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Safety Information

SML2281

Sigma-Aldrich

BAY 60-2770

≥98% (HPLC)

Synonym(s):

4-[((4-Carboxy-butyl)-{2-[5-fluoro-2-(4′-trifluoromethyl-biphenyl-4-ylmethoxy)-phenyl]-ethyl}-amino)-methyl]-benzoic acid, 4-[[(4-Carboxybutyl)[2-[5-fluoro-2-[[4′-(trifluoromethyl)[1,1′-biphenyl]-4-yl]methoxy]phenyl]ethyl]amino]methyl]benzoic acid

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About This Item

Empirical Formula (Hill Notation):
C35H33F4NO5
CAS Number:
1027642-43-8
Molecular Weight:
623.63
UNSPSC Code:
12352200
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

FC1=CC=C(OCC2=CC=C(C3=CC=C(C(F)(F)F)C=C3)C=C2)C(CCN(CC4=CC=C(C(O)=O)C=C4)CCCCC(O)=O)=C1

InChI

1S/C35H33F4NO5/c36-31-16-17-32(45-23-25-6-8-26(9-7-25)27-12-14-30(15-13-27)35(37,38)39)29(21-31)18-20-40(19-2-1-3-33(41)42)22-24-4-10-28(11-5-24)34(43)44/h4-17,21H,1-3,18-20,22-23H2,(H,41,42)(H,43,44)

InChI key

CRQMDXFUKDWARU-UHFFFAOYSA-N

Biochem/physiol Actions

BAY 60-2770 is a potent and selective soluble guanylyl cyclase (sGC) heme-independent activator that protects sGC from heme oxidation in smooth muscle tissues. BAY 60-2770 provides cardioprotection and limits the infarct size in rat ischaemia-reperfusion model. Also BAY 60-2770 Ameliorates of urethra dysfunction in high-fat fed obese mice.
Structurally, BAY 60-2770 comprises fluoro and trifluoromethyl moieties. It stimulates in vitro expressed α2/β1 isoform of nitric oxide sensitive guanylyl cyclase (NOsGC). BAY 60-2770 is reported to be effective in treating liver fibrosis and in lowering arterial pressures (both pulmonary and systemic) in animal studies. It elicits anti-aggregating and anti-adhesive effects on platelets and may have therapeutic potential to treat atherothrombotic events.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

SML2281-25MG:
SML2281-BULK:
SML2281-5MG:
SML2281-VAR:

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Vijay Kumar et al.
Biochemistry, 52(20), 3601-3608 (2013-04-26)
The soluble guanylyl cyclase (sGC) is an important receptor for nitric oxide (NO). Nitric oxide activates sGC several hundred fold to generate cGMP from GTP. Because of sGC's salutary roles in cardiovascular physiology, it has received substantial attention as a
Eduardo C Alexandre et al.
The Journal of pharmacology and experimental therapeutics, 349(1), 2-9 (2014-01-15)
Obesity has emerged as a major contributing risk factor for overactive bladder (OAB), but no study examined urethral smooth muscle (USM) dysfunction as a predisposing factor to obesity-induced OAB. This study investigated the USM relaxant machinery in obese mice and
Camila B Mendes-Silverio et al.
PloS one, 7(11), e47223-e47223 (2012-11-13)
Nitric oxide-independent soluble guanylyl cyclase (sGC) activators reactivate the haem-oxidized enzyme in vascular diseases. This study was undertaken to investigate the anti-platelet mechanisms of the haem-independent sGC activator BAY 60-2770 in human washed platelets. The hypothesis that sGC oxidation potentiates
Anne Sömmer et al.
Biochemical pharmacology, 147, 10-20 (2017-11-21)
Nitric oxide sensitive guanylyl cyclase (NOsGC), a hemoprotein and the major physiological receptor for nitric oxide (NO), is a heterodimer with the α1/β1 and α2/β1 isoforms known to be important for NO-signaling and conversion of GTP to cGMP in humans.
Alexander Kollau et al.
Molecular pharmacology, 93(2), 73-78 (2017-11-16)
Belonging to the class of so-called soluble guanylate cyclase (sGC) activators, cinaciguat and BAY 60-2770 are interesting therapeutic tools for the treatment of various cardiovascular pathologies. The drugs are supposed to preferentially stimulate oxidized or heme-depleted, but not native sGC.
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