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Terlipressin

CAS No.:
14636-12-5
Catalog Number:
AG019FSU
Molecular Formula:
C52H74N16O15S2
Molecular Weight:
1227.3722
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Purity
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Product Description
Catalog Number:
AG019FSU
Chemical Name:
Terlipressin
CAS Number:
14636-12-5
Molecular Formula:
C52H74N16O15S2
Molecular Weight:
1227.3722
MDL Number:
MFCD00155450
IUPAC Name:
(2S)-1-[(4R,7S,10S,13S,16S,19R)-19-[[2-[[2-[(2-aminoacetyl)amino]acetyl]amino]acetyl]amino]-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-benzyl-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]-N-[(2S)-6-amino-1-[(2-amino-2-oxoethyl)amino]-1-oxohexan-2-yl]pyrrolidine-2-carboxamide
InChI:
InChI=1S/C52H74N16O15S2/c53-17-5-4-9-31(45(76)60-23-41(57)72)63-51(82)38-10-6-18-68(38)52(83)37-27-85-84-26-36(61-44(75)25-59-43(74)24-58-42(73)22-54)50(81)65-34(20-29-11-13-30(69)14-12-29)48(79)64-33(19-28-7-2-1-3-8-28)47(78)62-32(15-16-39(55)70)46(77)66-35(21-40(56)71)49(80)67-37/h1-3,7-8,11-14,31-38,69H,4-6,9-10,15-27,53-54H2,(H2,55,70)(H2,56,71)(H2,57,72)(H,58,73)(H,59,74)(H,60,76)(H,61,75)(H,62,78)(H,63,82)(H,64,79)(H,65,81)(H,66,77)(H,67,80)/t31-,32-,33-,34-,35-,36-,37-,38-/m0/s1
InChI Key:
BENFXAYNYRLAIU-QSVFAHTRSA-N
SMILES:
NCCCC[C@@H](C(=O)NCC(=O)N)NC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CSSC[C@H](NC(=O)CNC(=O)CNC(=O)CN)C(=O)N[C@@H](Cc2ccc(cc2)O)C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)CC(=O)N)CCC(=O)N)Cc1ccccc1
EC Number:
238-680-8
Properties
Complexity:
2380  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
8  
Defined Bond Stereocenter Count:
0
Exact Mass:
1226.496g/mol
Formal Charge:
0
Heavy Atom Count:
85  
Hydrogen Bond Acceptor Count:
19  
Hydrogen Bond Donor Count:
16  
Isotope Atom Count:
0
Molecular Weight:
1227.381g/mol
Monoisotopic Mass:
1226.496g/mol
Rotatable Bond Count:
25  
Topological Polar Surface Area:
563A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-5.8  
Literature
Title Journal
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Predictors of response to terlipressin plus albumin in hepatorenal syndrome (HRS) type 1: relationship of serum creatinine to hemodynamics. Journal of hepatology 20110801
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Double-blind randomized multicenter study comparing the efficacy and safety of 10-day to 5-day terlipressin treatment of bleeding esophageal varices. Hepato-gastroenterology 20090101
Comparison of cardiac, hepatic, and renal effects of arginine vasopressin and noradrenaline during porcine fecal peritonitis: a randomized controlled trial. Critical care (London, England) 20090101
Synbeads porous-rigid methacrylic support: application to solid phase peptide synthesis and characterization of the polymeric matrix by FTIR microspectroscopy and high resolution magic angle spinning NMR. Journal of combinatorial chemistry 20090101
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Continuous terlipressin versus vasopressin infusion in septic shock (TERLIVAP): a randomized, controlled pilot study. Critical care (London, England) 20090101
Cutaneous necrosis secondary to terlipressin therapy. Acta dermato-venereologica 20090101
Arginine vasopressin in septic shock: supplement or substitute for norepinephrine? Critical care (London, England) 20090101
Terlipressin or europressin? Critical care (London, England) 20090101
Reversal of hepatorenal syndrome in cirrhotic patients with terlipressin plus albumin. First experience in Mexico. Annals of hepatology 20090101
Poor outcomes with treatment of hepatorenal syndrome type 1 with splanchnic vasoconstrictors and albumin: report of seven cases and review of the literature. Arquivos de gastroenterologia 20090101
Splanchnic hyposensitivity to glypressin in a hemorrhage-transfused common bile duct-ligated rat model of portal hypertension: role of nitric oxide and bradykinin. Hepato-gastroenterology 20090101
Embolization of cyanoacrylate glue in systemic circulation in a case of hepatocellular carcinoma: an autopsy report. Diagnostic pathology 20090101
Vasopressin in the pediatric cardiac intensive care unit: Myth or reality. Annals of pediatric cardiology 20090101
Effects of terlipressin on the aquaretic system: evidence of antidiuretic effects. American journal of physiology. Renal physiology 20081101
Efficacy and safety of terlipressin in cirrhotic patients with variceal bleeding or hepatorenal syndrome. Advances in therapy 20081101
Long-term outcome of patients treated with terlipressin for types 1 and 2 hepatorenal syndrome. Journal of gastroenterology and hepatology 20081001
Current place of vasopressin analogues in the treatment of septic shock. Current infectious disease reports 20080901
Updates in the pathogenesis, diagnosis and management of ectopic varices. Hepatology international 20080901
Prevention of paracentesis-induced circulatory dysfunction: midodrine vs albumin. A randomized pilot study. Liver international : official journal of the International Association for the Study of the Liver 20080801
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Dobutamine and terlipressin in patients with septic shock. British journal of anaesthesia 20080701
An open label, pilot, randomized controlled trial of noradrenaline versus terlipressin in the treatment of type 1 hepatorenal syndrome and predictors of response. The American journal of gastroenterology 20080701
Endoscopic reflectance spectrophotometry and visible light spectroscopy in clinical gastrointestinal studies. Digestive diseases and sciences 20080601
Impact of terlipressin on renal graft function. Shock (Augusta, Ga.) 20080601
A retrospective analysis of Terlipressin infusion in patients with refractory hypotension after cardiac surgery. The Journal of cardiovascular surgery 20080601
A case of ischemic skin necrosis after glypressin therapy in liver cirrhosis. The Korean journal of gastroenterology = Taehan Sohwagi Hakhoe chi 20080601
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Hot topics in liver intensive care. Transplantation proceedings 20080501
Terlipressin infusion induces ischemia of breast skin in a cirrothic patient with hepatorenal syndrome. Digestive and liver disease : official journal of the Italian Society of Gastroenterology and the Italian Association for the Study of the Liver 20080401
Significant improvement of portopulmonary hypertension after 1-week terlipressin treatment. Journal of hepatology 20080401
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Effects of short-term simultaneous infusion of dobutamine and terlipressin in patients with septic shock: the DOBUPRESS study. British journal of anaesthesia 20080401
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Employing dobutamine as a useful agent to reverse the terlipressin-linked impairments in cardiopulmonary hemodynamics and global oxygen transport in healthy and endotoxemic sheep. Shock (Augusta, Ga.) 20080101
Surviving Sepsis Campaign: international guidelines for management of severe sepsis and septic shock: 2008. Intensive care medicine 20080101
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Acute variceal bleeding: pharmacological treatment and primary/secondary prophylaxis. Best practice & research. Clinical gastroenterology 20080101
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Open, randomized, comparative study of efficacy and safety between Haemopressin and Glypressin in treating acute esophageal varices hemorrhage. Hepato-gastroenterology 20080101
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An economic evaluation of vasoactive agents used to treat acute bleeding oesophageal varices in Belgium. Acta gastro-enterologica Belgica 20080101
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Treatment of gastropathy and gastric antral vascular ectasia in patients with portal hypertension. Current treatment options in gastroenterology 20071201
Pharmacology, clinical efficacy and safety of terlipressin in esophageal varices bleeding, septic shock and hepatorenal syndrome. Expert review of gastroenterology & hepatology 20071201
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Continuous versus bolus infusion of terlipressin in ovine endotoxemia. Shock (Augusta, Ga.) 20071101
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Use of vasopressin after Caesarean section in idiopathic pulmonary arterial hypertension. British journal of anaesthesia 20071001
Ischaemic complications of Glypressin in liver disease: a case series. British journal of clinical pharmacology 20071001
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Comparison of terlipressin and noradrenalin on cerebral perfusion, intracranial pressure and cerebral extracellular concentrations of lactate and pyruvate in patients with acute liver failure in need of inotropic support. Journal of hepatology 20070901
Continuous low-dose infusion of terlipressin as a rescue therapy in meningococcal septic shock. The American journal of emergency medicine 20070901
Terlipressin and tricyclic antidepressant intoxication. The Netherlands journal of medicine 20070901
The use of terlipressin in a 14-year-old adolescent with catecholamine-resistant shock after severe traumatic brain injury. Acta anaesthesiologica Scandinavica 20070801
An economic evaluation of vasoactive agents used in the United Kingdom for acute bleeding oesophageal varices in patients with liver cirrhosis. Current medical research and opinion 20070701
Successful use of terlipressin in post-cardiac arrest resuscitation after an epinephrine-resistant anaphylactic shock to suxamethonium. Anesthesiology 20070701
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[Terlipressin and reversible intestinal ischaemia]. Ugeskrift for laeger 20070507
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Early use of terlipressin in catecholamine-resistant shock improves cerebral perfusion pressure in severe traumatic brain injury. Acta anaesthesiologica Scandinavica 20070401
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Cardiovascular collapse due to massive pulmonary thromboembolism during orthotopic liver transplantation. Journal of clinical anesthesia 20060801
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Switch therapy with ciprofloxacin vs. intravenous ceftazidime in the treatment of spontaneous bacterial peritonitis in patients with cirrhosis: similar efficacy at lower cost. Alimentary pharmacology & therapeutics 20060101
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A prospective double blind randomized study comparing the need for blood transfusion with terlipressin or a placebo during early excision and grafting of burns. Burns : journal of the International Society for Burn Injuries 20040501
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Update on ascites and hepatorenal syndrome. Digestive and liver disease : official journal of the Italian Society of Gastroenterology and the Italian Association for the Study of the Liver 20020801
Hepatorenal syndrome in patients with cirrhosis. Journal of gastroenterology and hepatology 20020701
Terlipressin for norepinephrine-resistant septic shock. Lancet (London, England) 20020406
Terlipressin in patients with cirrhosis and type 1 hepatorenal syndrome: a retrospective multicenter study. Gastroenterology 20020401
Terlipressin-ephedrine versus ephedrine to treat hypotension at the induction of anesthesia in patients chronically treated with angiotensin converting-enzyme inhibitors: a prospective, randomized, double-blinded, crossover study. Anesthesia and analgesia 20020401
Hemodynamic effects of a combination of octreotide and terlipressin in patients with viral hepatitis related cirrhosis. Scandinavian journal of gastroenterology 20020401
Increased plasma levels of neuropeptide Y in hepatorenal syndrome. Journal of hepatology 20020301
Variceal bleeding and portal hypertension: much to learn, much to explore. Endoscopy 20020201
Effect of terlipressin (Glypressin) on hepatorenal syndrome in cirrhotic patients: results of a multicentre pilot study. European journal of gastroenterology & hepatology 20020201
Comparison of the effect of terlipressin and albumin on arterial blood volume in patients with cirrhosis and tense ascites treated by paracentesis: a randomised pilot study. Gut 20020101
Emergency sclerotherapy versus medical interventions for bleeding oesophageal varices in cirrhotic patients. The Cochrane database of systematic reviews 20020101
Management of esophageal varices. Medicinski arhiv 20020101
[Physiopathology of refractory ascites and the hepatorenal syndrome]. Nefrologia : publicacion oficial de la Sociedad Espanola Nefrologia 20020101
[Vasoconstrictors in the treatment of hepatorenal syndrome]. Nefrologia : publicacion oficial de la Sociedad Espanola Nefrologia 20020101
Recently published papers: topical issues in pharmacology. Critical care (London, England) 20020101
Double-blind randomized, comparative multicenter study of the effect of terlipressin in the treatment of acute esophageal variceal and/or hypertensive gastropathy bleeding. Hepato-gastroenterology 20020101
Update on treatment of variceal hemorrhage. Digestive diseases (Basel, Switzerland) 20020101
Life, death, and varices. Gut 20011101
Recombinant activated factor VII (rFVIIa) acutely normalizes prothrombin time in patients with cirrhosis during bleeding from oesophageal varices. Scandinavian journal of gastroenterology 20011001
New method of cardiac output measurement using ultrasound velocity dilution in rats. Journal of applied physiology (Bethesda, Md. : 1985) 20010901
Drug therapy for portal hypertension. Gut 20010901
Comparative effects of the novel vasotocin analogue F-180 vs. vasopressin and terlipressin on systemic and splanchnic isolated vessels from portal hypertensive rats. Naunyn-Schmiedeberg's archives of pharmacology 20010901
Hemodynamic effects of terlipressin (a synthetic analog of vasopressin) in healthy and endotoxemic sheep. Critical care medicine 20010901
Terlipressin for treating intraoperative hypotension: can it unmask myocardial ischemia? Anesthesia and analgesia 20010701
Acute gastrointestinal bleeding: Part II. Critical care and resuscitation : journal of the Australasian Academy of Critical Care Medicine 20010601
Portal hypertension. Clinics in liver disease 20010501
Hemodynamic effects of a combination of prazosin and terlipressin in patients with viral cirrhosis. The American journal of gastroenterology 20010401
Management of acute variceal haemorrhage. European journal of gastroenterology & hepatology 20010401
[Treatment of esophageal varices]. Ugeskrift for laeger 20010312
Octreotide for acute esophageal variceal bleeding: a meta-analysis. Gastroenterology 20010301
Endoscopic Doppler ultrasound for measurement of azygos blood flow. Validation against thermodilution and assessment of pharmacological effects of terlipressin in portal hypertension. Scandinavian journal of gastroenterology 20010301
Vascular hyporesponsiveness in cirrhosis - many facets of a common problem! European journal of clinical investigation 20010201
Inhibition of prostacyclin by indomethacin ameliorates the splanchnic hyposensitivity to glypressin in haemorrhage-transfused common bile duct-ligated rats. European journal of clinical investigation 20010201
Pharmacologic therapy for portal hypertension. Current gastroenterology reports 20010201
Should the angiotensin II antagonists be discontinued before surgery? Anesthesia and analgesia 20010101
Terlipressin for acute esophageal variceal hemorrhage. The Cochrane database of systematic reviews 20010101
Long-term terlipressin administration improves renal function in cirrhotic patients with type 1 hepatorenal syndrome: a pilot study. Acta gastro-enterologica Belgica 20010101
European Society of Intensive Care Medicine 14th annual congress, 30 September-3 October 2001, Geneva, Switzerland. Critical care (London, England) 20010101
Hepatorenal syndrome in cirrhotic patients: terlipressine is a safe and efficient treatment; propranolol and digitalic treatments: precipitating and preventing factors? The American journal of gastroenterology 20001001
Adrenalin versus terlipressin: blood loss and cardiovascular side-effects in the vaginal part of laparoscopically-assisted vaginal hysterectomy or vaginal hysterectomy. Clinical and experimental obstetrics & gynecology 20000101
Restoration of the uricosuric effect of probenecid after triglycylvasopressine administration in a gouty patient. Clinical nephrology 19981001
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