terlipressin 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
vasoconstrictors, vasopressin derivatives	2967	14636-12-5

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: terlipressin glycylpressin glypressin remestyp triglycyl-8-lysine-vasopressin terlipressin acetate	Terlipressin is a synthetic vasopressin analogue with twice the selectivity for vasopressin V1 receptors versus V2 receptors. Terlipressin acts as both a prodrug for lysine-vasopressin, as well as having pharmacologic activity on its own. Terlipressin is thought to increase renal blood flow in patients with hepatorenal syndrome by reducing portal hypertension and blood circulation in portal vessels and increasing effective arterial volume and mean arterial pressure (MAP). It is used to control bleeding of ESOPHAGEAL VARICES and for the treatment of HEPATORENAL SYNDROME. Molecular weight: 1227.38 Formula: C52H74N16O15S2 CLOGP: -3.36 LIPINSKI: 3 HAC: 31 HDO: 16 TPSA: 512.85 ALOGS: -3.87 ROTB: 25 Status: ONP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

terlipressin
glycylpressin
glypressin
remestyp
triglycyl-8-lysine-vasopressin
terlipressin acetate

Terlipressin is a synthetic vasopressin analogue with twice the selectivity for vasopressin V1 receptors versus V2 receptors. Terlipressin acts as both a prodrug for lysine-vasopressin, as well as having pharmacologic activity on its own. Terlipressin is thought to increase renal blood flow in patients with hepatorenal syndrome by reducing portal hypertension and blood circulation in portal vessels and increasing effective arterial volume and mean arterial pressure (MAP). It is used to control bleeding of ESOPHAGEAL VARICES and for the treatment of HEPATORENAL SYNDROME.

Molecular weight: 1227.38
Formula: C52H74N16O15S2
CLOGP: -3.36
LIPINSKI: 3
HAC: 31
HDO: 16
TPSA: 512.85
ALOGS: -3.87
ROTB: 25

Status: ONP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

Dose	Unit	Route
12	mg	P

ADMET properties:

Property	Value	Reference
Vd (Volume of distribution)	0.24 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	8.20 mL/min/kg	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	0.90 hours	Lombardo F, Berellini G, Obach RS

Approvals:

Date	Agency	Company	Orphan
Sept. 14, 2022	FDA	MALLINCKRODT

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

FDA Adverse Event Reporting System (Geriatric)

None

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

Source	Code	Description
ATC	H01BA04	SYSTEMIC HORMONAL PREPARATIONS, EXCL. SEX HORMONES AND INSULINS PITUITARY AND HYPOTHALAMIC HORMONES AND ANALOGUES POSTERIOR PITUITARY LOBE HORMONES Vasopressin and analogues
MeSH PA	D000959	Antihypertensive Agents
MeSH PA	D002317	Cardiovascular Agents
MeSH PA	D014662	Vasoconstrictor Agents

Drug Use | Suggest Off label Use Form| |View source of the data|

Disease	Relation	SNOMED_ID	DOID
Hepatorenal syndrome	indication	51292008	DOID:11823
Ischemia	contraindication	52674009	DOID:326
Hypoxia	contraindication	389086002

🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	9.65	acidic
pKa2	11.89	acidic
pKa3	12.32	acidic
pKa4	12.71	acidic
pKa5	12.98	acidic
pKa6	13.08	acidic
pKa7	13.57	acidic
pKa8	13.58	acidic
pKa9	13.67	acidic
pKa10	13.96	acidic
pKa11	10.31	Basic
pKa12	7.93	Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Exclusivity date	Description
EQ 0.85MG BASE/VIAL	TERLIVAZ	MALLINCKRODT IRELAND	N022231	Sept. 14, 2022	RX	POWDER	INTRAVENOUS	Sept. 14, 2027	NEW CHEMICAL ENTITY

Bioactivity Summary:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Mechanism action	Bioact source	MoA source
Vasopressin V1a receptor	GPCR	P37288	V1AR_HUMAN	AGONIST	Ki	5.96		SCIENTIFIC LITERATURE	DRUG LABEL
Vasopressin V2 receptor	GPCR	P30518	V2R_HUMAN	AGONIST	Ki	5.16		SCIENTIFIC LITERATURE

External reference:

ID	Source
D06672	KEGG_DRUG
C0145185	UMLSCUI
CHEBI:135905	CHEBI
CHEMBL2135460	ChEMBL_ID
D000077585	MESH_DESCRIPTOR_UI
DB02638	DRUGBANK_ID
11241	IUPHAR_LIGAND_ID
5114	INN_ID
7Z5X49W53P	UNII
72081	PUBCHEM_CID
57048	RXNORM
004053	NDDF
013118	NDDF
325927008	SNOMEDCT_US
395899009	SNOMEDCT_US
734453002	SNOMEDCT_US

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Terlivaz	HUMAN PRESCRIPTION DRUG LABEL	1	43825-200	INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION	0.85 mg	INTRAVENOUS	NDA	30 sections