Terlipressin
Identification
- Summary
Terlipressin is a drug used to treat bleeding caused by esophageal varices.
- Generic Name
- Terlipressin
- DrugBank Accession Number
- DB02638
- Background
Terlipressin is an analogue of vasopressin used as a vasoactive drug in the management of hypotension which has been found to be effective when norepinephrine fails.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Terlipressin (DB02638)
- Weight
- Average: 1227.372
Monoisotopic: 1226.496097158 - Chemical Formula
- C52H74N16O15S2
- Synonyms
- Terlipresina
- Terlipressin
- Terlipressina
- Terlipressine
- Terlipressinum
Pharmacology
- Indication
Commonly used to stop bleeding of varices in the food pipe (oesophagus).
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- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Terlipressin is a medicine similar to a naturally occurring hormone present in the body, known as antidiuretic hormone (ADH) or vasopressin. ADH has two main effects in the body. Firstly, it causes narrowing of blood vessels (vasoconstriction), thereby limiting blood flow to a particular area of the body. It also acts on receptors in the kidney to retain water in the body, which helps to prevent excessive loss of water in the urine.
- Mechanism of action
Terlipressin, an analogue of vasopressin, acts on three different receptors, vasopressin receptor V1a (which initiates vasoconstriction, liver gluconeogenesis, platelet aggregation and release of factor VIII), vasopressin receptor V1b (which mediates corticotrophin secretion from the pituitary) and vasopressin receptor V2 which controls free water reabsorption in the renal medullar. The binding of terlipressin to the V2 receptor activates adenylate cyclase which causes the release of aquaporin 2 channels into the cells lining the renal medullar duct. This allows water to be reabsorbed down an osmotic gradient so the urine is more concentrated.
Target Actions Organism AVasopressin V2 receptor agonistHumans UVasopressin V1b receptor Not Available Humans UVasopressin V1a receptor stimulatorHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Approximately 30%
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcrivastine The risk or severity of QTc prolongation can be increased when Acrivastine is combined with Terlipressin. Adenosine The risk or severity of QTc prolongation can be increased when Adenosine is combined with Terlipressin. Ajmaline The risk or severity of QTc prolongation can be increased when Ajmaline is combined with Terlipressin. Alfuzosin The risk or severity of QTc prolongation can be increased when Alfuzosin is combined with Terlipressin. Alimemazine The risk or severity of QTc prolongation can be increased when Alimemazine is combined with Terlipressin. Amantadine The risk or severity of QTc prolongation can be increased when Amantadine is combined with Terlipressin. Amifampridine The risk or severity of QTc prolongation can be increased when Terlipressin is combined with Amifampridine. Amiodarone The risk or severity of QTc prolongation can be increased when Terlipressin is combined with Amiodarone. Amisulpride The risk or severity of QTc prolongation can be increased when Terlipressin is combined with Amisulpride. Amitriptyline The risk or severity of QTc prolongation can be increased when Amitriptyline is combined with Terlipressin. 
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- Not Available
Products
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Ingredient UNII CAS InChI Key Terlipressin acetate 4U092XZF0K Not Available MLECZWUGJYWVAV-NSECCGHPSA-N - International/Other Brands
- Glypressin (Ferring Pharmaceuticals) / Lucassin / Teripress (New Medicon Pharma)
Categories
- ATC Codes
- H01BA04 — Terlipressin
- Drug Categories
- Amino Acids, Peptides, and Proteins
- Cardiovascular Agents
- Hormones
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Moderate Risk QTc-Prolonging Agents
- Nerve Tissue Proteins
- Neuropeptides
- Oligopeptides
- Peptide Hormones
- Peptides
- Pituitary and Hypothalamic Hormones and Analogues
- Pituitary Hormones
- Pituitary Hormones, Posterior
- Posterior Pituitary Lobe Hormones
- Proteins
- QTc Prolonging Agents
- Systemic Hormonal Preparations, Excl. Sex Hormones and Insulins
- Vasoconstrictor Agents
- Vasopressin and Analogues
- Vasopressins
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as polypeptides. These are peptides containing ten or more amino acid residues.
- Kingdom
- Organic compounds
- Super Class
- Organic Polymers
- Class
- Polypeptides
- Sub Class
- Not Available
- Direct Parent
- Polypeptides
- Alternative Parents
- Cyclic peptides / Proline and derivatives / Macrolactams / N-acyl-alpha amino acids and derivatives / Alpha amino acid amides / Pyrrolidinecarboxamides / N-acylpyrrolidines / 1-hydroxy-2-unsubstituted benzenoids / Benzene and substituted derivatives / N-acyl amines show 11 more
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / Alpha-amino acid amide / Alpha-amino acid or derivatives / Amine / Amino acid or derivatives / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxamide group show 31 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 7Z5X49W53P
- CAS number
- 14636-12-5
- InChI Key
- BENFXAYNYRLAIU-QSVFAHTRSA-N
- 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
- IUPAC Name
- (2S)-6-amino-2-{[(2S)-1-[(4R,7S,10S,13S,16S,19R)-19-{2-[2-(2-aminoacetamido)acetamido]acetamido}-13-benzyl-10-(2-carbamoylethyl)-7-(carbamoylmethyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carbonyl]pyrrolidin-2-yl]formamido}-N-(carbamoylmethyl)hexanamide
- SMILES
- NCCCC[C@H](NC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CSSC[C@H](NC(=O)CNC(=O)CNC(=O)CN)C(=O)N[C@@H](CC2=CC=C(O)C=C2)C(=O)N[C@@H](CC2=CC=CC=C2)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N1)C(=O)NCC(N)=O
References
- General References
- Pesaturo AB, Jennings HR, Voils SA: Terlipressin: vasopressin analog and novel drug for septic shock. Ann Pharmacother. 2006 Dec;40(12):2170-7. Epub 2006 Dec 5. [Article]
- Klein M, Weksler N, Borer A, Koyfman L, Kesslin J, Gurman GM: Terlipressin facilitates transport of septic patients treated with norepinephrine. Isr Med Assoc J. 2006 Oct;8(10):691-3. [Article]
- Leone M, Charvet A, Delmas A, Albanese J, Martin C, Boyle WA: Terlipressin: a new therapeutic for calcium-channel blockers overdose. J Crit Care. 2005 Mar;20(1):114-5. [Article]
- Matok I, Vard A, Efrati O, Rubinshtein M, Vishne T, Leibovitch L, Adam M, Barzilay Z, Paret G: Terlipressin as rescue therapy for intractable hypotension due to septic shock in children. Shock. 2005 Apr;23(4):305-10. [Article]
- Kam PC, Williams S, Yoong FF: Vasopressin and terlipressin: pharmacology and its clinical relevance. Anaesthesia. 2004 Oct;59(10):993-1001. [Article]
- External Links
- Human Metabolome Database
- HMDB0015569
- PubChem Compound
- 72081
- PubChem Substance
- 46504626
- ChemSpider
- 65067
- 57048
- ChEBI
- 135905
- ChEMBL
- CHEMBL2135460
- Therapeutic Targets Database
- DAP000058
- PharmGKB
- PA164781020
- Wikipedia
- Terlipressin
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Prevention Acute Kidney Injury (AKI) / NGAL / Terlipressin / Transplantation, Liver 1 4 Completed Prevention Cirrhosis of the Liver / Upper Gastrointestinal Hemorrhage 1 4 Completed Treatment Acute Variceal Haemorrhage 1 4 Completed Treatment Bleeding / Varices, Esophageal 1 4 Completed Treatment Cirrhosis of the Liver / Hematemesis / Melena / Portal Hypertension 1 4 Completed Treatment Gastric and Esophageal Varices 1 4 Completed Treatment Hemorrhage / Portal Hypertension / Varices, Esophageal 1 4 Completed Treatment Variceal Bleeding, Cirrhosis 1 4 Completed Treatment Vasoconstrictor Choice on Acute Variceal Bleeding 1 4 Not Yet Recruiting Treatment Liver Cirrhosis Portal 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Solution Intravenous 0.85 mg Injection, powder, for solution Parenteral 1 MG/5ML Solution Intravenous 500 μg Injection, solution Parenteral Injection, powder, for solution Parenteral Injection, powder, lyophilized, for solution Intravenous 0.86 mg Injection Intravenous Injection, solution Intravenous Injection, powder, for solution Intravenous Solution Intravenous 1 mg Injection, solution Parenteral 0.2 MG/ML Injection, powder, for solution Injection, solution Parenteral 1 MG/8.5ML Injection, solution Parenteral 0.1 MG/ML Injection, powder, for solution Parenteral 1 MG Powder 1 mg/1vial Injection, solution 1 mg/8.5ml - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.167 mg/mL ALOGPS logP -1.6 ALOGPS logP -10 ChemAxon logS -3.9 ALOGPS pKa (Strongest Acidic) 9.43 ChemAxon pKa (Strongest Basic) 10.26 ChemAxon Physiological Charge 2 ChemAxon Hydrogen Acceptor Count 17 ChemAxon Hydrogen Donor Count 16 ChemAxon Polar Surface Area 512.85 Å2 ChemAxon Rotatable Bond Count 25 ChemAxon Refractivity 305.18 m3·mol-1 ChemAxon Polarizability 123.88 Å3 ChemAxon Number of Rings 4 ChemAxon Bioavailability 0 ChemAxon Rule of Five No ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule Yes ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.7085 Blood Brain Barrier - 0.8855 Caco-2 permeable - 0.7797 P-glycoprotein substrate Substrate 0.7307 P-glycoprotein inhibitor I Non-inhibitor 0.8042 P-glycoprotein inhibitor II Non-inhibitor 0.8977 Renal organic cation transporter Non-inhibitor 0.8004 CYP450 2C9 substrate Non-substrate 0.8292 CYP450 2D6 substrate Non-substrate 0.7878 CYP450 3A4 substrate Non-substrate 0.5247 CYP450 1A2 substrate Non-inhibitor 0.9358 CYP450 2C9 inhibitor Non-inhibitor 0.766 CYP450 2D6 inhibitor Non-inhibitor 0.8606 CYP450 2C19 inhibitor Non-inhibitor 0.7565 CYP450 3A4 inhibitor Non-inhibitor 0.7185 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8301 Ames test Non AMES toxic 0.736 Carcinogenicity Non-carcinogens 0.8513 Biodegradation Not ready biodegradable 0.9261 Rat acute toxicity 2.9218 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8955 hERG inhibition (predictor II) Inhibitor 0.6764
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Vasopressin receptor activity
- Specific Function
- Receptor for arginine vasopressin. The activity of this receptor is mediated by G proteins which activate adenylate cyclase. Involved in renal water reabsorption.
- Gene Name
- AVPR2
- Uniprot ID
- P30518
- Uniprot Name
- Vasopressin V2 receptor
- Molecular Weight
- 40278.57 Da
References
- Boson WL, Della Manna T, Damiani D, Miranda DM, Gadelha MR, Liberman B, Correa H, Romano-Silva MA, Friedman E, Silva FF, Ribeiro PA, De Marco L: Novel vasopressin type 2 (AVPR2) gene mutations in Brazilian nephrogenic diabetes insipidus patients. Genet Test. 2006 Fall;10(3):157-62. [Article]
- Slusarz MJ, Slusarz R, Ciarkowski J: Investigation of mechanism of desmopressin binding in vasopressin V2 receptor versus vasopressin V1a and oxytocin receptors: molecular dynamics simulation of the agonist-bound state in the membrane-aqueous system. Biopolymers. 2006 Apr 5;81(5):321-38. [Article]
- Bouley R, Hawthorn G, Russo LM, Lin HY, Ausiello DA, Brown D: Aquaporin 2 (AQP2) and vasopressin type 2 receptor (V2R) endocytosis in kidney epithelial cells: AQP2 is located in 'endocytosis-resistant' membrane domains after vasopressin treatment. Biol Cell. 2006 Apr;98(4):215-32. [Article]
- Yi X, Bouley R, Lin HY, Bechoua S, Sun TX, Del Re E, Shioda T, Raychowdhury MK, Lu HA, Abou-Samra AB, Brown D, Ausiello DA: Alix (AIP1) is a vasopressin receptor (V2R)-interacting protein that increases lysosomal degradation of the V2R. Am J Physiol Renal Physiol. 2007 May;292(5):F1303-13. Epub 2007 Feb 6. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Vasopressin receptor activity
- Specific Function
- Receptor for arginine vasopressin. The activity of this receptor is mediated by G proteins which activate a phosphatidyl-inositol-calcium second messenger system.
- Gene Name
- AVPR1B
- Uniprot ID
- P47901
- Uniprot Name
- Vasopressin V1b receptor
- Molecular Weight
- 46970.345 Da
References
- Young WS, Li J, Wersinger SR, Palkovits M: The vasopressin 1b receptor is prominent in the hippocampal area CA2 where it is unaffected by restraint stress or adrenalectomy. Neuroscience. 2006 Dec 28;143(4):1031-9. Epub 2006 Oct 4. [Article]
- Volpi S, Liu Y, Aguilera G: Vasopressin increases GAGA binding activity to the V1b receptor promoter through transactivation of the MAP kinase pathway. J Mol Endocrinol. 2006 Jun;36(3):581-90. [Article]
- Wersinger SR, Caldwell HK, Christiansen M, Young WS 3rd: Disruption of the vasopressin 1b receptor gene impairs the attack component of aggressive behavior in mice. Genes Brain Behav. 2007 Oct;6(7):653-60. Epub 2006 Dec 20. [Article]
- Slusarz MJ, Gieldon A, Slusarz R, Ciarkowski J: Analysis of interactions responsible for vasopressin binding to human neurohypophyseal hormone receptors-molecular dynamics study of the activated receptor-vasopressin-G(alpha) systems. J Pept Sci. 2006 Mar;12(3):180-9. [Article]
- Jurkevich A, Berghman LR, Cornett LE, Kuenzel WJ: Characterization and immunohistochemical visualization of the vasotocin VT2 receptor in the pituitary gland of the chicken, Gallus gallus. Gen Comp Endocrinol. 2005 Aug;143(1):82-91. Epub 2005 Mar 23. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Stimulator
- General Function
- Vasopressin receptor activity
- Specific Function
- Receptor for arginine vasopressin. The activity of this receptor is mediated by G proteins which activate a phosphatidyl-inositol-calcium second messenger system. Has been involved in social behavi...
- Gene Name
- AVPR1A
- Uniprot ID
- P37288
- Uniprot Name
- Vasopressin V1a receptor
- Molecular Weight
- 46799.105 Da
References
- Hiroyama M, Wang S, Aoyagi T, Oikawa R, Sanbe A, Takeo S, Tanoue A: Vasopressin promotes cardiomyocyte hypertrophy via the vasopressin V1A receptor in neonatal mice. Eur J Pharmacol. 2007 Mar 22;559(2-3):89-97. Epub 2006 Dec 29. [Article]
- Liedman R, Grant L, Igidbashian S, James I, McLeod A, Skillern L, Akerlund M: Intrauterine pressure, ischemia markers, and experienced pain during administration of a vasopressin V1a receptor antagonist in spontaneous and vasopressin-induced dysmenorrhea. Acta Obstet Gynecol Scand. 2006;85(2):207-11. [Article]
- Adikesavan NV, Mahmood SS, Stanley N, Xu Z, Wu N, Thibonnier M, Shoham M: A C-terminal segment of the V1R vasopressin receptor is unstructured in the crystal structure of its chimera with the maltose-binding protein. Acta Crystallogr Sect F Struct Biol Cryst Commun. 2005 Apr 1;61(Pt 4):341-5. Epub 2005 Mar 24. [Article]
- Hammock EA, Lim MM, Nair HP, Young LJ: Association of vasopressin 1a receptor levels with a regulatory microsatellite and behavior. Genes Brain Behav. 2005 Jul;4(5):289-301. [Article]
- Aoyagi T, Birumachi J, Hiroyama M, Fujiwara Y, Sanbe A, Yamauchi J, Tanoue A: Alteration of glucose homeostasis in V1a vasopressin receptor-deficient mice. Endocrinology. 2007 May;148(5):2075-84. Epub 2007 Feb 15. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Drug created on June 13, 2005 13:24 / Updated on May 22, 2021 06:01