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Details

Stereochemistry ACHIRAL
Molecular Formula C30H32F6N4O
Molecular Weight 578.5917
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NETUPITANT

SMILES

CN(C(=O)C(C)(C)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)C2=CN=C(C=C2C3=C(C)C=CC=C3)N4CCN(C)CC4

InChI

InChIKey=WAXQNWCZJDTGBU-UHFFFAOYSA-N
InChI=1S/C30H32F6N4O/c1-19-8-6-7-9-23(19)24-17-26(40-12-10-38(4)11-13-40)37-18-25(24)39(5)27(41)28(2,3)20-14-21(29(31,32)33)16-22(15-20)30(34,35)36/h6-9,14-18H,10-13H2,1-5H3

HIDE SMILES / InChI

Molecular Formula C30H32F6N4O
Molecular Weight 578.5917
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Fosnetupitant is a prodrug form of netupitant. Netupitant is a selective antagonist of human substance P/neurokinin 1 (NK-1) receptors. Upon intravenous administration, fosnetupitant is converted by phosphatases to its active form. It competitively binds to and blocks the activity of NK-1 receptors in the central nervous system, by inhibiting binding of substance P (SP) to NK-1 receptors. This prevents delayed emesis, which is associated with SP secretion. AKYNZEO® is a combination of palonosetron, a serotonin-3 receptor antagonist, and netupitant (capsules for oral use) or fosnetupitant (injections for intravenous use). AKYNZEO® for injection is indicated in combination with dexamethasone in adults for the prevention of acute and delayed nausea and vomiting associated with initial and repeat courses of highly emetogenic cancer chemotherapy.

CNS Activity

Approval Year

TargetsConditions

Conditions

PubMed

PubMed

TitleDatePubMed
Design and synthesis of a novel, achiral class of highly potent and selective, orally active neurokinin-1 receptor antagonists.
2006 Mar 1
Patents

Sample Use Guides

In Vivo Use Guide
One AKYNZEO (netupitant and palonosetron) capsule administered approximately 1 hour prior to the start of chemotherapy with dexamethasone 12 mg administered orally 30 minutes prior to chemotherapy on day 1 and 8 mg orally once daily on days 2 to 4 (for highly emetogenic chemotherapy, including cisplatin based chemotherapy) or on day 1 with not necessary administration of dexamethasone on days 2 to 4 (for anthracyclines and cyclophosphamide based chemotherapy and chemotherapy not considered highly emetogenic)
Route of Administration: Oral
In Vitro Use Guide
HEK-293 cells were incubated with 5 nM [3H]-netupitant for 40 min at room temperature.
Substance Class Chemical
Created
by admin
on Mon Oct 21 23:03:46 UTC 2019
Edited
by admin
on Mon Oct 21 23:03:46 UTC 2019
Record UNII
7732P08TIR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NETUPITANT
DASH   INN   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
NETUPITANT COMPONENT AKYNZEO CAPSULE
Brand Name English
NETUPITANT [USAN]
Common Name English
NETUPITANT [WHO-DD]
Common Name English
NETUPITANT [INN]
Common Name English
AKYNZEO CAPSULE COMPONENT NETUPITANT
Brand Name English
RO-67-3189/000
Code English
BENZENEACETAMIDE, N,.ALPHA.,.ALPHA.-TRIMETHYL-N-(4-(2-METHYLPHENYL)-6-(4-METHYL-1-PIPERAZINYL)-3-PYRIDINYL)-3,5-BIS(TRIFLUOROMETHYL)-
Systematic Name English
RO 67-3189/000
Code English
2-(3,5-BIS(TRIFLUOROMETHYL)PHENYL)-N,2-DIMETHYL-N-(4-(2-METHYLPHENYL)-6-(4-METHYLPIPERAZIN-1-YL)PYRIDIN-3-YL)PROPANAMIDE
Systematic Name English
RO-673189000
Code English
NETUPITANT [VANDF]
Common Name English
RO-67-3189
Code English
Classification Tree Code System Code
EMA ASSESSMENT REPORTS AKYNZEO (AUTHORIZED: NAUSEA)
Created by admin on Mon Oct 21 23:03:46 UTC 2019 , Edited by admin on Mon Oct 21 23:03:46 UTC 2019
NDF-RT N0000175786
Created by admin on Mon Oct 21 23:03:46 UTC 2019 , Edited by admin on Mon Oct 21 23:03:46 UTC 2019
NCI_THESAURUS C267
Created by admin on Mon Oct 21 23:03:46 UTC 2019 , Edited by admin on Mon Oct 21 23:03:46 UTC 2019
Code System Code Type Description
PUBCHEM
6451149
Created by admin on Mon Oct 21 23:03:46 UTC 2019 , Edited by admin on Mon Oct 21 23:03:46 UTC 2019
PRIMARY
INN
8409
Created by admin on Mon Oct 21 23:03:46 UTC 2019 , Edited by admin on Mon Oct 21 23:03:46 UTC 2019
PRIMARY
ChEMBL
CHEMBL206253
Created by admin on Mon Oct 21 23:03:46 UTC 2019 , Edited by admin on Mon Oct 21 23:03:46 UTC 2019
PRIMARY
NDF-RT
N0000190113
Created by admin on Mon Oct 21 23:03:46 UTC 2019 , Edited by admin on Mon Oct 21 23:03:46 UTC 2019
PRIMARY Breast Cancer Resistance Protein Inhibitors [MoA]
CAS
290297-26-6
Created by admin on Mon Oct 21 23:03:46 UTC 2019 , Edited by admin on Mon Oct 21 23:03:46 UTC 2019
PRIMARY
NDF-RT
N0000182141
Created by admin on Mon Oct 21 23:03:46 UTC 2019 , Edited by admin on Mon Oct 21 23:03:46 UTC 2019
PRIMARY Cytochrome P450 3A4 Inhibitors [MoA]
NDF-RT
N0000185503
Created by admin on Mon Oct 21 23:03:46 UTC 2019 , Edited by admin on Mon Oct 21 23:03:46 UTC 2019
PRIMARY P-Glycoprotein Inhibitors [MoA]
EVMPD
SUB130488
Created by admin on Mon Oct 21 23:03:46 UTC 2019 , Edited by admin on Mon Oct 21 23:03:46 UTC 2019
PRIMARY
EPA CompTox
290297-26-6
Created by admin on Mon Oct 21 23:03:46 UTC 2019 , Edited by admin on Mon Oct 21 23:03:46 UTC 2019
PRIMARY
IUPHAR
5742
Created by admin on Mon Oct 21 23:03:46 UTC 2019 , Edited by admin on Mon Oct 21 23:03:46 UTC 2019
PRIMARY
DRUG BANK
DB09048
Created by admin on Mon Oct 21 23:03:46 UTC 2019 , Edited by admin on Mon Oct 21 23:03:46 UTC 2019
PRIMARY
NCI_THESAURUS
C96745
Created by admin on Mon Oct 21 23:03:46 UTC 2019 , Edited by admin on Mon Oct 21 23:03:46 UTC 2019
PRIMARY
MESH
C508854
Created by admin on Mon Oct 21 23:03:46 UTC 2019 , Edited by admin on Mon Oct 21 23:03:46 UTC 2019
PRIMARY
RXCUI
1552337
Created by admin on Mon Oct 21 23:03:46 UTC 2019 , Edited by admin on Mon Oct 21 23:03:46 UTC 2019
PRIMARY RxNorm
Related Record Type Details
TRANSPORTER -> INHIBITOR
Netupitnat: Cmax/IC50= (1-1.5μM)/6 μM = (0.167-0.25)>0.1
METABOLIC ENZYME -> SUBSTRATE
MAJOR
TARGET -> INHIBITOR
Related Record Type Details
METABOLITE ACTIVE -> PARENT
of parent exposure
MAJOR
AUC
METABOLITE ACTIVE -> PARENT
of parent exposure
MAJOR
AUC
PRODRUG -> METABOLITE ACTIVE
Related Record Type Details
ACTIVE MOIETY