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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H26N2O5
Molecular Weight 386.4415
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OLODATEROL

SMILES

COC1=CC=C(CC(C)(C)NC[C@H](O)C2=C3OCC(=O)NC3=CC(O)=C2)C=C1

InChI

InChIKey=COUYJEVMBVSIHV-SFHVURJKSA-N
InChI=1S/C21H26N2O5/c1-21(2,10-13-4-6-15(27-3)7-5-13)22-11-18(25)16-8-14(24)9-17-20(16)28-12-19(26)23-17/h4-9,18,22,24-25H,10-12H2,1-3H3,(H,23,26)/t18-/m0/s1

HIDE SMILES / InChI

Molecular Formula C21H26N2O5
Molecular Weight 386.4415
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Olodaterol is a beta2-adrenoceptor agonist discovered by Boehringer Ingelheim and approved for the treatment of Chronic Obstructive Pulmonary Disease. The compound exerts its pharmacological effects by binding and activation of beta2-adrenoceptors after inhalation. Activation of these receptors in the airways results in a stimulation of intracellular adenyl cyclase, an enzyme that mediates the synthesis of cyclic-3’, 5’ adenosine monophosphate (cAMP). Elevated levels of cAMP induce bronchodilation by relaxation of airway smooth muscle cells. Olodaterol effect lasts for 24 hours.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.1 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
STRIVERDI RESPIMAT
PubMed

PubMed

TitleDatePubMed
Discovery of olodaterol, a novel inhaled beta2-adrenoceptor agonist with a 24 h bronchodilatory efficacy.
2010 Feb 15
Pharmacological characterization of olodaterol, a novel inhaled beta2-adrenoceptor agonist exerting a 24-hour-long duration of action in preclinical models.
2010 Jul
β₂-adrenoceptors and muscarinic receptors mediate opposing effects on endothelin-1 expression in human lung fibroblasts.
2012 Sep 15
Olodaterol: first global approval.
2013 Nov
Lung function efficacy and symptomatic benefit of olodaterol once daily delivered via Respimat® versus placebo and formoterol twice daily in patients with GOLD 2-4 COPD: results from two replicate 48-week studies.
2014
Olodaterol: a review of its use in chronic obstructive pulmonary disease.
2015 Apr
Patents

Sample Use Guides

In Vivo Use Guide
Two inhalations of STRIVERDI RESPIMAT once-daily at the same time of day. Inhalation spray: Each actuation from the mouthpiece contains 2.7 mcg olodaterol hydrochloride, equivalent to 2.5 mcg olodaterol. Two actuations equal one dose.
Route of Administration: Respiratory
In Vitro Use Guide
MRC-5 human lung fibroblasts were cultured in absence or presence of 10 nM olodaterol, followed by ß2-adrenoceptor mRNA determination by quantitative real time PCR
Substance Class Chemical
Created
by admin
on Mon Oct 21 21:51:09 UTC 2019
Edited
by admin
on Mon Oct 21 21:51:09 UTC 2019
Record UNII
VD2YSN1AFD
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OLODATEROL
DASH   INN   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
OLODATEROL HYDROCHLORIDE [JAN]
Common Name English
BI 1744
Code English
OLODATEROL [VANDF]
Common Name English
2H-1,4-BENZOXAZIN-3(4H)-ONE, 6-HYDROXY-8-((1R)-1-HYDROXY-2-((2-(4-METHOXYPHENYL)-1,1-DIMETHYLETHYL)AMINO)ETHYL)-
Systematic Name English
6-HYDROXY-8-((1R)-1-HYDROXY-2-((1-(4-METHOXYPHENYL)-2-METHYLPROPAN-2-YL)AMINO)ETHYL)-2H-1,4-BENZOXAZIN-3(4H)-ONE
Systematic Name English
6-HYDROXY-8-((1R)-1-HYDROXY-2-((2-(4-METHOXYPHENYL)-1,1-DIMETHYLETHYL)AMINO)ETHYL)-2H-1,4-BENZOXAZIN-3(4H)-ONE
Systematic Name English
OLODATEROL [INN]
Common Name English
BI-1744
Code English
OLODATEROL [WHO-DD]
Common Name English
OLODATEROL [USAN]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175779
Created by admin on Mon Oct 21 21:51:09 UTC 2019 , Edited by admin on Mon Oct 21 21:51:09 UTC 2019
WHO-ATC R03AL06
Created by admin on Mon Oct 21 21:51:09 UTC 2019 , Edited by admin on Mon Oct 21 21:51:09 UTC 2019
WHO-ATC R03AC19
Created by admin on Mon Oct 21 21:51:09 UTC 2019 , Edited by admin on Mon Oct 21 21:51:09 UTC 2019
WHO-VATC QR03AC19
Created by admin on Mon Oct 21 21:51:09 UTC 2019 , Edited by admin on Mon Oct 21 21:51:09 UTC 2019
Code System Code Type Description
INN
9174
Created by admin on Mon Oct 21 21:51:09 UTC 2019 , Edited by admin on Mon Oct 21 21:51:09 UTC 2019
PRIMARY
RXCUI
1546059
Created by admin on Mon Oct 21 21:51:09 UTC 2019 , Edited by admin on Mon Oct 21 21:51:09 UTC 2019
PRIMARY RxNorm
IUPHAR
7543
Created by admin on Mon Oct 21 21:51:09 UTC 2019 , Edited by admin on Mon Oct 21 21:51:09 UTC 2019
PRIMARY
DRUG BANK
DB09080
Created by admin on Mon Oct 21 21:51:09 UTC 2019 , Edited by admin on Mon Oct 21 21:51:09 UTC 2019
PRIMARY
CAS
868049-49-4
Created by admin on Mon Oct 21 21:51:09 UTC 2019 , Edited by admin on Mon Oct 21 21:51:09 UTC 2019
PRIMARY
ChEMBL
CHEMBL605846
Created by admin on Mon Oct 21 21:51:09 UTC 2019 , Edited by admin on Mon Oct 21 21:51:09 UTC 2019
PRIMARY
MESH
C549647
Created by admin on Mon Oct 21 21:51:09 UTC 2019 , Edited by admin on Mon Oct 21 21:51:09 UTC 2019
PRIMARY
WIKIPEDIA
Olodaterol
Created by admin on Mon Oct 21 21:51:09 UTC 2019 , Edited by admin on Mon Oct 21 21:51:09 UTC 2019
PRIMARY
PUBCHEM
11504295
Created by admin on Mon Oct 21 21:51:09 UTC 2019 , Edited by admin on Mon Oct 21 21:51:09 UTC 2019
PRIMARY
EVMPD
SUB36104
Created by admin on Mon Oct 21 21:51:09 UTC 2019 , Edited by admin on Mon Oct 21 21:51:09 UTC 2019
PRIMARY
LactMed
868049-49-4
Created by admin on Mon Oct 21 21:51:09 UTC 2019 , Edited by admin on Mon Oct 21 21:51:09 UTC 2019
PRIMARY
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