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Bimosiamose

CAS No.:
187269-40-5
Catalog Number:
AG00AW0U
Molecular Formula:
Molecular Weight:
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
99%
1 week
United States
$140
- +
5mg
99%
1 week
United States
$307
- +
Product Description
Catalog Number:
AG00AW0U
Chemical Name:
Bimosiamose
CAS Number:
187269-40-5
MDL Number:
MFCD00954185
IUPAC Name:
2-[3-[5-[6-[3-[3-(carboxymethyl)phenyl]-4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]hexyl]-2-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]phenyl]acetic acid
InChI:
InChI=1S/C46H54O16/c47-23-35-39(53)41(55)43(57)45(61-35)59-33-15-13-25(19-31(33)29-11-5-9-27(17-29)21-37(49)50)7-3-1-2-4-8-26-14-16-34(60-46-44(58)42(56)40(54)36(24-48)62-46)32(20-26)30-12-6-10-28(18-30)22-38(51)52/h5-6,9-20,35-36,39-48,53-58H,1-4,7-8,21-24H2,(H,49,50)(H,51,52)/t35-,36-,39-,40-,41+,42+,43+,44+,45+,46+/m1/s1
InChI Key:
RYWCQJDEHXJHRI-XJMXIVSISA-N
UNII:
97B5KCW80W
Properties
Complexity:
1270  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
10  
Defined Bond Stereocenter Count:
0
Exact Mass:
862.341g/mol
Formal Charge:
0
Heavy Atom Count:
62  
Hydrogen Bond Acceptor Count:
16  
Hydrogen Bond Donor Count:
10  
Isotope Atom Count:
0
Molecular Weight:
862.922g/mol
Monoisotopic Mass:
862.341g/mol
Rotatable Bond Count:
19  
Topological Polar Surface Area:
273A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
4.2  
Literature
Title Journal
Inhaled pan-selectin antagonist Bimosiamose attenuates airway inflammation in COPD. Pulmonary pharmacology & therapeutics 20130401
Efficacy of the pan-selectin antagonist Bimosiamose on ozone-induced airway inflammation in healthy subjects--a double blind, randomized, placebo-controlled, cross-over clinical trial. Pulmonary pharmacology & therapeutics 20111001
Discovery of 2-[1-(4-chlorophenyl)cyclopropyl]-3-hydroxy-8-(trifluoromethyl)quinoline-4-carboxylic acid (PSI-421), a P-selectin inhibitor with improved pharmacokinetic properties and oral efficacy in models of vascular injury. Journal of medicinal chemistry 20100826
The engagement of selectins and their ligands in colorectal cancer liver metastases. Journal of cellular and molecular medicine 20100101
Small molecule selectin inhibitor in global cerebral ischemia and controlled hemorrhagic shock. The Journal of trauma 20080901
Effects of the pan-selectin antagonist bimosiamose (TBC1269) in experimental human endotoxemia. Shock (Augusta, Ga.) 20080401
The pharmacokinetics of subcutaneously injected Bimosiamose disodium in healthy male volunteers. Biopharmaceutics & drug disposition 20071201
Tolerability and pharmacokinetics of inhaled bimosiamose disodium in healthy males. British journal of clinical pharmacology 20070401
Rational design of novel, potent small molecule pan-selectin antagonists. Journal of medicinal chemistry 20070322
Synthesis and biological evaluation of quinoline salicylic acids as P-selectin antagonists. Journal of medicinal chemistry 20070111
Selectin inhibitors and their proposed role in ischemia and reperfusion. Journal of investigative surgery : the official journal of the Academy of Surgical Research 20070101
Pan-selectin antagonism improves psoriasis manifestation in mice and man. Archives of dermatological research 20060201
Bimosiamose, an inhaled small-molecule pan-selectin antagonist, attenuates late asthmatic reactions following allergen challenge in mild asthmatics: a randomized, double-blind, placebo-controlled clinical cross-over-trial. Pulmonary pharmacology & therapeutics 20060101
Physiochemical properties, safety and pharmacokinetics of bimosiamose disodium after intravenous administration. International journal of clinical pharmacology and therapeutics 20051001
The anti-inflammatory effects of a selectin ligand mimetic, TBC-1269, are not a result of competitive inhibition of leukocyte rolling in vivo. Journal of leukocyte biology 20050101
Selectin antagonists : therapeutic potential in asthma and COPD. Treatments in respiratory medicine 20050101
Selectin inhibitor bimosiamose prolongs survival of kidney allografts by reduction in intragraft production of cytokines and chemokines. Journal of the American Society of Nephrology : JASN 20041101
Development of cell adhesion molecule antagonists as therapeutics for asthma and COPD. Pulmonary pharmacology & therapeutics 20040101
Selectin inhibition modulates Akt/MAPK signaling and chemokine expression after liver ischemia-reperfusion. Journal of investigative surgery : the official journal of the Academy of Surgical Research 20040101
Blockade of cell adhesion by a small molecule selectin antagonist attenuates myocardial ischemia/reperfusion injury. European journal of pharmacology 20031128
Small molecule selectin ligand inhibition improves outcome in ischemic acute renal failure. Kidney international 20011201
Targeting selectins for the treatment of respiratory diseases. Current opinion in investigational drugs (London, England : 2000) 20010701
Novel synthetic inhibitors of selectin-mediated cell adhesion: synthesis of 1,6-bis[3-(3-carboxymethylphenyl)-4-(2-alpha-D- mannopyranosyloxy)phenyl]hexane (TBC1269). Journal of medicinal chemistry 19980326
Properties