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Identification
NameTerlipressin
Accession NumberDB02638  (EXPT03310)
TypeSmall Molecule
GroupsApproved, Investigational
DescriptionTerlipressin 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
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
GlypressinFerring Pharmaceuticals
LucassinNot Available
TeripressNew Medicon Pharma
Brand mixturesNot Available
SaltsNot Available
Categories
UNII7Z5X49W53P
CAS number14636-12-5
WeightAverage: 1227.372
Monoisotopic: 1226.496097158
Chemical FormulaC52H74N16O15S2
InChI KeyBENFXAYNYRLAIU-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[[email protected]](NC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CSSC[[email protected]](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
IndicationCommonly used to stop bleeding of varices in the food pipe (oesophagus).
Structured Indications Not Available
PharmacodynamicsTerlipressin 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 actionTerlipressin, 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.
TargetKindPharmacological actionActionsOrganismUniProt ID
Vasopressin V1a receptorProteinunknown
stimulator
HumanP37288 details
Vasopressin V2 receptorProteinyes
agonist
HumanP30518 details
Vasopressin V1b receptorProteinunknownNot AvailableHumanP47901 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingApproximately 30%
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot 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
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
AtenololAtenolol may increase the hypotensive activities of Terlipressin.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
BethanidineBethanidine may increase the hypotensive activities of Terlipressin.Approved
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
BretyliumBretylium may increase the hypotensive activities of Terlipressin.Approved
BrimonidineBrimonidine may increase the hypotensive activities of Terlipressin.Approved
BrimonidineBrimonidine may increase the antihypertensive activities of Terlipressin.Approved
BupranololTerlipressin may increase the hypotensive activities of Bupranolol.Approved
CandesartanCandesartan 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
CilazaprilCilazapril may increase the hypotensive activities of Terlipressin.Approved
ClonidineClonidine may increase the hypotensive activities of Terlipressin.Approved
CryptenamineCryptenamine may increase the hypotensive activities of Terlipressin.Approved
CyclothiazideCyclothiazide may increase the hypotensive activities of Terlipressin.Approved
DebrisoquinTerlipressin may increase the hypotensive activities of Debrisoquin.Approved
DeserpidineTerlipressin may increase the hypotensive activities of Deserpidine.Approved
DiazoxideDiazoxide may increase the hypotensive activities of Terlipressin.Approved
DihydralazineTerlipressin may increase the hypotensive activities of Dihydralazine.Investigational
DiltiazemDiltiazem may increase the hypotensive 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
EnalaprilEnalapril may increase the hypotensive activities of Terlipressin.Approved, Vet Approved
EnalaprilatTerlipressin may increase the hypotensive activities of Enalaprilat.Approved
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
FosinoprilFosinopril may increase the hypotensive activities of Terlipressin.Approved
FurazolidoneFurazolidone may increase the hypotensive activities of Terlipressin.Approved, Vet Approved
GuanabenzGuanabenz may increase the hypotensive activities of Terlipressin.Approved
GuanadrelGuanadrel may increase the hypotensive activities of Terlipressin.Approved
GuanethidineGuanethidine may increase the hypotensive activities of Terlipressin.Approved
GuanfacineGuanfacine may increase the hypotensive activities of Terlipressin.Approved, Investigational
HexamethoniumTerlipressin may increase the hypotensive activities of Hexamethonium.Experimental
HydracarbazineHydracarbazine may increase the hypotensive activities of Terlipressin.Approved
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
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
IndoraminTerlipressin may increase the hypotensive activities of Indoramin.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
KetanserinTerlipressin may increase the hypotensive activities of Ketanserin.Investigational
LabetalolLabetalol may increase the hypotensive activities of Terlipressin.Approved
LacidipineTerlipressin may increase the hypotensive activities of Lacidipine.Approved
LatanoprostLatanoprost may increase the hypotensive activities of Terlipressin.Approved, Investigational
LercanidipineLercanidipine may increase the hypotensive activities of Terlipressin.Approved, Investigational
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
MacitentanTerlipressin may increase the hypotensive activities of Macitentan.Approved
ManidipineTerlipressin may increase the hypotensive activities of Manidipine.Approved
MebanazineMebanazine may increase the hypotensive activities of Terlipressin.Withdrawn
MecamylamineMecamylamine may increase the hypotensive activities of Terlipressin.Approved
MethyldopaMethyldopa may increase the hypotensive activities of Terlipressin.Approved
Methylene blueMethylene blue may increase the hypotensive activities of Terlipressin.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.Withdrawn
MinaprineMinaprine may increase the hypotensive activities of Terlipressin.Approved
MinoxidilMinoxidil may increase the hypotensive activities of Terlipressin.Approved
MoclobemideMoclobemide may increase the hypotensive activities of Terlipressin.Approved
MoexiprilMoexipril may increase the hypotensive activities of Terlipressin.Approved
MolsidomineMolsidomine may increase the hypotensive activities of Terlipressin.Approved
MoxonidineTerlipressin may increase the hypotensive activities of Moxonidine.Approved
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
NicorandilTerlipressin may increase the hypotensive activities of Nicorandil.Approved
NiguldipineTerlipressin may increase the hypotensive activities of Niguldipine.Experimental
NilvadipineTerlipressin may increase the hypotensive activities of Nilvadipine.Approved
NimodipineNimodipine may increase the hypotensive activities of Terlipressin.Approved
NisoldipineNisoldipine may increase the hypotensive activities of Terlipressin.Approved
NitrendipineNitrendipine may increase the hypotensive activities of Terlipressin.Approved
NitroprussideNitroprusside may increase the hypotensive activities of Terlipressin.Approved
ObinutuzumabTerlipressin may increase the hypotensive activities of Obinutuzumab.Approved
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
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
PinacidilTerlipressin may increase the hypotensive activities of Pinacidil.Withdrawn
PindololPindolol may increase the hypotensive activities of Terlipressin.Approved
PirlindolePirlindole may increase the hypotensive activities of Terlipressin.Approved
PivhydrazinePivhydrazine may increase the hypotensive activities of Terlipressin.Withdrawn
PolythiazidePolythiazide may increase the hypotensive activities of Terlipressin.Approved
PrazosinPrazosin may increase the hypotensive activities of Terlipressin.Approved
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
RilmenidineTerlipressin may increase the hypotensive activities of Rilmenidine.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
TelmisartanTelmisartan may increase the hypotensive activities of Terlipressin.Approved, Investigational
TemocaprilTerlipressin may increase the hypotensive activities of Temocapril.Experimental, Investigational
TiboloneTerlipressin may increase the hypotensive activities of Tibolone.Approved
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
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
Trans-2-PhenylcyclopropylamineTrans-2-Phenylcyclopropylamine may increase the hypotensive activities of Terlipressin.Experimental
TranylcypromineTranylcypromine may increase the hypotensive activities of Terlipressin.Approved
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
TrimazosinTerlipressin may increase the hypotensive activities of Trimazosin.Experimental
TrimethaphanTrimethaphan may increase the hypotensive activities of Terlipressin.Approved
UdenafilUdenafil may increase the antihypertensive activities of Terlipressin.Approved, Investigational
UnoprostoneTerlipressin may increase the hypotensive activities of Unoprostone.Approved
ValsartanValsartan may increase the hypotensive activities of Terlipressin.Approved, Investigational
VardenafilVardenafil may increase the antihypertensive activities of Terlipressin.Approved
VinpocetineTerlipressin may increase the hypotensive activities of Vinpocetine.Investigational
XylometazolineTerlipressin may increase the hypotensive activities of Xylometazoline.Approved
YohimbineYohimbine may decrease the antihypertensive activities of Terlipressin.Approved, Vet Approved
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
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
ATC CodesH01BA04
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as polypeptides. These are peptides containing ten or more amino acid residues.
KingdomOrganic compounds
Super ClassOrganic Polymers
ClassPolypeptides
Sub ClassNot Available
Direct ParentPolypeptides
Alternative Parents
Substituents
  • Polypeptide
  • Cyclic alpha peptide
  • N-acyl-alpha amino acid or derivatives
  • Macrolactam
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Pyrrolidine-2-carboxamide
  • Pyrrolidine carboxylic acid or derivatives
  • N-acylpyrrolidine
  • Phenol
  • Fatty acyl
  • Benzenoid
  • N-acyl-amine
  • Fatty amide
  • Monocyclic benzene moiety
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Cyclic alcohol
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Primary carboxylic acid amide
  • Organic disulfide
  • Lactam
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available

Targets

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 behaviors, including affiliation and attachment.
Gene Name:
AVPR1A
Uniprot ID:
P37288
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 ]
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
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
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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23