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Conivaptan

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Also known as Conivaptan HCl (Vaprisol)

Summary

Conivaptan (CHEMBL1755) is an approved small-molecule vasopressin receptor antagonist (ATC C03XA02) targeting AVPR1A and AVPR2; indicated across 5 conditions including cardiovascular disorder and cirrhosis of liver.

At a glance

  • Status: Approved (max clinical phase 4)
  • Modality: Small molecule
  • ATC class: C03XA02
  • Targets: 2 (AVPR1A, AVPR2)
  • Indications: 5 conditions
  • Clinical trials: 15
  • Chemistry: 498.6 Da · C32H26N4O2

Identifiers

Drug identity and classification

FieldValue
ChEMBL IDCHEMBL1755
NameConivaptan
TypeSmall molecule
Max phase4
FDA approvedno
PubChem CID151171
ChEBICHEBI:681850
ATCC03XA02
Molecular formulaC32H26N4O2
Molecular weight498.6
InChIKeyIKENVDNFQMCRTR-UHFFFAOYSA-N

SMILES: CC1=NC2=C(N1)CCN(C3=CC=CC=C32)C(=O)C4=CC=C(C=C4)NC(=O)C5=CC=CC=C5C6=CC=CC=C6

IUPAC name: N-[4-(2-methyl-4,5-dihydro-3H-imidazo[4,5-d][1]benzazepine-6-carbonyl)phenyl]-2-phenylbenzamide

ChEBI definition: The amide resulting from the formal condensation of 4-[(biphenyl-2-ylcarbonyl)amino]benzoic acid with the benzazepine nitrogen of 2-methyl-1,4,5,6-tetrahydroimidazo[4,5-d][1]benzazepine. It is an antagonist for two of the three types of arginine vasopressin (AVP) receptors, V1a and V2. It is used as its hydrochloride salt for the treatment of hyponatraemia (low blood sodium levels) caused by syndrome of inappropriate antidiuretic hormone (SIADH).

Pharmacological roles (ChEBI): vasopressin receptor antagonist, aquaretic.

Also known as: Conivaptan, conivaptan, CONIVAPTAN, Conivaptan HCl (Vaprisol)

Parent form; salt/anhydrous children: CHEMBL1201108

Patent coverage: 811 distinct patent families (3,108 SureChEMBL compound mentions), from 3 matched compound structure(s). One matched structure accounts for 3,039 (98%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

GeneTargetActionpAffinityCancer dependencyUniProt
AVPR1AV1A receptorAntagonist8.44.6%P37288
AVPR2V2 receptorAntagonist9.440%P30518

Broader ChEMBL bioactivity targets: 5 (assay-derived). Sample: Vasopressin V2 receptor, Vasopressin V1a receptor, Vasopressin V1a receptor, Vasopressin V2 receptor, Oxytocin receptor.

Bioactivity

ChEMBL activities: 9 potent at pChembl ≥ 5 of 9 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

TargetpChemblTypeValueUnitActivity ID
AVPR29.44Ki0.36nMCHEMBL_ACT_3309443
AVPR1A9.37Ki0.43nMCHEMBL_ACT_3309386
P305609.32Ki0.48nMCHEMBL_ACT_18561126
AVPR29.22Ki0.6nMCHEMBL_ACT_29072103
AVPR1A8.54Ki2.9nMCHEMBL_ACT_29072071
Q007888.52Ki3.04nMCHEMBL_ACT_18561124
AVPR1A8.52IC503nMCHEMBL_ACT_3309542
AVPR27.96IC5011nMCHEMBL_ACT_3309544
P705367.35Ki44.4nMCHEMBL_ACT_18561123

Target pathways

Aggregated over 2 target gene(s): AVPR1A, AVPR2.

Top Reactome pathways

8 total, by targets touching each:

PathwayTargetsGenes
Vasopressin-like receptors2AVPR1A, AVPR2
G alpha (q) signalling events1AVPR1A
G alpha (s) signalling events1AVPR2
Vasopressin regulates renal water homeostasis via Aquaporins1AVPR2
Defective AVP does not bind AVPR1A,B and causes neurohypophyseal diabetes insipidus (NDI)1AVPR1A
Cargo recognition for clathrin-mediated endocytosis1AVPR2
Clathrin-mediated endocytosis1AVPR2
Defective AVP does not bind AVPR2 and causes neurohypophyseal diabetes insipidus (NDI)1AVPR2

Dominant GO biological processes

GO termTargets
regulation of systemic arterial blood pressure by vasopressin2
positive regulation of systemic arterial blood pressure2
G protein-coupled receptor signaling pathway2
positive regulation of cell population proliferation2
telencephalon development2
cellular response to hormone stimulus2
positive regulation of vasoconstriction2
signal transduction2
positive regulation of blood pressure2
maternal aggressive behavior1
generation of precursor metabolites and energy1
positive regulation of cytosolic calcium ion concentration1
negative regulation of female receptivity1
grooming behavior1
blood circulation1

Indications & clinical

Indications

5 indications (1 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

IndicationTrial phaseMONDOEFO
cardiovascular disorder4MONDO:0004995EFO:0000319
cirrhosis of liver2MONDO:0005155EFO:0001422
heart failure2MONDO:0005252EFO:0003144
brain injury1MONDO:0043510MONDO:0043510

1 further indication record had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 15.

Phase distribution

PhaseTrials
PHASE44
PHASE34
PHASE23
PHASE12
Not specified2

Top trials by phase / activity

NCTPhaseStatusTitle
NCT00435591PHASE4COMPLETEDA Study of Multiple Dosing Regimens of IV Conivaptan in Subjects With Euvolemic or Hypervolemic Hyponatremia
NCT00727090PHASE4TERMINATEDUse of Conivaptan (Vaprisol) for Hyponatremic Neuro-ICU Patients
NCT00806910PHASE4WITHDRAWNDiuretic and Renal Effects of Vaprisol When Administered Along With Furosemide and Nesiritide Continuous Infusion
NCT01752543PHASE4COMPLETEDEffects on Exercise Hemodynamics of Vasopressin Blockade by Conivaptan Infusion in Heart Failure Patients
NCT00379847PHASE3COMPLETEDAn Open-Label Study of YM087 (Conivaptan) in Patients With Euvolemic or Hypervolemic Hyponatremia
NCT00478192PHASE3COMPLETEDStudy of Efficacy & Safety for 3 Infusion Regimens of IV Conivaptan in Subjects With Euvolemic or Hypervolemic Hyponatremia
NCT00684164PHASE3WITHDRAWNSafety and Efficacy of Conivaptan for the Correction of Hyponatremia in Neurological Patients
NCT00843986PHASE3TERMINATEDSafety and Efficacy of Conivaptan in Hyponatremic Patients With Symptomatic Acute Decompensated Heart Failure (ADHF)
NCT00057356PHASE2COMPLETEDSafety and Efficacy Study of YM087 (Conivaptan) in Patients With Acute Decompensated Heart Failure
NCT00592475PHASE2COMPLETEDA Study to Assess the Safety and Effects of Intravenous (IV) Conivaptan on the Hepatic Hemodynamic Response in Cirrhotic Patients
NCT01954290PHASE2WITHDRAWNStudy of Stroke Related Edema Treatments
NCT00930202PHASE1COMPLETEDStudy of the Safety and Efficacy of Conivaptan (Vaprisol®) to Raise Serum Sodium Levels in Patients With Severe Traumatic Brain Injury
NCT03000283PHASE1COMPLETEDConivaptan for the Reduction of Cerebral Edema in Intracerebral Hemorrhage- A Safety and Tolerability Study
NCT00811486Not specifiedWITHDRAWNBody Volume Regulation in Pulmonary Arterial Hypertension With Right Ventricular Failure
NCT00924014Not specifiedUNKNOWNComparing the Effects of Conivaptan and Diuretics on Plasma Neurohormones and Renal Blood Flow in Patients With Chronic Congestive Heart Failure

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

143 molecules share ≥1 primary target. Top 60 by shared-target count:

MoleculeSourceStatusShared targets
PIMOZIDEChEMBL + PubChemPhase 4 (approved)AVPR1A, AVPR2
RIFAMPINChEMBL + PubChemPhase 4 (approved)AVPR1A, AVPR2
TEGASERODChEMBL + PubChemPhase 4 (approved)AVPR1A, AVPR2
ATOSIBANChEMBLPhase 4 (approved)AVPR1A, AVPR2
BALSALAZIDEChEMBLPhase 4 (approved)AVPR1A, AVPR2
BOSUTINIBChEMBLPhase 4 (approved)AVPR1A, AVPR2
CARBETOCINChEMBLPhase 4 (approved)AVPR1A, AVPR2
CHLORHEXIDINEChEMBLPhase 4 (approved)AVPR1A, AVPR2
DESMOPRESSINChEMBLPhase 4 (approved)AVPR1A, AVPR2
FLUSPIRILENEChEMBLPhase 4 (approved)AVPR1A, AVPR2
MOZAVAPTANChEMBLPhase 4 (approved)AVPR1A, AVPR2
NITAZOXANIDEChEMBLPhase 4 (approved)AVPR1A, AVPR2
OXYTOCINChEMBLPhase 4 (approved)AVPR1A, AVPR2
PYRVINIUMChEMBLPhase 4 (approved)AVPR1A, AVPR2
RIFAXIMINChEMBLPhase 4 (approved)AVPR1A, AVPR2
TOLVAPTANChEMBLPhase 4 (approved)AVPR1A, AVPR2
VASOPRESSINChEMBLPhase 4 (approved)AVPR1A, AVPR2
BALOVAPTANChEMBLPhase 3AVPR1A, AVPR2
LIXIVAPTANChEMBLPhase 3AVPR1A, AVPR2
OTILONIUM BROMIDEChEMBLPhase 3AVPR1A, AVPR2
BENZETHONIUMChEMBLPhase 2AVPR1A, AVPR2
DOMIPHENChEMBLPhase 2AVPR1A, AVPR2
NELIVAPTANChEMBLPhase 2AVPR1A, AVPR2
ORNIPRESSINChEMBLPhase 2AVPR1A, AVPR2
PECAVAPTANChEMBLPhase 2AVPR1A, AVPR2
RELCOVAPTANChEMBLPhase 2AVPR1A, AVPR2
SELEPRESSINChEMBLPhase 2AVPR1A, AVPR2
AbirateronePubChemApprovedAVPR1A, AVPR2
acetylcysteinePubChemApprovedAVPR1A, AVPR2
Aclidinium BromidePubChemApprovedAVPR1A, AVPR2
AcyclovirPubChemApprovedAVPR1A, AVPR2
AfatinibPubChemApprovedAVPR1A, AVPR2
AllopurinolPubChemApprovedAVPR1A, AVPR2
AlmotriptanPubChemApprovedAVPR1A, AVPR2
AlogliptinPubChemApprovedAVPR1A, AVPR2
aminolevulinic acidPubChemApprovedAVPR1A, AVPR2
AnagrelidePubChemApprovedAVPR1A, AVPR2
ApixabanPubChemApprovedAVPR1A, AVPR2
AprepitantPubChemApprovedAVPR1A, AVPR2
BelzutifanPubChemApprovedAVPR1A, AVPR2
BosentanPubChemApprovedAVPR1A, AVPR2
ClofarabinePubChemApprovedAVPR1A, AVPR2
ClozapinePubChemApprovedAVPR1A, AVPR2
CrizotinibPubChemApprovedAVPR1A, AVPR2
DacarbazinePubChemApprovedAVPR1A, AVPR2
DesloratadinePubChemApprovedAVPR1A, AVPR2
Desoxycorticosterone PivalatePubChemApprovedAVPR1A, AVPR2
DidanosinePubChemApprovedAVPR1A, AVPR2
DihydroergotaminePubChemApprovedAVPR1A, AVPR2
ErythromycinPubChemApprovedAVPR1A, AVPR2
EthambutolPubChemApprovedAVPR1A, AVPR2
FidaxomicinPubChemApprovedAVPR1A, AVPR2
FulvestrantPubChemApprovedAVPR1A, AVPR2
GanciclovirPubChemApprovedAVPR1A, AVPR2
GefitinibPubChemApprovedAVPR1A, AVPR2
GlycopyrrolatePubChemApprovedAVPR1A, AVPR2
LeucovorinPubChemApprovedAVPR1A, AVPR2
LinagliptinPubChemApprovedAVPR1A, AVPR2
MethotrexatePubChemApprovedAVPR1A, AVPR2
OlanzapinePubChemApprovedAVPR1A, AVPR2

About this page

Generated deterministically by Sugi Atlas from primary biomedical databases via BioBTree. Every record on this page traces to a primary source.

Generated
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BioBTree
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Sources 30

This page pulls from 30 datasets indexed by BioBTree:

chebichembl_activitychembl_moleculechembl_targetcivic_evidenceclingen_dosageclinical_trialsdepmapefoensemblentrezgogoparentgtopdbgtopdb_interactiongtopdb_ligandhgncmeshmondomsigdbpatent_compoundpharmgkbpharmgkb_guidelinepubchempubchem_activityreactomereactomeparentrefseqtranscriptuniprot