BAY 41-2272

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

MedKoo CAT#: 522641

CAS#: 256376-24-6

Description: BAY 41-2272 is a a soluble guanylate cyclase stimulator (sGC stimulator). BAY 41-2272 inhibits platelet aggregation (IC50 = 36 nM), induces relaxation of phenylephrine-preconstricted rabbit aorta rings (IC50 = 304 nM), and reduces proliferation in smooth muscle.2,3 BAY 41-2272 is effective in vivo. BAY 41-2272 inhibits vascular smooth muscle growth through the cAMP-dependent protein kinase and cGMP-dependent protein kinase pathways. BAY 41-2272 inhibits the development of chronic hypoxic pulmonary hypertension in rats.


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BAY 41-2272 is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 522641
Name: BAY 41-2272
CAS#: 256376-24-6
Chemical Formula: C20H17FN6
Exact Mass: 360.1499
Molecular Weight: 360.3964
Elemental Analysis: C, 66.65; H, 4.75; F, 5.27; N, 23.32


Synonym: BAY 41-2272; BAY-41-2272; BAY41-2272; BAY412272; BAY-412272; BAY 412272.

IUPAC/Chemical Name: 5-cyclopropyl-2-[1-[(2-fluorophenyl)methyl]-1H-pyrazolo[3,4-b]pyridin-3-yl]-4-pyrimidinamine

InChi Key: ATOAHNRJAXSBOR-UHFFFAOYSA-N

InChi Code: InChI=1S/C20H17FN6/c21-16-6-2-1-4-13(16)11-27-20-14(5-3-9-23-20)17(26-27)19-24-10-15(12-7-8-12)18(22)25-19/h1-6,9-10,12H,7-8,11H2,(H2,22,24,25)

SMILES Code: NC1=NC(C2=NN(CC3=CC=CC=C3F)C4=NC=CC=C42)=NC=C1C5CC5


Technical Data

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, not in water

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).

Harmonized System Code:
293490


References

1: Vuckovic A, Herber-Jonat S, Flemmer AW, Strizek B, Engels AC, Jani JC. Antenatal BAY 41-2272 reduces pulmonary hypertension in the rabbit model of congenital diaphragmatic hernia. Am J Physiol Lung Cell Mol Physiol. 2016 Feb 12:ajplung.00178.2015. doi: 10.1152/ajplung.00178.2015. [Epub ahead of print] PubMed PMID: 26873974.

2: Soeiro-Pereira PV, Falcai A, Kubo CA, Antunes E, Condino-Neto A. BAY 41-2272 activates host defence against local and disseminated Candida albicans infections. Mem Inst Oswaldo Cruz. 2015 Feb;110(1):75-85. doi: 10.1590/0074-02760140255. Epub 2015 Jan 23. PubMed PMID: 25742266; PubMed Central PMCID: PMC4371220.

3: Nunes KP, Teixeira CE, Priviero FB, Toque HA, Webb RC. Beneficial effect of the soluble guanylyl cyclase stimulator BAY 41-2272 on impaired penile erection in db/db-/- type II diabetic and obese mice. J Pharmacol Exp Ther. 2015 May;353(2):330-9. doi: 10.1124/jpet.114.220970. Epub 2015 Mar 4. PubMed PMID: 25740897.

4: Soeiro-Pereira PV, Falcai A, Kubo CA, Antunes E, Condino-Neto A. BAY 41-2272 activates host defence against local and disseminated Candida albicans infections. Mem Inst Oswaldo Cruz. 2015 Jan 23:0. [Epub ahead of print] PubMed PMID: 25626456.

5: Füllhase C, Hennenberg M, Sandner P, Strittmatter F, Niedworok C, Bauer RM, Gratzke C, Soler R, Stief C, Andersson KE. Reduction of obstruction related bladder overactivity by the guanylyl cyclase modulators BAY 41-2272 and BAY 60-2770 alone or in combination with a phosphodiesterase type 5 inhibitor. Neurourol Urodyn. 2015 Nov;34(8):787-93. doi: 10.1002/nau.22665. Epub 2014 Sep 17. PubMed PMID: 25230878.

6: Miyaoka R, Mendes C, Schenka A, Gonzalez PG, de Nucci G, Antunes E, Monga M, Levi D'Ancona CA, Mónica FZ. BAY 41-2272, a soluble guanylate cyclase stimulator, relaxes isolated human ureter in a standardized in vitro model. Urology. 2014 Jan;83(1):256.e1-7. doi: 10.1016/j.urology.2013.09.005. Epub 2013 Nov 11. PubMed PMID: 24231204.

7: Yoo BK, Lamarre I, Rappaport F, Nioche P, Raman CS, Martin JL, Negrerie M. Picosecond to second dynamics reveals a structural transition in Clostridium botulinum NO-sensor triggered by the activator BAY-41-2272. ACS Chem Biol. 2012 Dec 21;7(12):2046-54. doi: 10.1021/cb3003539. Epub 2012 Oct 2. PubMed PMID: 23009307.

8: da Silva FH, Claudino MA, Báu FR, Rojas-Moscoso JA, Mónica FZ, De Nucci G, Antunes E. Vas deferens smooth muscle responses to the nitric oxide-independent soluble guanylate cyclase stimulator BAY 41-2272. Eur J Pharmacol. 2012 Aug 5;688(1-3):49-55. doi: 10.1016/j.ejphar.2012.05.009. Epub 2012 May 22. PubMed PMID: 22634166.

9: Cosyns SM, Lefebvre RA. Mechanism of relaxation and interaction with nitric oxide of the soluble guanylate cyclase stimulator BAY 41-2272 in mouse gastric fundus and colon. Eur J Pharmacol. 2012 Jul 5;686(1-3):104-15. doi: 10.1016/j.ejphar.2012.04.049. Epub 2012 May 2. PubMed PMID: 22575520.

10: Adderley SP, Joshi CN, Martin DN, Tulis DA. Phosphodiesterases Regulate BAY 41-2272-Induced VASP Phosphorylation in Vascular Smooth Muscle Cells. Front Pharmacol. 2012 Feb 7;3:10. doi: 10.3389/fphar.2012.00010. eCollection 2012. PubMed PMID: 22347188; PubMed Central PMCID: PMC3273712.

11: Soeiro-Pereira PV, Falcai A, Kubo CA, Oliveira-Júnior EB, Marques OC, Antunes E, Condino-Neto A. BAY 41-2272, a soluble guanylate cyclase agonist, activates human mononuclear phagocytes. Br J Pharmacol. 2012 Jul;166(5):1617-30. doi: 10.1111/j.1476-5381.2011.01764.x. PubMed PMID: 22044316; PubMed Central PMCID: PMC3419906.

12: Joshi CN, Martin DN, Fox JC, Mendelev NN, Brown TA, Tulis DA. The soluble guanylate cyclase stimulator BAY 41-2272 inhibits vascular smooth muscle growth through the cAMP-dependent protein kinase and cGMP-dependent protein kinase pathways. J Pharmacol Exp Ther. 2011 Nov;339(2):394-402. doi: 10.1124/jpet.111.183400. Epub 2011 Aug 8. PubMed PMID: 21825001; PubMed Central PMCID: PMC3199990.

13: Mónica FZ, Reges R, Cohen D, Silva FH, De Nucci G, D'Ancona CA, Antunes E. Long-term administration of BAY 41-2272 prevents bladder dysfunction in nitric oxide-deficient rats. Neurourol Urodyn. 2011 Mar;30(3):456-60. doi: 10.1002/nau.20992. Epub 2010 Dec 3. PubMed PMID: 21412825.

14: D'Ancona CA, Mónica FZ, Reges R, Cohen D, Silva FH, Nucci GD, Antunes E. Administration of BAY 41-2272 prevents bladder dysfunction in nitric-oxide deficient rats. Einstein (Sao Paulo). 2010 Dec;8(4):404-9. doi: 10.1590/S1679-45082010AO1789. English, Portuguese. PubMed PMID: 26760319.

15: Roger S, Badier-Commander C, Paysant J, Cordi A, Verbeuren TJ, Félétou M. The anti-aggregating effect of BAY 41-2272, a stimulator of soluble guanylyl cyclase, requires the presence of nitric oxide. Br J Pharmacol. 2010 Nov;161(5):1044-58. doi: 10.1111/j.1476-5381.2010.00943.x. PubMed PMID: 20977455; PubMed Central PMCID: PMC2998686.

16: Claudino MA, da Silva FH, Mónica FZ, Rojas-Moscoso JA, De Nucci G, Antunes E. Long-term oral treatment with BAY 41-2272 ameliorates impaired corpus cavernosum relaxations in a nitric oxide-deficient rat model. BJU Int. 2011 Jul;108(1):116-22. doi: 10.1111/j.1464-410X.2010.09776.x. Epub 2010 Oct 15. PubMed PMID: 20950311.

17: Thorsen LB, Eskildsen-Helmond Y, Zibrandtsen H, Stasch JP, Simonsen U, Laursen BE. BAY 41-2272 inhibits the development of chronic hypoxic pulmonary hypertension in rats. Eur J Pharmacol. 2010 Nov 25;647(1-3):147-54. doi: 10.1016/j.ejphar.2010.08.032. Epub 2010 Sep 7. PubMed PMID: 20828552.

18: Toque HA, Mónica FZ, Morganti RP, De Nucci G, Antunes E. Mechanisms of relaxant activity of the nitric oxide-independent soluble guanylyl cyclase stimulator BAY 41-2272 in rat tracheal smooth muscle. Eur J Pharmacol. 2010 Oct 25;645(1-3):158-64. doi: 10.1016/j.ejphar.2010.07.028. Epub 2010 Jul 27. PubMed PMID: 20670622.

19: Pal B, Kitagawa T. Binding of YC-1/BAY 41-2272 to soluble guanylate cyclase: A new perspective to the mechanism of activation. Biochem Biophys Res Commun. 2010 Jul 2;397(3):375-9. doi: 10.1016/j.bbrc.2010.05.122. Epub 2010 May 27. Review. PubMed PMID: 20513359.

20: Báu FR, Mónica FZ, Priviero FB, Baldissera L Jr, de Nucci G, Antunes E. Evaluation of the relaxant effect of the nitric oxide-independent soluble guanylyl cyclase stimulator BAY 41-2272 in isolated detrusor smooth muscle. Eur J Pharmacol. 2010 Jul 10;637(1-3):171-7. doi: 10.1016/j.ejphar.2010.04.008. Epub 2010 Apr 23. PubMed PMID: 20399768.