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Details

Stereochemistry ABSOLUTE
Molecular Formula 2C21H29Cl2N3O2.C4H4O4
Molecular Weight 968.832
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of PICUMETEROL FUMARATE

SMILES

OC(=O)\C=C\C(O)=O.NC1=C(Cl)C=C(C=C1Cl)[C@@H](O)CNCCCCCCOCCC2=NC=CC=C2.NC3=C(Cl)C=C(C=C3Cl)[C@@H](O)CNCCCCCCOCCC4=NC=CC=C4

InChI

InChIKey=MZHXOYZUNRCUCP-MMSVOLSESA-N
InChI=1S/2C21H29Cl2N3O2.C4H4O4/c2*22-18-13-16(14-19(23)21(18)24)20(27)15-25-9-4-1-2-6-11-28-12-8-17-7-3-5-10-26-17;5-3(6)1-2-4(7)8/h2*3,5,7,10,13-14,20,25,27H,1-2,4,6,8-9,11-12,15,24H2;1-2H,(H,5,6)(H,7,8)/b;;2-1+/t2*20-;/m00./s1

HIDE SMILES / InChI

Molecular Formula C21H29Cl2N3O2
Molecular Weight 426.38
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Picumeterol (GR114297A) is a potent and highly selective beta2-adrenoceptor agonist with a longer duration of action than salbutamol, but shorter than salmeterol. Picumeterol is the (R)-isomer of the racemic entity GR63411B, and picumeterol has been shown to be about 40 times more potent than the (S)-isomer (GR114744A) in various in vitro pharmacological models of beta2-agonist activity. Picumeterol is of potential value in the treatment of asthma and related diseases in man following inhalation administration. In the clinical studies, the bronchodilator potencies of picumeterol and GR 63411B were similar. However, both drugs were short-acting, which is at odds with their activity in vitro. These compounds display dissociation between bronchodilator activity and protection against methacholine-induced bronchoconstriction.

Approval Year

PubMed

PubMed

TitleDatePubMed
Kinetics and disposition of picumeterol in animals.
1995 Sep
Some pharmacodynamic aspects on long-acting beta-adrenoceptor agonists.
1996 Jun
Picumeterol: dissociation of improvement in lung function and reduction of airways hyperresponsiveness in asthmatics.
1997 Feb
Analysis of the Indacaterol-Regulated Transcriptome in Human Airway Epithelial Cells Implicates Gene Expression Changes in the Adverse and Therapeutic Effects of β(2)-Adrenoceptor Agonists.
2018 Jul
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:30:36 UTC 2023
Edited
by admin
on Fri Dec 15 16:30:36 UTC 2023
Record UNII
0SUN4UF93Y
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PICUMETEROL FUMARATE
USAN  
USAN  
Official Name English
GR 114297A
Code English
BENZENEMETHANOL, 4-AMINO-3,5-DICHLORO-.ALPHA.-(((6-(2-(2-PYRIDINYL)ETHOXY)HEXYL)AMINO)METHYL)-, (R)-, (E)-2-BUTENEDIOATE (2:1) (SALT)
Common Name English
PICUMETEROL FUMARATE [USAN]
Common Name English
GR-114297A
Code English
(-)-(R)-4-AMINO-3,5-DICHLORO-.ALPHA.-(((6-(2-(2-PYRIDYL)ETHOXY)HEXYL)AMINO)METHYL)BENZYL ALCOHOL, FUMARATE (2:1) (SALT)
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C48149
Created by admin on Fri Dec 15 16:30:36 UTC 2023 , Edited by admin on Fri Dec 15 16:30:36 UTC 2023
Code System Code Type Description
ChEMBL
CHEMBL2110947
Created by admin on Fri Dec 15 16:30:36 UTC 2023 , Edited by admin on Fri Dec 15 16:30:36 UTC 2023
PRIMARY
NCI_THESAURUS
C76544
Created by admin on Fri Dec 15 16:30:36 UTC 2023 , Edited by admin on Fri Dec 15 16:30:36 UTC 2023
PRIMARY
USAN
CC-54
Created by admin on Fri Dec 15 16:30:36 UTC 2023 , Edited by admin on Fri Dec 15 16:30:36 UTC 2023
PRIMARY
PUBCHEM
10350952
Created by admin on Fri Dec 15 16:30:36 UTC 2023 , Edited by admin on Fri Dec 15 16:30:36 UTC 2023
PRIMARY
FDA UNII
0SUN4UF93Y
Created by admin on Fri Dec 15 16:30:36 UTC 2023 , Edited by admin on Fri Dec 15 16:30:36 UTC 2023
PRIMARY
CAS
130641-37-1
Created by admin on Fri Dec 15 16:30:36 UTC 2023 , Edited by admin on Fri Dec 15 16:30:36 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY