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116649-85-5,MFCD00887606
Catalog No.:AA000CV2

116649-85-5 | 9H-Carbazole-9-propanoic acid, 3-[[(4-fluorophenyl)sulfonyl]amino]-1,2,3,4-tetrahydro-, (3R)-

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  • Technical Information
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Technical Information
Catalog Number:
AA000CV2
Chemical Name:
9H-Carbazole-9-propanoic acid, 3-[[(4-fluorophenyl)sulfonyl]amino]-1,2,3,4-tetrahydro-, (3R)-
CAS Number:
116649-85-5
Molecular Formula:
C21H21FN2O4S
Molecular Weight:
416.4658
MDL Number:
MFCD00887606
SMILES:
OC(=O)CCn1c2CC[C@H](Cc2c2c1cccc2)NS(=O)(=O)c1ccc(cc1)F
Properties
Properties
 
Form:
Solid  
MP:
134-138°C  
Storage:
Keep in dry area;2-8℃;  

Computed Properties
 
Complexity:
689  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Heavy Atom Count:
29  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
6  
XLogP3:
2.9  

Literature

Title: Prostaglandin D2 toxicity in primary neurons is mediated through its bioactive cyclopentenone metabolites.

Journal: Neurotoxicology 20131201

Title: Asymmetric chemoenzymatic synthesis of ramatroban using lipases and oxidoreductases.

Journal: The Journal of organic chemistry 20120518

Title: Induction of apoptosis in non-small cell lung carcinoma A549 cells by PGD₂ metabolite, 15d-PGJ₂.

Journal: Cell biology international 20111101

Title: Discovery of potent, selective, and orally bioavailable alkynylphenoxyacetic acid CRTH2 (DP2) receptor antagonists for the treatment of allergic inflammatory diseases.

Journal: Journal of medicinal chemistry 20111027

Title: Zwitterionic CRTh2 antagonists.

Journal: Journal of medicinal chemistry 20110324

Title: Discovery of MK-7246, a selective CRTH2 antagonist for the treatment of respiratory diseases.

Journal: Bioorganic & medicinal chemistry letters 20110101

Title: Prostaglandin D₂ receptor CRTH2 antagonists for the treatment of inflammatory diseases.

Journal: Progress in medicinal chemistry 20110101

Title: Prophylactic effects of the histamine H1 receptor antagonist epinastine and the dual thromboxane A2 receptor and chemoattractant receptor-homologous molecule expressed on Th2 cells antagonist ramatroban on allergic rhinitis model in mice.

Journal: Biological & pharmaceutical bulletin 20110101

Title: CRTH2 mediates the activation of human Th2 cells in response to PGD(2) released from IgE/anti-IgE treated nasal polyp tissue.

Journal: Allergy 20100301

Title: Identification and characterisation of new inhibitors for the human hematopoietic prostaglandin D2 synthase.

Journal: European journal of medicinal chemistry 20100201

Title: [CRTH2 antagonist ameliorates airway inflammation in rats with asthma].

Journal: Zhejiang da xue xue bao. Yi xue ban = Journal of Zhejiang University. Medical sciences 20100101

Title: 7-Azaindole-3-acetic acid derivatives: potent and selective CRTh2 receptor antagonists.

Journal: Bioorganic & medicinal chemistry letters 20090815

Title: Evidence that 13-14 di-hydro, 15-keto prostaglandin D(2)-induced airway eosinophilia in guinea-pigs is independent of interleukin-5.

Journal: Inflammation research : official journal of the European Histamine Research Society ... [et al.] 20090201

Title: IL-16 variability and modulation by antiallergic drugs in a murine experimental allergic rhinitis model.

Journal: International archives of allergy and immunology 20090101

Title: A novel antagonist of prostaglandin D2 blocks the locomotion of eosinophils and basophils.

Journal: European journal of clinical investigation 20080901

Title: CRTH2 plays an essential role in the pathophysiology of Cry j 1-induced pollinosis in mice.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20080415

Title: Discovery of a new class of potent, selective, and orally bioavailable CRTH2 (DP2) receptor antagonists for the treatment of allergic inflammatory diseases.

Journal: Journal of medicinal chemistry 20080410

Title: The role of prostaglandin E and thromboxane-prostanoid receptors in the response to prostaglandin E2 in the aorta of Wistar Kyoto rats and spontaneously hypertensive rats.

Journal: Cardiovascular research 20080401

Title: Antagonists of the prostaglandin D2 receptor CRTH2.

Journal: Drug news & perspectives 20080101

Title: Participation in cysteinyl leukotrienes and thromboxane A2 in nasal congestion model in Brown Norway rats.

Journal: International immunopharmacology 20071101

Title: A paracrine role for chemoattractant receptor-homologous molecule expressed on T helper type 2 cells (CRTH2) in mediating chemotactic activation of CRTH2+ CD4+ T helper type 2 lymphocytes.

Journal: Immunology 20070801

Title: Interactive effect of histamine and prostaglandin D2 on nasal allergic symptoms in rats.

Journal: European journal of pharmacology 20070112

Title: Antagonism of the prostaglandin D2 receptor CRTH2 attenuates asthma pathology in mouse eosinophilic airway inflammation.

Journal: Respiratory research 20070101

Title: Successful treatment of eosinophilic otitis media using ramatroban: report of two cases.

Journal: Auris, nasus, larynx 20061201

Title: Involvement of cyclooxygenase-2 in allergic nasal inflammation in rats.

Journal: International immunopharmacology 20061101

Title: A dominant role for chemoattractant receptor-homologous molecule expressed on T helper type 2 (Th2) cells (CRTH2) in mediating chemotaxis of CRTH2+ CD4+ Th2 lymphocytes in response to mast cell supernatants.

Journal: Immunology 20061101

Title: Hierarchy of eosinophil chemoattractants: role of p38 mitogen-activated protein kinase.

Journal: European journal of immunology 20060901

Title: Prostanoids as pharmacological targets in COPD and asthma.

Journal: European journal of pharmacology 20060308

Title: Prostaglandin D2 causes preferential induction of proinflammatory Th2 cytokine production through an action on chemoattractant receptor-like molecule expressed on Th2 cells.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20051115

Title: CRTH2-specific binding characteristics of [3H]ramatroban and its effects on PGD2-, 15-deoxy-Delta12, 14-PGJ2- and indomethacin-induced agonist responses.

Journal: European journal of pharmacology 20051107

Title: Effects of fexofenadine hydrochloride in a guinea pig model of antigen-induced rhinitis.

Journal: Pharmacology 20051001

Title: Identification of determinants of ligand binding affinity and selectivity in the prostaglandin D2 receptor CRTH2.

Journal: The Journal of biological chemistry 20050916

Title: Inhibitory effect of the 4-aminotetrahydroquinoline derivatives, selective chemoattractant receptor-homologous molecule expressed on T helper 2 cell antagonists, on eosinophil migration induced by prostaglandin D2.

Journal: The Journal of pharmacology and experimental therapeutics 20050701

Title: Isosteric ramatroban analogs: selective and potent CRTH-2 antagonists.

Journal: Bioorganic & medicinal chemistry letters 20050315

Title: Prostaglandin D2-induced eosinophilic airway inflammation is mediated by CRTH2 receptor.

Journal: The Journal of pharmacology and experimental therapeutics 20050301

Title: Structural determinants of arylacetic acid nonsteroidal anti-inflammatory drugs necessary for binding and activation of the prostaglandin D2 receptor CRTH2.

Journal: Molecular pharmacology 20050301

Title: Minor structural modifications convert the dual TP/CRTH2 antagonist ramatroban into a highly selective and potent CRTH2 antagonist.

Journal: Journal of medicinal chemistry 20050224

Title: Participation of chemical mediators in the development of experimental allergic conjunctivitis in rats.

Journal: International immunopharmacology 20041101

Title: CRTH2 is a prominent effector in contact hypersensitivity-induced neutrophil inflammation.

Journal: International immunology 20040701

Title: Pharmacokinetic analysis of ramatroban using a recirculatory model with enterohepatic circulation by measuring portal and systemic blood concentration difference in Sprague-Dawley and Eisai hyperbilirubinemic rats.

Journal: Pharmaceutical research 20040601

Title: [Study of thromboxane A2 antagonist reduction in the treatment of patients with perennial allergic rhinitis].

Journal: Arerugi = [Allergy] 20040601

Title: Evaluation of anti-platelet aggregatory effects of aspirin, cilostazol and ramatroban on platelet-rich plasma and whole blood.

Journal: Blood coagulation & fibrinolysis : an international journal in haemostasis and thrombosis 20040301

Title: 11-Dehydro-thromboxane B2, a stable thromboxane metabolite, is a full agonist of chemoattractant receptor-homologous molecule expressed on TH2 cells (CRTH2) in human eosinophils and basophils.

Journal: The Journal of biological chemistry 20040227

Title: Ramatroban (BAY u 3405): a novel dual antagonist of TXA2 receptor and CRTh2, a newly identified prostaglandin D2 receptor.

Journal: Cardiovascular drug reviews 20040101

Title: Chemoattractant receptor-homologous molecule expressed on Th2 cells activation in vivo increases blood leukocyte counts and its blockade abrogates 13,14-dihydro-15-keto-prostaglandin D2-induced eosinophilia in rats.

Journal: The Journal of pharmacology and experimental therapeutics 20031101

Title: [The 3 effective cases of cough variant asthma with ramatroban].

Journal: Arerugi = [Allergy] 20031101

Title: Ramatroban, a TP receptor antagonist, improves vascular responses to acetylcholine in hypercholesterolemic rabbits in vivo.

Journal: European journal of pharmacology 20030502

Title: An orally bioavailable small molecule antagonist of CRTH2, ramatroban (BAY u3405), inhibits prostaglandin D2-induced eosinophil migration in vitro.

Journal: The Journal of pharmacology and experimental therapeutics 20030401

Title: Ramatroban, a thromboxane A2 receptor antagonist, prevents macrophage accumulation and neointimal formation after balloon arterial injury in cholesterol-fed rabbits.

Journal: Journal of cardiovascular pharmacology 20030401

Title: The role of chemical mediators in eosinophil infiltration in allergic rhinitis in mice.

Journal: International immunopharmacology 20030401

Title: Participation of chemical mediators other than histamine in nasal allergy signs: a study using mice lacking histamine H(1) receptors.

Journal: European journal of pharmacology 20020809

Title: Thromboxane A2 inhibition: therapeutic potential in bronchial asthma.

Journal: American journal of respiratory medicine : drugs, devices, and other interventions 20020101

Title: Prostanoid EP(1)- and TP-receptors involved in the contraction of human pulmonary veins.

Journal: British journal of pharmacology 20011201

Title: [Ramatroban (Baynas): a review of its pharmacological and clinical profile].

Journal: Nihon yakurigaku zasshi. Folia pharmacologica Japonica 20011201

Title: Differential effects of prostacyclin and iloprost in the isolated carotid artery of the guinea-pig.

Journal: European journal of pharmacology 20010824

Title: Necessity of thromboxane A2 for initiation of platelet-mediated contact sensitivity: dual activation of platelets and vascular endothelial cells.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20010101

Title: Synthesis and biological evaluation of new tetrahydronaphthalene derivatives as thromboxane receptor antagonists.

Journal: Bioorganic & medicinal chemistry letters 19980602

Title: Binding characteristics of the new thromboxane A2/prostaglandin H2 receptor antagonist [3H]BAY U 3405 to washed human platelets and platelet membranes.

Journal: Biochemical pharmacology 19920804

Title: Stearns BA, et al. Novel tricyclic antagonists of the prostaglandin D2 receptor DP2 with efficacy in a murine modelof allergic rhinitis. Bioorg Med Chem Lett. 2009 Aug 15;19(16):4647-51.

Title: Sugimoto H, et al. An orally bioavailable small molecule antagonist of CRTH2, ramatroban (BAY u3405), inhibits prostaglandin D2-induced eosinophil migration in vitro. J Pharmacol Exp Ther. 2003 Apr;305(1):347-52.

Title: Haba R, et al. Central CRTH2, a second prostaglandin D2 receptor, mediates emotional impairment in the lipopolysaccharide and tumor-induced sickness behavior model. J Neurosci. 2014 Feb 12;34(7):2514-23.

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Tags:116649-85-5 Molecular Formula|116649-85-5 MDL|116649-85-5 SMILES|116649-85-5 9H-Carbazole-9-propanoic acid, 3-[[(4-fluorophenyl)sulfonyl]amino]-1,2,3,4-tetrahydro-, (3R)-