Terlipressin

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.^[1]

Terlipressin

Clinical data
Trade names	Terlivaz
AHFS/Drugs.com	International Drug Names
Routes of administration	Intravenous
ATC code	H01BA04 (WHO)
Legal status
Legal status	US: ℞-only[1][2]
Pharmacokinetic data
Protein binding	~30%
Identifiers
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
CAS Number	14636-12-5 Y
PubChem CID	72081
DrugBank	DB02638 Y
ChemSpider	65067 Y
UNII	7Z5X49W53P
KEGG	D06672 Y
CompTox Dashboard (EPA)	DTXSID7048952
ECHA InfoCard	100.035.149
Chemical and physical data
Formula	C52H74N16O15S2
Molar mass	1227.38 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C(N)CNC(=O)[C@@H](NC(=O)[C@H]4N(C(=O)[C@H]1NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)CN)CSSC1)Cc2ccc(O)cc2)Cc3ccccc3)CCC(=O)N)CC(=O)N)CCC4)CCCCN
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 Y Key:BENFXAYNYRLAIU-QSVFAHTRSA-N Y
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Terlipressin was approved for medical use in the United States in 2022.^[1][3][4] The US Food and Drug Administration (FDA) considers it to be a first-in-class medication.^[4][5]

Medical uses

Terlipressin is indicated to improve kidney function in adults with hepatorenal syndrome with rapid reduction in kidney function.^[1]

Indications for use include norepinephrine-resistant septic shock^[6] although, 2021 Surviving Sepsis Guidelines recommend against its use for adults with septic shock^[7] and hepatorenal syndrome.^[8] In addition, it is used to treat bleeding esophageal varices.^[9]

Contraindications

Terlipressin is contraindicated in people experiencing hypoxia or worsening respiratory symptoms and in people with ongoing coronary, peripheral or mesenteric ischemia.^[1] Terlipressin may cause fetal harm when used during pregnancy.^[1]

Society and culture

Terlipressin is available in United States,^[10] New Zealand,^[11] Australia, the European Union,^[12] India, Indonesia, Pakistan, UAE. It is sold under various brand names including Glypressin and Terlivaz.