U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C21H26N2O5
Molecular Weight 386.4423
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OLODATEROL

SMILES

CC(C)(Cc1ccc(cc1)OC)NC[C@@]([H])(c2cc(cc3c2OCC(=N3)O)O)O

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 386.4423
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: http://www.drugdevelopment-technology.com/projects/striverdi-respimat-for-the-maintenance-treatment-of-copd/; http://www.ncbi.nlm.nih.gov/pubmed/?term=20371707

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
Target ID: P07550|||Q53GA6|||Q9UCZ3
Gene ID: 154
Gene Symbol: ADRB2
Target Organism: Homo sapiens (Human)
0.100000000000000006 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
STRIVERDI RESPIMAT

Approved Use

The long-term, once-daily maintenance bronchodilator treatment of airflow obstruction in patients with chronic obstructive pulmonary disease (COPD), including chronic bronchitis and/or emphysema. Is not indicated to treat acute deterioration of COPD and asthma.

Launch Date

1406764800000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
5.92 pg/mL
5 μg 1 times / day multiple, respiratory
dose: 5 μg
route of administration: Respiratory
experiment type: MULTIPLE
co-administered:
OLODATEROL HYDROCHLORIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
13.1 pg/mL
10 μg 1 times / day multiple, respiratory
dose: 10 μg
route of administration: Respiratory
experiment type: MULTIPLE
co-administered:
OLODATEROL HYDROCHLORIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
104 pg × h/mL
5 μg 1 times / day multiple, respiratory
dose: 5 μg
route of administration: Respiratory
experiment type: MULTIPLE
co-administered:
OLODATEROL HYDROCHLORIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
160 pg × h/mL
10 μg 1 times / day multiple, respiratory
dose: 10 μg
route of administration: Respiratory
experiment type: MULTIPLE
co-administered:
OLODATEROL HYDROCHLORIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
7.5 h
5 μg 1 times / day unknown, unknown
dose: 5 μg
route of administration: UNKNOWN
experiment type: UNKNOWN
co-administered:
OLODATEROL HYDROCHLORIDE plasma
Homo sapiens
population: UNHEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
40%
5 μg 1 times / day unknown, unknown
dose: 5 μg
route of administration: UNKNOWN
experiment type: UNKNOWN
co-administered:
OLODATEROL HYDROCHLORIDE plasma
Homo sapiens
population: UNHEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no [IC50 >100 uM]
no [IC50 >100 uM]
no [IC50 >100 uM]
no [IC50 >100 uM]
no [IC50 >100 uM]
no [IC50 >100 uM]
no [IC50 >100 uM]
no [IC50 >100 uM]
no [IC50 >100 uM]
no [IC50 >100 uM]
no
no
no
no
no
no
weak [IC50 100 uM]
weak [IC50 365 uM]
yes [Ki 1.92 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
minor
yes (co-administration study)
Comment: Ketoconazole: Co-administration of 400 mg ketoconazole once a day for 14 days increased olodaterol Cmax by 66% and AUC0-1 by 68%.
Page: 8
weak
no (co-administration study)
Comment: Co-administration of 400 mg fluconazole once a day for 14 days had no relevant effect on systemic exposure to olodaterol.
Page: 8
yes
yes
yes
yes
yes
yes
Tox targets

Tox targets

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
Curator's Comment:: For oral inhalation only
Two inhalations of STRIVERDI RESPIMAT once-daily at the
Route of Administration: Respiratory
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 Sat Jun 26 14:50:56 UTC 2021
Edited
by admin
on Sat Jun 26 14:50:56 UTC 2021
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 [MI]
Common Name English
OLODATEROL [USAN]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175779
Created by admin on Sat Jun 26 14:50:56 UTC 2021 , Edited by admin on Sat Jun 26 14:50:56 UTC 2021
WHO-ATC R03AL06
Created by admin on Sat Jun 26 14:50:56 UTC 2021 , Edited by admin on Sat Jun 26 14:50:56 UTC 2021
WHO-ATC R03AC19
Created by admin on Sat Jun 26 14:50:56 UTC 2021 , Edited by admin on Sat Jun 26 14:50:56 UTC 2021
WHO-VATC QR03AC19
Created by admin on Sat Jun 26 14:50:56 UTC 2021 , Edited by admin on Sat Jun 26 14:50:56 UTC 2021
Code System Code Type Description
INN
9174
Created by admin on Sat Jun 26 14:50:56 UTC 2021 , Edited by admin on Sat Jun 26 14:50:56 UTC 2021
PRIMARY
RXCUI
1546059
Created by admin on Sat Jun 26 14:50:56 UTC 2021 , Edited by admin on Sat Jun 26 14:50:56 UTC 2021
PRIMARY RxNorm
IUPHAR
7543
Created by admin on Sat Jun 26 14:50:56 UTC 2021 , Edited by admin on Sat Jun 26 14:50:56 UTC 2021
PRIMARY
DRUG BANK
DB09080
Created by admin on Sat Jun 26 14:50:56 UTC 2021 , Edited by admin on Sat Jun 26 14:50:56 UTC 2021
PRIMARY
CAS
868049-49-4
Created by admin on Sat Jun 26 14:50:56 UTC 2021 , Edited by admin on Sat Jun 26 14:50:56 UTC 2021
PRIMARY
ChEMBL
CHEMBL605846
Created by admin on Sat Jun 26 14:50:56 UTC 2021 , Edited by admin on Sat Jun 26 14:50:56 UTC 2021
PRIMARY
MERCK INDEX
M11957
Created by admin on Sat Jun 26 14:50:56 UTC 2021 , Edited by admin on Sat Jun 26 14:50:56 UTC 2021
PRIMARY
MESH
C549647
Created by admin on Sat Jun 26 14:50:56 UTC 2021 , Edited by admin on Sat Jun 26 14:50:56 UTC 2021
PRIMARY
FDA UNII
VD2YSN1AFD
Created by admin on Sat Jun 26 14:50:56 UTC 2021 , Edited by admin on Sat Jun 26 14:50:56 UTC 2021
PRIMARY
WIKIPEDIA
Olodaterol
Created by admin on Sat Jun 26 14:50:56 UTC 2021 , Edited by admin on Sat Jun 26 14:50:56 UTC 2021
PRIMARY
NCI_THESAURUS
C170249
Created by admin on Sat Jun 26 14:50:56 UTC 2021 , Edited by admin on Sat Jun 26 14:50:56 UTC 2021
PRIMARY
DRUG CENTRAL
4814
Created by admin on Sat Jun 26 14:50:56 UTC 2021 , Edited by admin on Sat Jun 26 14:50:56 UTC 2021
PRIMARY
PUBCHEM
11504295
Created by admin on Sat Jun 26 14:50:56 UTC 2021 , Edited by admin on Sat Jun 26 14:50:56 UTC 2021
PRIMARY
LACTMED
Olodaterol
Created by admin on Sat Jun 26 14:50:56 UTC 2021 , Edited by admin on Sat Jun 26 14:50:56 UTC 2021
PRIMARY
EVMPD
SUB36104
Created by admin on Sat Jun 26 14:50:56 UTC 2021 , Edited by admin on Sat Jun 26 14:50:56 UTC 2021
PRIMARY
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Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
Tmax PHARMACOKINETIC INHALED ADMINISTRATION