571170-77-9,MFCD11042421
Catalog No.:AA00ECB4

571170-77-9 | Laropiprant

Pack Size
Purity
Availability
Price(USD)
Quantity
  
1mg
≥98%
in stock  
$82.00   $57.00
- +
5mg
≥98%
in stock  
$199.00   $139.00
- +
10mg
≥98%
in stock  
$356.00   $249.00
- +
25mg
≥98%
in stock  
$782.00   $547.00
- +
50mg
99% (HPLC)
in stock  
$1,434.00   $1,004.00
- +
100mg
99% (HPLC)
in stock  
$2,435.00   $1,705.00
- +
500mg
99% (HPLC)
in stock  
$7,722.00   $5,405.00
- +
1000mg
99% (HPLC)
in stock  
$12,318.00   $8,623.00
- +
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
Technical Information
Catalog Number:
AA00ECB4
Chemical Name:
Laropiprant
CAS Number:
571170-77-9
Molecular Formula:
C21H19ClFNO4S
Molecular Weight:
435.8963
MDL Number:
MFCD11042421
SMILES:
OC(=O)C[C@H]1CCc2c1n(Cc1ccc(cc1)Cl)c1c2cc(cc1S(=O)(=O)C)F
Properties
Computed Properties
 
Complexity:
721  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Heavy Atom Count:
29  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
5  
XLogP3:
3.5  

Downstream Synthesis Route

[1]Campos,KevinR.;Journet,Michel;Lee,Sandra;Grabowski,EdwardJ.J.;Tillyer,RichardD.[JournalofOrganicChemistry,2005,vol.70,#1,p.268-274]

[2]Sturino,ClaudioF.;O'Neill,Gary;Lachance,Nicolas;Boyd,Michael;Berthelette,Carl;Labelle,Marc;Li,Lianhai;Roy,Bruno;Scheigetz,John;Tsou,Nancy;Aubin,Yves;Bateman,KevinP.;Chauret,Nathalie;Day,StephenH.;Lévesque,Jean-François;Seto,Carmai;Silva,JoseH.;Trimble,LairdA.;Carriere,Marie-Claude;Denis,Danielle;Greig,Gillian;Kargman,Stacia;Lamontagne,Sonia;Mathieu,Marie-Claude;Sawyer,Nicole;Slipetz,Deborah;Abraham,WilliamM.;Jones,Tom;McAuliffe,Malia;Piechuta,Hana;Nicoll-Griffith,DeborahA.;Wang,Zhaoyin;Zamboni,Robert;Young,RobertN.;Metters,KathleenM.[JournalofMedicinalChemistry,2007,vol.50,#4,p.794-806]

[3]CurrentPatentAssignee:MERCK&COINC-WO2006/57922,2006,A2Locationinpatent:Page/Pagecolumn77-78

[1]Shafiee,Ali;Upadhyay,Veena;Corley,EdwardG.;Biba,Mirlinda;Zhao,Dalian;Marcoux,Jean-Francois;Campos,KevinR.;Journet,Michel;King,AnthonyO.;Larsen,RobD.;Grabowski,EdwardJ.J.;Volante,RalphP.;Tillyer,RichardD.[TetrahedronAsymmetry,2005,vol.16,#18,p.3094-3098]

800381-16-2    20277-69-4    104-83-6   
4-(4-chloro-benzyl)-7-fluoro-5-methanesulfonyl-1,2,3,4-tetrahydro-cyclopenta<i>b</i>indol-3-yl-aceticacid 
  571170-77-9 

[1]Shafiee,Ali;Upadhyay,Veena;Corley,EdwardG.;Biba,Mirlinda;Zhao,Dalian;Marcoux,Jean-Francois;Campos,KevinR.;Journet,Michel;King,AnthonyO.;Larsen,RobD.;Grabowski,EdwardJ.J.;Volante,RalphP.;Tillyer,RichardD.[TetrahedronAsymmetry,2005,vol.16,#18,p.3094-3098]

571170-77-9   
4-(4-chloro-benzyl)-7-fluoro-5-methanesulfonyl-1-oxo-1,2,3,4-tetrahydro-cyclopenta<i>b</i>indol-3-yl-aceticacid 
 
(1R,3R)-4-(4-Chloro-benzyl)-7-fluoro-1-hydroxy-5-methanesulfonyl-1,2,3,4-tetrahydro-cyclopentabindol-3-yl-aceticacid 
 
(1S,3R)-4-(4-Chloro-benzyl)-7-fluoro-1-hydroxy-5-methanesulfonyl-1,2,3,4-tetrahydro-cyclopentabindol-3-yl-aceticacid 

[1]Nicoll-Griffith,DeborahA.;Seto,Carmai;Aubin,Yves;Levesque,JeanFrancois;Chauret,Nathalie;Day,Stephen;Silva,JoseM.;Trimble,LairdA.;Truchon,Jean-Francois;Berthelette,Carl;Lachance,Nicolas;Wang,Zhaoyin;Sturino,Claudio;Braun,Matt;Zamboni,Robert;Young,RobertN.[BioorganicandMedicinalChemistryLetters,2007,vol.17,#2,p.301-304]

866215-99-8   
4-(4-chloro-benzyl)-7-fluoro-5-methanesulfonyl-1,2,3,4-tetrahydro-cyclopenta<i>b</i>indol-3-yl-aceticacid 
  571170-77-9 

[1]Tellers,DavidM.;McWilliams,J.Christopher;Humphrey,Guy;Journet,Michel;DiMichele,Lisa;Hinksmon,Joseph;McKeown,ArleneE.;Rosner,Thorsten;Sun,Yongkui;Tillyer,RichardD.[JournaloftheAmericanChemicalSociety,2006,vol.128,#51,p.17063-17073]

[2]Tellers,DavidM.;McWilliams,J.Christopher;Humphrey,Guy;Journet,Michel;DiMichele,Lisa;Hinksmon,Joseph;McKeown,ArleneE.;Rosner,Thorsten;Sun,Yongkui;Tillyer,RichardD.[JournaloftheAmericanChemicalSociety,2006,vol.128,#51,p.17063-17073]

Literature

Title: Effectiveness and safety of laropiprant on niacin-induced flushing.

Journal: The American journal of cardiology 20120915

Title: Extended-release niacin/laropiprant effects on lipoprotein subfractions in patients with type 2 diabetes mellitus.

Journal: Metabolic syndrome and related disorders 20120801

Title: Cost-effectiveness of extended-release niacin/laropiprant added to a stable simvastatin dose in secondary prevention patients not at cholesterol goal in Germany.

Journal: The European journal of health economics : HEPAC : health economics in prevention and care 20120601

Title: Consistency of extended-release niacin/laropiprant effects on Lp(a), ApoB, non-HDL-C, Apo A1, and ApoB/ApoA1 ratio across patient subgroups.

Journal: American journal of cardiovascular drugs : drugs, devices, and other interventions 20120601

Title: Extended-release niacin with laropiprant : a review on efficacy, clinical effectiveness and safety.

Journal: Expert opinion on pharmacotherapy 20120601

Title: Bullous drug eruption secondary to nicotinic acid/laropiprant.

Journal: Annals of the Academy of Medicine, Singapore 20120301

Title: Safety and tolerability of extended-release niacin with laropiprant.

Journal: Expert opinion on drug safety 20120101

Title: Lipid disorders in elderly hypertensive patients.

Journal: International journal of hypertension 20120101

Title: Attenuation of niacin-induced prostaglandin D(2) generation by omega-3 fatty acids in THP-1 macrophages and Langerhans dendritic cells.

Journal: Journal of inflammation research 20120101

Title: Effects of coadministered extended-release niacin/laropiprant and simvastatin on lipoprotein subclasses in patients with dyslipidemia.

Journal: Journal of clinical lipidology 20120101

Title: Laropiprant attenuates EP3 and TP prostanoid receptor-mediated thrombus formation.

Journal: PloS one 20120101

Title: Familial hypercholesterolemia: present and future management.

Journal: Current cardiology reports 20111201

Title: Paradoxical decrease in serum high-density lipoprotein cholesterol with Tredaptive® (m/r nicotinic acid 1 g and laropiprant 20 mg).

Journal: Annals of clinical biochemistry 20111101

Title: Progress in HDL-based therapies for atherosclerosis.

Journal: Current atherosclerosis reports 20111001

Title: Pleiotropic effects of nicotinic acid: beyond high density lipoprotein cholesterol elevation.

Journal: Current vascular pharmacology 20110701

Title: Sustained hypophosphatemic effect of once-daily niacin/laropiprant in dyslipidemic CKD stage 3 patients.

Journal: American journal of kidney diseases : the official journal of the National Kidney Foundation 20110601

Title: Triglyceride-rich lipoproteins and high-density lipoprotein cholesterol in patients at high risk of cardiovascular disease: evidence and guidance for management.

Journal: European heart journal 20110601

Title: The resurgence of niacin: from nicotinic acid to niaspan/laropiprant.

Journal: The Israel Medical Association journal : IMAJ 20110601

Title: Extended-release niacin/laropiprant lipid-altering consistency across patient subgroups.

Journal: International journal of clinical practice 20110401

Title: The causes and consequences of low levels of high density lipoproteins in patients with diabetes.

Journal: Diabetes & metabolism journal 20110401

Title: Pharmacokinetics of laropiprant, a selective prostaglandin D2 receptor 1 antagonist, in patients with moderate hepatic impairment.

Journal: Journal of clinical pharmacology 20110301

Title: The effects of laropiprant, a selective prostaglandin D₂ receptor 1 antagonist, on the antiplatelet activity of clopidogrel or aspirin.

Journal: Platelets 20110101

Title: Add-on-Statin Extended Release Nicotinic Acid/Laropiprant but Not the Switch to High-Dose Rosuvastatin Lowers Blood Pressure: An Open-Label Randomized Study.

Journal: International journal of hypertension 20110101

Title: Treating statin-intolerant patients.

Journal: Diabetes, metabolic syndrome and obesity : targets and therapy 20110101

Title: Extended-release niacin/laropiprant lowers serum phosphorus concentrations in patients with type 2 diabetes.

Journal: Journal of clinical lipidology 20110101

Title: Extended release niacin-laropiprant in patients with hypercholesterolemia or mixed dyslipidemias improves clinical parameters.

Journal: Clinical Medicine Insights. Cardiology 20110101

Title: Biological roles and therapeutic potential of hydroxy-carboxylic Acid receptors.

Journal: Frontiers in endocrinology 20110101

Title: Single therapeutic and supratherapeutic doses of laropiprant, a selective prostaglandin D2 receptor 1 antagonist, do not prolong the QTcF interval in healthy volunteers.

Journal: Journal of clinical pharmacology 20101101

Title: Pharmacomodulation of high-density lipoprotein metabolism as a therapeutic intervention for atherosclerotic disease.

Journal: Current cardiology reports 20101101

Title: Induction of prostaglandin D2 through the p38 MAPK pathway is responsible for the antipruritic activity of sertaconazole nitrate.

Journal: The Journal of investigative dermatology 20101001

Title: HDL and LDL as therapeutic targets for cardiovascular disease prevention: the possible role of niacin.

Journal: Nutrition, metabolism, and cardiovascular diseases : NMCD 20101001

Title: Management of hypertriglyceridemia in the diabetic patient.

Journal: Current diabetes reports 20100801

Title: Effects of laropiprant, a selective prostaglandin D2 receptor 1 antagonist, on the steady-state pharmacokinetics of digoxin in healthy adult subjects.

Journal: Journal of clinical pharmacology 20100701

Title: Laropiprant plus niacin for dyslipidemia and prevention of cardiovascular disease.

Journal: Expert opinion on pharmacotherapy 20100701

Title: [Hyperlipoproteinaemia and dyslipoproteinaemia II. Therapy: non-pharmacological and pharmacological approaches].

Journal: Vnitrni lekarstvi 20100701

Title: Niacin and laropiprant.

Journal: Drugs of today (Barcelona, Spain : 1998) 20100601

Title: Mast cell-derived prostaglandin D2 controls hyaluronan synthesis in human orbital fibroblasts via DP1 activation: implications for thyroid eye disease.

Journal: The Journal of biological chemistry 20100521

Title: Efficacy and safety of extended-release niacin/laropiprant plus statin vs. doubling the dose of statin in patients with primary hypercholesterolaemia or mixed dyslipidaemia.

Journal: International journal of clinical practice 20100501

Title: Hypophosphatemic effect of niacin in patients without renal failure: a randomized trial.

Journal: Clinical journal of the American Society of Nephrology : CJASN 20100401

Title: A new paradigm for managing dyslipidemia with combination therapy: laropiprant + niacin + simvastatin.

Journal: Expert opinion on investigational drugs 20100301

Title: Nicotinic acid + larodiorant. Laropiprant adds its own adverse effects.

Journal: Prescrire international 20100201

Title: Cholesteryl ester transfer protein: at the heart of the action of lipid-modulating therapy with statins, fibrates, niacin, and cholesteryl ester transfer protein inhibitors.

Journal: European heart journal 20100101

Title: Effects of extended release niacin/laropiprant, laropiprant, extended release niacin and placebo on platelet aggregation and bleeding time in healthy subjects.

Journal: Platelets 20100101

Title: Niacin, an old drug with new perspectives for the management of dyslipidaemia.

Journal: Acta clinica Belgica 20100101

Title: Critical appraisal of laropiprant and extended-release niacin combination in the management of mixed dyslipidemias and primary hypercholesterolemia.

Journal: Therapeutics and clinical risk management 20100101

Title: Safety of extended-release niacin/laropiprant in patients with dyslipidemia.

Journal: Journal of clinical lipidology 20100101

Title: Efficacy and tolerability of extended-release niacin/laropiprant in dyslipidemic patients with metabolic syndrome.

Journal: Journal of clinical lipidology 20100101

Title: Low high-density lipoprotein cholesterol: current status and future strategies for management.

Journal: Vascular health and risk management 20100101

Title: Treatment of dyslipidemia in patients with type 2 diabetes.

Journal: Lipids in health and disease 20100101

Title: Recent advances in preventing cardiovascular disorders by managing lipid levels.

Journal: F1000 medicine reports 20100101

Title: High density lipoproteins-based therapies for cardiovascular disease.

Journal: Journal of cardiovascular disease research 20100101

Title: Safety and efficacy of laropiprant and extended-release niacin combination in the management of mixed dyslipidemias and primary hypercholesterolemia.

Journal: Drug, healthcare and patient safety 20100101

Title: Current strategies and recent advances in the therapy of hypercholesterolemia.

Journal: Atherosclerosis. Supplements 20091229

Title: What's the deal with niacin development: is laropiprant add-on therapy a winning strategy to beat a straight flush?

Journal: Current opinion in lipidology 20091201

Title: Laropiprant in combination with extended-release niacin does not alter urine 11-dehydrothromboxane B2, a marker of in vivo platelet function, in healthy, hypercholesterolemic, and diabetic subjects.

Journal: Journal of clinical pharmacology 20091201

Title: Clinical studies of the DP1 antagonist laropiprant in asthma and allergic rhinitis.

Journal: The Journal of allergy and clinical immunology 20091101

Title: Mechanisms of flushing due to niacin and abolition of these effects.

Journal: Journal of clinical hypertension (Greenwich, Conn.) 20091101

Title: The mechanism and mitigation of niacin-induced flushing.

Journal: International journal of clinical practice 20090901

Title: Extended-release niacin (nicotinic acid)/laropiprant.

Journal: Drugs 20090820

Title: Nephropathy and other topics.

Journal: Diabetes care 20090801

Title: Flushing profile of extended-release niacin/laropiprant versus gradually titrated niacin extended-release in patients with dyslipidemia with and without ischemic cardiovascular disease.

Journal: The American journal of cardiology 20090701

Title: Discovery of potent and selective DP1 receptor antagonists in the azaindole series.

Journal: Bioorganic & medicinal chemistry letters 20090415

Title: Effects of aspirin when added to the prostaglandin D2 receptor antagonist laropiprant on niacin-induced flushing symptoms.

Journal: Journal of clinical pharmacology 20090401

Title: Does nicotinic acid (niacin) lower blood pressure?

Journal: International journal of clinical practice 20090101

Title: Niacin: an old drug rejuvenated.

Journal: Current atherosclerosis reports 20090101

Title: A review of trials evaluating nonstatin lipid-lowering therapies.

Journal: Current atherosclerosis reports 20090101

Title: High-density lipoprotein cholesterol: current perspective for clinicians.

Journal: Angiology 20090101

Title: Blood pressure-lowering effects of extended-release niacin alone and extended-release niacin/laropiprant combination: a post hoc analysis of a 24-week, placebo-controlled trial in dyslipidemic patients.

Journal: Clinical therapeutics 20090101

Title: Pharmacokinetics of laropiprant and glucuronide metabolite in patients with severe renal insufficiency.

Journal: American journal of therapeutics 20090101

Title: Management of complex lipid abnormalities with a fixed dose combination of simvastatin and extended release niacin.

Journal: Vascular health and risk management 20090101

Title: Influence of laropiprant, a selective prostaglandin D2 receptor 1 antagonist, on the pharmacokinetics and pharmacodynamics of warfarin.

Journal: American journal of therapeutics 20090101

Title: Flushing profile of extended-release niacin/laropiprant at initiation of therapy in Asian lipid clinic patients.

Journal: Cardiology 20090101

Title: Drug-drug noninteractions.

Journal: Cardiovascular therapeutics 20090101

Title: Effects of laropiprant, a selective prostaglandin D(2) receptor 1 antagonist, on the pharmacokinetics of rosiglitazone.

Journal: Cardiovascular therapeutics 20090101

Title: Effect of laropiprant, a PGD2 receptor 1 antagonist, on estradiol and norgestimate pharmacokinetics after oral contraceptive administration in women.

Journal: American journal of therapeutics 20090101

Title: Review of extended-release niacin/laropiprant fixed combination in the treatment of mixed dyslipidemia and primary hypercholesterolemia.

Journal: Vascular health and risk management 20090101

Title: Lipid-modifying efficacy of extended release niacin/laropiprant in Asian patients with primary hypercholesterolemia or mixed hyperlipidemia.

Journal: Journal of clinical lipidology 20090101

Title: Lipid-modifying efficacy and tolerability of extended-release niacin/laropiprant in patients with primary hypercholesterolaemia or mixed dyslipidaemia.

Journal: International journal of clinical practice 20081201

Title: Extended-release niacin/laropiprant: reducing niacin-induced flushing to better realize the benefit of niacin in improving cardiovascular risk factors.

Journal: Cardiology clinics 20081101

Title: Targeting multiple dyslipidemias with fixed combinations--focus on extended release niacin and simvastatin.

Journal: Vascular health and risk management 20081001

Title: Nicotinic acid: recent developments.

Journal: Current opinion in cardiology 20080701

Title: Pharmacokinetics, pharmacodynamics, and safety of a prostaglandin D2 receptor antagonist.

Journal: Clinical pharmacology and therapeutics 20080601

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology 20080601

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology 20080501

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology 20080401

Title: Effects of laropiprant on nicotinic acid-induced flushing in patients with dyslipidemia.

Journal: The American journal of cardiology 20080301

Title: Gateways to clinical trials. July-August 2008.

Journal: Methods and findings in experimental and clinical pharmacology 20080101

Title: Molecule of the Month. TREDAPTIVE (nicotinic acid/laropiprant): a new lipid-modifying therapy for the treatment of LDL-C, HDL-C and triglycerides.

Journal: Current topics in medicinal chemistry 20080101

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology 20071201

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology 20071001

Title: Absorption, metabolism, and excretion of [(14)C]MK-0524, a prostaglandin D(2) receptor antagonist, in humans.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20070701

Title: Suppression of niacin-induced vasodilation with an antagonist to prostaglandin D2 receptor subtype 1.

Journal: Clinical pharmacology and therapeutics 20070601

Title: Metabolic activation of indole-containing prostaglandin D2 receptor 1 antagonists: impacts of glutathione trapping and glucuronide conjugation on covalent binding.

Journal: Bioorganic & medicinal chemistry letters 20070601

Title: The pharmacokinetics and disposition of MK-0524, a Prosglandin D2 Receptor 1 antagonist, in rats, dogs and monkeys.

Journal: Xenobiotica; the fate of foreign compounds in biological systems 20070501

Title: Discovery of a potent and selective prostaglandin D2 receptor antagonist, [(3R)-4-(4-chloro-benzyl)-7-fluoro-5-(methylsulfonyl)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]-acetic acid (MK-0524).

Journal: Journal of medicinal chemistry 20070222

Title: Metabolism of MK-0524, a prostaglandin D2 receptor 1 antagonist, in microsomes and hepatocytes from preclinical species and humans.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20070201

Title: In vitro biotransformations of the prostaglandin D2 (DP) antagonist MK-0524 and synthesis of metabolites.

Journal: Bioorganic & medicinal chemistry letters 20070115

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology 20070101

Title: Body temperatures and heart rates of laboratory rats and Belding squirrels (Spermophilus beldingi) during behavioral thermoregulation.

Journal: Comparative biochemistry and physiology. A, Comparative physiology 19751201

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Related Products of 571170-77-9
Tags:571170-77-9 Molecular Formula|571170-77-9 MDL|571170-77-9 SMILES|571170-77-9 Laropiprant
Catalog No.: AA00ECB4
571170-77-9,MFCD11042421
571170-77-9 | Laropiprant
Pack Size: 1mg
Purity: ≥98%
in stock
$82.00 $57.00
Pack Size: 5mg
Purity: ≥98%
in stock
$199.00 $139.00
Pack Size: 10mg
Purity: ≥98%
in stock
$356.00 $249.00
Pack Size: 25mg
Purity: ≥98%
in stock
$782.00 $547.00
Pack Size: 50mg
Purity: 99% (HPLC)
in stock
$1,434.00 $1,004.00
Pack Size: 100mg
Purity: 99% (HPLC)
in stock
$2,435.00 $1,705.00
Pack Size: 500mg
Purity: 99% (HPLC)
in stock
$7,722.00 $5,405.00
Pack Size: 1000mg
Purity: 99% (HPLC)
in stock
$12,318.00 $8,623.00
Quantity
- +
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Technical Information
Catalog Number: AA00ECB4
Chemical Name: Laropiprant
CAS Number: 571170-77-9
Molecular Formula: C21H19ClFNO4S
Molecular Weight: 435.8963
MDL Number: MFCD11042421
SMILES: OC(=O)C[C@H]1CCc2c1n(Cc1ccc(cc1)Cl)c1c2cc(cc1S(=O)(=O)C)F
Properties
Complexity: 721  
Covalently-Bonded Unit Count: 1  
Defined Atom Stereocenter Count: 1  
Heavy Atom Count: 29  
Hydrogen Bond Acceptor Count: 5  
Hydrogen Bond Donor Count: 1  
Rotatable Bond Count: 5  
XLogP3: 3.5  
Downstream Synthesis Route
571170-92-8    571170-77-9 

[1]Campos,KevinR.;Journet,Michel;Lee,Sandra;Grabowski,EdwardJ.J.;Tillyer,RichardD.[JournalofOrganicChemistry,2005,vol.70,#1,p.268-274]

[2]Sturino,ClaudioF.;O'Neill,Gary;Lachance,Nicolas;Boyd,Michael;Berthelette,Carl;Labelle,Marc;Li,Lianhai;Roy,Bruno;Scheigetz,John;Tsou,Nancy;Aubin,Yves;Bateman,KevinP.;Chauret,Nathalie;Day,StephenH.;Lévesque,Jean-François;Seto,Carmai;Silva,JoseH.;Trimble,LairdA.;Carriere,Marie-Claude;Denis,Danielle;Greig,Gillian;Kargman,Stacia;Lamontagne,Sonia;Mathieu,Marie-Claude;Sawyer,Nicole;Slipetz,Deborah;Abraham,WilliamM.;Jones,Tom;McAuliffe,Malia;Piechuta,Hana;Nicoll-Griffith,DeborahA.;Wang,Zhaoyin;Zamboni,Robert;Young,RobertN.;Metters,KathleenM.[JournalofMedicinalChemistry,2007,vol.50,#4,p.794-806]

[3]CurrentPatentAssignee:MERCK&amp;COINC-WO2006/57922,2006,A2Locationinpatent:Page/Pagecolumn77-78

393509-05-2    20277-69-4    571170-77-9 

[1]Shafiee,Ali;Upadhyay,Veena;Corley,EdwardG.;Biba,Mirlinda;Zhao,Dalian;Marcoux,Jean-Francois;Campos,KevinR.;Journet,Michel;King,AnthonyO.;Larsen,RobD.;Grabowski,EdwardJ.J.;Volante,RalphP.;Tillyer,RichardD.[TetrahedronAsymmetry,2005,vol.16,#18,p.3094-3098]

800381-16-2    20277-69-4    104-83-6   
4-(4-chloro-benzyl)-7-fluoro-5-methanesulfonyl-1,2,3,4-tetrahydro-cyclopenta<i>b</i>indol-3-yl-aceticacid 
  571170-77-9 

[1]Shafiee,Ali;Upadhyay,Veena;Corley,EdwardG.;Biba,Mirlinda;Zhao,Dalian;Marcoux,Jean-Francois;Campos,KevinR.;Journet,Michel;King,AnthonyO.;Larsen,RobD.;Grabowski,EdwardJ.J.;Volante,RalphP.;Tillyer,RichardD.[TetrahedronAsymmetry,2005,vol.16,#18,p.3094-3098]

571170-77-9   
4-(4-chloro-benzyl)-7-fluoro-5-methanesulfonyl-1-oxo-1,2,3,4-tetrahydro-cyclopenta<i>b</i>indol-3-yl-aceticacid 
 
(1R,3R)-4-(4-Chloro-benzyl)-7-fluoro-1-hydroxy-5-methanesulfonyl-1,2,3,4-tetrahydro-cyclopentabindol-3-yl-aceticacid 
 
(1S,3R)-4-(4-Chloro-benzyl)-7-fluoro-1-hydroxy-5-methanesulfonyl-1,2,3,4-tetrahydro-cyclopentabindol-3-yl-aceticacid 

[1]Nicoll-Griffith,DeborahA.;Seto,Carmai;Aubin,Yves;Levesque,JeanFrancois;Chauret,Nathalie;Day,Stephen;Silva,JoseM.;Trimble,LairdA.;Truchon,Jean-Francois;Berthelette,Carl;Lachance,Nicolas;Wang,Zhaoyin;Sturino,Claudio;Braun,Matt;Zamboni,Robert;Young,RobertN.[BioorganicandMedicinalChemistryLetters,2007,vol.17,#2,p.301-304]

866215-99-8   
4-(4-chloro-benzyl)-7-fluoro-5-methanesulfonyl-1,2,3,4-tetrahydro-cyclopenta<i>b</i>indol-3-yl-aceticacid 
  571170-77-9 

[1]Tellers,DavidM.;McWilliams,J.Christopher;Humphrey,Guy;Journet,Michel;DiMichele,Lisa;Hinksmon,Joseph;McKeown,ArleneE.;Rosner,Thorsten;Sun,Yongkui;Tillyer,RichardD.[JournaloftheAmericanChemicalSociety,2006,vol.128,#51,p.17063-17073]

[2]Tellers,DavidM.;McWilliams,J.Christopher;Humphrey,Guy;Journet,Michel;DiMichele,Lisa;Hinksmon,Joseph;McKeown,ArleneE.;Rosner,Thorsten;Sun,Yongkui;Tillyer,RichardD.[JournaloftheAmericanChemicalSociety,2006,vol.128,#51,p.17063-17073]

Literature fold

Title: Effectiveness and safety of laropiprant on niacin-induced flushing.

Journal: The American journal of cardiology20120915

Title: Extended-release niacin/laropiprant effects on lipoprotein subfractions in patients with type 2 diabetes mellitus.

Journal: Metabolic syndrome and related disorders20120801

Title: Cost-effectiveness of extended-release niacin/laropiprant added to a stable simvastatin dose in secondary prevention patients not at cholesterol goal in Germany.

Journal: The European journal of health economics : HEPAC : health economics in prevention and care20120601

Title: Consistency of extended-release niacin/laropiprant effects on Lp(a), ApoB, non-HDL-C, Apo A1, and ApoB/ApoA1 ratio across patient subgroups.

Journal: American journal of cardiovascular drugs : drugs, devices, and other interventions20120601

Title: Extended-release niacin with laropiprant : a review on efficacy, clinical effectiveness and safety.

Journal: Expert opinion on pharmacotherapy20120601

Title: Bullous drug eruption secondary to nicotinic acid/laropiprant.

Journal: Annals of the Academy of Medicine, Singapore20120301

Title: Safety and tolerability of extended-release niacin with laropiprant.

Journal: Expert opinion on drug safety20120101

Title: Lipid disorders in elderly hypertensive patients.

Journal: International journal of hypertension20120101

Title: Attenuation of niacin-induced prostaglandin D(2) generation by omega-3 fatty acids in THP-1 macrophages and Langerhans dendritic cells.

Journal: Journal of inflammation research20120101

Title: Effects of coadministered extended-release niacin/laropiprant and simvastatin on lipoprotein subclasses in patients with dyslipidemia.

Journal: Journal of clinical lipidology20120101

Title: Laropiprant attenuates EP3 and TP prostanoid receptor-mediated thrombus formation.

Journal: PloS one20120101

Title: Familial hypercholesterolemia: present and future management.

Journal: Current cardiology reports20111201

Title: Paradoxical decrease in serum high-density lipoprotein cholesterol with Tredaptive® (m/r nicotinic acid 1 g and laropiprant 20 mg).

Journal: Annals of clinical biochemistry20111101

Title: Progress in HDL-based therapies for atherosclerosis.

Journal: Current atherosclerosis reports20111001

Title: Pleiotropic effects of nicotinic acid: beyond high density lipoprotein cholesterol elevation.

Journal: Current vascular pharmacology20110701

Title: Sustained hypophosphatemic effect of once-daily niacin/laropiprant in dyslipidemic CKD stage 3 patients.

Journal: American journal of kidney diseases : the official journal of the National Kidney Foundation20110601

Title: Triglyceride-rich lipoproteins and high-density lipoprotein cholesterol in patients at high risk of cardiovascular disease: evidence and guidance for management.

Journal: European heart journal20110601

Title: The resurgence of niacin: from nicotinic acid to niaspan/laropiprant.

Journal: The Israel Medical Association journal : IMAJ20110601

Title: Extended-release niacin/laropiprant lipid-altering consistency across patient subgroups.

Journal: International journal of clinical practice20110401

Title: The causes and consequences of low levels of high density lipoproteins in patients with diabetes.

Journal: Diabetes & metabolism journal20110401

Title: Pharmacokinetics of laropiprant, a selective prostaglandin D2 receptor 1 antagonist, in patients with moderate hepatic impairment.

Journal: Journal of clinical pharmacology20110301

Title: The effects of laropiprant, a selective prostaglandin D₂ receptor 1 antagonist, on the antiplatelet activity of clopidogrel or aspirin.

Journal: Platelets20110101

Title: Add-on-Statin Extended Release Nicotinic Acid/Laropiprant but Not the Switch to High-Dose Rosuvastatin Lowers Blood Pressure: An Open-Label Randomized Study.

Journal: International journal of hypertension20110101

Title: Treating statin-intolerant patients.

Journal: Diabetes, metabolic syndrome and obesity : targets and therapy20110101

Title: Extended-release niacin/laropiprant lowers serum phosphorus concentrations in patients with type 2 diabetes.

Journal: Journal of clinical lipidology20110101

Title: Extended release niacin-laropiprant in patients with hypercholesterolemia or mixed dyslipidemias improves clinical parameters.

Journal: Clinical Medicine Insights. Cardiology20110101

Title: Biological roles and therapeutic potential of hydroxy-carboxylic Acid receptors.

Journal: Frontiers in endocrinology20110101

Title: Single therapeutic and supratherapeutic doses of laropiprant, a selective prostaglandin D2 receptor 1 antagonist, do not prolong the QTcF interval in healthy volunteers.

Journal: Journal of clinical pharmacology20101101

Title: Pharmacomodulation of high-density lipoprotein metabolism as a therapeutic intervention for atherosclerotic disease.

Journal: Current cardiology reports20101101

Title: Induction of prostaglandin D2 through the p38 MAPK pathway is responsible for the antipruritic activity of sertaconazole nitrate.

Journal: The Journal of investigative dermatology20101001

Title: HDL and LDL as therapeutic targets for cardiovascular disease prevention: the possible role of niacin.

Journal: Nutrition, metabolism, and cardiovascular diseases : NMCD20101001

Title: Management of hypertriglyceridemia in the diabetic patient.

Journal: Current diabetes reports20100801

Title: Effects of laropiprant, a selective prostaglandin D2 receptor 1 antagonist, on the steady-state pharmacokinetics of digoxin in healthy adult subjects.

Journal: Journal of clinical pharmacology20100701

Title: Laropiprant plus niacin for dyslipidemia and prevention of cardiovascular disease.

Journal: Expert opinion on pharmacotherapy20100701

Title: [Hyperlipoproteinaemia and dyslipoproteinaemia II. Therapy: non-pharmacological and pharmacological approaches].

Journal: Vnitrni lekarstvi20100701

Title: Niacin and laropiprant.

Journal: Drugs of today (Barcelona, Spain : 1998)20100601

Title: Mast cell-derived prostaglandin D2 controls hyaluronan synthesis in human orbital fibroblasts via DP1 activation: implications for thyroid eye disease.

Journal: The Journal of biological chemistry20100521

Title: Efficacy and safety of extended-release niacin/laropiprant plus statin vs. doubling the dose of statin in patients with primary hypercholesterolaemia or mixed dyslipidaemia.

Journal: International journal of clinical practice20100501

Title: Hypophosphatemic effect of niacin in patients without renal failure: a randomized trial.

Journal: Clinical journal of the American Society of Nephrology : CJASN20100401

Title: A new paradigm for managing dyslipidemia with combination therapy: laropiprant + niacin + simvastatin.

Journal: Expert opinion on investigational drugs20100301

Title: Nicotinic acid + larodiorant. Laropiprant adds its own adverse effects.

Journal: Prescrire international20100201

Title: Cholesteryl ester transfer protein: at the heart of the action of lipid-modulating therapy with statins, fibrates, niacin, and cholesteryl ester transfer protein inhibitors.

Journal: European heart journal20100101

Title: Effects of extended release niacin/laropiprant, laropiprant, extended release niacin and placebo on platelet aggregation and bleeding time in healthy subjects.

Journal: Platelets20100101

Title: Niacin, an old drug with new perspectives for the management of dyslipidaemia.

Journal: Acta clinica Belgica20100101

Title: Critical appraisal of laropiprant and extended-release niacin combination in the management of mixed dyslipidemias and primary hypercholesterolemia.

Journal: Therapeutics and clinical risk management20100101

Title: Safety of extended-release niacin/laropiprant in patients with dyslipidemia.

Journal: Journal of clinical lipidology20100101

Title: Efficacy and tolerability of extended-release niacin/laropiprant in dyslipidemic patients with metabolic syndrome.

Journal: Journal of clinical lipidology20100101

Title: Low high-density lipoprotein cholesterol: current status and future strategies for management.

Journal: Vascular health and risk management20100101

Title: Treatment of dyslipidemia in patients with type 2 diabetes.

Journal: Lipids in health and disease20100101

Title: Recent advances in preventing cardiovascular disorders by managing lipid levels.

Journal: F1000 medicine reports20100101

Title: High density lipoproteins-based therapies for cardiovascular disease.

Journal: Journal of cardiovascular disease research20100101

Title: Safety and efficacy of laropiprant and extended-release niacin combination in the management of mixed dyslipidemias and primary hypercholesterolemia.

Journal: Drug, healthcare and patient safety20100101

Title: Current strategies and recent advances in the therapy of hypercholesterolemia.

Journal: Atherosclerosis. Supplements20091229

Title: What's the deal with niacin development: is laropiprant add-on therapy a winning strategy to beat a straight flush?

Journal: Current opinion in lipidology20091201

Title: Laropiprant in combination with extended-release niacin does not alter urine 11-dehydrothromboxane B2, a marker of in vivo platelet function, in healthy, hypercholesterolemic, and diabetic subjects.

Journal: Journal of clinical pharmacology20091201

Title: Clinical studies of the DP1 antagonist laropiprant in asthma and allergic rhinitis.

Journal: The Journal of allergy and clinical immunology20091101

Title: Mechanisms of flushing due to niacin and abolition of these effects.

Journal: Journal of clinical hypertension (Greenwich, Conn.)20091101

Title: The mechanism and mitigation of niacin-induced flushing.

Journal: International journal of clinical practice20090901

Title: Extended-release niacin (nicotinic acid)/laropiprant.

Journal: Drugs20090820

Title: Nephropathy and other topics.

Journal: Diabetes care20090801

Title: Flushing profile of extended-release niacin/laropiprant versus gradually titrated niacin extended-release in patients with dyslipidemia with and without ischemic cardiovascular disease.

Journal: The American journal of cardiology20090701

Title: Discovery of potent and selective DP1 receptor antagonists in the azaindole series.

Journal: Bioorganic & medicinal chemistry letters20090415

Title: Effects of aspirin when added to the prostaglandin D2 receptor antagonist laropiprant on niacin-induced flushing symptoms.

Journal: Journal of clinical pharmacology20090401

Title: Does nicotinic acid (niacin) lower blood pressure?

Journal: International journal of clinical practice20090101

Title: Niacin: an old drug rejuvenated.

Journal: Current atherosclerosis reports20090101

Title: A review of trials evaluating nonstatin lipid-lowering therapies.

Journal: Current atherosclerosis reports20090101

Title: High-density lipoprotein cholesterol: current perspective for clinicians.

Journal: Angiology20090101

Title: Blood pressure-lowering effects of extended-release niacin alone and extended-release niacin/laropiprant combination: a post hoc analysis of a 24-week, placebo-controlled trial in dyslipidemic patients.

Journal: Clinical therapeutics20090101

Title: Pharmacokinetics of laropiprant and glucuronide metabolite in patients with severe renal insufficiency.

Journal: American journal of therapeutics20090101

Title: Management of complex lipid abnormalities with a fixed dose combination of simvastatin and extended release niacin.

Journal: Vascular health and risk management20090101

Title: Influence of laropiprant, a selective prostaglandin D2 receptor 1 antagonist, on the pharmacokinetics and pharmacodynamics of warfarin.

Journal: American journal of therapeutics20090101

Title: Flushing profile of extended-release niacin/laropiprant at initiation of therapy in Asian lipid clinic patients.

Journal: Cardiology20090101

Title: Drug-drug noninteractions.

Journal: Cardiovascular therapeutics20090101

Title: Effects of laropiprant, a selective prostaglandin D(2) receptor 1 antagonist, on the pharmacokinetics of rosiglitazone.

Journal: Cardiovascular therapeutics20090101

Title: Effect of laropiprant, a PGD2 receptor 1 antagonist, on estradiol and norgestimate pharmacokinetics after oral contraceptive administration in women.

Journal: American journal of therapeutics20090101

Title: Review of extended-release niacin/laropiprant fixed combination in the treatment of mixed dyslipidemia and primary hypercholesterolemia.

Journal: Vascular health and risk management20090101

Title: Lipid-modifying efficacy of extended release niacin/laropiprant in Asian patients with primary hypercholesterolemia or mixed hyperlipidemia.

Journal: Journal of clinical lipidology20090101

Title: Lipid-modifying efficacy and tolerability of extended-release niacin/laropiprant in patients with primary hypercholesterolaemia or mixed dyslipidaemia.

Journal: International journal of clinical practice20081201

Title: Extended-release niacin/laropiprant: reducing niacin-induced flushing to better realize the benefit of niacin in improving cardiovascular risk factors.

Journal: Cardiology clinics20081101

Title: Targeting multiple dyslipidemias with fixed combinations--focus on extended release niacin and simvastatin.

Journal: Vascular health and risk management20081001

Title: Nicotinic acid: recent developments.

Journal: Current opinion in cardiology20080701

Title: Pharmacokinetics, pharmacodynamics, and safety of a prostaglandin D2 receptor antagonist.

Journal: Clinical pharmacology and therapeutics20080601

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology20080601

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology20080501

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology20080401

Title: Effects of laropiprant on nicotinic acid-induced flushing in patients with dyslipidemia.

Journal: The American journal of cardiology20080301

Title: Gateways to clinical trials. July-August 2008.

Journal: Methods and findings in experimental and clinical pharmacology20080101

Title: Molecule of the Month. TREDAPTIVE (nicotinic acid/laropiprant): a new lipid-modifying therapy for the treatment of LDL-C, HDL-C and triglycerides.

Journal: Current topics in medicinal chemistry20080101

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology20071201

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology20071001

Title: Absorption, metabolism, and excretion of [(14)C]MK-0524, a prostaglandin D(2) receptor antagonist, in humans.

Journal: Drug metabolism and disposition: the biological fate of chemicals20070701

Title: Suppression of niacin-induced vasodilation with an antagonist to prostaglandin D2 receptor subtype 1.

Journal: Clinical pharmacology and therapeutics20070601

Title: Metabolic activation of indole-containing prostaglandin D2 receptor 1 antagonists: impacts of glutathione trapping and glucuronide conjugation on covalent binding.

Journal: Bioorganic & medicinal chemistry letters20070601

Title: The pharmacokinetics and disposition of MK-0524, a Prosglandin D2 Receptor 1 antagonist, in rats, dogs and monkeys.

Journal: Xenobiotica; the fate of foreign compounds in biological systems20070501

Title: Discovery of a potent and selective prostaglandin D2 receptor antagonist, [(3R)-4-(4-chloro-benzyl)-7-fluoro-5-(methylsulfonyl)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]-acetic acid (MK-0524).

Journal: Journal of medicinal chemistry20070222

Title: Metabolism of MK-0524, a prostaglandin D2 receptor 1 antagonist, in microsomes and hepatocytes from preclinical species and humans.

Journal: Drug metabolism and disposition: the biological fate of chemicals20070201

Title: In vitro biotransformations of the prostaglandin D2 (DP) antagonist MK-0524 and synthesis of metabolites.

Journal: Bioorganic & medicinal chemistry letters20070115

Title: Gateways to clinical trials.

Journal: Methods and findings in experimental and clinical pharmacology20070101

Title: Body temperatures and heart rates of laboratory rats and Belding squirrels (Spermophilus beldingi) during behavioral thermoregulation.

Journal: Comparative biochemistry and physiology. A, Comparative physiology19751201

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