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Netupitant

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Also known as Netupitant component of akynzeoNetupitant component of akynzeo capsuleRO-673189000

Summary

Netupitant (CHEMBL206253) is an approved small-molecule neurokinin-1 receptor antagonist targeting TACR1; indicated across 2 conditions including neoplasm.

At a glance

  • Status: Approved (max clinical phase 4)
  • Modality: Small molecule
  • Targets: 1 (TACR1)
  • Indications: 2 conditions
  • Clinical trials: 16
  • Chemistry: 578.6 Da · C30H32F6N4O

Identifiers

Drug identity and classification

FieldValue
ChEMBL IDCHEMBL206253
NameNetupitant
TypeSmall molecule
Max phase4
FDA approvedno
PubChem CID6451149
ChEBICHEBI:85155
Molecular formulaC30H32F6N4O
Molecular weight578.6
InChIKeyWAXQNWCZJDTGBU-UHFFFAOYSA-N

SMILES: CC1=CC=CC=C1C2=CC(=NC=C2N(C)C(=O)C(C)(C)C3=CC(=CC(=C3)C(F)(F)F)C(F)(F)F)N4CCN(CC4)C

IUPAC name: 2-[3,5-bis(trifluoromethyl)phenyl]-N,2-dimethyl-N-[4-(2-methylphenyl)-6-(4-methylpiperazin-1-yl)-3-pyridinyl]propanamide

ChEBI definition: A monocarboxylic acid amide obtained by formal condensation of the carboxy group of 2-[3,5-bis(trifluoromethyl)phenyl]-2-methylpropanoic acid with the secondary amino group of N-methyl-4-(2-methylphenyl)-6-(4-methylpiperazin-1-yl)pyridin-3-amine; an antiemetic used in combination with palonosetron hydrochloride (under the trade name Akynzeo) to treat nausea and vomiting in patients undergoing cancer chemotherapy.

Pharmacological roles (ChEBI): antiemetic, neurokinin-1 receptor antagonist.

Also known as: Netupitant, Netupitant component of akynzeo, Netupitant component of akynzeo capsule, RO-673189000, NETUPITANT

Patent coverage: 830 distinct patent families (2,133 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 2,119 (99%) 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
TACR1NK1 receptorAntagonist9.020.7%P25103

Broader ChEMBL bioactivity targets: 1 (assay-derived). Sample: Substance-P receptor.

Bioactivity

ChEMBL activities: 2 potent at pChembl ≥ 5 of 2 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

TargetpChemblTypeValueUnitActivity ID
TACR19.02IC500.95nMCHEMBL_ACT_13508448
TACR19.02Ki0.95nMCHEMBL_ACT_1693497

Target pathways

Aggregated over 1 target gene(s): TACR1.

Top Reactome pathways

4 total, by targets touching each:

PathwayTargetsGenes
Tachykinin receptors bind tachykinins1TACR1
G alpha (q) signalling events1TACR1
Cargo recognition for clathrin-mediated endocytosis1TACR1
Clathrin-mediated endocytosis1TACR1

Dominant GO biological processes

GO termTargets
aggressive behavior1
positive regulation of leukocyte migration1
angiotensin-mediated drinking behavior1
inflammatory response1
adenylate cyclase-activating G protein-coupled receptor signaling pathway1
phospholipase C-activating G protein-coupled receptor signaling pathway1
positive regulation of cytosolic calcium ion concentration1
phospholipase C-activating tachykinin receptor signaling pathway1
tachykinin receptor signaling pathway1
long-term memory1
associative learning1
detection of abiotic stimulus1
response to ozone1
positive regulation of epithelial cell migration1
response to auditory stimulus1

Indications & clinical

Indications

2 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
neoplasm2MONDO:0005070MONDO:0004992

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

Clinical trials

Total trials: 16.

Phase distribution

PhaseTrials
PHASE37
PHASE25
PHASE42
PHASE2/PHASE31
Not specified1

Top trials by phase / activity

NCTPhaseStatusTitle
NCT06726291PHASE4RECRUITINGAkynzeo as Antiemetic Treatment in Patients With Endometrial Cancer
NCT04817189PHASE4COMPLETEDOral Akynzeo® vs Standard of Care in Preventing CINV in High-risk MEC Patients (MyRisk)
NCT01339260PHASE3COMPLETEDAn Efficacy and Safety Study of Oral Netupitant and Palonosetron for the Prevention of Nausea and Vomiting
NCT01376297PHASE3COMPLETEDA Safety Study of Oral Netupitant and Palonosetron for the Prevention of Nausea and Vomiting
NCT02517021PHASE3COMPLETEDA Safety Study of Intravenous Pro-Netupitant and Palonosetron Combination for the Prevention of Nausea and Vomiting
NCT03040726PHASE2/PHASE3COMPLETEDNetupitant and Palonosetron Hydrochloride in Preventing Chronic Nausea and Vomiting in Patients With Cancer
NCT03367572PHASE3COMPLETEDTreatment of Refractory Nausea and Vomiting in Patients With Breast Cancer
NCT03403712PHASE3COMPLETEDA Study to Assess the Safety and the Efficacy of IV Fosnetupitant/Palonosetron (260 mg/0.25 mg) Combination Compared to Oral Netupitant/Palonosetron (300 mg/0.5 mg) Combination for the Prevention of CINV in AC Chemotherapy in Women With Breast Cancer
NCT04201769PHASE3UNKNOWNDexamethasone-sparing Approach Including NEPA Against Emesis Caused by Cisplatin
NCT06331520PHASE3COMPLETEDNEPA Combined With Olanzapine, Dexamethasone-sparing for the Effect of CINV in Patients Receiving HEC Regimens
NCT03008213PHASE2TERMINATEDCombination of Netupitant and Palonosetron (Akynzeo®) in the Treatment of Refractory CINV
NCT03097588PHASE2COMPLETEDNetupitant and Palonosetron Hydrochloride in Preventing Chemotherapy Induced Nausea and Vomiting in Patients With Cancer Undergoing BEAM Conditioning Regimen Before Stem Cell Transplant
NCT03204279PHASE2COMPLETEDPK/PD Study of Netupitant and Palonosetron in Pediatric Patients for Prevention of Chemotherapy-induced Nausea and Vomiting
NCT03862144PHASE2COMPLETEDNEPA to Prevent Chemotherapy Induced Nausea and Vomiting in Patients With Breast Cancer
NCT04669132PHASE2COMPLETEDEfficacy of Olanzapine, Netupitant and Palonosetron in Controlling Nausea and Vomiting Associated With Highly Emetogenic Chemotherapy in Patients With Breast Cancer
NCT03649230Not specifiedCOMPLETEDObservational Study on the Use of Akynzeo® in Patients Receiving HEC

Clinical evidence (CIViC)

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

Pharmacology

Pharmacogenomics

No PharmGKB pharmacogenomic data curated for this drug.

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.

44 molecules share ≥1 primary target. Top 44 by shared-target count:

MoleculeSourceStatusShared targets
ACLIDINIUM BROMIDEChEMBL + PubChemPhase 4 (approved)TACR1
FIDAXOMICINChEMBL + PubChemPhase 4 (approved)TACR1
ROLAPITANTChEMBL + PubChemPhase 4 (approved)TACR1
AMOXAPINEChEMBLPhase 4 (approved)TACR1
APREPITANTChEMBLPhase 4 (approved)TACR1
ARIPIPRAZOLEChEMBLPhase 4 (approved)TACR1
ASTEMIZOLEChEMBLPhase 4 (approved)TACR1
BOSUTINIBChEMBLPhase 4 (approved)TACR1
CARVEDILOLChEMBLPhase 4 (approved)TACR1
CLOTRIMAZOLEChEMBLPhase 4 (approved)TACR1
CYCLOSPORINEChEMBLPhase 4 (approved)TACR1
DEXTROMETHORPHANChEMBLPhase 4 (approved)TACR1
DOXAZOSINChEMBLPhase 4 (approved)TACR1
ECONAZOLEChEMBLPhase 4 (approved)TACR1
HALOPERIDOLChEMBLPhase 4 (approved)TACR1
ITRACONAZOLEChEMBLPhase 4 (approved)TACR1
LANSOPRAZOLEChEMBLPhase 4 (approved)TACR1
MICONAZOLEChEMBLPhase 4 (approved)TACR1
NEFAZODONEChEMBLPhase 4 (approved)TACR1
NILOTINIBChEMBLPhase 4 (approved)TACR1
PAROXETINEChEMBLPhase 4 (approved)TACR1
RITONAVIRChEMBLPhase 4 (approved)TACR1
TAMOXIFENChEMBLPhase 4 (approved)TACR1
TERFENADINEChEMBLPhase 4 (approved)TACR1
THIOTHIXENEChEMBLPhase 4 (approved)TACR1
TRAZODONEChEMBLPhase 4 (approved)TACR1
CASOPITANTChEMBLPhase 3TACR1
SAREDUTANTChEMBLPhase 3TACR1
SERLOPITANTChEMBLPhase 3TACR1
BEFETUPITANTChEMBLPhase 2TACR1
DAPITANTChEMBLPhase 2TACR1
DNK333ChEMBLPhase 2TACR1
LANEPITANTChEMBLPhase 2TACR1
ORVEPITANTChEMBLPhase 2TACR1
OSANETANTChEMBLPhase 2TACR1
SPERGUALINChEMBLPhase 2TACR1
TALNETANTChEMBLPhase 2TACR1
TELMAPITANTChEMBLPhase 2TACR1
VESTIPITANTChEMBLPhase 2TACR1
VOFOPITANTChEMBLPhase 2TACR1
AlogliptinPubChemApprovedTACR1
BelzutifanPubChemApprovedTACR1
PropoxyphenePubChemApprovedTACR1
Tiotropium Bromide MonohydratePubChemApprovedTACR1

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
Atlas version
v1.1.2
BioBTree
v2.0.2

Sources 30

This page pulls from 30 datasets indexed by BioBTree:

chebichembl_activitychembl_moleculechembl_targetcivic_evidenceclingen_dosageclinical_trialsdepmapefoensemblentrezgogoparentgtopdbgtopdb_interactiongtopdb_ligandhgncmeshmondomsigdbpatent_compoundpharmgkbpharmgkb_guidelinepubchempubchem_activityreactomereactomeparentrefseqtranscriptuniprot