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

Details

Stereochemistry ABSOLUTE
Molecular Formula C26H30NO4S2
Molecular Weight 484.6538
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 1

SHOW SMILES / InChI
Structure of ACLIDINIUM

SMILES

c1ccc(cc1)OCCC[N+]23CCC([H])(CC2)[C@]([H])(C3)OC(=O)C(c4cccs4)(c5cccs5)O

InChI

InChIKey=ASMXXROZKSBQIH-VITNCHFBSA-N
InChI=1S/C26H30NO4S2/c28-25(26(29,23-9-4-17-32-23)24-10-5-18-33-24)31-22-19-27(14-11-20(22)12-15-27)13-6-16-30-21-7-2-1-3-8-21/h1-5,7-10,17-18,20,22,29H,6,11-16,19H2/q+1/t20?,22-,27?/m0/s1

HIDE SMILES / InChI

Molecular Formula C26H29NO4S2
Molecular Weight 483.6459
Charge 0
Count
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: description was created based on several sources, including: | http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Public_assessment_report/human/002706/WC500132734.pdf | http://www.ncbi.nlm.nih.gov/pubmed/?term=24587893 | https://www.ncbi.nlm.nih.gov/pubmed/19710368

Aclidinium is a long-acting, competitive, and reversible anticholinergic drug that is specific for the acetylcholine muscarinic receptors. It binds to all 5 muscarinic receptor subtypes to a similar affinity. It has a much higher propensity to bind to muscarinic receptors than nicotinic receptors. FDA approved on July 24, 2012. Aclidinium's effects on the airways are mediated through the M3 receptor at the smooth muscle to cause bronchodilation. Prevention of acetylcholine-induced bronchoconstriction effects was dose-dependent and lasted longer than 24 hours.

CNS Activity

Curator's Comment:: The polar nature of aclidinium bromide makes it unlikely to cross the blood brain barrier

Originator

Curator's Comment:: In 2015 AstraZeneca acquired the development and commercial rights in the US and Canada to Tudorza Pressair (aclidinium bromide inhalation powder).

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
TUDORZA PRESSAIR

Approved Use

Indicated for the long-term maintenance treatment of bronchospasm associated with chronic obstructive pulmonary disease (COPD), including chronic bronchitis and emphysema

Launch Date

1.34300159E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
194.2 pg/mL
400 μg single, oral
dose: 400 μg
route of administration: Oral
experiment type: SINGLE
co-administered:
ACLIDINIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
240.5 pg/mL
400 μg 2 times / day steady-state, oral
dose: 400 μg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
ACLIDINIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
386.7 pg × h/mL
400 μg single, oral
dose: 400 μg
route of administration: Oral
experiment type: SINGLE
co-administered:
ACLIDINIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
468.4 pg × h/mL
400 μg 2 times / day steady-state, oral
dose: 400 μg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
ACLIDINIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
5.9 h
400 μg single, oral
dose: 400 μg
route of administration: Oral
experiment type: SINGLE
co-administered:
ACLIDINIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
17 h
400 μg 2 times / day steady-state, oral
dose: 400 μg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
ACLIDINIUM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
400 ug single, intravenous
Dose: 400 ug
Route: intravenous
Route: single
Dose: 400 ug
Sources:
healthy, 30 years (range: 24-43 years)
n = 6
Health Status: healthy
Age Group: 30 years (range: 24-43 years)
Sex: M
Population Size: 6
Sources:
800 ug 2 times / day steady, respiratory
Highest studied dose
Dose: 800 ug, 2 times / day
Route: respiratory
Route: steady
Dose: 800 ug, 2 times / day
Sources:
healthy, 39.3 years (range: 18-45 years)
n = 8
Health Status: healthy
Age Group: 39.3 years (range: 18-45 years)
Sex: M+F
Population Size: 8
Sources:
Other AEs: Muscle spasm, Dysgeusia...
Other AEs:
Muscle spasm (12.5%)
Dysgeusia (12.5%)
Somnolence (12.5%)
Sources:
6000 ug single, respiratory
Highest studied dose
Dose: 6000 ug
Route: respiratory
Route: single
Dose: 6000 ug
Sources:
healthy
n = 16
Health Status: healthy
Population Size: 16
Sources:
200 ug 2 times / day steady, respiratory
Recommended
Dose: 200 ug, 2 times / day
Route: respiratory
Route: steady
Dose: 200 ug, 2 times / day
Sources: Page: p. 101
unhealthy
n = 891
Health Status: unhealthy
Condition: COPD
Population Size: 891
Sources: Page: p. 101
Disc. AE: Non-cardiac chest pain, Headache...
AEs leading to
discontinuation/dose reduction:
Non-cardiac chest pain (0.3%)
Headache (0.2%)
Dyspnea (0.2%)
COPD (2%)
Pruritus (0.2%)
Syncope (0.2%)
Sources: Page: p. 101
200 ug 2 times / day steady, respiratory
Dose: 200 ug, 2 times / day
Route: respiratory
Route: steady
Dose: 200 ug, 2 times / day
Sources: Page: p. 101
unhealthy
n = 448
Health Status: unhealthy
Condition: COPD
Population Size: 448
Sources: Page: p. 101
Disc. AE: Fatigue, Non-cardiac chest pain...
AEs leading to
discontinuation/dose reduction:
Fatigue (0.4%)
Non-cardiac chest pain (0.2%)
Dizziness (0.4%)
Dyspnea (0.2%)
COPD (2.9%)
Pruritus (0.2%)
Sources: Page: p. 101
AEs

AEs

AESignificanceDosePopulation
Dysgeusia 12.5%
800 ug 2 times / day steady, respiratory
Highest studied dose
Dose: 800 ug, 2 times / day
Route: respiratory
Route: steady
Dose: 800 ug, 2 times / day
Sources:
healthy, 39.3 years (range: 18-45 years)
n = 8
Health Status: healthy
Age Group: 39.3 years (range: 18-45 years)
Sex: M+F
Population Size: 8
Sources:
Muscle spasm 12.5%
800 ug 2 times / day steady, respiratory
Highest studied dose
Dose: 800 ug, 2 times / day
Route: respiratory
Route: steady
Dose: 800 ug, 2 times / day
Sources:
healthy, 39.3 years (range: 18-45 years)
n = 8
Health Status: healthy
Age Group: 39.3 years (range: 18-45 years)
Sex: M+F
Population Size: 8
Sources:
Somnolence 12.5%
800 ug 2 times / day steady, respiratory
Highest studied dose
Dose: 800 ug, 2 times / day
Route: respiratory
Route: steady
Dose: 800 ug, 2 times / day
Sources:
healthy, 39.3 years (range: 18-45 years)
n = 8
Health Status: healthy
Age Group: 39.3 years (range: 18-45 years)
Sex: M+F
Population Size: 8
Sources:
Dyspnea 0.2%
Disc. AE
200 ug 2 times / day steady, respiratory
Recommended
Dose: 200 ug, 2 times / day
Route: respiratory
Route: steady
Dose: 200 ug, 2 times / day
Sources: Page: p. 101
unhealthy
n = 891
Health Status: unhealthy
Condition: COPD
Population Size: 891
Sources: Page: p. 101
Headache 0.2%
Disc. AE
200 ug 2 times / day steady, respiratory
Recommended
Dose: 200 ug, 2 times / day
Route: respiratory
Route: steady
Dose: 200 ug, 2 times / day
Sources: Page: p. 101
unhealthy
n = 891
Health Status: unhealthy
Condition: COPD
Population Size: 891
Sources: Page: p. 101
Pruritus 0.2%
Disc. AE
200 ug 2 times / day steady, respiratory
Recommended
Dose: 200 ug, 2 times / day
Route: respiratory
Route: steady
Dose: 200 ug, 2 times / day
Sources: Page: p. 101
unhealthy
n = 891
Health Status: unhealthy
Condition: COPD
Population Size: 891
Sources: Page: p. 101
Syncope 0.2%
Disc. AE
200 ug 2 times / day steady, respiratory
Recommended
Dose: 200 ug, 2 times / day
Route: respiratory
Route: steady
Dose: 200 ug, 2 times / day
Sources: Page: p. 101
unhealthy
n = 891
Health Status: unhealthy
Condition: COPD
Population Size: 891
Sources: Page: p. 101
Non-cardiac chest pain 0.3%
Disc. AE
200 ug 2 times / day steady, respiratory
Recommended
Dose: 200 ug, 2 times / day
Route: respiratory
Route: steady
Dose: 200 ug, 2 times / day
Sources: Page: p. 101
unhealthy
n = 891
Health Status: unhealthy
Condition: COPD
Population Size: 891
Sources: Page: p. 101
COPD 2%
Disc. AE
200 ug 2 times / day steady, respiratory
Recommended
Dose: 200 ug, 2 times / day
Route: respiratory
Route: steady
Dose: 200 ug, 2 times / day
Sources: Page: p. 101
unhealthy
n = 891
Health Status: unhealthy
Condition: COPD
Population Size: 891
Sources: Page: p. 101
Dyspnea 0.2%
Disc. AE
200 ug 2 times / day steady, respiratory
Dose: 200 ug, 2 times / day
Route: respiratory
Route: steady
Dose: 200 ug, 2 times / day
Sources: Page: p. 101
unhealthy
n = 448
Health Status: unhealthy
Condition: COPD
Population Size: 448
Sources: Page: p. 101
Non-cardiac chest pain 0.2%
Disc. AE
200 ug 2 times / day steady, respiratory
Dose: 200 ug, 2 times / day
Route: respiratory
Route: steady
Dose: 200 ug, 2 times / day
Sources: Page: p. 101
unhealthy
n = 448
Health Status: unhealthy
Condition: COPD
Population Size: 448
Sources: Page: p. 101
Pruritus 0.2%
Disc. AE
200 ug 2 times / day steady, respiratory
Dose: 200 ug, 2 times / day
Route: respiratory
Route: steady
Dose: 200 ug, 2 times / day
Sources: Page: p. 101
unhealthy
n = 448
Health Status: unhealthy
Condition: COPD
Population Size: 448
Sources: Page: p. 101
Dizziness 0.4%
Disc. AE
200 ug 2 times / day steady, respiratory
Dose: 200 ug, 2 times / day
Route: respiratory
Route: steady
Dose: 200 ug, 2 times / day
Sources: Page: p. 101
unhealthy
n = 448
Health Status: unhealthy
Condition: COPD
Population Size: 448
Sources: Page: p. 101
Fatigue 0.4%
Disc. AE
200 ug 2 times / day steady, respiratory
Dose: 200 ug, 2 times / day
Route: respiratory
Route: steady
Dose: 200 ug, 2 times / day
Sources: Page: p. 101
unhealthy
n = 448
Health Status: unhealthy
Condition: COPD
Population Size: 448
Sources: Page: p. 101
COPD 2.9%
Disc. AE
200 ug 2 times / day steady, respiratory
Dose: 200 ug, 2 times / day
Route: respiratory
Route: steady
Dose: 200 ug, 2 times / day
Sources: Page: p. 101
unhealthy
n = 448
Health Status: unhealthy
Condition: COPD
Population Size: 448
Sources: Page: p. 101
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no [IC50 90 uM]
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
yes [IC50 2.4 uM]
Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Inhalation by design: novel tertiary amine muscarinic M₃ receptor antagonists with slow off-rate binding kinetics for inhaled once-daily treatment of chronic obstructive pulmonary disease.
2011 Oct 13
Perampanel.
2013 Apr
Long-acting muscarinic receptor antagonists for the treatment of chronic airway diseases.
2014 Mar
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment:: Aclidinium bromide inhalation powder
One inhalation of TUDORZA PRESSAIR 400 mcg twice daily. For oral inhalation only.
Route of Administration: Other
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Jun 26 16:10:10 UTC 2021
Edited
by admin
on Sat Jun 26 16:10:10 UTC 2021
Record UNII
K17VY42F6C
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ACLIDINIUM
VANDF   WHO-DD  
Common Name English
(3R)-3-(2-HYDROXY(DI-2-THIENYL)ACETOXY)-1-(3-PHENOXYPROPYL)-1-AZONIABICYCLO(2.2.2)OCTANE
Systematic Name English
ACLIDINIUM [VANDF]
Common Name English
ACLIDINIUM CATION
Common Name English
ACLIDINIUM ION
Common Name English
ACLIDINIUM [WHO-DD]
Common Name English
1-AZONIABICYCLO(2.2.2)OCTANE, 3-((HYDROXYDI-2-THIENYLACETYL)OXY)-1-(3-PHENOXYPROPYL)-, (3R)-
Systematic Name English
Classification Tree Code System Code
EMA ASSESSMENT REPORTS BRIMICA GENUAIR ( AUTHORIZED: PLUMONARY DISEASE, CRONIC OBSTRUCTIVE)
Created by admin on Sat Jun 26 16:10:11 UTC 2021 , Edited by admin on Sat Jun 26 16:10:11 UTC 2021
WHO-ATC R03BB05
Created by admin on Sat Jun 26 16:10:11 UTC 2021 , Edited by admin on Sat Jun 26 16:10:11 UTC 2021
NDF-RT N0000175574
Created by admin on Sat Jun 26 16:10:11 UTC 2021 , Edited by admin on Sat Jun 26 16:10:11 UTC 2021
NCI_THESAURUS C29704
Created by admin on Sat Jun 26 16:10:11 UTC 2021 , Edited by admin on Sat Jun 26 16:10:11 UTC 2021
WHO-ATC R03AL05
Created by admin on Sat Jun 26 16:10:11 UTC 2021 , Edited by admin on Sat Jun 26 16:10:11 UTC 2021
Code System Code Type Description
CAS
727649-81-2
Created by admin on Sat Jun 26 16:10:11 UTC 2021 , Edited by admin on Sat Jun 26 16:10:11 UTC 2021
PRIMARY
PUBCHEM
11434515
Created by admin on Sat Jun 26 16:10:11 UTC 2021 , Edited by admin on Sat Jun 26 16:10:11 UTC 2021
PRIMARY
EPA CompTox
727649-81-2
Created by admin on Sat Jun 26 16:10:11 UTC 2021 , Edited by admin on Sat Jun 26 16:10:11 UTC 2021
PRIMARY
DRUG BANK
DB08897
Created by admin on Sat Jun 26 16:10:11 UTC 2021 , Edited by admin on Sat Jun 26 16:10:11 UTC 2021
PRIMARY
LACTMED
Aclidinium
Created by admin on Sat Jun 26 16:10:11 UTC 2021 , Edited by admin on Sat Jun 26 16:10:11 UTC 2021
PRIMARY
IUPHAR
7449
Created by admin on Sat Jun 26 16:10:11 UTC 2021 , Edited by admin on Sat Jun 26 16:10:11 UTC 2021
PRIMARY
EVMPD
SUB71686
Created by admin on Sat Jun 26 16:10:11 UTC 2021 , Edited by admin on Sat Jun 26 16:10:11 UTC 2021
PRIMARY
WIKIPEDIA
Aclidinium
Created by admin on Sat Jun 26 16:10:11 UTC 2021 , Edited by admin on Sat Jun 26 16:10:11 UTC 2021
PRIMARY
RXCUI
1303098
Created by admin on Sat Jun 26 16:10:11 UTC 2021 , Edited by admin on Sat Jun 26 16:10:11 UTC 2021
PRIMARY RxNorm
NCI_THESAURUS
C79894
Created by admin on Sat Jun 26 16:10:11 UTC 2021 , Edited by admin on Sat Jun 26 16:10:11 UTC 2021
PRIMARY
FDA UNII
K17VY42F6C
Created by admin on Sat Jun 26 16:10:11 UTC 2021 , Edited by admin on Sat Jun 26 16:10:11 UTC 2021
PRIMARY
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