor of the inducible nitric-oxide synthase. Mol Pharmacol. 2006 Jan;69(1):328-37. Epub 2005 Oct 13. PubMed PMID: 16223957.
