Terlipressin

H01B - Posterior pituitary lobe hormones ATC H01BA04 Protein approved 2022 Parenteral Prodrug First-in-class Natural product Black-box warning

Active form: Lypressin.

JFDA label: Glypressin

⚠ Black-Box Warning

Mechanism of Action

Binding Agent of Vasopressin V1 receptor — Vasopressin V1 receptor binding agent; Binding Agent of Vasopressin V2 receptor — Vasopressin V2 receptor binding agent

Target	Action	Gene / class
Vasopressin V1 receptor efficacy	BINDING AGENT
Vasopressin V2 receptor efficacy	BINDING AGENT	AVPR2

Indications

Approved

Hepatorenal Syndrome — hepatorenal syndrome
Renal Insufficiency — kidney failure

Off-label

Hemoptysis
Hemorrhage
Liver Cirrhosis
Liver Failure
Shock, Septic

Adverse Reactions

Very Common >10%Common 1–10%Uncommon 0.1–1% Rare 0.01–0.1%Very Rare <0.01%Not Known

Cardiac disorders (9)

Rare Acute coronary syndrome · Atrial fibrillation · Bradycardia · Cardiac disorder · Cardiac failure · Myocardial infarction · Tachycardia · Ventricular extrasystoles · Ventricular fibrillation

Vascular disorders (2)

Rare Hot flush · Hypertension

Nervous system disorders (1)

Rare Headache

Metabolism and nutrition disorders (1)

Rare Hyponatraemia

Gastrointestinal disorders (6)

Rare Abdominal pain · Diarrhoea · Gastrointestinal disorder · Intestinal ischaemia · Nausea · Vomiting

Skin and subcutaneous tissue disorders (2)

Rare Skin disorder · Skin exfoliation

Reproductive system and breast disorders (2)

Rare Pregnancy · Uterine hypertonus

General disorders and administration site conditions (14)

Rare Angiopathy · Chest pain · Cyanosis · Fluid overload · Injection site necrosis · Malnutrition · Menopausal symptoms · Mesenteric vascular insufficiency · Nervous system disorder · Pallor · Peripheral ischaemia · Skin necrosis · Torsade de pointes · Vasoconstriction

Respiratory, thoracic and mediastinal disorders (4)

Rare Dyspnoea · Pulmonary oedema · Respiratory distress · Respiratory failure

Pregnancy & Lactation

Pregnancy

Chemistry & Properties

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
CAS	14636-12-5
PubChem CID	72081
InChIKey	`BENFXAYNYRLAIU-QSVFAHTRSA-N`

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](Cc2ccc(O)cc2)C(=O)N[C@@H](Cc2ccccc2)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N1)C(=O)NCC(N)=O

Biology & Pharmacokinetics

Pharmacokinetics predicted

Bioavailability	70.0%
Half-life	1.681 h
Volume of distribution	0.197 L/kg
Protein binding	-2.0%
BBB penetrant	No

Enzyme interactions

Enzyme	Role	Detail
CYP2C19	Substrate	—

Transporters

BCRP (Inhibitor)BSEP (Inhibitor)BSEP (Inhibitor)MRP1 (Inhibitor)MRP2 (Inhibitor)MRP3 (Inhibitor)MRP4 (Inhibitor)OATP1B1 (Inhibitor)OATP1B3 (Inhibitor)P-gp (Inhibitor)P-gp (Substrate)

Registered Products (1)

Brand	Form / strength	Pack	Agent	Citizen (JOD)
Glypressin	Ampoule 1 mg/8.5 ml	5 amp	Petra Drug Store	—