PICUMETEROL FUMARATE

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9131949 | https://www.ncbi.nlm.nih.gov/pubmed/8553692 | Milne, G.W.A. (2018) Drugs: Synonyms and Properties, retrieved from: https://books.google.ru/books?id=xUlaDwAAQBAJ

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

Title	Date	PubMed
Kinetics and disposition of picumeterol in animals.	1995 Sep	8553692
Some pharmacodynamic aspects on long-acting beta-adrenoceptor agonists.	1996 Jun	8853286
Picumeterol: dissociation of improvement in lung function and reduction of airways hyperresponsiveness in asthmatics.	1997 Feb	9131949
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	29653961

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:30:36 GMT 2023` Edited by `admin` on `Fri Dec 15 16:30:36 GMT 2023`
Record UNII	0SUN4UF93Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PICUMETEROL FUMARATE

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