Identification

Name
Terlipressin
Accession Number
DB02638  (EXPT03310)
Type
Small Molecule
Groups
Approved, Investigational
Description

Terlipressin is an analogue of vasopressin used as a vasoactive drug in the management of hypotension. It has been found to be effective when norepinephrine does not help. [Wikipedia]

Structure
Thumb
Synonyms
  • Terlipressin
  • Terlipressina
  • Terlipressine
  • Terlipressinum
Product Ingredients
IngredientUNIICASInChI Key
Terlipressin acetate4U092XZF0KNot AvailableMLECZWUGJYWVAV-NSECCGHPSA-N
International/Other Brands
Glypressin (Ferring Pharmaceuticals) / Lucassin / Teripress (New Medicon Pharma)
Categories
UNII
7Z5X49W53P
CAS number
14636-12-5
Weight
Average: 1227.372
Monoisotopic: 1226.496097158
Chemical Formula
C52H74N16O15S2
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

Pharmacology

Indication

Commonly used to stop bleeding of varices in the food pipe (oesophagus).

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.

TargetActionsOrganism
AVasopressin V2 receptor
agonist
Human
UVasopressin V1b receptorNot AvailableHuman
UVasopressin V1a receptor
stimulator
Human
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
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypotensive activities of Terlipressin.Experimental
AcebutololAcebutolol may increase the hypotensive activities of Terlipressin.Approved, Investigational
AcemetacinThe therapeutic efficacy of Terlipressin can be decreased when used in combination with Acemetacin.Approved, Experimental, Investigational
AlfuzosinAlfuzosin may increase the hypotensive activities of Terlipressin.Approved, Investigational
AliskirenTerlipressin may increase the hypotensive activities of Aliskiren.Approved, Investigational
AlprenololAlprenolol may increase the hypotensive activities of Terlipressin.Approved, Withdrawn
AmbrisentanTerlipressin may increase the hypotensive activities of Ambrisentan.Approved, Investigational
AmifostineTerlipressin may increase the hypotensive activities of Amifostine.Approved, Investigational
AmlodipineAmlodipine may increase the hypotensive activities of Terlipressin.Approved
AmphetamineAmphetamine may increase the hypotensive activities of Terlipressin.Approved, Illicit, Investigational
AtenololAtenolol may increase the hypotensive activities of Terlipressin.Approved
AvanafilAvanafil may increase the antihypertensive activities of Terlipressin.Approved
BarnidipineTerlipressin may increase the antihypertensive activities of Barnidipine.Approved
BenazeprilBenazepril may increase the hypotensive activities of Terlipressin.Approved, Investigational
BendroflumethiazideBendroflumethiazide may increase the hypotensive activities of Terlipressin.Approved
BenmoxinBenmoxin may increase the hypotensive activities of Terlipressin.Withdrawn
BepridilBepridil may increase the hypotensive activities of Terlipressin.Approved, Withdrawn
BetaxololBetaxolol may increase the hypotensive activities of Terlipressin.Approved, Investigational
BethanidineBethanidine may increase the hypotensive activities of Terlipressin.Approved
BietaserpineBietaserpine may increase the hypotensive activities of Terlipressin.Experimental
BimatoprostBimatoprost may increase the hypotensive activities of Terlipressin.Approved, Investigational
BisoprololBisoprolol may increase the hypotensive activities of Terlipressin.Approved
BosentanBosentan may increase the hypotensive activities of Terlipressin.Approved, Investigational
BQ-123Terlipressin may increase the hypotensive activities of BQ-123.Investigational
BretyliumBretylium may increase the hypotensive activities of Terlipressin.Approved
BrimonidineBrimonidine may increase the antihypertensive activities of Terlipressin.Approved
BrofaromineBrofaromine may increase the hypotensive activities of Terlipressin.Experimental
BupranololTerlipressin may increase the hypotensive activities of Bupranolol.Approved
CadralazineCadralazine may increase the hypotensive activities of Terlipressin.Experimental
CafedrineTerlipressin may increase the hypotensive activities of Cafedrine.Investigational
CandesartanTerlipressin may increase the hypotensive activities of Candesartan.Experimental
Candesartan cilexetilCandesartan cilexetil may increase the hypotensive activities of Terlipressin.Approved
CandoxatrilCandoxatril may increase the hypotensive activities of Terlipressin.Experimental
CaptoprilCaptopril may increase the hypotensive activities of Terlipressin.Approved
CaroxazoneCaroxazone may increase the hypotensive activities of Terlipressin.Withdrawn
CarteololCarteolol may increase the hypotensive activities of Terlipressin.Approved
CarvedilolCarvedilol may increase the hypotensive activities of Terlipressin.Approved, Investigational
CeliprololTerlipressin may increase the hypotensive activities of Celiprolol.Approved, Investigational
ChlorothiazideChlorothiazide may increase the hypotensive activities of Terlipressin.Approved, Vet Approved
ChlorthalidoneChlorthalidone may increase the hypotensive activities of Terlipressin.Approved
CicletanineTerlipressin may increase the hypotensive activities of Cicletanine.Investigational
CilazaprilCilazapril may increase the hypotensive activities of Terlipressin.Approved
ClonidineClonidine may increase the hypotensive activities of Terlipressin.Approved
CloranololTerlipressin may increase the hypotensive activities of Cloranolol.Experimental
CryptenamineCryptenamine may increase the hypotensive activities of Terlipressin.Approved
CyclopenthiazideTerlipressin may increase the hypotensive activities of Cyclopenthiazide.Experimental
CyclothiazideCyclothiazide may increase the hypotensive activities of Terlipressin.Approved
DebrisoquinDebrisoquin may increase the hypotensive activities of Terlipressin.Approved, Investigational
DelamanidTerlipressin may increase the QTc-prolonging activities of Delamanid.Approved, Investigational
DelaprilTerlipressin may increase the hypotensive activities of Delapril.Investigational
DeserpidineTerlipressin may increase the hypotensive activities of Deserpidine.Approved
DeutetrabenazineTerlipressin may increase the QTc-prolonging activities of Deutetrabenazine.Approved, Investigational
DiazoxideDiazoxide may increase the hypotensive activities of Terlipressin.Approved
DiethylnorspermineTerlipressin may increase the hypotensive activities of Diethylnorspermine.Investigational
DihydralazineDihydralazine may increase the hypotensive activities of Terlipressin.Approved, Investigational
DiltiazemDiltiazem may increase the hypotensive activities of Terlipressin.Approved, Investigational
DipyridamoleDipyridamole may increase the antihypertensive activities of Terlipressin.Approved
DorzolamideDorzolamide may increase the hypotensive activities of Terlipressin.Approved
DoxazosinDoxazosin may increase the hypotensive activities of Terlipressin.Approved
EfonidipineTerlipressin may increase the hypotensive activities of Efonidipine.Approved, Investigational
EnalaprilEnalapril may increase the hypotensive activities of Terlipressin.Approved, Vet Approved
EnalaprilatTerlipressin may increase the hypotensive activities of Enalaprilat.Approved
EndralazineEndralazine may increase the hypotensive activities of Terlipressin.Experimental
EpanololTerlipressin may increase the hypotensive activities of Epanolol.Experimental
EpoprostenolEpoprostenol may increase the hypotensive activities of Terlipressin.Approved
EprosartanEprosartan may increase the hypotensive activities of Terlipressin.Approved
FelodipineFelodipine may increase the hypotensive activities of Terlipressin.Approved, Investigational
FenoldopamFenoldopam may increase the hypotensive activities of Terlipressin.Approved
Ferulic acidTerlipressin may increase the hypotensive activities of Ferulic acid.Experimental
FosinoprilFosinopril may increase the hypotensive activities of Terlipressin.Approved
FostamatinibFostamatinib may increase the antihypertensive activities of Terlipressin.Approved, Investigational
FurazolidoneFurazolidone may increase the hypotensive activities of Terlipressin.Approved, Investigational, Vet Approved
GuanabenzGuanabenz may increase the hypotensive activities of Terlipressin.Approved, Investigational
GuanadrelGuanadrel may increase the hypotensive activities of Terlipressin.Approved
GuanazodineTerlipressin may increase the hypotensive activities of Guanazodine.Experimental
GuanethidineGuanethidine may increase the hypotensive activities of Terlipressin.Approved
GuanfacineGuanfacine may increase the hypotensive activities of Terlipressin.Approved, Investigational
GuanoclorTerlipressin may increase the hypotensive activities of Guanoclor.Experimental
GuanoxabenzTerlipressin may increase the hypotensive activities of Guanoxabenz.Experimental
GuanoxanTerlipressin may increase the hypotensive activities of Guanoxan.Experimental
HarmalineHarmaline may increase the hypotensive activities of Terlipressin.Experimental
HexamethoniumTerlipressin may increase the hypotensive activities of Hexamethonium.Experimental
HydracarbazineHydracarbazine may increase the hypotensive activities of Terlipressin.Experimental
HydralazineHydralazine may increase the hypotensive activities of Terlipressin.Approved
HydrochlorothiazideHydrochlorothiazide may increase the hypotensive activities of Terlipressin.Approved, Vet Approved
HydroflumethiazideHydroflumethiazide may increase the hypotensive activities of Terlipressin.Approved, Investigational
IloprostIloprost may increase the hypotensive activities of Terlipressin.Approved, Investigational
ImidaprilTerlipressin may increase the hypotensive activities of Imidapril.Investigational
IndapamideIndapamide may increase the hypotensive activities of Terlipressin.Approved
IndenololTerlipressin may increase the hypotensive activities of Indenolol.Withdrawn
IndoraminIndoramin may increase the hypotensive activities of Terlipressin.Withdrawn
IproclozideIproclozide may increase the hypotensive activities of Terlipressin.Withdrawn
IproniazidIproniazid may increase the hypotensive activities of Terlipressin.Withdrawn
IrbesartanIrbesartan may increase the hypotensive activities of Terlipressin.Approved, Investigational
IsocarboxazidIsocarboxazid may increase the hypotensive activities of Terlipressin.Approved
IsradipineIsradipine may increase the hypotensive activities of Terlipressin.Approved, Investigational
KetanserinKetanserin may increase the hypotensive activities of Terlipressin.Investigational
LabetalolLabetalol may increase the hypotensive activities of Terlipressin.Approved
LacidipineTerlipressin may increase the hypotensive activities of Lacidipine.Approved, Investigational
LatanoprostLatanoprost may increase the hypotensive activities of Terlipressin.Approved, Investigational
LercanidipineLercanidipine may increase the hypotensive activities of Terlipressin.Approved, Investigational
LinsidomineTerlipressin may increase the hypotensive activities of Linsidomine.Experimental
LisinoprilLisinopril may increase the hypotensive activities of Terlipressin.Approved, Investigational
LofexidineTerlipressin may increase the hypotensive activities of Lofexidine.Approved, Investigational
LosartanLosartan may increase the hypotensive activities of Terlipressin.Approved
MacimorelinTerlipressin may increase the QTc-prolonging activities of Macimorelin.Approved, Investigational
MacitentanTerlipressin may increase the hypotensive activities of Macitentan.Approved
ManidipineTerlipressin may increase the hypotensive activities of Manidipine.Approved, Investigational
MebanazineMebanazine may increase the hypotensive activities of Terlipressin.Withdrawn
MecamylamineMecamylamine may increase the hypotensive activities of Terlipressin.Approved, Investigational
MethoserpidineTerlipressin may increase the hypotensive activities of Methoserpidine.Experimental
MethyldopaMethyldopa may increase the hypotensive activities of Terlipressin.Approved
Methylene blueMethylene blue may increase the hypotensive activities of Terlipressin.Approved, Investigational
MethylphenidateMethylphenidate may decrease the antihypertensive activities of Terlipressin.Approved, Investigational
MetipranololMetipranolol may increase the hypotensive activities of Terlipressin.Approved
MetolazoneMetolazone may increase the hypotensive activities of Terlipressin.Approved
MetoprololMetoprolol may increase the hypotensive activities of Terlipressin.Approved, Investigational
MetyrosineTerlipressin may increase the hypotensive activities of Metyrosine.Approved
MibefradilMibefradil may increase the hypotensive activities of Terlipressin.Investigational, Withdrawn
MinaprineMinaprine may increase the hypotensive activities of Terlipressin.Approved
MinoxidilMinoxidil may increase the hypotensive activities of Terlipressin.Approved, Investigational
MirodenafilMirodenafil may increase the antihypertensive activities of Terlipressin.Investigational
MoclobemideMoclobemide may increase the hypotensive activities of Terlipressin.Approved, Investigational
MoexiprilMoexipril may increase the hypotensive activities of Terlipressin.Approved
MolsidomineMolsidomine may increase the hypotensive activities of Terlipressin.Approved, Investigational
MoxonidineMoxonidine may increase the hypotensive activities of Terlipressin.Approved, Investigational
MuzolimineTerlipressin may increase the hypotensive activities of Muzolimine.Experimental
NadololNadolol may increase the hypotensive activities of Terlipressin.Approved
NaftopidilTerlipressin may increase the hypotensive activities of Naftopidil.Investigational
NebivololTerlipressin may increase the hypotensive activities of Nebivolol.Approved, Investigational
NialamideNialamide may increase the hypotensive activities of Terlipressin.Withdrawn
NicardipineNicardipine may increase the hypotensive activities of Terlipressin.Approved, Investigational
NicorandilTerlipressin may increase the hypotensive activities of Nicorandil.Approved, Investigational
NiguldipineTerlipressin may increase the hypotensive activities of Niguldipine.Experimental
NilvadipineTerlipressin may increase the hypotensive activities of Nilvadipine.Approved, Investigational
NimodipineNimodipine may increase the hypotensive activities of Terlipressin.Approved, Investigational
NisoldipineNisoldipine may increase the hypotensive activities of Terlipressin.Approved
NitrendipineNitrendipine may increase the hypotensive activities of Terlipressin.Approved, Investigational
NitroprussideNitroprusside may increase the hypotensive activities of Terlipressin.Approved, Investigational
ObinutuzumabTerlipressin may increase the hypotensive activities of Obinutuzumab.Approved, Investigational
OctamoxinOctamoxin may increase the hypotensive activities of Terlipressin.Withdrawn
OlmesartanOlmesartan may increase the hypotensive activities of Terlipressin.Approved, Investigational
OmapatrilatOmapatrilat may increase the hypotensive activities of Terlipressin.Investigational
OxprenololOxprenolol may increase the hypotensive activities of Terlipressin.Approved
PargylinePargyline may increase the hypotensive activities of Terlipressin.Approved
Patent BlueThe therapeutic efficacy of Terlipressin can be decreased when used in combination with Patent Blue.Approved
PenbutololPenbutolol may increase the hypotensive activities of Terlipressin.Approved, Investigational
PentoliniumPentolinium may increase the hypotensive activities of Terlipressin.Approved
PentoxifyllinePentoxifylline may increase the hypotensive activities of Terlipressin.Approved, Investigational
PerindoprilPerindopril may increase the hypotensive activities of Terlipressin.Approved
PhenelzinePhenelzine may increase the hypotensive activities of Terlipressin.Approved
PheniprazinePheniprazine may increase the hypotensive activities of Terlipressin.Withdrawn
PhenoxybenzaminePhenoxybenzamine may increase the hypotensive activities of Terlipressin.Approved
PhenoxypropazinePhenoxypropazine may increase the hypotensive activities of Terlipressin.Withdrawn
PhentolaminePhentolamine may increase the hypotensive activities of Terlipressin.Approved
PinacidilPinacidil may increase the hypotensive activities of Terlipressin.Approved
PindololPindolol may increase the hypotensive activities of Terlipressin.Approved, Investigational
PirlindolePirlindole may increase the hypotensive activities of Terlipressin.Approved
PitolisantThe risk or severity of QTc prolongation can be increased when Terlipressin is combined with Pitolisant.Approved, Investigational
PivhydrazinePivhydrazine may increase the hypotensive activities of Terlipressin.Withdrawn
Platelet Activating FactorPlatelet Activating Factor may increase the hypotensive activities of Terlipressin.Experimental
PolythiazidePolythiazide may increase the hypotensive activities of Terlipressin.Approved
PrazosinPrazosin may increase the hypotensive activities of Terlipressin.Approved
ProcaineProcaine may increase the hypotensive activities of Terlipressin.Approved, Investigational, Vet Approved
ProcarbazineProcarbazine may increase the hypotensive activities of Terlipressin.Approved, Investigational
PropranololPropranolol may increase the hypotensive activities of Terlipressin.Approved, Investigational
QuinaprilQuinapril may increase the hypotensive activities of Terlipressin.Approved, Investigational
QuinineQuinine may increase the hypotensive activities of Terlipressin.Approved
RamiprilRamipril may increase the hypotensive activities of Terlipressin.Approved
RasagilineRasagiline may increase the hypotensive activities of Terlipressin.Approved
RemikirenRemikiren may increase the hypotensive activities of Terlipressin.Approved
RescinnamineTerlipressin may increase the hypotensive activities of Rescinnamine.Approved
ReserpineReserpine may increase the hypotensive activities of Terlipressin.Approved, Investigational
RibociclibThe risk or severity of QTc prolongation can be increased when Ribociclib is combined with Terlipressin.Approved, Investigational
RilmenidineRilmenidine may increase the hypotensive activities of Terlipressin.Approved, Investigational
RiociguatTerlipressin may increase the hypotensive activities of Riociguat.Approved
RituximabTerlipressin may increase the hypotensive activities of Rituximab.Approved
SafrazineSafrazine may increase the hypotensive activities of Terlipressin.Withdrawn
SaprisartanSaprisartan may increase the hypotensive activities of Terlipressin.Experimental
SelegilineSelegiline may increase the hypotensive activities of Terlipressin.Approved, Investigational, Vet Approved
SelexipagTerlipressin may increase the hypotensive activities of Selexipag.Approved
SildenafilSildenafil may increase the antihypertensive activities of Terlipressin.Approved, Investigational
SitaxentanTerlipressin may increase the hypotensive activities of Sitaxentan.Approved, Investigational, Withdrawn
SpiraprilSpirapril may increase the hypotensive activities of Terlipressin.Approved
TadalafilTadalafil may increase the antihypertensive activities of Terlipressin.Approved, Investigational
TalinololTerlipressin may increase the hypotensive activities of Talinolol.Investigational
TelmisartanTelmisartan may increase the hypotensive activities of Terlipressin.Approved, Investigational
TemocaprilTerlipressin may increase the hypotensive activities of Temocapril.Experimental, Investigational
TetrahydropalmatineTerlipressin may increase the hypotensive activities of Tetrahydropalmatine.Investigational
TheodrenalineTerlipressin may increase the hypotensive activities of Theodrenaline.Investigational
TheophyllineTheophylline may increase the antihypertensive activities of Terlipressin.Approved
TiboloneTerlipressin may increase the hypotensive activities of Tibolone.Approved, Investigational
TicrynafenTerlipressin may increase the hypotensive activities of Ticrynafen.Withdrawn
TimololTimolol may increase the hypotensive activities of Terlipressin.Approved
TolazolineTolazoline may increase the hypotensive activities of Terlipressin.Approved, Vet Approved
TolonidineTerlipressin may increase the hypotensive activities of Tolonidine.Experimental
ToloxatoneToloxatone may increase the hypotensive activities of Terlipressin.Approved
TorasemideTorasemide may increase the hypotensive activities of Terlipressin.Approved
TrandolaprilTrandolapril may increase the hypotensive activities of Terlipressin.Approved
TranylcypromineTranylcypromine may increase the hypotensive activities of Terlipressin.Approved, Investigational
TravoprostTravoprost may increase the hypotensive activities of Terlipressin.Approved
TreprostinilTreprostinil may increase the hypotensive activities of Terlipressin.Approved, Investigational
TrichlormethiazideTrichlormethiazide may increase the hypotensive activities of Terlipressin.Approved, Vet Approved
TrimazosinTrimazosin may increase the hypotensive activities of Terlipressin.Experimental
TrimethaphanTrimethaphan may increase the hypotensive activities of Terlipressin.Approved, Investigational
UdenafilUdenafil may increase the antihypertensive activities of Terlipressin.Approved, Investigational
UnoprostoneTerlipressin may increase the hypotensive activities of Unoprostone.Approved, Investigational
UrapidilUrapidil may increase the hypotensive activities of Terlipressin.Investigational
ValsartanValsartan may increase the hypotensive activities of Terlipressin.Approved, Investigational
VardenafilVardenafil may increase the antihypertensive activities of Terlipressin.Approved
VincamineTerlipressin may increase the hypotensive activities of Vincamine.Experimental
VinpocetineTerlipressin may increase the hypotensive activities of Vinpocetine.Investigational
XipamideTerlipressin may increase the hypotensive activities of Xipamide.Experimental
XylometazolineTerlipressin may increase the hypotensive activities of Xylometazoline.Approved, Investigational
YohimbineYohimbine may decrease the antihypertensive activities of Terlipressin.Approved, Investigational, Vet Approved
ZofenoprilTerlipressin may increase the hypotensive activities of Zofenopril.Experimental
Food Interactions
Not Available

References

General References
  1. 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. [PubMed:17148649]
  2. 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. [PubMed:17125115]
  3. 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. [PubMed:16015526]
  4. 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. [PubMed:15803052]
  5. Kam PC, Williams S, Yoong FF: Vasopressin and terlipressin: pharmacology and its clinical relevance. Anaesthesia. 2004 Oct;59(10):993-1001. [PubMed:15488059]
External Links
Human Metabolome Database
HMDB0015569
PubChem Compound
72081
PubChem Substance
46504626
ChemSpider
65067
ChEBI
135905
ChEMBL
CHEMBL2135460
Therapeutic Targets Database
DAP000058
PharmGKB
PA164781020
Wikipedia
Terlipressin
ATC Codes
H01BA04 — Terlipressin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1, 2CompletedTreatmentHepatorenal Syndrome Type 11
2CompletedPreventionHepatectomy, Surgical Blood Loss, Terlipressin1
2CompletedTreatmentBlood Loss / Terlipressin1
2CompletedTreatmentCompensated Cirrhosis and Portal Hypertension1
2CompletedTreatmentHemodynamics, Liver, Terlipressin1
2CompletedTreatmentShock, Septic1
2RecruitingTreatmentAscites Hepatic / Liver Cirrhosis1
2RecruitingTreatmentHepatic Failure / Liver Resection1
2RecruitingTreatmentPortal Vein Pressure1
2RecruitingTreatmentTerlipressin Adverse Reaction / Transplantation, Liver1
2Unknown StatusSupportive CareShock, Septic1
2WithdrawnPreventionRenal Failure1
2, 3CompletedNot AvailableAscites / Liver Cirrhosis1
2, 3CompletedTreatmentLiver Cirrhosis / Shock, Septic1
3CompletedTreatmentHepatorenal Syndrome Type 1 / HRS1
3CompletedTreatmentHepatorenal Syndrome2
3CompletedTreatmentLiver Cirrhosis1
3CompletedTreatmentSafety and Efficacy of Terlipressin and Noradrenaline and Predictive Factors of Response in Type 2 HRS1
3Not Yet RecruitingPreventionBronchial Endoscopy1
3RecruitingTreatmentHepatorenal Syndrome1
3RecruitingTreatmentRefractory Shock / Shock, Septic1
3TerminatedTreatmentSepsis-associated Hypotension / Shock, Septic1
4Active Not RecruitingTreatmentHepatorenal Syndrome Type I / Liver Cirrhosis1
4CompletedPreventionAcute Kidney Injury (AKI) / NGAL / Terlipressin / Transplantation, Liver1
4CompletedTreatmentGastric and Esophageal Varices1
4CompletedTreatmentHaematemesis / Liver Cirrhosis / Melena / Portal Hypertension1
4CompletedTreatmentHemorrhage / Portal Hypertension / Varices, Esophageal1
4CompletedTreatmentVariceal Bleeding, Cirrhosis1
4CompletedTreatmentVasoconstrictor Choice on Acute Variceal Bleeding1
4Not Yet RecruitingTreatmentShock, Septic1
4RecruitingPreventionHepatorenal Syndrome1
4SuspendedTreatmentHepatorenal Syndrome / Liver Cirrhosis1
4Unknown StatusTreatmentEsophageal Variceal Rebleeding1
Not AvailableCompletedTreatmentAcute on Chronic Liver Failure1
Not AvailableCompletedTreatmentCirrhosis With Septic Shock2
Not AvailableCompletedTreatmentHepatorenal Syndrome1
Not AvailableNot Yet RecruitingTreatmentEsophageal and Gastric Varices / Gastroesophageal variceal hemorrhage prophylaxis / Haemorrhage / Liver Cirrhosis / Portal Hypertension1
Not AvailableRecruitingPreventionArterial Hypotension1
Not AvailableRecruitingTreatmentAcute Variceal Bleeding1
Not AvailableRecruitingTreatmentLiver Cirrhosis1
Not AvailableUnknown StatusNot AvailableEsophageal and Gastric Varices / Hemorrhage / Liver Cirrhosis1
Not AvailableUnknown StatusTreatmentShock, Septic1
Not AvailableUnknown StatusTreatmentShock, Septic / Terlipressin1
Not AvailableWithdrawnTreatmentHepatorenal Syndrome1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.167 mg/mLALOGPS
logP-1.6ALOGPS
logP-10ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)9.43ChemAxon
pKa (Strongest Basic)10.26ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count16ChemAxon
Polar Surface Area512.85 Å2ChemAxon
Rotatable Bond Count25ChemAxon
Refractivity305.18 m3·mol-1ChemAxon
Polarizability123.88 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.7085
Blood Brain Barrier-0.8855
Caco-2 permeable-0.7797
P-glycoprotein substrateSubstrate0.7307
P-glycoprotein inhibitor INon-inhibitor0.8042
P-glycoprotein inhibitor IINon-inhibitor0.8977
Renal organic cation transporterNon-inhibitor0.8004
CYP450 2C9 substrateNon-substrate0.8292
CYP450 2D6 substrateNon-substrate0.7878
CYP450 3A4 substrateNon-substrate0.5247
CYP450 1A2 substrateNon-inhibitor0.9358
CYP450 2C9 inhibitorNon-inhibitor0.766
CYP450 2D6 inhibitorNon-inhibitor0.8606
CYP450 2C19 inhibitorNon-inhibitor0.7565
CYP450 3A4 inhibitorNon-inhibitor0.7185
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8301
Ames testNon AMES toxic0.736
CarcinogenicityNon-carcinogens0.8513
BiodegradationNot ready biodegradable0.9261
Rat acute toxicity2.9218 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8955
hERG inhibition (predictor II)Inhibitor0.6764
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Polypeptide / Cyclic alpha peptide / Proline or derivatives / Macrolactam / N-acyl-alpha amino acid or derivatives / Alpha-amino acid amide / N-substituted-alpha-amino acid / Alpha-amino acid or derivatives / N-acylpyrrolidine / Pyrrolidine carboxylic acid or derivatives
show 31 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
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
  1. 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. [PubMed:17020465]
  2. 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. [PubMed:16333859]
  3. 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. [PubMed:16563128]
  4. 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. [PubMed:17287200]
Kind
Protein
Organism
Human
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
  1. 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. [PubMed:17027167]
  2. 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. [PubMed:16720725]
  3. 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. [PubMed:17284170]
  4. 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. [PubMed:16114100]
  5. 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. [PubMed:15993108]
Kind
Protein
Organism
Human
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
  1. 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. [PubMed:17275806]
  2. 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. [PubMed:16532916]
  3. 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. [PubMed:16511036]
  4. 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. [PubMed:16011575]
  5. 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. [PubMed:17303660]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Drug created on June 13, 2005 07:24 / Updated on July 02, 2018 20:58