Structure via PubChem · Public domain (PubChem)
terlipressin
Sign in to saveAlso known as SID124896640, Terlipressine, H-Gly-Gly-Gly-Cys(1)-Tyr-Phe-Gln-Asn-Cys(1)-Pro-Lys-Gly-NH2
Terlipressin, sold under the brand name Terlivaz among others, is an analogue of vasopressin used as a vasoactive drug in the management of low blood pressure. It has been found to be effective when norepinephrine does not help. Terlipressin is a vasopressin receptor agonist.
In the Vinony graph
Vinony's link graph records 75 inbound references to terlipressin, and connects out to arginine vasopressin, lithium and medication.
It is catalogued under topics including Antidiuretics, Antihypotensive agents and ECHA InfoCard ID from Wikidata.
Vinony links it to 18 Wikipedia language editions.
Key facts
- Drug.verifiedrevid
- 470602469
- Drug.image
- terlipressin.png
- Drug.image_class
- skin-invert-image
- Drug.tradename
- Terlivaz
- Drug.routes_of_administration
- Intravenous
- Drug.ATC_prefix
- H01
- Drug.ATC_suffix
- BA04
- Drug.legal_US
- Rx-only
- Drug.protein_bound
- ~30%
- Drug.CAS_number
- 14636-12-5
- Drug.PubChem
- 72081
- Drug.DrugBank
- DB02638
- Drug.ChemSpiderID
- 65067
- Drug.UNII
- 7Z5X49W53P
- Drug.KEGG
- D06672
- Drug.IUPAC_name
- 1-{[(4R,7S,10S,13S,16S,19R)-19-{[({[(aminoacetyl)amino]acetyl}amino)acetyl]amino}-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-benzyl-16-(4-hydroxybenzyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-4-yl]carbonyl}-L-prolyl-N-(2-amino-2-oxoethyl)-L-lysinamide
- Drug.C
- 52
- Drug.H
- 74
via Wikipedia infobox
Chemical data
- Formula
- C52H74N16O15S2
- Molecular weight
- 1227.4 g/mol
- 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
- SMILES
- C1C[C@H](N(C1)C(=O)[C@@H]2CSSC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N2)CC(=O)N)CCC(=O)N)CC3=CC=CC=C3)CC4=CC=C(C=C4)O)NC(=O)CNC(=O)CNC(=O)CN)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N
- InChIKey
- BENFXAYNYRLAIU-QSVFAHTRSA-N
- XLogP
- -5.8
- Polar surface area
- 563 Ų
- H-bond donors
- 16
- H-bond acceptors
- 19
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Protein
- First approval
- 2022
- Admin. routes
- parenteral
- Indications
- cirrhosis of liver, septic shock, hemorrhage, kidney failure
via ChEMBL · EBI
Research
1,380 papers- Terlipressin plus Albumin for the Treatment of Type 1 Hepatorenal Syndrome.The New England journal of medicine · 2021
- Terlipressin for hepatorenal syndrome.Current opinion in gastroenterology · 2024
- Terlipressin in the management of liver disease.Expert opinion on pharmacotherapy · 2023
- Terlipressin given by continuous intravenous infusion versus intravenous boluses in the treatment of hepatorenal syndrome: A randomized controlled study.Hepatology (Baltimore, Md.) · 2016
- Terlipressin Acetate.American journal of health-system pharmacy : AJHP : official journal of the American Society of Health-System Pharmacists · 2023
via PubMed
Wikidata facts
- Subclass of
- peptide
- Mass
- 1226.496
- Has use
- medication
Show 6 more facts
- chemical formula
- C₅₂H₇₄N₁₆O₁₅S₂
- canonical SMILES
- C1CC(N(C1)C(=O)C2CSSCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N2)CC(=O)N)CCC(=O)N)CC3=CC=CC=C3)CC4=CC=C(C=C4)O)NC(=O)CNC(=O)CNC(=O)CN)C(=O)NC(CCCCN)C(=O)NCC(=O)N
- isomeric SMILES
- C1C[C@H](N(C1)C(=O)[C@@H]2CSSC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N2)CC(=O)N)CCC(=O)N)CC3=CC=CC=C3)CC4=CC=C(C=C4)O)NC(=O)CNC(=O)CNC(=O)CN)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N
- defined daily dose
- 12
- medical condition treated
- hepatorenal syndrome
- legal status (medicine)
- boxed warning
Sources (7)
via Wikidata · CC0
~4 min read
Encyclopedic overview
5 sectionsContents
- Medical uses
- Contraindications
- Society and culture
- References
- External links
{{Infobox drug | verifiedrevid = 470602469 | image = terlipressin.png | image_class = skin-invert-image | alt =
| tradename = Terlivaz | Drugs.com = | pregnancy_category = | routes_of_administration = Intravenous | ATC_prefix = H01 | ATC_suffix = BA04 | ATC_supplemental =
Excerpted from Wikipedia’s “terlipressin” article, available under the CC BY-SA 4.0 licence.