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Details

Stereochemistry ABSOLUTE
Molecular Formula C31H35Cl2F6N3O3
Molecular Weight 682.524
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BURAPITANT

SMILES

CC(C)(C1CCN(CC[C@]2(CN(CCO2)C(=O)CC3=CC(=CC(=C3)C(F)(F)F)C(F)(F)F)C4=CC=C(Cl)C(Cl)=C4)CC1)C(N)=O

InChI

InChIKey=ZLNYUCXXSDDIFU-LJAQVGFWSA-N
InChI=1S/C31H35Cl2F6N3O3/c1-28(2,27(40)44)20-5-8-41(9-6-20)10-7-29(21-3-4-24(32)25(33)17-21)18-42(11-12-45-29)26(43)15-19-13-22(30(34,35)36)16-23(14-19)31(37,38)39/h3-4,13-14,16-17,20H,5-12,15,18H2,1-2H3,(H2,40,44)/t29-/m0/s1

HIDE SMILES / InChI

Molecular Formula C31H35Cl2F6N3O3
Molecular Weight 682.524
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Burapitant (SSR-240,600) is a drug developed by Sanofi-Aventis which was one of the first compounds developed that acts as a potent and selective antagonist for the NK1 receptor. Burapitant inhibited the binding of radioactive substance P to tachykinin NK1 receptors in human lymphoblastic IM9 cells, human astrocytoma U373MG cells, and human brain cortex. It also showed a subnanomolar affinity for guinea pig NK1 receptors but was less potent on rat and gerbil NK1 receptors. Burapitant inhibited [Sar(9),Met(O2)(11)]substance P-induced inositol monophosphate formation in human astrocytoma U373MG cells. Burapitant (0.1-10 mg/kg i.p. or p.o.) antagonized the excitatory effect of i.c.v. infusion of [Sar(9),Met(O2)(11)]substance P (SP) on the release of acetylcholine in the striatum of anesthetized and awake guinea pigs. This antagonistic action was still observed after repeated administration of Burapitant (5 days, 10 mg/kg p.o., once a day). Burapitant (10 mg/kg i.p.) inhibited the phosphorylation of the cAMP response element-binding protein in various brain regions induced by i.c.v. administration of [Sar9,Met(O2)(11)]SP. While burapitant itself did not proceed beyond early clinical trials and was never developed for clinical use in humans, promising animal results from this and related compounds have led to a number of novel drugs from this class that has now been introduced into medical use.

Approval Year

PubMed

PubMed

TitleDatePubMed
SSR240600 [(R)-2-(1-[2-[4-[2-[3,5-bis(trifluoromethyl)phenyl]acetyl]-2-(3,4-dichlorophenyl)-2-morpholinyl]ethyl]-4-piperidinyl)-2-methylpropanamide], a centrally active nonpeptide antagonist of the tachykinin neurokinin 1 receptor: II. Neurochemical and behavioral characterization.
2002 Dec
Patents

Sample Use Guides

10 mg/kg p.o., once a day
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Sat Dec 16 16:20:06 GMT 2023
Edited
by admin
on Sat Dec 16 16:20:06 GMT 2023
Record UNII
E35SK332MS
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BURAPITANT
INN  
INN  
Official Name English
SSR-240600
Code English
SSR240600
Common Name English
2-(1-(2-((2R)-4-(2-(3,5-BIS(TRIFLUOROMETHYL)PHENYL)ACETYL)-2-(3,4-DICHLOROPHENYL)MORPHOLIN-2-YL)ETHYL)PIPERIDIN-4-YL)-2-METHYLPROPANAMIDE
Systematic Name English
burapitant [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C267
Created by admin on Sat Dec 16 16:20:06 GMT 2023 , Edited by admin on Sat Dec 16 16:20:06 GMT 2023
Code System Code Type Description
WIKIPEDIA
Burapitant
Created by admin on Sat Dec 16 16:20:06 GMT 2023 , Edited by admin on Sat Dec 16 16:20:06 GMT 2023
PRIMARY
FDA UNII
E35SK332MS
Created by admin on Sat Dec 16 16:20:06 GMT 2023 , Edited by admin on Sat Dec 16 16:20:06 GMT 2023
PRIMARY
PUBCHEM
23649599
Created by admin on Sat Dec 16 16:20:06 GMT 2023 , Edited by admin on Sat Dec 16 16:20:06 GMT 2023
PRIMARY
SMS_ID
300000034146
Created by admin on Sat Dec 16 16:20:06 GMT 2023 , Edited by admin on Sat Dec 16 16:20:06 GMT 2023
PRIMARY
CAS
299427-93-3
Created by admin on Sat Dec 16 16:20:06 GMT 2023 , Edited by admin on Sat Dec 16 16:20:06 GMT 2023
NON-SPECIFIC STEREOCHEMISTRY
EPA CompTox
DTXSID10968465
Created by admin on Sat Dec 16 16:20:06 GMT 2023 , Edited by admin on Sat Dec 16 16:20:06 GMT 2023
PRIMARY
ChEMBL
CHEMBL3544947
Created by admin on Sat Dec 16 16:20:06 GMT 2023 , Edited by admin on Sat Dec 16 16:20:06 GMT 2023
PRIMARY
INN
9138
Created by admin on Sat Dec 16 16:20:06 GMT 2023 , Edited by admin on Sat Dec 16 16:20:06 GMT 2023
PRIMARY
NCI_THESAURUS
C90718
Created by admin on Sat Dec 16 16:20:06 GMT 2023 , Edited by admin on Sat Dec 16 16:20:06 GMT 2023
PRIMARY
CAS
537034-22-3
Created by admin on Sat Dec 16 16:20:06 GMT 2023 , Edited by admin on Sat Dec 16 16:20:06 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY