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152918-18-8,MFCD00671785
Catalog No.:AA00ABL9

152918-18-8 | Ib-meca

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1mg
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2mg
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5mg
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10mg
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25mg
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00ABL9
Chemical Name:
Ib-meca
CAS Number:
152918-18-8
Molecular Formula:
C18H19IN6O4
Molecular Weight:
510.2857
MDL Number:
MFCD00671785
SMILES:
CNC(=O)[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2NCc1cccc(c1)I
Properties
Computed Properties
 
Complexity:
589  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Heavy Atom Count:
29  
Hydrogen Bond Acceptor Count:
8  
Hydrogen Bond Donor Count:
4  
Rotatable Bond Count:
5  
XLogP3:
0.9  

Literature

Title: Targeting the A3 adenosine receptor for glaucoma treatment (review).

Journal: Molecular medicine reports 20130601

Title: Synthesis and structure-activity relationship studies in serotonin 5-HT(1A) receptor agonists based on fused pyrrolidone scaffolds.

Journal: European journal of medicinal chemistry 20130501

Title: Medicinal chemistry of A₃ adenosine receptor modulators: pharmacological activities and therapeutic implications.

Journal: Journal of medicinal chemistry 20120628

Title: Treatment of plaque-type psoriasis with oral CF101: data from an exploratory randomized phase 2 clinical trial.

Journal: Journal of the European Academy of Dermatology and Venereology : JEADV 20120301

Title: Molecular mechanisms of A3 adenosine receptor-induced G1 cell cycle arrest and apoptosis in androgen-dependent and independent prostate cancer cell lines: involvement of intrinsic pathway.

Journal: Journal of cancer research and clinical oncology 20111001

Title: Inhibition of cyclooxygenase-2 promotes the stimulatory action of adenosine A₃ receptor agonist on hematopoiesis in sublethally γ-irradiated mice.

Journal: Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie 20110901

Title: The role of adenosine receptors in rheumatoid arthritis.

Journal: Autoimmunity reviews 20101201

Title: Activation of A1, A2A, or A3 adenosine receptors attenuates lung ischemia-reperfusion injury.

Journal: The Journal of thoracic and cardiovascular surgery 20100801

Title: Activation of adenosine A(3) receptors supports hematopoiesis-stimulating effects of granulocyte colony-stimulating factor in sublethally irradiated mice.

Journal: International journal of radiation biology 20100801

Title: Multivalent dendrimeric and monomeric adenosine agonists attenuate cell death in HL-1 mouse cardiomyocytes expressing the A(3) receptor.

Journal: Biochemical pharmacology 20100715

Title: Induction of apoptosis by A3 adenosine receptor agonist N-(3-iodobenzyl)-adenosine-5'-N-methylcarboxamide in human leukaemia cells: a possible involvement of intracellular mechanism.

Journal: Acta physiologica (Oxford, England) 20100601

Title: Synthesis and evaluation of new N6-substituted adenosine-5'-N-methylcarboxamides as A3 adenosine receptor agonists.

Journal: Bioorganic & medicinal chemistry 20100501

Title: Compensatory upregulation of the adenosine system following phenylephrine-induced hypertrophy in cultured rat ventricular myocytes.

Journal: American journal of physiology. Heart and circulatory physiology 20100201

Title: 2-Dialkynyl derivatives of (N)-methanocarba nucleosides: 'Clickable' A(3) adenosine receptor-selective agonists.

Journal: Bioorganic & medicinal chemistry 20100115

Title: Activation of adenosine low-affinity A3 receptors inhibits the enteric short interplexus neural circuit triggered by histamine.

Journal: American journal of physiology. Gastrointestinal and liver physiology 20091201

Title: Design and synthesis of N(6)-substituted-4'-thioadenosine-5'-uronamides as potent and selective human A(3) adenosine receptor agonists.

Journal: Bioorganic & medicinal chemistry 20091201

Title: Adenosine A(3) receptor suppresses prostate cancer metastasis by inhibiting NADPH oxidase activity.

Journal: Neoplasia (New York, N.Y.) 20091101

Title: Cardioprotection induced by adenosine A1 receptor agonists in a cardiac cell ischemia model involves cooperative activation of adenosine A2A and A2B receptors by endogenous adenosine.

Journal: Journal of cardiovascular pharmacology 20090501

Title: Activation of adenosine A(3) receptors potentiates stimulatory effects of IL-3, SCF, and GM-CSF on mouse granulocyte-macrophage hematopoietic progenitor cells.

Journal: Physiological research 20090101

Title: A3 adenosine receptor: pharmacology and role in disease.

Journal: Handbook of experimental pharmacology 20090101

Title: Stimulation of ANP secretion by 2-Cl-IB-MECA through A(3) receptor and CaMKII.

Journal: Peptides 20081201

Title: cis-4-(Piperazin-1-yl)-5,6,7a,8,9,10,11,11a-octahydrobenzofuro[2,3-h]quinazolin-2-amine (A-987306), a new histamine H4R antagonist that blocks pain responses against carrageenan-induced hyperalgesia.

Journal: Journal of medicinal chemistry 20081127

Title: Structure-activity relationships of truncated D- and l-4'-thioadenosine derivatives as species-independent A3 adenosine receptor antagonists.

Journal: Journal of medicinal chemistry 20081023

Title: Adenosine A(2A) receptor dynamics studied with the novel fluorescent agonist Alexa488-APEC.

Journal: European journal of pharmacology 20080820

Title: Identification of a potent, selective, and orally active leukotriene a4 hydrolase inhibitor with anti-inflammatory activity.

Journal: Journal of medicinal chemistry 20080724

Title: Homeostatic action of adenosine A3 and A1 receptor agonists on proliferation of hematopoietic precursor cells.

Journal: Experimental biology and medicine (Maywood, N.J.) 20080701

Title: Design of (N)-methanocarba adenosine 5'-uronamides as species-independent A3 receptor-selective agonists.

Journal: Bioorganic & medicinal chemistry letters 20080501

Title: The anti-inflammatory effect of A3 adenosine receptor agonists: a novel targeted therapy for rheumatoid arthritis.

Journal: Expert opinion on investigational drugs 20071001

Title: Adenosine A(3) receptor agonist acts as a homeostatic regulator of bone marrow hematopoiesis.

Journal: Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie 20070701

Title: Rapid stimulation of presynaptic serotonin transport by A(3) adenosine receptors.

Journal: The Journal of pharmacology and experimental therapeutics 20070701

Title: Structure-activity relationship study of prion inhibition by 2-aminopyridine-3,5-dicarbonitrile-based compounds: parallel synthesis, bioactivity, and in vitro pharmacokinetics.

Journal: Journal of medicinal chemistry 20070111

Title: Overexpression of A3 adenosine receptor in peripheral blood mononuclear cells in rheumatoid arthritis: involvement of nuclear factor-kappaB in mediating receptor level.

Journal: The Journal of rheumatology 20070101

Title: Expression of adenosine receptors in cardiac fibroblasts as a function of insulin and glucose level.

Journal: Archives of biochemistry and biophysics 20061101

Title: Modulation of cardiac sarcoplasmic reticulum calcium release by aenosine: a protein kinase C- dependent pathway.

Journal: Molecular and cellular biochemistry 20060801

Title: ADOA3R as a therapeutic target in experimental colitis: proof by validated high-density oligonucleotide microarray analysis.

Journal: Inflammatory bowel diseases 20060801

Title: N6-(3-iodobenzyl)-adenosine-5'-N-methylcarboxamide confers cardioprotection at reperfusion by inhibiting mitochondrial permeability transition pore opening via glycogen synthase kinase 3 beta.

Journal: The Journal of pharmacology and experimental therapeutics 20060701

Title: Effects of adenosine A(3) receptor agonist on bone marrow granulocytic system in 5-fluorouracil-treated mice.

Journal: European journal of pharmacology 20060524

Title: The synthesis of highly potent, selective, and water-soluble agonists at the human adenosine A3 receptor.

Journal: Bioorganic & medicinal chemistry letters 20060501

Title: N6-ethyl-2-alkynyl NECAs, selective human A3 adenosine receptor agonists.

Journal: Bioorganic & medicinal chemistry letters 20060501

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

Title: Radioligand binding and functional responses of ligands for human recombinant adenosine A(3) receptors.

Journal: Autonomic & autacoid pharmacology 20060401

Title: Adenosine receptors as therapeutic targets.

Journal: Nature reviews. Drug discovery 20060301

Title: The PI3K-NF-kappaB signal transduction pathway is involved in mediating the anti-inflammatory effect of IB-MECA in adjuvant-induced arthritis.

Journal: Arthritis research & therapy 20060101

Title: IB-MECA, an A3 adenosine receptor agonist prevents bone resorption in rats with adjuvant induced arthritis.

Journal: Clinical and experimental rheumatology 20060101

Title: Methotrexate enhances the anti-inflammatory effect of CF101 via up-regulation of the A3 adenosine receptor expression.

Journal: Arthritis research & therapy 20060101

Title: IB-MECA and cardioprotection.

Journal: Cardiovascular drug reviews 20060101

Title: 2-n-Butyl-9-methyl-8-[1,2,3]triazol-2-yl-9H-purin-6-ylamine and analogues as A2A adenosine receptor antagonists. Design, synthesis, and pharmacological characterization.

Journal: Journal of medicinal chemistry 20051103

Title: G(i)-protein-dependent inhibition of IL-12 production is mediated by activation of the phosphatidylinositol 3-kinase-protein 3 kinase B/Akt pathway and JNK.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20050901

Title: Induction of apoptosis by the adenosine derivative IB-MECA in parental or multidrug-resistant HL-60 leukemia cells: possible relationship to the effects on inhibitor of apoptosis protein levels.

Journal: Chemotherapy 20050801

Title: (N)-methanocarba 2,N6-disubstituted adenine nucleosides as highly potent and selective A3 adenosine receptor agonists.

Journal: Journal of medicinal chemistry 20050324

Title: Synthesis, biological evaluation, and molecular modeling of ribose-modified adenosine analogues as adenosine receptor agonists.

Journal: Journal of medicinal chemistry 20050310

Title: Inhibition of phenylephrine-induced cardiomyocyte hypertrophy by activation of multiple adenosine receptor subtypes.

Journal: The Journal of pharmacology and experimental therapeutics 20050101

Title: CF101, an agonist to the A3 adenosine receptor, enhances the chemotherapeutic effect of 5-fluorouracil in a colon carcinoma murine model.

Journal: Neoplasia (New York, N.Y.) 20050101

Title: Mesangial cell apoptosis induced by stimulation of the adenosine A3 receptor: signaling and apoptotic events.

Journal: Journal of investigative medicine : the official publication of the American Federation for Clinical Research 20050101

Title: Activation of A3 adenosine receptor provides lung protection against ischemia-reperfusion injury associated with reduction in apoptosis.

Journal: American journal of transplantation : official journal of the American Society of Transplantation and the American Society of Transplant Surgeons 20041201

Title: Activation of A3 adenosine receptors attenuates lung injury after in vivo reperfusion.

Journal: Anesthesiology 20041101

Title: Synthesis and biological evaluation of novel N6-[4-(substituted)sulfonamidophenylcarbamoyl]adenosine-5'-uronamides as A3 adenosine receptor agonists.

Journal: Journal of medicinal chemistry 20041021

Title: Design and synthesis of 3'-ureidoadenosine-5'-uronamides: effects of the 3'-ureido group on binding to the A3 adenosine receptor.

Journal: Bioorganic & medicinal chemistry letters 20041004

Title: Negative chronotropic response to adenosine receptor stimulation in rat right atria after run training.

Journal: Clinical and experimental pharmacology & physiology 20041001

Title: 2-Pyrazolyl-N(6)-substituted adenosine derivatives as high affinity and selective adenosine A(3) receptor agonists.

Journal: Journal of medicinal chemistry 20040909

Title: Role of adenosine A1 receptor in the regulation of gastrin release.

Journal: The Journal of pharmacology and experimental therapeutics 20040801

Title: An adenosine analog (IB-MECA) inhibits anchorage-dependent cell growth of various human breast cancer cell lines.

Journal: The international journal of biochemistry & cell biology 20040801

Title: A2A adenosine receptor activation improves survival in mouse models of endotoxemia and sepsis.

Journal: The Journal of infectious diseases 20040515

Title: An agonist to the A3 adenosine receptor inhibits colon carcinoma growth in mice via modulation of GSK-3 beta and NF-kappa B.

Journal: Oncogene 20040401

Title: Effects of stable adenosine receptor agonists on bone marrow hematopoietic cells as inferred from the cytotoxic action of 5-fluorouracil.

Journal: Physiological research 20040101

Title: A3 adenosine receptor activation in melanoma cells: association between receptor fate and tumor growth inhibition.

Journal: The Journal of biological chemistry 20031024

Title: Inhibition of primary colon carcinoma growth and liver metastasis by the A3 adenosine receptor agonist CF101.

Journal: British journal of cancer 20031020

Title: An adenosine analogue, IB-MECA, down-regulates estrogen receptor alpha and suppresses human breast cancer cell proliferation.

Journal: Cancer research 20031001

Title: Protection from myocardial stunning by ischaemia and hypoxia with the adenosine A3 receptor agonist, IB-MECA.

Journal: European journal of pharmacology 20030923

Title: N6-substituted D-4'-thioadenosine-5'-methyluronamides: potent and selective agonists at the human A3 adenosine receptor.

Journal: Journal of medicinal chemistry 20030828

Title: A3 adenosine receptor agonist IB-MECA reduces myocardial ischemia-reperfusion injury in dogs.

Journal: American journal of physiology. Heart and circulatory physiology 20030801

Title: Protein kinase C-delta mediates adenosine A3 receptor-induced delayed cardioprotection in mouse.

Journal: American journal of physiology. Heart and circulatory physiology 20030701

Title: Activation of murine lung mast cells by the adenosine A3 receptor.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20030701

Title: Adenosine affects expression of membrane molecules, cytokine and chemokine release, and the T-cell stimulatory capacity of human dendritic cells.

Journal: Blood 20030515

Title: The adenosine A3 receptor agonist, N6-(3-iodobenzyl)-adenosine-5'-N-methyluronamide, is protective in two murine models of colitis.

Journal: European journal of pharmacology 20030418

Title: The influence of adenosine A3 receptor agonist: IB-MECA, on scopolamine- and MK-801-induced memory impairment.

Journal: Behavioural brain research 20030417

Title: A3 adenosine receptor knockout mice are protected against ischemia- and myoglobinuria-induced renal failure.

Journal: American journal of physiology. Renal physiology 20030201

Title: Pharmacological analysis of calcium responses mediated by the human A3 adenosine receptor in monocyte-derived dendritic cells and recombinant cells.

Journal: Molecular pharmacology 20030201

Title: 3'-Aminoadenosine-5'-uronamides: discovery of the first highly selective agonist at the human adenosine A3 receptor.

Journal: Journal of medicinal chemistry 20030130

Title: Positive coupling of atypical adenosine A3 receptors on human eosinophils to adenylyl cyclase.

Journal: Biochemical and biophysical research communications 20030117

Title: Targeting the A3 adenosine receptor for cancer therapy: inhibition of prostate carcinoma cell growth by A3AR agonist.

Journal: Anticancer research 20030101

Title: Contractile responses to adenosine, R-PIA and ovalbumen in passively sensitized guinea-pig isolated airways.

Journal: British journal of pharmacology 20021101

Title: Structural determinants of A(3) adenosine receptor activation: nucleoside ligands at the agonist/antagonist boundary.

Journal: Journal of medicinal chemistry 20020926

Title: Knockout of A3 adenosine receptors reduces mouse intraocular pressure.

Journal: Investigative ophthalmology & visual science 20020901

Title: Evidence for involvement of Wnt signaling pathway in IB-MECA mediated suppression of melanoma cells.

Journal: Oncogene 20020606

Title: Effects of adenosine receptor agonists on guinea-pig isolated working hearts and the role of endothelium and NO.

Journal: The Journal of pharmacy and pharmacology 20020601

Title: Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells.

Journal: The Journal of biological chemistry 20020419

Title: Adenosine A(3) receptor-mediated potentiation of mucociliary transport and epithelial ciliary motility.

Journal: American journal of physiology. Lung cellular and molecular physiology 20020301

Title: Late preconditioning elicited by activation of adenosine A(3) receptor in heart: role of NF- kappa B, iNOS and mitochondrial K(ATP) channel.

Journal: Journal of molecular and cellular cardiology 20020301

Title: Regulation of glycogen metabolism in hepatocytes through adenosine receptors. Role of Ca2+ and cAMP.

Journal: European journal of pharmacology 20020222

Title: A(3) adenosine receptors in human neutrophils and promyelocytic HL60 cells: a pharmacological and biochemical study.

Journal: Molecular pharmacology 20020201

Title: Apparent activation of cardiovascular A1 adenosine receptors by A3 agonists.

Journal: American journal of physiology. Heart and circulatory physiology 20020201

Title: Binding thermodynamics at the human A(3) adenosine receptor.

Journal: Biochemical pharmacology 20020115

Title: Inhibition of human mast cell activation with the novel selective adenosine A(2B) receptor antagonist 3-isobutyl-8-pyrrolidinoxanthine (IPDX)(2).

Journal: Biochemical pharmacology 20011101

Title: Adenosine-mediated hypotension in in vivo guinea-pig: receptors involved and role of NO.

Journal: British journal of pharmacology 20011001

Title: The plasma protein extravasation induced by adenosine and its analogues in the rat dorsal skin: evidence for the involvement of capsaicin sensitive primary afferent neurones and mast cells.

Journal: British journal of pharmacology 20010901

Title: Pharmacological characterization of adenosine receptors in PGT-beta mouse pineal gland tumour cells.

Journal: British journal of pharmacology 20010901

Title: Role of adenosine in ischemic preconditioning in rats depends critically on the duration of the stimulus and involves both A(1) and A(3) receptors.

Journal: Cardiovascular research 20010901

Title: Protection of IB-MECA against myocardial stunning in conscious rabbits is not mediated by the A1 adenosine receptor.

Journal: Basic research in cardiology 20010901

Title: Right thing at a wrong time? Adenosine A3 receptors and cerebroprotection in stroke.

Journal: Annals of the New York Academy of Sciences 20010601

Title: Regulation of p42/p44 mitogen-activated protein kinase by the human adenosine A3 receptor in transfected CHO cells.

Journal: European journal of pharmacology 20010518

Title: A3 adenosine receptor stimulation modulates sarcoplasmic reticulum Ca(2+) release in rat heart.

Journal: Cardiovascular research 20010401

Title: Adenosine inhibits neutrophil vascular endothelial growth factor release and transendothelial migration via A2B receptor activation.

Journal: Shock (Augusta, Ga.) 20010401

Title: A(1) or A(3) adenosine receptors induce late preconditioning against infarction in conscious rabbits by different mechanisms.

Journal: Circulation research 20010316

Title: A3 adenosine receptor activation triggers phosphorylation of protein kinase B and protects rat basophilic leukemia 2H3 mast cells from apoptosis.

Journal: Molecular pharmacology 20010101

Title: [(3)H]MRE 3008F20: a novel antagonist radioligand for the pharmacological and biochemical characterization of human A(3) adenosine receptors.

Journal: Molecular pharmacology 20000501

Title: Activation of the A3 adenosine receptor affects cell cycle progression and cell growth.

Journal: Naunyn-Schmiedeberg's archives of pharmacology 20000301

Title: Characterization of human A(2B) adenosine receptors: radioligand binding, western blotting, and coupling to G(q) in human embryonic kidney 293 cells and HMC-1 mast cells.

Journal: Molecular pharmacology 19991001

Title: Structure-activity relationships and molecular modeling of 3, 5-diacyl-2,4-dialkylpyridine derivatives as selective A3 adenosine receptor antagonists.

Journal: Journal of medicinal chemistry 19980813

Title: 2'-C-Methyl analogues of selective adenosine receptor agonists: synthesis and binding studies.

Journal: Journal of medicinal chemistry 19980507

Title: Comparative pharmacology of human adenosine receptor subtypes - characterization of stably transfected receptors in CHO cells.

Journal: Naunyn-Schmiedeberg's archives of pharmacology 19980101

Title: Canine mast cell adenosine receptors: cloning and expression of the A3 receptor and evidence that degranulation is mediated by the A2B receptor.

Journal: Molecular pharmacology 19971101

Title: Site-directed mutagenesis identifies residues involved in ligand recognition in the human A2a adenosine receptor.

Journal: The Journal of biological chemistry 19950609

Title: The effects of adenosine A3 receptor stimulation on seizures in mice.

Journal: European journal of pharmacology 19950224

Title: 2-Substitution of N6-benzyladenosine-5'-uronamides enhances selectivity for A3 adenosine receptors.

Journal: Journal of medicinal chemistry 19941014

Title: Structure-activity relationships of N6-benzyladenosine-5'-uronamides as A3-selective adenosine agonists.

Journal: Journal of medicinal chemistry 19940304

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Tags:152918-18-8 Molecular Formula|152918-18-8 MDL|152918-18-8 SMILES|152918-18-8 Ib-meca