Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C26H30NO4S2.Br |
Molecular Weight | 564.555 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Br-].OC(C(=O)O[C@H]1C[N+]3(CCCOC2=CC=CC=C2)CCC1CC3)(C4=CC=CS4)C5=CC=CS5
InChI
InChIKey=XLAKJQPTOJHYDR-QTQXQZBYSA-M
InChI=1S/C26H30NO4S2.BrH/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;1H/q+1;/p-1/t20?,22-,27?;/m0./s1
Molecular Formula | C26H29NO4S2 |
Molecular Weight | 483.643 |
Charge | 0 |
Count |
|
Stereochemistry | EPIMERIC |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Molecular Formula | BrH |
Molecular Weight | 80.912 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionCurator'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
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
Sources: http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Public_assessment_report/human/002706/WC500132734.pdf
Curator's Comment: The polar nature of aclidinium bromide makes it unlikely to cross the blood brain barrier
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
0.14 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Secondary | TUDORZA PRESSAIR Approved UseIndicated for the long-term maintenance treatment of bronchospasm associated with chronic obstructive pulmonary disease (COPD), including chronic bronchitis and emphysema Launch Date2012 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
194.2 pg/mL DRUG LABEL https://pubmed.ncbi.nlm.nih.gov/22366196/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22366196/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
386.7 pg × h/mL DRUG LABEL https://pubmed.ncbi.nlm.nih.gov/22366196/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22366196/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5.9 h DRUG LABEL https://pubmed.ncbi.nlm.nih.gov/22366196/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22366196/ |
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
Dose | Population | Adverse 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%) Sources: Dysgeusia (12.5%) Somnolence (12.5%) |
6000 ug single, respiratory Highest studied dose Dose: 6000 ug Route: respiratory Route: single Dose: 6000 ug Sources: |
healthy n = 16 |
|
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%) Sources: Page: p. 101Headache (0.2%) Dyspnea (0.2%) COPD (2%) Pruritus (0.2%) Syncope (0.2%) |
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%) Sources: Page: p. 101Non-cardiac chest pain (0.2%) Dizziness (0.4%) Dyspnea (0.2%) COPD (2.9%) Pruritus (0.2%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
Page: 9.0 |
unlikely |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202450Orig1s000PharmR.pdf#page=147 Page: 147.0 |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
|
Long-acting muscarinic receptor antagonists for the treatment of chronic airway diseases. | 2014 Mar |
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:54:09 GMT 2023
by
admin
on
Fri Dec 15 15:54:09 GMT 2023
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Record UNII |
UQW7UF9N91
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Record Status |
Validated (UNII)
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C29704
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EMA ASSESSMENT REPORTS |
DUAKLIR GENUAIR (AUTHORIZED: PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
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EMA ASSESSMENT REPORTS |
BRETARIS GENUAIR (AUTHORIZED: ASTHMA, PULMONARY DISEASE, CHRONIC OBSTRUCTIVE)
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WHO-ATC |
R03BB05
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WHO-VATC |
QR03BB05
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EMA ASSESSMENT REPORTS |
EKLIRA GENUAIR (AUTHORIZED: PULMONARY DISEASE, CHRONIC OBSTRUCTIVE )
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8544
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CHEMBL1194325
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ACLIDINIUM BROMIDE
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UQW7UF9N91
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C75999
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DBSALT000003
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SUB71687
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UQW7UF9N91
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DTXSID30185854
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TT-113
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100000135704
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65344
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4484
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C542859
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1303097
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m1376
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320345-99-1
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11519741
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