OLODATEROL HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H26N2O5.ClH
Molecular Weight	422.902
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=KCEHVJZZIGJAAW-FERBBOLQSA-N

InChI=1S/C21H26N2O5.ClH/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);1H/t18-;/m0./s1

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C21H26N2O5
Molecular Weight	386.4415
Charge	0
Count

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

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/203108s000lbl.pdf
Curator's Comment: description was created based on several sources, including 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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Beta-2 adrenergic receptor 209 Target ID: P07550\|\|\|Q53GA6\|\|\|Q9UCZ3 Gene ID: 154.0 Gene Symbol: ADRB2 Target Organism: Homo sapiens (Human) Sources: http://www.ncbi.nlm.nih.gov/pubmed/?term=20371707	Agonist 2752		0.1 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Chronic obstructive pulmonary disease 175 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/203108s000lbl.pdf	Primary		Approved 8583	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 2014

C_max

Value	Dose	Co-administered	Analyte	Population
5.92 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26316741	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26316741	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

Value	Dose	Co-administered	Analyte	Population
104 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26316741	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26316741	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
7.5 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/203108s008lbl.pdf	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
40% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/203108s008lbl.pdf	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

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946 inhibitor 2252 inducer 1087	substrate 1193 inhibitor 2438 inducer 440	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1741 BCRP 910 CYP1A1 132 CYP1A2 2153 CYP2A6 879 CYP2B6 926 CYP2C8 1057 CYP2C19 2057 CYP2E1 1060 CYP4A11 21	CYP2C8 810 UGT2B7 456 UGT1A1 479 UGT1A7 249 UGT1A9 423 P-gp 2052	CYP1A2 832 CYP2B6 669 CYP2C8 198 CYP2C19 329

Drug as perpetrator

Target	Modality	Activity
CYP1A1 272	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/203108Orig1s000ClinPharmR.pdf#page=26 Page: 26.0	no [IC50 >100 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/203108Orig1s000ClinPharmR.pdf#page=26 Page: 26.0	no [IC50 >100 uM]
CYP2A6 911	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/203108Orig1s000ClinPharmR.pdf#page=26 Page: 26.0	no [IC50 >100 uM]
CYP2B6 1160	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/203108Orig1s000ClinPharmR.pdf#page=26 Page: 26.0	no [IC50 >100 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/203108Orig1s000ClinPharmR.pdf#page=26 Page: 26.0	no [IC50 >100 uM]
CYP2C8 1117	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/203108Orig1s000ClinPharmR.pdf#page=26 Page: 26.0	no [IC50 >100 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/203108Orig1s000ClinPharmR.pdf#page=26 Page: 26.0	no [IC50 >100 uM]
CYP2E1 1146	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/203108Orig1s000ClinPharmR.pdf#page=26 Page: 26.0	no [IC50 >100 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/203108Orig1s000ClinPharmR.pdf#page=26 Page: 26.0	no [IC50 >100 uM]
CYP4A11 25	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/203108Orig1s000ClinPharmR.pdf#page=26 Page: 26.0	no [IC50 >100 uM]
CYP1A2 2333	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/203108Orig1s000ClinPharmR.pdf#page=26 Page: 26.0	no
CYP2B6 1160	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/203108Orig1s000ClinPharmR.pdf#page=26 Page: 26.0	no
CYP2C19 2141	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/203108Orig1s000ClinPharmR.pdf#page=26 Page: 26.0	no
CYP2C8 1117	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/203108Orig1s000ClinPharmR.pdf#page=26 Page: 26.0	no
CYP2C9 2497	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/203108Orig1s000ClinPharmR.pdf#page=26 Page: 26.0	no
CYP3A4 2633	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/203108Orig1s000ClinPharmR.pdf#page=26 Page: 26.0	no
BCRP 985	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/203108Orig1s000ClinPharmR.pdf#page=25 Page: 25.0	weak [IC50 100 uM]
P-gp 1932	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/203108Orig1s000ClinPharmR.pdf#page=25 Page: 25.0	weak [IC50 365 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/203108Orig1s000ClinPharmR.pdf#page=26 Page: 26.0	yes [Ki 1.92 uM]

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP3A4 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/203108s000lbl.pdf#page=8 Page: 8.0	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%. Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/203108s000lbl.pdf#page=8 Page: 8.0
CYP2C9 1193	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/203108s000lbl.pdf#page=8 Page: 8.0	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. Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/203108s000lbl.pdf#page=8 Page: 8.0
CYP2C8 810	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/203108s000lbl.pdf#page=8 Page: 8.0	yes
P-gp 2052	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/203108Orig1s000ClinPharmR.pdf#page=3 Page: 3.0	yes
UGT1A1 479	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/203108s000lbl.pdf#page=8 Page: 8.0	yes
UGT1A7 249	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/203108s000lbl.pdf#page=8 Page: 8.0	yes
UGT1A9 423	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/203108s000lbl.pdf#page=8 Page: 8.0	yes
UGT2B7 456	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/203108s000lbl.pdf#page=8 Page: 8.0	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/203108Orig1s000PharmR.pdf#page=54 Page: 54.0

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:82700	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:82700
ChemicalBook	CB52484977	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB52484977
MolPort	MolPort-044-183-629	https://www.molport.com/shop/molecule-link/MolPort-044-183-629
ZINC	ZINC000034636383	http://zinc15.docking.org/substances/ZINC000034636383

PubMed

Title	Date	PubMed
Olodaterol: a review of its use in chronic obstructive pulmonary disease.	2015-04	25773742
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	25045258
Olodaterol: first global approval.	2013-11	24158691
Endothelin-1 enhances β₂-adrenoceptor gene transcription in human lung fibroblasts.	2012-10-15	22483689
β₂-adrenoceptors and muscarinic receptors mediate opposing effects on endothelin-1 expression in human lung fibroblasts.	2012-09-15	22796455
Pharmacological characterization of olodaterol, a novel inhaled beta2-adrenoceptor agonist exerting a 24-hour-long duration of action in preclinical models.	2010-07	20371707
Discovery of olodaterol, a novel inhaled beta2-adrenoceptor agonist with a 24 h bronchodilatory efficacy.	2010-02-15	20096576

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 Mar 31 18:18:37 GMT 2025` Edited by `admin` on `Mon Mar 31 18:18:37 GMT 2025`
Record UNII	65R445W3V9
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

STRIVERDI RESPIMAT

Preferred Name

English

OLODATEROL HYDROCHLORIDE

Official Name

English

OLODATEROL HYDROCHLORIDE [VANDF]

Common Name

English

OLODATEROL HYDROCHLORIDE [MI]

Common Name

English

6-HYDROXY-8-((1R)-1-HYDROXY-2-((2-(4-METHOXYPHENYL)-1,1-DIMETHYLETHYL)AMINO)ETHYL)- 2H-1,4-BENZOXAZIN-3(4H)-ONE HYDROCHLORIDE

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 hydrochloride

Systematic Name

English

BI 1744 CL

Code

English

2H-1,4-BENZOXAZIN-3(4H)-ONE, 6-HYDROXY-8-((1R)-1-HYDROXY-2-((2-(4-METHOXYPHENYL)- 1,1-DIMETHYLETHYL)AMINO)ETHYL)-, HYDROCHLORIDE (1:1)

Systematic Name

English

BI-1744-CL

Code

English

OLODATEROL HYDROCHLORIDE [ORANGE BOOK]

Common Name

English

Olodaterol hydrochloride [WHO-DD]

Common Name

English

OLODATEROL HYDROCHLORIDE [USAN]

Common Name

English

BI-1744 CL

Code

English

Code System Code Type Description

PUBCHEM

11711522