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Terutroban

CAS No.:
165538-40-9
Catalog Number:
AG001W7T
Molecular Formula:
C20H22ClNO4S
Molecular Weight:
407.9110
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
5mg
≥98%
1 week
United States
$139
- +
10mg
99%
1 week
United States
$165
- +
50mg
99%
1 week
United States
$523
- +
Product Description
Catalog Number:
AG001W7T
Chemical Name:
Terutroban
CAS Number:
165538-40-9
Molecular Formula:
C20H22ClNO4S
Molecular Weight:
407.9110
MDL Number:
MFCD28411833
IUPAC Name:
3-[(6R)-6-[(4-chlorophenyl)sulfonylamino]-2-methyl-5,6,7,8-tetrahydronaphthalen-1-yl]propanoic acid
InChI:
InChI=1S/C20H22ClNO4S/c1-13-2-3-14-12-16(6-9-19(14)18(13)10-11-20(23)24)22-27(25,26)17-7-4-15(21)5-8-17/h2-5,7-8,16,22H,6,9-12H2,1H3,(H,23,24)/t16-/m1/s1
InChI Key:
HWEOXFSBSQIWSY-MRXNPFEDSA-N
SMILES:
OC(=O)CCc1c(C)ccc2c1CC[C@H](C2)NS(=O)(=O)c1ccc(cc1)Cl
UNII:
A6WX9391D8
Properties
Complexity:
612  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Defined Bond Stereocenter Count:
0
Exact Mass:
407.096g/mol
Formal Charge:
0
Heavy Atom Count:
27  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
407.909g/mol
Monoisotopic Mass:
407.096g/mol
Rotatable Bond Count:
6  
Topological Polar Surface Area:
91.8A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
4.1  
Literature
Title Journal
Antiplatelet treatment in primary and secondary stroke prevention in women. European journal of internal medicine 20121001
Why the United States Center for Medicare and Medicaid Services (CMS) should not extend reimbursement indications for carotid artery angioplasty/stenting. Brain and behavior 20120301
Effects of terutroban, a thromboxane/prostaglandin endoperoxide receptor antagonist, on retinal vascularity in diabetic rats. Diabetes/metabolism research and reviews 20120201
Asymptomatic and symptomatic carotid stenosis: an obsolete classification? Stroke research and treatment 20120101
Increased atherothrombotic burden in patients with diabetes mellitus and acute coronary syndrome: a review of antiplatelet therapy. Cardiology research and practice 20120101
Aging-shifted prostaglandin profile in endothelium as a factor in cardiovascular disorders. Journal of aging research 20120101
Thromboxane receptors antagonists and/or synthase inhibitors. Handbook of experimental pharmacology 20120101
Antiplatelet therapy: terutroban does not out-PERFORM aspirin in secondary prevention. Nature reviews. Cardiology 20110621
Vascular events after stroke: terutroban fails to PERFORM. Lancet (London, England) 20110611
Terutroban versus aspirin in patients with cerebral ischaemic events (PERFORM): a randomised, double-blind, parallel-group trial. Lancet (London, England) 20110611
Daily administration of the TP receptor antagonist terutroban improved endothelial function in high-cardiovascular-risk patients with atherosclerosis. British journal of clinical pharmacology 20110601
Design, data management, and population baseline characteristics of the PERFORM magnetic resonance imaging project. Journal of neurology 20110501
New therapeutic approaches to combat arterial thrombosis: better drugs for old targets, novel targets, and future prospects. Molecular interventions 20110401
Terutroban, a thromboxane/prostaglandin endoperoxide receptor antagonist, prevents hypertensive vascular hypertrophy and fibrosis. American journal of physiology. Heart and circulatory physiology 20110301
Placebo - More hatred than love. Journal of neurosciences in rural practice 20110101
Platelet function in patients with diabetes mellitus: from a theoretical to a practical perspective. International journal of endocrinology 20110101
Dexmedetomidine induces both relaxations and contractions, via different {alpha}2-adrenoceptor subtypes, in the isolated mesenteric artery and aorta of the rat. The Journal of pharmacology and experimental therapeutics 20101201
Thromboxane Antagonism with terutroban in Peripheral Arterial Disease: the TAIPAD study. Journal of thrombosis and haemostasis : JTH 20101101
Controversies and future perspectives of antiplatelet therapy in secondary stroke prevention. Journal of cellular and molecular medicine 20101001
Terutroban, a thromboxane/prostaglandin endoperoxide receptor antagonist, increases survival in stroke-prone rats by preventing systemic inflammation and endothelial dysfunction: comparison with aspirin and rosuvastatin. The Journal of pharmacology and experimental therapeutics 20100701
Antiplatelet drugs--do we need new options? With a reappraisal of direct thromboxane inhibitors. Drugs 20100507
Rationale, design and population baseline characteristics of the PERFORM vascular project: an ancillary study of the Prevention of cerebrovascular and cardiovascular Events of ischemic origin with teRutroban in patients with a history oF ischemic strOke or tRansient ischeMic attack (PERFORM) trial. Cardiovascular drugs and therapy 20100401
Pharmacokinetic, pharmacodynamic and clinical profile of novel antiplatelet drugs targeting vascular diseases. British journal of pharmacology 20100201
[Update on new antithrombotic treatments]. Revue medicale suisse 20100120
Novel antiplatelet agents in the prevention of cardiovascular complications--focus on ticagrelor. Vascular health and risk management 20100101
Emerging antiplatelet agents, differential pharmacology, and clinical utility. Journal of blood medicine 20100101
New antiplatelet agents: why they are needed. European journal of internal medicine 20091201
New antiplatelet agents. Current opinion in hematology 20090901
New antiplatelet drugs: beyond aspirin and clopidogrel. International journal of clinical practice 20090501
Update on oral antiplatelet therapy: principles, problems and promises. Future cardiology 20090501
Rationale and design of a randomized, double-blind, parallel-group study of terutroban 30 mg/day versus aspirin 100 mg/day in stroke patients: the prevention of cerebrovascular and cardiovascular events of ischemic origin with terutroban in patients with a history of ischemic stroke or transient ischemic attack (PERFORM) study. Cerebrovascular diseases (Basel, Switzerland) 20090101
The Prevention of cerebrovascular and cardiovascular Events of ischemic origin with teRutroban in patients with a history oF ischemic strOke or tRansient ischeMic attack (PERFORM) study: baseline characteristics of the population. Cerebrovascular diseases (Basel, Switzerland) 20090101
TP receptor antagonism: a new concept in atherothrombosis and stroke prevention. Cerebrovascular diseases (Basel, Switzerland) 20090101
Rationale and design of the Prevention of Cerebrovascular and Cardiovascular Events of Ischemic Origin with Terutroban in Patients with a History of Ischemic Stroke or Transient Ischemic Attack (PERFORM) Study. Cerebrovascular diseases (Basel, Switzerland) 20090101
Effect of the thromboxane prostaglandin receptor antagonist terutroban on arterial thrombogenesis after repeated administration in patients treated for the prevention of ischemic stroke. Cerebrovascular diseases (Basel, Switzerland) 20090101
Hypertension and the absence of EDHF-mediated responses favour endothelium-dependent contractions in renal arteries of the rat. British journal of pharmacology 20080901
Negative effects of rofecoxib treatment on cardiac function after ischemia-reperfusion injury in APOE3Leiden mice are prevented by combined treatment with thromboxane prostanoid-receptor antagonist S18886 (terutroban). Critical care medicine 20080901
Selective COX-2 inhibitors: new insights into mechanisms of side effects? Critical care medicine 20080901
Antiplatelet therapy for secondary prevention of noncardioembolic ischemic stroke: a critical review. Stroke 20080501
Thromboxane receptor activation mediates isoprostane-induced increases in amyloid pathology in Tg2576 mice. The Journal of neuroscience : the official journal of the Society for Neuroscience 20080430
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. Cardiovascular research 20080401
Two isoforms of cyclooxygenase contribute to augmented endothelium-dependent contractions in femoral arteries of 1-year-old rats. Acta pharmacologica Sinica 20080201
The selective TP receptor antagonist, S18886 (terutroban), attenuates renal damage in the double transgenic rat model of hypertension. American journal of nephrology 20080101
Altered TP receptor function in isolated, perfused kidneys of nondiabetic and diabetic ApoE-deficient mice. American journal of physiology. Renal physiology 20080101
Increased spontaneous tone in renal arteries of spontaneously hypertensive rats. American journal of physiology. Heart and circulatory physiology 20070901
A thromboxane A2/prostaglandin H2 receptor antagonist (S18886) shows high antithrombotic efficacy in an experimental model of stent-induced thrombosis. Thrombosis and haemostasis 20070901
Renal effects of S18886 (Terutroban), a TP receptor antagonist, in an experimental model of type 2 diabetes. Diabetes 20070401
Preclinical evaluation of S18886 in an experimental model of coronary arterial thrombosis. Journal of cardiovascular pharmacology 20061101
TP receptor as a therapeutic target in atherosclerosis and related cardiovascular diseases. Recent patents on cardiovascular drug discovery 20061101
[Terutroban and endothelial TP receptors in atherogenesis]. Medecine sciences : M/S 20060401
Thromboxane A2/prostaglandin H2 receptor activation mediates angiotensin II-induced postischemic neovascularization. Arteriosclerosis, thrombosis, and vascular biology 20060301
The thromboxane receptor antagonist S18886 attenuates renal oxidant stress and proteinuria in diabetic apolipoprotein E-deficient mice. Diabetes 20060101
Experimental models of thrombosis and atherosclerosis. Therapie 20060101
The thromboxane A2 receptor antagonist S18886 prevents enhanced atherogenesis caused by diabetes mellitus. Circulation 20051108
S18886, a selective TP receptor antagonist, inhibits development of atherosclerosis in rabbits. Atherosclerosis 20051101
Atherosclerosis regression and TP receptor inhibition: effect of S18886 on plaque size and composition--a magnetic resonance imaging study. European heart journal 20050801
The specific thromboxane receptor antagonist S18886: pharmacokinetic and pharmacodynamic studies. Journal of thrombosis and haemostasis : JTH 20050701
Antithrombotic properties of the thromboxane A2/prostaglandin H2 receptor antagonist S18886 on prevention of platelet-dependent cyclic flow reductions in dogs. Journal of cardiovascular pharmacology 20050501
Cyclooxygenases, thromboxane, and atherosclerosis: plaque destabilization by cyclooxygenase-2 inhibition combined with thromboxane receptor antagonism. Circulation 20050125
Improved endothelial function by the thromboxane A2 receptor antagonist S 18886 in patients with coronary artery disease treated with aspirin. Journal of the American College of Cardiology 20030402
S-18886 Servier. Current opinion in investigational drugs (London, England : 2000) 20020901
Role of prostacyclin in the cardiovascular response to thromboxane A2. Science (New York, N.Y.) 20020419
Synthesis and biological evaluation of new tetrahydronaphthalene derivatives as thromboxane receptor antagonists. Bioorganic & medicinal chemistry letters 19980602
Properties