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Linaclotide

CAS No.:
851199-59-2
Catalog Number:
AG00G3R9
Molecular Formula:
C59H79N15O21S6
Molecular Weight:
1526.7365
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
≥95%
1 week
United States
$119
- +
5mg
≥95%
1 week
United States
$265
- +
10mg
≥95%
1 week
United States
$432
- +
Product Description
Catalog Number:
AG00G3R9
Chemical Name:
Linaclotide
CAS Number:
851199-59-2
Molecular Formula:
C59H79N15O21S6
Molecular Weight:
1526.7365
MDL Number:
MFCD20526656
IUPAC Name:
(2S)-2-[[(1R,4S,7S,13S,16R,21R,24R,27S,30S,33R,38R,44S)-21-amino-13-(2-amino-2-oxoethyl)-27-(2-carboxyethyl)-44-[(1R)-1-hydroxyethyl]-30-[(4-hydroxyphenyl)methyl]-4-methyl-3,6,12,15,22,25,28,31,40,43,46,51-dodecaoxo-18,19,35,36,48,49-hexathia-2,5,11,14,23,26,29,32,39,42,45,52-dodecazatetracyclo[22.22.4.216,33.07,11]dopentacontane-38-carbonyl]amino]-3-(4-hydroxyphenyl)propanoic acid
InChI:
InChI=1S/C59H79N15O21S6/c1-26-47(82)69-41-25-101-99-22-38-52(87)65-33(13-14-45(80)81)49(84)66-34(16-28-5-9-30(76)10-6-28)50(85)71-40(54(89)72-39(23-97-96-20-32(60)48(83)70-38)53(88)67-35(18-43(61)78)58(93)74-15-3-4-42(74)56(91)63-26)24-100-98-21-37(64-44(79)19-62-57(92)46(27(2)75)73-55(41)90)51(86)68-36(59(94)95)17-29-7-11-31(77)12-8-29/h5-12,26-27,32-42,46,75-77H,3-4,13-25,60H2,1-2H3,(H2,61,78)(H,62,92)(H,63,91)(H,64,79)(H,65,87)(H,66,84)(H,67,88)(H,68,86)(H,69,82)(H,70,83)(H,71,85)(H,72,89)(H,73,90)(H,80,81)(H,94,95)/t26-,27+,32-,33-,34-,35-,36-,37-,38-,39-,40-,41-,42-,46-/m0/s1
InChI Key:
KXGCNMMJRFDFNR-WDRJZQOASA-N
SMILES:
OC(=O)CC[C@H]1NC(=O)[C@@H]2CSSC[C@@H]3NC(=O)[C@H](C)NC(=O)[C@H]4N(C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC1=O)Cc1ccc(cc1)O)CSSC[C@H](NC(=O)CNC(=O)C(NC3=O)[C@H](O)C)C(=O)N[C@H](C(=O)O)Cc1ccc(cc1)O)CSSC[C@@H](C(=O)N2)N)CC(=O)N)CCC4
Properties
Complexity:
3030  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
14  
Defined Bond Stereocenter Count:
0
Exact Mass:
1525.39g/mol
Formal Charge:
0
Heavy Atom Count:
101  
Hydrogen Bond Acceptor Count:
28  
Hydrogen Bond Donor Count:
19  
Isotope Atom Count:
0
Molecular Weight:
1526.725g/mol
Monoisotopic Mass:
1525.39g/mol
Rotatable Bond Count:
13  
Topological Polar Surface Area:
726A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-6.8  
Literature
Title Journal
Current and emerging treatments for irritable bowel syndrome with constipation and chronic idiopathic constipation: focus on prosecretory agents. Pharmacotherapy 20150601
Metabolic and toxicological considerations for the latest drugs used to treat irritable bowel syndrome. Expert opinion on drug metabolism & toxicology 20130401
Pharmacologic properties, metabolism, and disposition of linaclotide, a novel therapeutic peptide approved for the treatment of irritable bowel syndrome with constipation and chronic idiopathic constipation. The Journal of pharmacology and experimental therapeutics 20130101
Pharmacology and clinical potential of guanylyl cyclase C agonists in the treatment of ulcerative colitis. Drug design, development and therapy 20130101
Linaclotide: first global approval. Drugs 20121112
Recent advances in the management of difficult constipation. Current gastroenterology reports 20120801
Linaclotide in the management of gastrointestinal tract disorders. Drugs of today (Barcelona, Spain : 1998) 20120301
Contrasting effects of linaclotide and lubiprostone on restitution of epithelial cell barrier properties and cellular homeostasis after exposure to cell stressors. BMC pharmacology 20120101
Linaclotide: a novel approach to the treatment of irritable bowel syndrome. The Annals of pharmacotherapy 20111201
Chronic constipation: current treatment options. Canadian journal of gastroenterology = Journal canadien de gastroenterologie 20111001
New treatment options for chronic constipation: mechanisms, efficacy and safety. Canadian journal of gastroenterology = Journal canadien de gastroenterologie 20111001
Two randomized trials of linaclotide for chronic constipation. The New England journal of medicine 20110811
Linaclotide, a synthetic guanylate cyclase C agonist, for the treatment of functional gastrointestinal disorders associated with constipation. Expert review of gastroenterology & hepatology 20110601
The pharmacokinetics, pharmacodynamics, clinical efficacy, safety and tolerability of linaclotide. Expert opinion on drug metabolism & toxicology 20110501
Effect of laxatives and pharmacological therapies in chronic idiopathic constipation: systematic review and meta-analysis. Gut 20110201
IBS in 2010: advances in pathophysiology, diagnosis and treatment. Nature reviews. Gastroenterology & hepatology 20110201
Optimized Fmoc solid-phase synthesis of the cysteine-rich peptide linaclotide. Biopolymers 20110101
Linaclotide, through activation of guanylate cyclase C, acts locally in the gastrointestinal tract to elicit enhanced intestinal secretion and transit. European journal of pharmacology 20101215
Linaclotide improves abdominal pain and bowel habits in a phase IIb study of patients with irritable bowel syndrome with constipation. Gastroenterology 20101201
Emerging pharmacologic therapies for irritable bowel syndrome. Current gastroenterology reports 20101001
Molecule of the month. Linaclotide acetate. Drug news & perspectives 20101001
Bacterial heat-stable enterotoxins: translation of pathogenic peptides into novel targeted diagnostics and therapeutics. Toxins 20100801
Constipation: Linaclotide--a stimulating new drug for chronic constipation. Nature reviews. Gastroenterology & hepatology 20100701
[New drugs for the treatment of constipation]. Medizinische Klinik (Munich, Germany : 1983) 20100701
Linaclotide is a potent and selective guanylate cyclase C agonist that elicits pharmacological effects locally in the gastrointestinal tract. Life sciences 20100508
Guanylate cyclase C-mediated antinociceptive effects of linaclotide in rodent models of visceral pain. Neurogastroenterology and motility : the official journal of the European Gastrointestinal Motility Society 20100301
Efficacy of linaclotide for patients with chronic constipation. Gastroenterology 20100301
Taking a lesson from microbial diarrheagenesis in the management of chronic constipation. Gastroenterology 20100301
Linaclotide - a secretagogue and antihyperalgesic agent - what next? Neurogastroenterology and motility : the official journal of the European Gastrointestinal Motility Society 20100301
The use of novel promotility and prosecretory agents for the treatment of chronic idiopathic constipation and irritable bowel syndrome with constipation. Advances in therapy 20090501
Pilot study on the effect of linaclotide in patients with chronic constipation. The American journal of gastroenterology 20090101
Effect of 5 days linaclotide on transit and bowel function in females with constipation-predominant irritable bowel syndrome. Gastroenterology 20070901
Linaclotide, a new direction in the treatment of irritable bowel syndrome and chronic constipation. Current opinion in molecular therapeutics 20070801
Properties