TERLIPRESSIN

Synonyms. Terlipressin; N-(N-(N-Glycylglycyl)glycyl)-8-L-lysinevasopressin; Terlipressin; Terlipressina; Terlipressine; Terlipressinum; (2S)-1-((4S,7S,10S,13S,16S,19S)-19-((2-((2-((2-Aminoacetyl) amino)acetyl)amino) acetyl)amino)-13-benzyl-10-(2-carbamoylethyl)-7-(carbamoylmethyl)- 16-((4-hydroxy phenyl)methyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane- 4-carbonyl)-N-((1S)-5-amino-1-(carbamoylmethylcarbamoyl) pentyl)pyrrolidine-2-carboxamide;

TERLIPRESSIN

 

PRODUCT IDENTIFICATION

CAS RN

14636-12-5

EINECS RN

238-680-8

FORMULA

C52H74N16O15S2

MOLE WEIGHT

1227.37

H.S CODE

2933.99.7900

SMILES

NC(CNC([C@@H](NC([C@H]1N(C([C@H]2NC([C@@H](NC(=O) [C@H](CCC (=O)N)NC([C@@H] (NC([C@@H](NC([C@@H](NC (CNC (CNC(CN)=O)=O)=O) CSSC2)=O)Cc2ccc (cc2)O)=O) Cc2ccccc2)=O)CC(=O)N)=O)=O)CCC1) =O)C CC CN) =O)=O

CLASSIFICATION

Antihypertensive agent, Cardiovascular agent, Vasoconstrictor

EXTRA NOTES

 

 

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE.

powder

MELTING POINT

 

BOILING POINT

 

DENSITY

 

SOLUBILITY IN WATER

Insoluble (Press Cake), Soluble (Finished)

SOLVENT SOLUBILITY  

VAPOR DENSITY

 

log P(octanol-water)

 

VAPOR PRESSURE

 

AUTOIGNITION TEMP

 
pH

 

REFRACTIVE INDEX

 

FLASH POINT

 

 

STABILITY AND REACTIVITY
STABILITY Stable under normal conditions.

INCOMPATIBLE MATERIALS

Strong oxidizing agents

POLYMERIZATION

Has not been reported

NFPA RATINGS

Health: 2,Flammability:1, Reactivity: 0

 

EXTERNAL LINKS & GENERAL DESCRIPTION

Wikipedia Linking - Terlipressin

Google Scholar Search - Terlipressin

Drug Information Portal (U.S. National Library of Medicine) - Terlipressin

PubChem Compound Summary - Terlipressin

Drug Bank -  Terlipressin

KEGG (Kyoto Encyclopedia of Genes and Genomes) - Terlipressin

http://www.ebi.ac.uk/ - Terlipressin

http://www.ncbi.nlm.nih.gov/ - Terlipressin

http://www.singhealthacademy.edu.sg/
Background: Vasodilatory septic shock unresponsive to fluid resuscitation requires the addition of vasopressors. Catecholamines remain the first line vasopressor therapy, but treatment failure is a potential problem. Vasopressin and its analogue, terlipressin, have been used for this indication.
Objective: This systematic review aims to evaluate the effects of vasopressin and terlipressin on mortality and morbidity outcomes in patients with vasodilatory shock. Secondary outcomes include the effects of vasopressin and terlipressin on haemodynamic stability and organ function.
Method: A computerised search of MEDLINE from January 1966 till June 2010 and screening of references of relevant articles were conducted. Only prospective, randomised controlled trials comparing vasopressin or terlipressin versus standard vasopressors or placebo were included.
Results: Seven studies using vasopressin, three using terlipressin and one using both were identified. Four vasopressin trials assessing mortality and morbidity outcomes showed a trend towards benefit for mortality in adults but possibly adverse outcomes in a small paediatric study. No data was available on the long-term mortality and morbidity outcomes of terlipressin. Vasopressin and terlipressin were similar to standard vasopressors in maintaining haemodynamic parameters, while allowing a beneficial catecholamine-sparing effect. These agents also had a neutral to positive effect on organ function.
Conclusion: Vasopressin and terlipressin was comparable to conventional agents in the maintenance of haemodynamic stability and organ function in vasodilatory shock. Since morbidity and mortality data do not differentiate vasopressin and terlipressin from catecholamines, their role remains unclear. More large studies evaluating the long-term outcomes in this group of patients are required.

http://www.wjgnet.com/
Hepatorenal syndrome (HRS) is a reversible form of functional renal failure that occurs with advanced hepatic cirrhosis and liver failure. Despite mounting research in HRS, its etiology and medical therapy has not been resolved. HRS encompasses 2 distinct types. Type 1 is characterized by the rapid development of renal failure that occurs within 2 wk and involves a doubling of initial serum creatinine. Type 2 has a more insidious onset and is often associated with ascites. Animal studies have shown that both forms, in particular type 1 HRS, are often precipitated by bacterial infections and circulatory changes. The prognosis for HRS remains very poor. Type 1 and 2 both have an expected survival time of 2 wk and 6 mo, respectively. Progression of liver cirrhosis and the resultant portal hypertension leads to the pooling of blood in the splanchnic vascular bed. The ensuing hyperdynamic circulation causes an ineffective circulatory volume which subsequently activates neurohormonal systems. Primarily the sympathetic nervous system and the renin angiotensin system are activated, which, in the early stages of HRS, maintain adequate circulation. Both advanced cirrhosis and prolonged activation of neurohormonal mechanisms result in fatal complications. Locally produced nitric oxide may have the potential to induce a deleterious vasodilatory effect on the splanchnic circulation. Currently medical therapy is aimed at reducing splanchnic vasodilation to resolve the ineffective circulation and maintain good renal perfusion pressure. Terlipressin, a vasopressin analogue, has shown potential benefit in the treatment of HRS. It prolongs both survival time and has the ability to reverse HRS in the majority of patients. In this review we aim to focus on the pathogenesis of HRS and its treatment with terlipressin vs other drugs.

 

SALES SPECIFICATION

APPEARANCE

white powder

ASSAY

95.0~105.0% (on Anhydrous, Acetic Acid free basis)

OPTICAL ROTATION

-95° ~ -105° (c=1, 1% HAc)

WATER

10.0% max (Karl Fischer)

ACETATE CONTENT

15.0% max (HPLC)

AMINO ACID COMPOSITION

±10% theoretical

INDIVIDUAL IMPURITY

1.0% max (HPLC)

PEPTIDE CONTENT

80% min (by %N)

BACTERIAL ENDOTOXINS

5EU/mg max

 

TRANSPORT & REGULATORY INFORMATION

UN NO.

Not known

HAZARD CLASS

 
PACKING GROUP  

 

SAFETY INFORMATION

HAZARD OVERVIEW

Avoid contact and inhalation. May causes eye irritation. May causes skin irritation. May cause gastrointestinal irritation. May causes respiratory tract irritation

HAZARD CODES

 

RISK PHRASES

 

SAFETY PHRASES

22-24/25

 

PACKING