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Identification
- Summary
Tiotropium is a long-acting bronchodilator used in the management of chronic obstructive pulmonary disease (COPD).
- Brand Names
- Inspiolto Respimat, Spiriva, Spiriva Respimat, Stiolto
- Generic Name
- Tiotropium
- DrugBank Accession Number
- DB01409
- Background
Tiotropium is a long-acting, antimuscarinic bronchodilator used in the management of chronic obstructive pulmonary disease (COPD) and asthma.1,2,3,4,5 Tiotropium acts mainly on M3 muscarinic receptors located in the airways to produce smooth muscle relaxation and bronchodilation.1,2,3,4,5
Tiotropium is more specific for the subset of muscarinic receptors commonly found in the lungs than ipratropium.1
Tiotropium was granted FDA approval on 30 January 2004.2
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Tiotropium (DB01409)
- Weight
- Average: 392.512
Monoisotopic: 392.099024577 - Chemical Formula
- C19H22NO4S2
- Synonyms
- Not Available
- External IDs
- BA 679 BR
- BA-679 BR
Pharmacology
- Indication
Tiotropium powder for inhalation is indicated for the maintenance of bronchospasm in COPD and to prevent exacerbations of COPD.2 A combination tiotropium and olodaterol metered inhalation spray is indicated for maintenance of COPD.3 A tiotropium inhalation spray is indicated for the maintenance of bronchospasm in COPD, to prevent exacerbations of COPD, and to treat asthma in patients 12 or more years old.4 A tiotropium metered inhalation spray is indicated for the maintenance of bronchospasm in COPD, to prevent exacerbations of COPD, and to treat asthma in patients 6 or more years old.5
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Asthma •••••••••••• ••••• Management of Asthma •••••••••••• •••••• ••••••• Used in combination to manage Bronchitis Combination Product in combination with: Mometasone furoate (DB14512) •••••••••••• Used in combination to treat Bronchoconstriction Combination Product in combination with: Formoterol (DB00983) •••••••••••• Used in combination to prevent Bronchoconstriction Combination Product in combination with: Formoterol (DB00983) •••••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Tiotropium is a long acting antimuscarinic that causes bronchodilation.1,2,3,4,5 The effects of tiotropium last over 24 hours and there is a wide therapeutic index as overdoses are uncommon even at doses well above the recommended maximum.2,3,4,5
- Mechanism of action
Tiotropium is an antagonist of muscarinic receptors M1 to M5.1,2,3,4,5 Inhibition of the M3 receptor in the smooth muscle of the lungs leads to relaxation of smooth muscle and bronchodilation.1,2,3,4,5
Target Actions Organism AMuscarinic acetylcholine receptor M3 antagonistHumans UMuscarinic acetylcholine receptor M1 antagonistHumans UMuscarinic acetylcholine receptor M2 antagonistHumans UMuscarinic acetylcholine receptor M4 Not Available Humans UMuscarinic acetylcholine receptor M5 Not Available Humans - Absorption
33% of an inhaled solution reaches systemic circulation, while oral solutions have a bioavailability of 2-3%.1,3,4,5 A dry powder for inhalation is 19.5% bioavailable.1,2 Tiotropium metered spray for inhalation reaches a maximum concentration in 5-7 minutes.3,4,5
- Volume of distribution
The volume of distribution of tiotropium is 32L/kg.1,2,3,4,5
- Protein binding
- Metabolism
Tiotropium is not heavily metabolized in the body.2,3,4,5 74% of an intravenous dose is excreted in the urine as unchanged drug.2,3,4,5 Tiotropium is nonenzymatically cleaved to the inactive metabolites N-methylscopine and dithienylglycolic acid.2,3,4,5 In vitro experiments show cytochrome P-450 dependent oxidation and glutathione conjugation to further metabolites.2,3,4,5
Hover over products below to view reaction partners
- Route of elimination
74% of intravenous tiotropium was excreted unchanged in urine.1,2,3,4,5 14% of a dry powder inhalation dose was excreted unchanged in the urine.1 24 hour urinary excretion after 21 days of 5µg once daily inhalation in patients with COPD is 18.6% and in patients with asthma is 12.8%.2,3,4,5
- Half-life
The terminal half life of tiotropium is 24 hours in patients with COPD and 44 hours in patients with asthma.4,5
- Clearance
The total clearance of tiotropium is 880mL/min in healthy subjects receiving 5µg daily.1,2 The renal clearance of tiotropium was 669mL/min.1 Patients <65 years old demonstrated a clearance of 365mL/min while patients ≥65 demonstrated a clearance of 271mL/min.2 This decreased clearance is not associated with increased AUC or Cmax.3,4,5
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Symptoms of overdose include altered mental status, tremors, abdominal pain, and severe constipation.2 However, doses of up to 282µg did not lead to systemic anticholinergic effects in a trial of 6 patients.3,4,5 In case of overdose, stop tiotropium and being symptomatic and supportive therapy.2,3,4,5
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Abacavir may decrease the excretion rate of Tiotropium which could result in a higher serum level. Abametapir The serum concentration of Tiotropium can be increased when it is combined with Abametapir. Abatacept The metabolism of Tiotropium can be increased when combined with Abatacept. Abiraterone The metabolism of Tiotropium can be decreased when combined with Abiraterone. Acebutolol The metabolism of Tiotropium can be decreased when combined with Acebutolol. - Food Interactions
- Take with or without food. Food is not expected to interfere with absorption.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Tiotropium bromide XX112XZP0J 136310-93-5 DQHNAVOVODVIMG-RGECMCKFSA-M Tiotropium bromide monohydrate L64SXO195N 411207-31-3 MQLXPRBEAHBZTK-SEINRUQRSA-M - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Spiriva Capsule 18 ug/1 Oral; Respiratory (inhalation) A-S Medication Solutions 2005-10-11 Not applicable US 
Spiriva Capsule 18 mcg Respiratory (inhalation) Boehringer Ingelheim 2002-11-21 Not applicable Canada 
Spiriva Capsule 18 ug/1 Oral; Respiratory (inhalation) Lake Erie Medical &Surgical Supply Dba Quality Care Products Llc 2005-10-11 2014-12-31 US Spiriva Capsule 18 ug/1 Oral; Respiratory (inhalation) Physicians Total Care, Inc. 2004-07-14 Not applicable US Spiriva HandiHaler Capsule 18 ug/1 Oral; Respiratory (inhalation) Boehringer Ingelheim Pharmaceuticals, Inc. 2005-10-11 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Apo-tiotropium Capsule 18 mcg Respiratory (inhalation) Apotex Corporation Not applicable Not applicable Canada Lupin-tiotropium Capsule 18 mcg Respiratory (inhalation) Lupin Pharmaceuticals, Inc. 2023-12-18 Not applicable Canada Tiotropium Bromide Capsule 18 ug/1 Oral; Respiratory (inhalation) Lupin Pharmaceuticals, Inc. 2023-08-16 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image AERODAY 18/12 MCG INHALASYON IÇIN TOZ IÇEREN BLISTER, 60 DOZ Tiotropium bromide (18 mcg) + Formoterol fumarate (12 mcg) Powder Respiratory (inhalation) NEUTEC İNHALER İLAÇ SAN. VE TİC. A.Ş. 2013-12-13 Not applicable Turkey 
DUESONIT 18/200 MCG INHALASYON ICIN TOZ ICEREN KAPSUL, 120 ADET Tiotropium (18 mcg) + Ciclesonide (200 mcg) Powder Respiratory (inhalation) NEUTEC İLAÇ SAN. TİC. A.Ş. 2012-04-26 Not applicable Turkey DUESONIT 18/200 MCG INHALASYON ICIN TOZ ICEREN KAPSUL, 60 ADET Tiotropium (18 mcg) + Ciclesonide (200 mcg) Powder Respiratory (inhalation) NEUTEC İLAÇ SAN. TİC. A.Ş. 2012-04-26 Not applicable Turkey DUESONIT 18/400 MCG INHALASYON ICIN TOZ ICEREN KAPSUL, 120 ADET Tiotropium (18 mcg) + Ciclesonide (400 mcg) Powder Respiratory (inhalation) NEUTEC İLAÇ SAN. TİC. A.Ş. 2012-04-26 Not applicable Turkey DUESONIT 18/400 MCG INHALASYON ICIN TOZ ICEREN KAPSUL, 60 ADET Tiotropium (18 mcg) + Ciclesonide (400 mcg) Powder Respiratory (inhalation) NEUTEC İLAÇ SAN. TİC. A.Ş. 2012-04-26 Not applicable Turkey
Categories
- ATC Codes
- R03AL06 — Olodaterol and tiotropium bromide
- R03AL — Adrenergics in combination with anticholinergics incl. triple combinations with corticosteroids
- R03A — ADRENERGICS, INHALANTS
- R03 — DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
- R — RESPIRATORY SYSTEM
- R03BB — Anticholinergics
- R03B — OTHER DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES, INHALANTS
- R03 — DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
- R — RESPIRATORY SYSTEM
- R03BB — Anticholinergics
- R03B — OTHER DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES, INHALANTS
- R03 — DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
- R — RESPIRATORY SYSTEM
- Drug Categories
- Adrenergics, Inhalants
- Agents producing tachycardia
- Agents to Treat Airway Disease
- Alkaloids
- Anti-Asthmatic Agents
- Anticholinergic Agents
- Antimuscarinics Antispasmodics
- Autonomic Agents
- Aza Compounds
- Azabicyclo Compounds
- Bronchodilator Agents
- Cholinergic Agents
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Drugs for Obstructive Airway Diseases
- Drugs that are Mainly Renally Excreted
- Muscarinic Antagonists
- Neurotransmitter Agents
- Parasympatholytics
- Peripheral Nervous System Agents
- Respiratory System Agents
- Scopolamine Derivatives
- Tropanes
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as morpholines. These are organic compounds containing a morpholine moiety, which consists of a six-member aliphatic saturated ring with the formula C4H9NO, where the oxygen and nitrogen atoms lie at positions 1 and 4, respectively.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Oxazinanes
- Sub Class
- Morpholines
- Direct Parent
- Morpholines
- Alternative Parents
- Piperidines / N-alkylpyrrolidines / Thiophenes / Tetraalkylammonium salts / Tertiary alcohols / Heteroaromatic compounds / Carboxylic acid esters / Azacyclic compounds / Oxacyclic compounds / Dialkyl ethers show 10 more
- Substituents
- Alcohol / Amine / Aromatic alcohol / Aromatic heteropolycyclic compound / Azacycle / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Dialkyl ether / Ether show 21 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 0EB439235F
- CAS number
- 186691-13-4
- InChI Key
- LERNTVKEWCAPOY-DZZGSBJMSA-N
- InChI
- InChI=1S/C19H22NO4S2/c1-20(2)12-9-11(10-13(20)17-16(12)24-17)23-18(21)19(22,14-5-3-7-25-14)15-6-4-8-26-15/h3-8,11-13,16-17,22H,9-10H2,1-2H3/q+1/t11-,12-,13+,16-,17+
- IUPAC Name
- (1R,2R,4S,5S,7R)-7-{[2-hydroxy-2,2-bis(thiophen-2-yl)acetyl]oxy}-9,9-dimethyl-3-oxa-9-azatricyclo[3.3.1.0^{2,4}]nonan-9-ium
- SMILES
- [H][C@]12O[C@@]1([H])[C@]1([H])C[C@@]([H])(C[C@@]2([H])[N+]1(C)C)OC(=O)C(O)(C1=CC=CS1)C1=CC=CS1
References
- Synthesis Reference
Rolf Banholzer, "Crystalline tiotropium bromide monohydrate, processes for the preparation thereof, and pharmaceutical compositions." U.S. Patent US20020169321, issued November 14, 2002.
US20020169321- General References
- Price D, Sharma A, Cerasoli F: Biochemical properties, pharmacokinetics and pharmacological response of tiotropium in chronic obstructive pulmonary disease patients. Expert Opin Drug Metab Toxicol. 2009 Apr;5(4):417-24. doi: 10.1517/17425250902828337 . [Article]
- FDA Drug Approval Package: Tiotropium Bromide Powder for Inhalation [Link]
- FDA Approved Drug Products: Tiotropium and Olodaterol Metered Inhalation Spray [Link]
- FDA Approved Drug Products: Tiotropium Inhalation Spray [Link]
- FDA Approved Drug Products: Tiotropium Metered Inhalation Spray [Link]
- External Links
- PubChem Compound
- 5487427
- PubChem Substance
- 46504448
- ChemSpider
- 19618474
- BindingDB
- 50239981
- 69120
- ChEBI
- 90960
- ChEMBL
- CHEMBL1900528
- ZINC
- ZINC000100008319
- Therapeutic Targets Database
- DAP000344
- PharmGKB
- PA164769056
- PDBe Ligand
- 0HK
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Tiotropium
- PDB Entries
- 4daj / 4u14 / 4u15 / 5cxv / 5dsg / 6ol9
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Not Available Angle-Closure Glaucoma / Chronic Obstructive Pulmonary Disease (COPD) 1 somestatus stop reason just information to hide Not Available Completed Not Available Asthma 4 somestatus stop reason just information to hide Not Available Completed Not Available Asthma / Obesity 1 somestatus stop reason just information to hide Not Available Completed Not Available Bronchodilation / Cardiovascular Disease (CVD) / Chronic Obstructive Pulmonary Disease (COPD) / Smoking 1 somestatus stop reason just information to hide Not Available Completed Not Available Chronic Obstructive Pulmonary Disease (COPD) 41 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Boehringer Ingelheim Ltd.
- Diversified Healthcare Services Inc.
- Physicians Total Care Inc.
- Dosage Forms
Form Route Strength Powder Respiratory (inhalation) Powder Respiratory (inhalation) 00156 Mg Capsule Oral 10 Mikrogramm Powder Respiratory (inhalation) 18 mcg Powder Respiratory (inhalation) 12 mcg Capsule; powder Respiratory (inhalation) Suspension Respiratory (inhalation) 18 mcg Powder Buccal 15.600 mcg Solution Oral Solution Respiratory (inhalation) 2.5 MICROGRAMMI/2.5MICROGRAMMI Solution Respiratory (inhalation) 0.0025 mg/actuation Aerosol, metered Respiratory (inhalation) Solution Respiratory (inhalation) Capsule Oral; Respiratory (inhalation) 18 ug/1 Powder Respiratory (inhalation) 10 mg Powder, metered Respiratory (inhalation) 18 MCG Solution Oral 0.226 mg Capsule Respiratory (inhalation) 18 mcg Powder Respiratory (inhalation) Powder Respiratory (inhalation) 18 Mikrogramm Aerosol Respiratory (inhalation) 3.124 MG Aerosol Respiratory (inhalation) 3.124 mcg Solution Respiratory (inhalation) 2.5 mcg Solution Respiratory (inhalation) 2.5 MICROGRAMMI Solution Respiratory (inhalation) 2.5 mcg / act Spray, metered Respiratory (inhalation) 1.562 ug/1 Spray, metered Respiratory (inhalation) 3.124 ug/1 Solution Respiratory (inhalation) 2.5 Mikrogramm Aerosol, metered Respiratory (inhalation) 2.5 mcg Solution Respiratory (inhalation) 0.0025 mg Capsule Respiratory (inhalation) 18 Mikrogramm Spray, metered Respiratory (inhalation) Capsule, coated Respiratory (inhalation) 0.0236 mg/capsule Capsule Respiratory (inhalation) Capsule Respiratory (inhalation) Capsule Respiratory (inhalation) 0.013 mg Capsule, coated Respiratory (inhalation) 18 mcg Capsule, coated Respiratory (inhalation) 1800000 mcg Powder, metered Respiratory (inhalation) 10 MCG Suspension Respiratory (inhalation) 0.016 % Aerosol Respiratory (inhalation) 2.5 mcg/1dose Aerosol Respiratory (inhalation) - Prices
Unit description Cost Unit Spiriva HandiHaler 30 18 mcg capsule Box 223.07USD box Spiriva HandiHaler 5 18 mcg capsule Box 63.64USD box Spiriva HandiHaler 6 18 mcg capsule Box 41.99USD box Spiriva 18 mcg cp-handihaler 6.31USD inhaler Spiriva 18 mcg Capsule 2.2USD capsule DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5478578 No 1995-12-26 2012-12-26 US CA2066248 No 1998-08-04 2010-09-08 Canada US6908928 Yes 2005-06-21 2022-03-24 US US7070800 Yes 2006-07-04 2022-07-22 US US8022082 Yes 2011-09-20 2026-07-19 US USRE39820 Yes 2007-09-04 2018-07-30 US US7642268 Yes 2010-01-05 2022-03-24 US US7694676 Yes 2010-04-13 2027-09-12 US US6777423 Yes 2004-08-17 2022-03-24 US US7309707 Yes 2007-12-18 2022-03-24 US USRE38912 Yes 2005-12-06 2022-04-11 US US6453795 Yes 2002-09-24 2017-06-05 US US8733341 Yes 2014-05-27 2031-04-16 US US9027967 Yes 2015-05-12 2027-10-01 US US7104470 Yes 2006-09-12 2017-04-04 US US7246615 Yes 2007-07-24 2016-12-01 US US7896264 Yes 2011-03-01 2025-11-26 US US7988001 Yes 2011-08-02 2022-02-04 US US7802568 Yes 2010-09-28 2019-08-26 US US6149054 Yes 2000-11-21 2017-06-16 US US6726124 Yes 2004-04-27 2017-04-04 US US7396341 Yes 2008-07-08 2027-04-10 US US6846413 Yes 2005-01-25 2019-02-28 US US6176442 Yes 2001-01-23 2016-12-01 US US7837235 Yes 2010-11-23 2028-09-13 US US5964416 Yes 1999-10-12 2017-04-04 US US7284474 Yes 2007-10-23 2025-02-26 US US6977042 Yes 2005-12-20 2019-02-28 US US6988496 Yes 2006-01-24 2020-08-23 US US8044046 No 2011-10-25 2023-11-10 US US8034809 No 2011-10-11 2025-05-12 US US7220742 No 2007-05-22 2025-05-12 US US7491719 No 2009-02-17 2023-11-10 US US7056916 No 2006-06-06 2023-12-07 US US7727984 No 2010-06-01 2023-11-10 US US7786111 No 2010-08-31 2023-11-10 US US9010323 No 2015-04-21 2030-04-19 US
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source logP -1.8 Chemaxon pKa (Strongest Acidic) 10.35 Chemaxon pKa (Strongest Basic) -4.3 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 59.06 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 109.18 m3·mol-1 Chemaxon Polarizability 39.52 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.9173 Blood Brain Barrier + 0.5208 Caco-2 permeable + 0.5294 P-glycoprotein substrate Substrate 0.7153 P-glycoprotein inhibitor I Non-inhibitor 0.7514 P-glycoprotein inhibitor II Non-inhibitor 0.9762 Renal organic cation transporter Non-inhibitor 0.7256 CYP450 2C9 substrate Non-substrate 0.6633 CYP450 2D6 substrate Non-substrate 0.7533 CYP450 3A4 substrate Substrate 0.6615 CYP450 1A2 substrate Non-inhibitor 0.7787 CYP450 2C9 inhibitor Non-inhibitor 0.812 CYP450 2D6 inhibitor Non-inhibitor 0.8368 CYP450 2C19 inhibitor Non-inhibitor 0.7284 CYP450 3A4 inhibitor Non-inhibitor 0.7752 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9289 Ames test Non AMES toxic 0.6133 Carcinogenicity Non-carcinogens 0.9221 Biodegradation Not ready biodegradable 0.9319 Rat acute toxicity 2.6249 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9957 hERG inhibition (predictor II) Non-inhibitor 0.8947
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-03kc-1900000000-02d8f650f9450c4bd904 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 176.4108 predictedDeepCCS 1.0 (2019) [M-H]- 176.4108 predictedDeepCCS 1.0 (2019) [M-H]- 176.4108 predictedDeepCCS 1.0 (2019) [M+H]+ 178.30621 predictedDeepCCS 1.0 (2019) [M+H]+ 178.30621 predictedDeepCCS 1.0 (2019) [M+H]+ 178.30621 predictedDeepCCS 1.0 (2019) [M+Na]+ 183.99887 predictedDeepCCS 1.0 (2019) [M+Na]+ 183.99887 predictedDeepCCS 1.0 (2019) [M+Na]+ 183.99887 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
- Specific Function
- acetylcholine binding
- Gene Name
- CHRM3
- Uniprot ID
- P20309
- Uniprot Name
- Muscarinic acetylcholine receptor M3
- Molecular Weight
- 66127.445 Da
References
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Hansel TT, Barnes PJ: Tiotropium bromide: a novel once-daily anticholinergic bronchodilator for the treatment of COPD. Drugs Today (Barc). 2002 Sep;38(9):585-600. [Article]
- Barnes PJ: Tiotropium bromide. Expert Opin Investig Drugs. 2001 Apr;10(4):733-40. [Article]
- Barnes PJ, Belvisi MG, Mak JC, Haddad EB, O'Connor B: Tiotropium bromide (Ba 679 BR), a novel long-acting muscarinic antagonist for the treatment of obstructive airways disease. Life Sci. 1995;56(11-12):853-9. [Article]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
- Specific Function
- G protein-coupled acetylcholine receptor activity
- Gene Name
- CHRM1
- Uniprot ID
- P11229
- Uniprot Name
- Muscarinic acetylcholine receptor M1
- Molecular Weight
- 51420.375 Da
References
- Hansel TT, Barnes PJ: Tiotropium bromide: a novel once-daily anticholinergic bronchodilator for the treatment of COPD. Drugs Today (Barc). 2002 Sep;38(9):585-600. [Article]
- Barnes PJ: Tiotropium bromide. Expert Opin Investig Drugs. 2001 Apr;10(4):733-40. [Article]
- Barnes PJ, Belvisi MG, Mak JC, Haddad EB, O'Connor B: Tiotropium bromide (Ba 679 BR), a novel long-acting muscarinic antagonist for the treatment of obstructive airways disease. Life Sci. 1995;56(11-12):853-9. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is adenylate cyclase inhibition. Signaling promotes phospholipase C activity, leading to the release of inositol trisphosphate (IP3); this then triggers calcium ion release into the cytosol
- Specific Function
- arrestin family protein binding
- Gene Name
- CHRM2
- Uniprot ID
- P08172
- Uniprot Name
- Muscarinic acetylcholine receptor M2
- Molecular Weight
- 51714.605 Da
References
- Hansel TT, Barnes PJ: Tiotropium bromide: a novel once-daily anticholinergic bronchodilator for the treatment of COPD. Drugs Today (Barc). 2002 Sep;38(9):585-600. [Article]
- Barnes PJ, Belvisi MG, Mak JC, Haddad EB, O'Connor B: Tiotropium bromide (Ba 679 BR), a novel long-acting muscarinic antagonist for the treatment of obstructive airways disease. Life Sci. 1995;56(11-12):853-9. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is inhibition of adenylate cyclase
- Specific Function
- G protein-coupled acetylcholine receptor activity
- Gene Name
- CHRM4
- Uniprot ID
- P08173
- Uniprot Name
- Muscarinic acetylcholine receptor M4
- Molecular Weight
- 53048.65 Da
References
- Glossop PA, Watson CA, Price DA, Bunnage ME, Middleton DS, Wood A, James K, Roberts D, Strang RS, Yeadon M, Perros-Huguet C, Clarke NP, Trevethick MA, Machin I, Stuart EF, Evans SM, Harrison AC, Fairman DA, Agoram B, Burrows JL, Feeder N, Fulton CK, Dillon BR, Entwistle DA, Spence FJ: Inhalation by design: novel tertiary amine muscarinic M(3) receptor antagonists with slow off-rate binding kinetics for inhaled once-daily treatment of chronic obstructive pulmonary disease. J Med Chem. 2011 Oct 13;54(19):6888-904. doi: 10.1021/jm200884j. Epub 2011 Sep 20. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
- Specific Function
- G protein-coupled acetylcholine receptor activity
- Gene Name
- CHRM5
- Uniprot ID
- P08912
- Uniprot Name
- Muscarinic acetylcholine receptor M5
- Molecular Weight
- 60073.205 Da
References
- Glossop PA, Watson CA, Price DA, Bunnage ME, Middleton DS, Wood A, James K, Roberts D, Strang RS, Yeadon M, Perros-Huguet C, Clarke NP, Trevethick MA, Machin I, Stuart EF, Evans SM, Harrison AC, Fairman DA, Agoram B, Burrows JL, Feeder N, Fulton CK, Dillon BR, Entwistle DA, Spence FJ: Inhalation by design: novel tertiary amine muscarinic M(3) receptor antagonists with slow off-rate binding kinetics for inhaled once-daily treatment of chronic obstructive pulmonary disease. J Med Chem. 2011 Oct 13;54(19):6888-904. doi: 10.1021/jm200884j. Epub 2011 Sep 20. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of fatty acids, steroids and retinoids (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:19965576, PubMed:20972997). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 20-hydroxyeicosatetraenoic acid ethanolamide (20-HETE-EA) and 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:18698000, PubMed:21289075). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Catalyzes the oxidative transformations of all-trans retinol to all-trans retinal, a precursor for the active form all-trans-retinoic acid (PubMed:10681376). Also involved in the oxidative metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants
- Specific Function
- anandamide 11,12 epoxidase activity
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Keam SJ, Keating GM: Tiotropium bromide. A review of its use as maintenance therapy in patients with COPD. Treat Respir Med. 2004;3(4):247-68. [Article]
- Mosley JF 2nd, Smith LL, Dutton BN: Tiotropium Bromide/Olodaterol (Stiolto Respimat): Once-Daily Combination Therapy for the Maintenance of COPD. P T. 2016 Feb;41(2):97-102. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
- Specific Function
- 1,8-cineole 2-exo-monooxygenase activity
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Keam SJ, Keating GM: Tiotropium bromide. A review of its use as maintenance therapy in patients with COPD. Treat Respir Med. 2004;3(4):247-68. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine (PubMed:10454528, PubMed:10525100, PubMed:10966938, PubMed:17509700, PubMed:20722056, PubMed:33124720). Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Relative uptake activity ratio of carnitine to TEA is 11.3 (PubMed:10454528, PubMed:10525100, PubMed:10966938). In intestinal epithelia, transports the quorum-sensing pentapeptide CSF (competence and sporulation factor) from Bacillus Subtilis wich induces cytoprotective heat shock proteins contributing to intestinal homeostasis (PubMed:18005709). May also contribute to regulate the transport of organic compounds in testis across the blood-testis-barrier (Probable)
- Specific Function
- (R)-carnitine transmembrane transporter activity
- Gene Name
- SLC22A5
- Uniprot ID
- O76082
- Uniprot Name
- Organic cation/carnitine transporter 2
- Molecular Weight
- 62751.08 Da
References
- Nakamura T, Nakanishi T, Haruta T, Shirasaka Y, Keogh JP, Tamai I: Transport of ipratropium, an anti-chronic obstructive pulmonary disease drug, is mediated by organic cation/carnitine transporters in human bronchial epithelial cells: implications for carrier-mediated pulmonary absorption. Mol Pharm. 2010 Feb 1;7(1):187-95. doi: 10.1021/mp900206j. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Transporter that mediates the transport of endogenous and microbial zwitterions and organic cations (PubMed:10215651, PubMed:15107849, PubMed:15795384, PubMed:16729965, PubMed:20601551, PubMed:22206629, PubMed:22569296, PubMed:29530864). Functions as a Na(+)-dependent and pH-dependent high affinity microbial symporter of potent food-derived antioxidant ergothioeine (PubMed:15795384, PubMed:29530864, PubMed:33124720). Transports one sodium ion with one ergothioeine molecule (By similarity). Involved in the absorption of ergothioneine from the luminal/apical side of the small intestine and renal tubular cells, and into non-parenchymal liver cells, thereby contributing to maintain steady-state ergothioneine level in the body (PubMed:20601551). Also mediates the bidirectional transport of acetycholine, although the exact transport mechanism has not been fully identified yet (PubMed:22206629). Most likely exports anti-inflammatory acetylcholine in non-neuronal tissues, thereby contributing to the non-neuronal cholinergic system (PubMed:22206629, PubMed:22569296). Displays a general physiological role linked to better survival by controlling inflammation and oxidative stress, which may be related to ergothioneine and acetycholine transports (PubMed:15795384, PubMed:22206629). May also function as a low-affinity Na(+)-dependent transporter of L-carnitine through the mitochondrial membrane, thereby maintaining intracellular carnitine homeostasis (PubMed:10215651, PubMed:15107849, PubMed:16729965). May contribute to regulate the transport of cationic compounds in testis across the blood-testis-barrier (PubMed:35307651)
- Specific Function
- acetylcholine transmembrane transporter activity
- Gene Name
- SLC22A4
- Uniprot ID
- Q9H015
- Uniprot Name
- Solute carrier family 22 member 4
- Molecular Weight
- 62154.48 Da
References
- Nakamura T, Nakanishi T, Haruta T, Shirasaka Y, Keogh JP, Tamai I: Transport of ipratropium, an anti-chronic obstructive pulmonary disease drug, is mediated by organic cation/carnitine transporters in human bronchial epithelial cells: implications for carrier-mediated pulmonary absorption. Mol Pharm. 2010 Feb 1;7(1):187-95. doi: 10.1021/mp900206j. [Article]
Drug created at July 17, 2007 12:36 / Updated at November 01, 2024 00:04