Home Other Building Blocks MK 0974, Telcagepant

MK 0974, Telcagepant

CAS No.:
781649-09-0
Catalog Number:
AG00G3P4
Molecular Formula:
C26H27F5N6O3
Molecular Weight:
566.5230
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
≥98%
1 week
United States
$133
- +
2mg
99%
1 week
United States
$232
- +
5mg
99%
1 week
United States
$323
- +
10mg
99%
1 week
United States
$523
- +
50mg
99%
1 week
United States
$2057
- +
100mg
99%
1 week
United States
$3473
- +
Product Description
Catalog Number:
AG00G3P4
Chemical Name:
MK 0974, Telcagepant
CAS Number:
781649-09-0
Molecular Formula:
C26H27F5N6O3
Molecular Weight:
566.5230
MDL Number:
MFCD22741412
IUPAC Name:
N-[(3R,6S)-6-(2,3-difluorophenyl)-2-oxo-1-(2,2,2-trifluoroethyl)azepan-3-yl]-4-(2-oxo-3H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxamide
InChI:
InChI=1S/C26H27F5N6O3/c27-18-4-1-3-17(21(18)28)15-6-7-19(23(38)36(13-15)14-26(29,30)31)33-24(39)35-11-8-16(9-12-35)37-20-5-2-10-32-22(20)34-25(37)40/h1-5,10,15-16,19H,6-9,11-14H2,(H,33,39)(H,32,34,40)/t15-,19-/m1/s1
InChI Key:
CGDZXLJGHVKVIE-DNVCBOLYSA-N
SMILES:
O=C(N1CCC(CC1)n1c(=O)[nH]c2c1cccn2)N[C@@H]1CC[C@H](CN(C1=O)CC(F)(F)F)c1cccc(c1F)F
UNII:
D42O649ALL
Properties
Complexity:
948  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Defined Bond Stereocenter Count:
0
Exact Mass:
566.206g/mol
Formal Charge:
0
Heavy Atom Count:
40  
Hydrogen Bond Acceptor Count:
9  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
566.533g/mol
Monoisotopic Mass:
566.206g/mol
Rotatable Bond Count:
4  
Topological Polar Surface Area:
97.9A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
3  
Literature
Title Journal
Identification of potent CNS-penetrant thiazolidinones as novel CGRP receptor antagonists. Bioorganic & medicinal chemistry letters 20140201
CGRP receptor antagonism and migraine therapy. Current protein & peptide science 20130801
Management of acute and chronic migraine. Current opinion in supportive and palliative care 20120601
CGRP receptor antagonists: an expanding drug class for acute migraine? Expert opinion on investigational drugs 20120601
[Therapy and prophylaxis of migraine]. MMW Fortschritte der Medizin 20120419
A randomized, placebo-controlled study of the effects of telcagepant on exercise time in patients with stable angina. Clinical pharmacology and therapeutics 20120301
Randomized, controlled study of telcagepant in patients with migraine and coronary artery disease. Headache 20120201
High-throughput polymer monolith in-tip SPME fiber preparation and application in drug analysis. Bioanalysis 20111201
ACS chemical neuroscience molecule spotlight on Telcagepant (MK-0974). ACS chemical neuroscience 20110720
Optimal balance of efficacy and tolerability of oral triptans and telcagepant: a review and a clinical comment. The journal of headache and pain 20110601
Treatment of migraine: update on new therapies. Current opinion in neurology 20110601
Effect of telcagepant on spontaneous ischemia in cardiovascular patients in a randomized study. Headache 20110601
EuroQol (EQ-5D) health utility scores for patients with migraine. Quality of life research : an international journal of quality of life aspects of treatment, care and rehabilitation 20110501
Orally bioavailable imidazoazepanes as calcitonin gene-related peptide (CGRP) receptor antagonists: discovery of MK-2918. Bioorganic & medicinal chemistry letters 20110501
The potent calcitonin gene-related peptide receptor antagonist, telcagepant, does not affect nitroglycerin-induced vasodilation in healthy men. British journal of clinical pharmacology 20110501
Possible site of action of CGRP antagonists in migraine. Cephalalgia : an international journal of headache 20110401
Randomized controlled study of telcagepant plus ibuprofen or acetaminophen in migraine. Headache 20110401
Pain freedom at 2 hours in migraine after telcagepant 300 mg. CNS drugs 20110301
Current understanding and treatment of headache disorders: five new things. Neurology 20110215
Sustained pain freedom and no adverse events as an endpoint in clinical trials of acute migraine treatments: application to patient-level data from a trial of the CGRP receptor antagonist, telcagepant, and zolmitriptan. Cephalalgia : an international journal of headache 20110201
Antimigraine efficacy of telcagepant based on patient's historical triptan response. Headache 20110101
Excellent tolerability but relatively low initial clinical efficacy of telcagepant in migraine. Headache 20110101
Long-term tolerability of telcagepant for acute treatment of migraine in a randomized trial. Headache 20110101
Single- and multiple-dose pharmacokinetics and tolerability of telcagepant, an oral calcitonin gene-related peptide receptor antagonist, in adults. Journal of clinical pharmacology 20101201
Randomized, controlled trial of telcagepant over four migraine attacks. Cephalalgia : an international journal of headache 20101201
[Calcitonin gene-related peptide and migraine. Increases understanding of physiopathology can lead to new drug therapy]. Lakartidningen 20101201
Effect of the calcitonin gene-related peptide (CGRP) receptor antagonist telcagepant in human cranial arteries. Cephalalgia : an international journal of headache 20101001
Asymmetric hydrogenation of protected allylic amines. Organic letters 20100917
Crystal structure of the ectodomain complex of the CGRP receptor, a class-B GPCR, reveals the site of drug antagonism. Structure (London, England : 1993) 20100908
Characterization of the calcitonin gene-related peptide receptor antagonist telcagepant (MK-0974) in human isolated coronary arteries. The Journal of pharmacology and experimental therapeutics 20100901
New drugs in migraine treatment and prophylaxis: telcagepant and topiramate. Lancet (London, England) 20100821
Calcitonin gene-related peptide (CGRP) receptor antagonists in the treatment of migraine. CNS drugs 20100701
Calcitonin gene-related peptide receptor antagonists for migraine. Expert opinion on investigational drugs 20100701
Comparison of the vasoconstrictor effects of the calcitonin gene-related peptide receptor antagonist telcagepant (MK-0974) and zolmitriptan in human isolated coronary arteries. Journal of cardiovascular pharmacology 20100501
CGRP receptor antagonism and migraine. Neurotherapeutics : the journal of the American Society for Experimental NeuroTherapeutics 20100401
Mapping the CGRP receptor ligand binding domain: tryptophan-84 of RAMP1 is critical for agonist and antagonist binding. Biochemical and biophysical research communications 20100326
Randomized, controlled trial of telcagepant for the acute treatment of migraine. Neurology 20100323
Non-peptidic antagonists of the CGRP receptor, BIBN4096BS and MK-0974, interact with the calcitonin receptor-like receptor via methionine-42 and RAMP1 via tryptophan-74. Biochemical and biophysical research communications 20100101
Inhibition of capsaicin-induced increase in dermal blood flow by the oral CGRP receptor antagonist, telcagepant (MK-0974). British journal of clinical pharmacology 20100101
Is there an inherent limit to the efficacy of calcitonin gene-related peptide receptor antagonists in the acute treatment of migraine? A comment. The journal of headache and pain 20091201
New drugs for migraine. The journal of headache and pain 20091201
The role of CGRP in the pathophysiology of migraine and efficacy of CGRP receptor antagonists as acute antimigraine drugs. Pharmacology & therapeutics 20091201
Is there an inherent limit to acute migraine treatment efficacy? The journal of headache and pain 20091201
Calcitonin gene-related peptide receptor antagonists for the treatment of migraine: a patent review. Expert opinion on therapeutic patents 20091201
CGRP antagonists: hope for a new era in acute migraine treatment. Acta neurologica Belgica 20091201
Optimization of azepanone calcitonin gene-related peptide (CGRP) receptor antagonists: development of novel spiropiperidines. Bioorganic & medicinal chemistry letters 20091115
Randomized, controlled trial of telcagepant for the acute treatment of migraine. Neurology 20090922
[Migraine can signal a risk for heart and brain]. MMW Fortschritte der Medizin 20090910
The identification of potent, orally bioavailable tricyclic CGRP receptor antagonists. Bioorganic & medicinal chemistry letters 20090815
Telcagepant, a calcitonin gene-related peptide antagonist for the treatment of migraine. Current opinion in investigational drugs (London, England : 2000) 20090701
Elimination of diastereomer interference to determine Telcagepant (MK-0974) in human plasma using on-line turbulent-flow technology and off-line solid-phase extraction coupled with liquid chromatography/tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20090601
A flexible and high throughput liquid chromatography-tandem mass spectrometric assay for the quantitation of telcagepant in human plasma. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20090515
[CGRP antagonists: novel concept for treatment of migraine]. Medizinische Monatsschrift fur Pharmazeuten 20090501
Migraine: Telcagepant provides new hope for people with migraine. Nature reviews. Neurology 20090501
[Gepants: the beginning of a new age in the symptomatic treatment of migraine?]. Revista de neurologia 20090401
An oral calcitonin gene-related peptide receptor antagonist for acute migraine management: sign of a possible new chapter in headache medicine. Current neurology and neuroscience reports 20090301
Molecule of the month. Telcagepant. Drug news & perspectives 20090301
CGRP receptors in the control of pain and inflammation. Current opinion in pharmacology 20090201
Examining the binding properties of MK-0974: a CGRP receptor antagonist for the acute treatment of migraine. European journal of pharmacology 20090114
Preclinical pharmacokinetics of MK-0974, an orally active calcitonin-gene related peptide (CGRP)-receptor antagonist, mechanism of dose dependency and species differences. Xenobiotica; the fate of foreign compounds in biological systems 20090101
Calcitonin gene-related peptide receptor antagonists for the treatment of migraine. Progress in medicinal chemistry 20090101
Efficacy and tolerability of MK-0974 (telcagepant), a new oral antagonist of calcitonin gene-related peptide receptor, compared with zolmitriptan for acute migraine: a randomised, placebo-controlled, parallel-treatment trial. Lancet (London, England) 20081220
CGRP-receptor antagonism in migraine treatment. Lancet (London, England) 20081220
Reversed-phase chiral liquid chromatography on polysaccharide-based stationary phase coupled with tandem mass spectrometry for simultaneous determination of four stereoisomers of MK-0974 in human plasma. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20081001
Clinical and preclinical rationale for CGRP-receptor antagonists in the treatment of migraine. Headache 20080901
Synthesis of the (3R,6S)-3-amino-6-(2,3-difluorophenyl)azepan-2-one of telcagepant (MK-0974), a calcitonin gene-related peptide receptor antagonist for the treatment of migraine headache. Organic letters 20080807
Randomized controlled trial of an oral CGRP receptor antagonist, MK-0974, in acute treatment of migraine. Neurology 20080415
[A new therapeutic principle for migraine]. Ugeskrift for laeger 20080317
Strategies on efficient method development of on-line extraction assays for determination of MK-0974 in human plasma and urine using turbulent-flow chromatography and tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20080215
Pharmacological characterization of MK-0974 [N-[(3R,6S)-6-(2,3-difluorophenyl)-2-oxo-1-(2,2,2-trifluoroethyl)azepan-3-yl]-4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxamide], a potent and orally active calcitonin gene-related peptide receptor antagonist for the treatment of migraine. The Journal of pharmacology and experimental therapeutics 20080201
Treatment of migraine attacks based on the interaction with the trigemino-cerebrovascular system. The journal of headache and pain 20080201
The tortuous road to an ideal CGRP function blocker for the treatment of migraine. Current topics in medicinal chemistry 20080101
Potent, orally bioavailable calcitonin gene-related peptide receptor antagonists for the treatment of migraine: discovery of N-[(3R,6S)-6-(2,3-difluorophenyl)-2-oxo-1- (2,2,2-trifluoroethyl)azepan-3-yl]-4- (2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin- 1-yl)piperidine-1-carboxamide (MK-0974). Journal of medicinal chemistry 20071115
CGRP antagonists: unravelling the role of CGRP in migraine. Trends in pharmacological sciences 20071101
Properties