Explore a selection of our essential drug information below, or:
Identification
- Summary
Oxybutynin is an antimuscarinic agent that reduces detrusor muscle activity, relaxing the bladder and preventing the urge to void.
- Brand Names
- Ditropan, Gelnique, Kentera, Oxytrol
- Generic Name
- Oxybutynin
- DrugBank Accession Number
- DB01062
- Background
Overactive bladder (OAB) is a common condition negatively impacting the lives of millions of patients worldwide. Due to its urinary symptoms that include nocturia, urgency, and frequency, this condition causes social embarrassment and a poor quality of life.4,5
Oxybutynin, also marketed as Ditropan XL, is an anticholinergic medication used for the relief of overactive bladder symptoms that has been optimized for high levels of safety and efficacy since initial FDA approval in 1975.2,14 This drug relieves undesirable urinary symptoms, increasing the quality of life for patients affected by OAB. It is often used as first-line therapy for OAB.3
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Oxybutynin (DB01062)
- Weight
- Average: 357.4864
Monoisotopic: 357.230393863 - Chemical Formula
- C22H31NO3
- Synonyms
- 4-(Diethylamino)-2-butynyl alpha-phenylcyclohexaneglycolic acid ester
- 4-Diethylamino-2-butinyl alpha-cyclohexylmandelat
- 4-Diethylamino-2-butynyl alpha-phenylcyclohexaneglycolate
- Oxibutinina
- Oxybutynin
- Oxybutynine
- Oxybutyninum
Pharmacology
- Indication
Oxybutynin is indicated for the symptomatic treatment of overactive bladder, which causes urge urinary incontinence and frequency, and urgency. Oxybutynin may also be used for children aged 6 and above for the symptomatic management of detrusor muscle overactivity which has been found to be related to a neurological condition. Spina bifida is an example of a neurological condition in which oxybutynin may be used to control urinary symptoms.14 On occasion, oxybutynin may be used off-label to relieve bladder spasms associated with ureteral stents or urinary catheters.12
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 Treatment of Bladder spasm ••• ••••• Symptomatic treatment of Overactive bladder (oab) •••••••••••• ••••••• •••••••• ••••••• Treatment of Detruser overactivity •••••••••••• ••••••••• ••••••• •••••••• •••••••• ••••••• •••• ••••••• •••••••• ••••••• - 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
Oxybutynin exerts antispasmodic actions on the bladder, relieving the uncomfortable symptoms of overactive bladder, including urinary urgency and frequency. These actions occur through the inhibition of muscarinic receptors.
A note on angioedema and anticholinergic effects
Symptoms of angioedema may occur with oxybutynin therapy. If angioedema is suspected, discontinue oxybutynin immediately and provide appropriate medical treatment.14 In addition, anticholinergic effects may occur with the administration of this drug. Some symptoms may include hallucinations, confusion, agitation, and drowsiness. It is advisable to avoid operating heavy machinery before the response to oxybutynin has been monitored. Dose adjustments may be required.14
- Mechanism of action
Oxybutynin acts to relax the bladder by inhibiting the muscarinic action of acetylcholine on smooth muscle, and not skeletal muscle.14 The active of oxybutynin is metabolite is N-desethyloxybutynin. It competitively inhibits the postganglionic type 1, 2 and 3 muscarinic receptors. The above actions lead to increased urine capacity in the bladder, decreasing urinary urgency and frequency. In addition, oxybutynin delays the initial desire to void.12,14
Target Actions Organism AMuscarinic acetylcholine receptor M3 antagonistHumans AMuscarinic acetylcholine receptor M2 antagonistHumans AMuscarinic acetylcholine receptor M1 antagonistHumans - Absorption
Oxybutynin should be swallowed whole with the help of liquids.14 A pharmacokinetic study revealed that oxybutynin was rapidly absorbed, and peak concentrations were reached within about 1 hour of administration, measured at 8.2 ngml-1 and AUC was 16 ngml-1.1 The biovailability of oxybutynin is about 6%, and the plasma concentration of the active metabolite, desethyloxybutynin is 5 to 12 times greater than that of oxybutynin.2 Bioavailability is increased in the elderly.3 Food has been shown to increase the exposure to controlled-release oxybutynin.7
- Volume of distribution
Oxybutynin has a wide volume of distribution of 193 L.14 In rats, oxybutynin penetrates the central nervous system.11
- Protein binding
Oxybutynin enantiomers are more than 97% bound to plasma proteins, primarily to alpha-1 acid glycoprotein.8,14
- Metabolism
Oxybutynin is heavily metabolized by the CYP3A4 enzyme system3 in both the liver and the wall of the intestine. It undergoes first-pass metabolism, and its resulting primary active metabolite, N-desethyloxybutynin circulates. It is active at the muscarinic receptors in both the bladder and the salivary gland.2 Hepatic biotransformation also produces its major inactive metabolite, phenylcyclohexylglycolic acid.3
Hover over products below to view reaction partners
- Route of elimination
Oxybutynin is heavily cleared by the liver.1 Under 0.1% of an administered dose is found as unchanged drug in the urine. Less than 0.1% of a single dose of oxybutynin is excreted as desethyloxybutynin.1,14
- Half-life
The plasma elimination half-life is about 2 hours. In the elderly, the elimination half-life is prolonged up to 5 hours.2,3
- Clearance
Not Available
- 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
The acute oral LD50 in rats is 460 mg/kg.13
Overdose information
An overdose with oxybutynin may manifest clinically as CNS overactivity, fever, palpitations, cardiac arrhythmias, urinary retention, respiratory failure, paralysis, in addition to coma.12,14 Provide supportive care immediately. Activated charcoal in addition to a cathartic agent should be administered. There have been 2 reports of an overdose with a 100 mg dose of oxybutynin. One case was a 13-year-old boy and another was a 34-year-old woman. Alcohol was also ingested simultaneously in both cases. The patients received supportive treatment and fully recovered.12
- 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 softwareAbametapir The serum concentration of Oxybutynin can be increased when it is combined with Abametapir. Abatacept The metabolism of Oxybutynin can be increased when combined with Abatacept. Abemaciclib The serum concentration of Abemaciclib can be increased when it is combined with Oxybutynin. Acalabrutinib The serum concentration of Acalabrutinib can be increased when it is combined with Oxybutynin. Acebutolol The metabolism of Acebutolol can be decreased when combined with Oxybutynin. - Food Interactions
- Avoid alcohol.
- Take with or without food.
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 Oxybutynin chloride L9F3D9RENQ 1508-65-2 SWIJYDAEGSIQPZ-UHFFFAOYSA-N - Product Images
- International/Other Brands
- Lenditro / Lyrinel XL
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Albert Oxybutynin Tablet 5 mg Oral Aventis Pharma Ltd. 1996-11-21 2002-07-29 Canada 
Ditropan Tablet 5 mg/1 Oral Alza 1975-07-16 2012-03-19 US 
Ditropan Syrup 5 mg/5mL Oral Ortho-McNeil Pharmaceutical, Inc. 2006-08-29 2006-08-29 US Ditropan Syrup 1mg/ml Syrup 1 mg / mL Oral Janssen Pharmaceuticals 1993-12-31 2007-02-21 Canada Ditropan Tablets 5mg Tablet 5 mg Oral Janssen Pharmaceuticals 1993-12-31 2006-08-04 Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Apo-oxybutynin Tablet 5 mg Oral Apotex Corporation 1995-12-31 Not applicable Canada Apo-oxybutynin Syrup 1 mg / mL Oral Apotex Corporation 1997-04-28 Not applicable Canada Ava-oxybutynin Tablet 5 mg Oral Avanstra Inc 2011-08-22 2014-08-21 Canada Dom-oxybutynin 5 Mg Tablets Tablet 5 mg Oral Dominion Pharmacal 1999-12-16 Not applicable Canada Mylan-oxybutynin Tablet 5 mg Oral Mylan Pharmaceuticals 1997-04-24 2016-06-28 Canada - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Oxytrol For Women Patch 3.9 mg/1d Transdermal Bayer Healthcare Llc. 2013-08-19 2016-01-15 US Oxytrol for Women Patch 3.9 mg/1d Transdermal Allergan, Inc. 2016-01-01 Not applicable US Oxytrol For Women Patch 3.9 mg/1d Transdermal Actavis Pharma, Inc. 2016-01-01 2020-01-31 US Oxytrol For Women Patch 3.9 mg/1d Transdermal Bayer Healthcare Llc. 2013-08-19 2016-01-15 US
Categories
- ATC Codes
- G04BD04 — Oxybutynin
- Drug Categories
- Acids, Carbocyclic
- Agents producing tachycardia
- Anticholinergic Agents
- Autonomic Agents
- Cytochrome P-450 CYP2C8 Inhibitors
- Cytochrome P-450 CYP2C8 Inhibitors (moderate)
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A5 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Drugs for Urinary Frequency and Incontinence
- Genito Urinary System and Sex Hormones
- Genitourinary Agents
- Hydroxy Acids
- Muscarinic Antagonists
- Neurotransmitter Agents
- Parasympatholytics
- Peripheral Nervous System Agents
- Urological Agents
- Urologicals
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Not Available
- Direct Parent
- Benzene and substituted derivatives
- Alternative Parents
- Tertiary alcohols / Trialkylamines / Carboxylic acid esters / Amino acids and derivatives / Monocarboxylic acids and derivatives / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds / Aromatic alcohols
- Substituents
- Alcohol / Amine / Amino acid or derivatives / Aromatic alcohol / Aromatic homomonocyclic compound / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Hydrocarbon derivative / Monocarboxylic acid or derivatives
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- tertiary alcohol, tertiary amine, acetate ester, acetylenic compound (CHEBI:7856)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- K9P6MC7092
- CAS number
- 5633-20-5
- InChI Key
- XIQVNETUBQGFHX-UHFFFAOYSA-N
- InChI
- InChI=1S/C22H31NO3/c1-3-23(4-2)17-11-12-18-26-21(24)22(25,19-13-7-5-8-14-19)20-15-9-6-10-16-20/h5,7-8,13-14,20,25H,3-4,6,9-10,15-18H2,1-2H3
- IUPAC Name
- 4-(diethylamino)but-2-yn-1-yl 2-cyclohexyl-2-hydroxy-2-phenylacetate
- SMILES
- CCN(CC)CC#CCOC(=O)C(O)(C1CCCCC1)C1=CC=CC=C1
References
- Synthesis Reference
Masakatsu Shibasaki, "Method of producing oxybutynin and its derivatives." U.S. Patent US20040006243, issued January 08, 2004.
US20040006243- General References
- Douchamps J, Derenne F, Stockis A, Gangji D, Juvent M, Herchuelz A: The pharmacokinetics of oxybutynin in man. Eur J Clin Pharmacol. 1988;35(5):515-20. doi: 10.1007/bf00558247. [Article]
- Kennelly MJ: A comparative review of oxybutynin chloride formulations: pharmacokinetics and therapeutic efficacy in overactive bladder. Rev Urol. 2010 Winter;12(1):12-9. [Article]
- Yarker YE, Goa KL, Fitton A: Oxybutynin. A review of its pharmacodynamic and pharmacokinetic properties, and its therapeutic use in detrusor instability. Drugs Aging. 1995 Mar;6(3):243-62. doi: 10.2165/00002512-199506030-00007. [Article]
- Willis-Gray MG, Dieter AA, Geller EJ: Evaluation and management of overactive bladder: strategies for optimizing care. Res Rep Urol. 2016 Jul 27;8:113-22. doi: 10.2147/RRU.S93636. eCollection 2016. [Article]
- Plata M, Bravo-Balado A, Robledo D, Trujillo CG, Caicedo JI, Catano JG, Arenas J, Rondon M, Londono D: Prevalence of lower urinary tract symptoms and overactive bladder in men and women over 18 years old: The Colombian overactive bladder and lower urinary tract symptoms (COBaLT) study. Neurourol Urodyn. 2019 Jan;38(1):200-207. doi: 10.1002/nau.23828. Epub 2018 Sep 24. [Article]
- Aprile S, Canavesi R, Matucci R, Bellucci C, Del Grosso E, Grosa G: New insights in the metabolism of oxybutynin: evidence of N-oxidation of propargylamine moiety and rearrangement to enaminoketone. Xenobiotica. 2018 May;48(5):478-487. doi: 10.1080/00498254.2017.1342288. Epub 2017 Jul 6. [Article]
- Guay DR: Clinical pharmacokinetics of drugs used to treat urge incontinence. Clin Pharmacokinet. 2003;42(14):1243-85. doi: 10.2165/00003088-200342140-00004. [Article]
- Shibukawa A, Ishizawa N, Kimura T, Sakamoto Y, Ogita K, Matsuo Y, Kuroda Y, Matayatsu C, Nakagawa T, Wainer IW: Plasma protein binding study of oxybutynin by high-performance frontal analysis. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Feb 25;768(1):177-88. [Article]
- Sathyan G, Chancellor MB, Gupta SK: Effect of OROS controlled-release delivery on the pharmacokinetics and pharmacodynamics of oxybutynin chloride. Br J Clin Pharmacol. 2001 Oct;52(4):409-17. doi: 10.1046/j.0306-5251.2001.01463.x. [Article]
- Lukkari E, Hakonen T, Neuvonen PJ: The pharmacokinetics of oxybutynin is unaffected by gender and contraceptive steroids. Eur J Clin Pharmacol. 1998 Jan;53(5):351-4. doi: 10.1007/s002280050392. [Article]
- Callegari E, Malhotra B, Bungay PJ, Webster R, Fenner KS, Kempshall S, LaPerle JL, Michel MC, Kay GG: A comprehensive non-clinical evaluation of the CNS penetration potential of antimuscarinic agents for the treatment of overactive bladder. Br J Clin Pharmacol. 2011 Aug;72(2):235-46. doi: 10.1111/j.1365-2125.2011.03961.x. [Article]
- Jennifer Dwyer; Chad A. LaGrange (2019). Oxybutinin. StatPearls Publishing.
- HMDB MSDS, Oxybutinin [Link]
- Ditropan XL FDA label [Link]
- External Links
- Human Metabolome Database
- HMDB0015195
- KEGG Drug
- D00465
- KEGG Compound
- C07360
- PubChem Compound
- 4634
- PubChem Substance
- 46508005
- ChemSpider
- 4473
- BindingDB
- 50165019
- 32675
- ChEBI
- 7856
- ChEMBL
- CHEMBL1231
- Therapeutic Targets Database
- DAP001128
- PharmGKB
- PA164746030
- Guide to Pharmacology
- GtP Drug Page
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Oxybutynin
- MSDS
- Download (73 KB)
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 Hyperhidrosis 1 somestatus stop reason just information to hide Not Available Completed Not Available Overactive Bladder Syndrome (OABS) 2 somestatus stop reason just information to hide Not Available Completed Not Available Overactive Bladder Syndrome (OABS) / Urinary Bladder Diseases / Urological Diseases 1 somestatus stop reason just information to hide Not Available Completed Treatment Axillary Hyperhidrosis / Osmidrosis 1 somestatus stop reason just information to hide Not Available Completed Treatment Hyperhidrosis 2 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Alza Corp.
- Atlantic Biologicals Corporation
- Cardinal Health
- Dept Health Central Pharmacy
- Dispensing Solutions
- Global Pharmaceuticals
- Goldline Laboratories Inc.
- Impax Laboratories Inc.
- Janssen-Ortho Inc.
- Liberty Pharmaceuticals
- Major Pharmaceuticals
- McNeil Laboratories
- Medisca Inc.
- Murfreesboro Pharmaceutical Nursing Supply
- Mylan
- Ortho Mcneil Janssen Pharmaceutical Inc.
- Physicians Total Care Inc.
- Pliva Inc.
- Qualitest
- Redpharm Drug
- Remedy Repack
- Resource Optimization and Innovation LLC
- Schwarz Pharma Inc.
- Teva Pharmaceutical Industries Ltd.
- UDL Laboratories
- USL Pharma Inc.
- Vangard Labs Inc.
- Vintage Pharmaceuticals Inc.
- Watson Pharmaceuticals
- Dosage Forms
Form Route Strength Syrup Oral 100 mg Tablet, coated Oral 5 mg Syrup Oral 1 mg / mL Tablet, extended release Oral 10 mg/1 Tablet, extended release Oral 10 mg Tablet, extended release Oral 5 mg/1 Tablet Oral 5 mg Gel Topical 10 % Gel Transdermal 100 mg/1g Gel Transdermal 28 mg/.92g Spray, metered Topical 100 mg / g Tablet Oral Gel Transdermal 4 mg/24hr Gel Transdermal 90.7 mg/g Patch, extended release Transdermal 3.9 mg/24hr Patch Transdermal 3.9 mg/24h Tablet Oral 10 MG Syrup Oral 0.1 g Syrup Oral 100.000 mg Tablet Oral 5.000 mg Solution Oral 5 mg/5mL Syrup Oral 5 mg/5mL Tablet Oral 2.5 mg/1 Tablet Oral 5 mg/1 Tablet, extended release Oral 15 mg/1 Tablet, film coated, extended release Oral 10 mg/1 Tablet, film coated, extended release Oral 15 mg/1 Tablet, film coated, extended release Oral 5 mg/1 Patch Transdermal 3.9 mg / 24 hour Patch Transdermal 3.9 mg/1d Tablet Oral 5 mg / tab Syrup Oral 5 mg / 5 mL Tablet Oral 2.5 mg Tablet, film coated Oral 5 mg Tablet Oral 5.510 mg Tablet Oral 10.000 mg Tablet, extended release Oral 15 mg Solution Intravesical 1 MG/ML Syrup Oral Tablet, extended release Oral 5 mg Patch Transdermal 73.5 mg - Prices
Unit description Cost Unit Oxybutynin chloride powder 54.47USD g Oxytrol 3.9 mg/24hr Patches 20.87USD patch Oxytrol 3.9 mg/24hr patch 20.06USD patch Gelnique 10% gel sachets 5.17USD g Ditropan XL 15 mg 24 Hour tablet 4.59USD tablet Ditropan XL 10 mg 24 Hour tablet 4.47USD tablet Ditropan XL 5 mg 24 Hour tablet 4.47USD tablet Ditropan xl 15 mg tablet 4.23USD tablet Ditropan xl 10 mg tablet 4.13USD tablet Ditropan xl 5 mg tablet 4.13USD tablet Ditropan xl 5 mg tablet sa 4.13USD tablet Oxybutynin Chloride 15 mg 24 Hour tablet 3.5USD tablet Oxybutynin Chloride 10 mg 24 Hour tablet 3.42USD tablet Oxybutynin Chloride 5 mg 24 Hour tablet 3.2USD tablet Ditropan 5 mg tablet 1.15USD tablet Oxybutynin Chloride 5 mg tablet 0.57USD tablet Ditropan 5 mg/5ml Syrup 0.26USD ml Apo-Oxybutynin 5 mg Tablet 0.26USD tablet Mylan-Oxybutynin 5 mg Tablet 0.26USD tablet Novo-Oxybutynin 5 mg Tablet 0.26USD tablet Nu-Oxybutyn 5 mg Tablet 0.26USD tablet Pms-Oxybutynin 5 mg Tablet 0.26USD tablet Oxybutynin Chloride 5 mg/5ml Syrup 0.21USD ml Oxybutynin 5 mg tablet 0.17USD tablet Pms-Oxybutynin 2.5 mg Tablet 0.14USD tablet Pms-Oxybutynin 1 mg/ml Syrup 0.08USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5164190 No 1992-11-17 2010-12-11 US CA2218714 No 2005-08-23 2016-05-08 Canada US6743441 No 2004-06-01 2020-04-26 US US7081249 No 2006-07-25 2020-04-26 US US7081250 No 2006-07-25 2020-04-26 US US7081251 No 2006-07-25 2020-04-26 US US7081252 No 2006-07-25 2020-04-26 US US7179483 No 2007-02-20 2020-04-26 US US7198801 No 2007-04-03 2022-06-25 US US7029694 No 2006-04-18 2020-04-26 US US8241662 No 2012-08-14 2020-04-26 US US8920392 No 2014-12-30 2031-03-26 US US9259388 No 2016-02-16 2029-11-06 US US6262115 Yes 2001-07-17 2015-11-22 US US5912268 Yes 1999-06-15 2015-11-22 US US5840754 Yes 1998-11-24 2015-11-22 US US5674895 Yes 1997-10-07 2015-11-22 US US10272061 No 2019-04-30 2020-04-26 US US10449173 No 2019-10-22 2029-11-06 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 122-124 https://www.chemicalbook.com/ChemicalProductProperty_US_CB0178112.aspx water solubility 50 mg/mL https://www.chemicalbook.com/ChemicalProductProperty_US_CB0178112.aspx logP 4.3 http://www.hmdb.ca/metabolites/HMDB0015195 logS -4.6 http://www.hmdb.ca/metabolites/HMDB0015195 pKa 8.04 https://www.chemicalbook.com/ChemicalProductProperty_US_CB2767266.aspx - Predicted Properties
Property Value Source Water Solubility 0.01 mg/mL ALOGPS logP 4.36 ALOGPS logP 4.44 Chemaxon logS -4.6 ALOGPS pKa (Strongest Acidic) 11.53 Chemaxon pKa (Strongest Basic) 8.77 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 49.77 Å2 Chemaxon Rotatable Bond Count 10 Chemaxon Refractivity 105.26 m3·mol-1 Chemaxon Polarizability 41.37 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9225 Blood Brain Barrier + 0.9418 Caco-2 permeable + 0.5989 P-glycoprotein substrate Substrate 0.7244 P-glycoprotein inhibitor I Inhibitor 0.6809 P-glycoprotein inhibitor II Inhibitor 0.7244 Renal organic cation transporter Non-inhibitor 0.558 CYP450 2C9 substrate Non-substrate 0.812 CYP450 2D6 substrate Non-substrate 0.7985 CYP450 3A4 substrate Non-substrate 0.5213 CYP450 1A2 substrate Inhibitor 0.9106 CYP450 2C9 inhibitor Inhibitor 0.8949 CYP450 2D6 inhibitor Inhibitor 0.8932 CYP450 2C19 inhibitor Inhibitor 0.8994 CYP450 3A4 inhibitor Inhibitor 0.796 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.7137 Ames test Non AMES toxic 0.9132 Carcinogenicity Non-carcinogens 0.7038 Biodegradation Not ready biodegradable 0.9878 Rat acute toxicity 2.9059 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9548 hERG inhibition (predictor II) Inhibitor 0.7337
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 199.5471772 predictedDarkChem Lite v0.1.0 [M-H]- 183.7358 predictedDeepCCS 1.0 (2019) [M+H]+ 200.2975772 predictedDarkChem Lite v0.1.0 [M+H]+ 186.0938 predictedDeepCCS 1.0 (2019) [M+Na]+ 200.4172772 predictedDarkChem Lite v0.1.0 [M+Na]+ 192.47394 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
- Baldwin CM, Keating GM: Transdermal oxybutynin. Drugs. 2009;69(3):327-37. doi: 10.2165/00003495-200969030-00008. [Article]
- Ito Y, Oyunzul L, Yoshida A, Fujino T, Noguchi Y, Yuyama H, Ohtake A, Suzuki M, Sasamata M, Matsui M, Yamada S: Comparison of muscarinic receptor selectivity of solifenacin and oxybutynin in the bladder and submandibular gland of muscarinic receptor knockout mice. Eur J Pharmacol. 2009 Aug 1;615(1-3):201-6. doi: 10.1016/j.ejphar.2009.04.068. Epub 2009 May 13. [Article]
- Sinha S, Gupta S, Malhotra S, Krishna NS, Meru AV, Babu V, Bansal V, Garg M, Kumar N, Chugh A, Ray A: AE9C90CB: a novel, bladder-selective muscarinic receptor antagonist for the treatment of overactive bladder. Br J Pharmacol. 2010 Jul;160(5):1119-27. doi: 10.1111/j.1476-5381.2010.00752.x. [Article]
- Oki T, Kageyama A, Takagi Y, Uchida S, Yamada S: Comparative evaluation of central muscarinic receptor binding activity by oxybutynin, tolterodine and darifenacin used to treat overactive bladder. J Urol. 2007 Feb;177(2):766-70. [Article]
- Maruyama S, Oki T, Otsuka A, Shinbo H, Ozono S, Kageyama S, Mikami Y, Araki I, Takeda M, Masuyama K, Yamada S: Human muscarinic receptor binding characteristics of antimuscarinic agents to treat overactive bladder. J Urol. 2006 Jan;175(1):365-9. [Article]
- Yarker YE, Goa KL, Fitton A: Oxybutynin. A review of its pharmacodynamic and pharmacokinetic properties, and its therapeutic use in detrusor instability. Drugs Aging. 1995 Mar;6(3):243-62. doi: 10.2165/00002512-199506030-00007. [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]
- Jennifer Dwyer; Chad A. LaGrange (2019). Oxybutinin. StatPearls Publishing.
- 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 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
- Dmochowski R: Improving the tolerability of anticholinergic agents in the treatment of overactive bladder. Drug Saf. 2005;28(7):583-600. [Article]
- Nelson CP, Nahorski SR, Challiss RA: Constitutive activity and inverse agonism at the M2 muscarinic acetylcholine receptor. J Pharmacol Exp Ther. 2006 Jan;316(1):279-88. Epub 2005 Sep 27. [Article]
- Ito Y, Oyunzul L, Yoshida A, Fujino T, Noguchi Y, Yuyama H, Ohtake A, Suzuki M, Sasamata M, Matsui M, Yamada S: Comparison of muscarinic receptor selectivity of solifenacin and oxybutynin in the bladder and submandibular gland of muscarinic receptor knockout mice. Eur J Pharmacol. 2009 Aug 1;615(1-3):201-6. doi: 10.1016/j.ejphar.2009.04.068. Epub 2009 May 13. [Article]
- Sinha S, Gupta S, Malhotra S, Krishna NS, Meru AV, Babu V, Bansal V, Garg M, Kumar N, Chugh A, Ray A: AE9C90CB: a novel, bladder-selective muscarinic receptor antagonist for the treatment of overactive bladder. Br J Pharmacol. 2010 Jul;160(5):1119-27. doi: 10.1111/j.1476-5381.2010.00752.x. [Article]
- Oki T, Kageyama A, Takagi Y, Uchida S, Yamada S: Comparative evaluation of central muscarinic receptor binding activity by oxybutynin, tolterodine and darifenacin used to treat overactive bladder. J Urol. 2007 Feb;177(2):766-70. [Article]
- Yarker YE, Goa KL, Fitton A: Oxybutynin. A review of its pharmacodynamic and pharmacokinetic properties, and its therapeutic use in detrusor instability. Drugs Aging. 1995 Mar;6(3):243-62. doi: 10.2165/00002512-199506030-00007. [Article]
- Jennifer Dwyer; Chad A. LaGrange (2019). Oxybutinin. StatPearls Publishing.
- 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
- G protein-coupled acetylcholine receptor activity
- Gene Name
- CHRM1
- Uniprot ID
- P11229
- Uniprot Name
- Muscarinic acetylcholine receptor M1
- Molecular Weight
- 51420.375 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Sinha S, Gupta S, Malhotra S, Krishna NS, Meru AV, Babu V, Bansal V, Garg M, Kumar N, Chugh A, Ray A: AE9C90CB: a novel, bladder-selective muscarinic receptor antagonist for the treatment of overactive bladder. Br J Pharmacol. 2010 Jul;160(5):1119-27. doi: 10.1111/j.1476-5381.2010.00752.x. [Article]
- Oki T, Kageyama A, Takagi Y, Uchida S, Yamada S: Comparative evaluation of central muscarinic receptor binding activity by oxybutynin, tolterodine and darifenacin used to treat overactive bladder. J Urol. 2007 Feb;177(2):766-70. [Article]
- Maruyama S, Oki T, Otsuka A, Shinbo H, Ozono S, Kageyama S, Mikami Y, Araki I, Takeda M, Masuyama K, Yamada S: Human muscarinic receptor binding characteristics of antimuscarinic agents to treat overactive bladder. J Urol. 2006 Jan;175(1):365-9. [Article]
- Yarker YE, Goa KL, Fitton A: Oxybutynin. A review of its pharmacodynamic and pharmacokinetic properties, and its therapeutic use in detrusor instability. Drugs Aging. 1995 Mar;6(3):243-62. doi: 10.2165/00002512-199506030-00007. [Article]
- Jennifer Dwyer; Chad A. LaGrange (2019). Oxybutinin. StatPearls Publishing.
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- 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
- Yaich M, Popon M, Medard Y, Aigrain EJ: In-vitro cytochrome P450 dependent metabolism of oxybutynin to N-deethyloxybutynin in humans. Pharmacogenetics. 1998 Oct;8(5):449-51. [Article]
- Lukkari E, Taavitsainen P, Juhakoski A, Pelkonen O: Cytochrome P450 specificity of metabolism and interactions of oxybutynin in human liver microsomes. Pharmacol Toxicol. 1998 Apr;82(4):161-6. doi: 10.1111/j.1600-0773.1998.tb01418.x. [Article]
- Kennelly MJ: A comparative review of oxybutynin chloride formulations: pharmacokinetics and therapeutic efficacy in overactive bladder. Rev Urol. 2010 Winter;12(1):12-9. [Article]
- McCrery RJ, Appell RA: Oxybutynin: an overview of the available formulations. Ther Clin Risk Manag. 2006 Mar;2(1):19-24. [Article]
- Ditropan XL FDA label [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:11093772, PubMed:14559847, PubMed:15766564, PubMed:19965576, PubMed:7574697). 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:11093772, PubMed:14559847, PubMed:15766564, PubMed:19965576, PubMed:7574697). Primarily catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) with a preference for the last double bond (PubMed:15766564, PubMed:19965576, PubMed:7574697). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes all trans-retinoic acid toward its 4-hydroxylated form (PubMed:11093772). Displays 16-alpha hydroxylase activity toward estrogen steroid hormones, 17beta-estradiol (E2) and estrone (E1) (PubMed:14559847). Plays a role in the oxidative metabolism of xenobiotics. It is the principal enzyme responsible for the metabolism of the anti-cancer drug paclitaxel (taxol) (PubMed:26427316)
- Specific Function
- arachidonic acid epoxygenase activity
- Gene Name
- CYP2C8
- Uniprot ID
- P10632
- Uniprot Name
- Cytochrome P450 2C8
- Molecular Weight
- 55824.275 Da
References
- Walsky RL, Gaman EA, Obach RS: Examination of 209 drugs for inhibition of cytochrome P450 2C8. J Clin Pharmacol. 2005 Jan;45(1):68-78. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- 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
- Lukkari E, Taavitsainen P, Juhakoski A, Pelkonen O: Cytochrome P450 specificity of metabolism and interactions of oxybutynin in human liver microsomes. Pharmacol Toxicol. 1998 Apr;82(4):161-6. doi: 10.1111/j.1600-0773.1998.tb01418.x. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of steroid hormones and vitamins (PubMed:10681376, PubMed:11093772, PubMed:12865317, PubMed:2732228). 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:10681376, PubMed:11093772, PubMed:12865317, PubMed:2732228). Exhibits high catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes 6beta-hydroxylation of the steroid hormones testosterone, progesterone, and androstenedione (PubMed:2732228). Catalyzes the oxidative conversion 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 all trans-retinoic acid (atRA) to 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Also involved in the oxidative metabolism of xenobiotics, including calcium channel blocking drug nifedipine and immunosuppressive drug cyclosporine (PubMed:2732228)
- Specific Function
- aromatase activity
- Gene Name
- CYP3A5
- Uniprot ID
- P20815
- Uniprot Name
- Cytochrome P450 3A5
- Molecular Weight
- 57108.065 Da
References
- Lukkari E, Taavitsainen P, Juhakoski A, Pelkonen O: Cytochrome P450 specificity of metabolism and interactions of oxybutynin in human liver microsomes. Pharmacol Toxicol. 1998 Apr;82(4):161-6. doi: 10.1111/j.1600-0773.1998.tb01418.x. [Article]
- Mizushima H, Takanaka K, Abe K, Fukazawa I, Ishizuka H: Stereoselective pharmacokinetics of oxybutynin and N-desethyloxybutynin in vitro and in vivo. Xenobiotica. 2007 Jan;37(1):59-73. doi: 10.1080/00498250600976088. [Article]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Functions as a transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in the body. Appears to function in modulating the activity of the immune system during the acute-phase reaction
- Specific Function
- Not Available
- Gene Name
- ORM1
- Uniprot ID
- P02763
- Uniprot Name
- Alpha-1-acid glycoprotein 1
- Molecular Weight
- 23539.43 Da
References
- Shibukawa A, Ishizawa N, Kimura T, Sakamoto Y, Ogita K, Matsuo Y, Kuroda Y, Matayatsu C, Nakagawa T, Wainer IW: Plasma protein binding study of oxybutynin by high-performance frontal analysis. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Feb 25;768(1):177-88. [Article]
- Shibukaw A, Yoshikawa Y, Kimura T, Kuroda Y, Nakagawa T, Wainer IW: Binding study of desethyloxybutynin using high-performance frontal analysis method. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Feb 25;768(1):189-97. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Binds water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs (Probable). Its main function is the regulation of the colloidal osmotic pressure of blood (Probable). Major zinc transporter in plasma, typically binds about 80% of all plasma zinc (PubMed:19021548). Major calcium and magnesium transporter in plasma, binds approximately 45% of circulating calcium and magnesium in plasma (By similarity). Potentially has more than two calcium-binding sites and might additionally bind calcium in a non-specific manner (By similarity). The shared binding site between zinc and calcium at residue Asp-273 suggests a crosstalk between zinc and calcium transport in the blood (By similarity). The rank order of affinity is zinc > calcium > magnesium (By similarity). Binds to the bacterial siderophore enterobactin and inhibits enterobactin-mediated iron uptake of E.coli from ferric transferrin, and may thereby limit the utilization of iron and growth of enteric bacteria such as E.coli (PubMed:6234017). Does not prevent iron uptake by the bacterial siderophore aerobactin (PubMed:6234017)
- Specific Function
- antioxidant activity
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Albumin
- Molecular Weight
- 69365.94 Da
References
- Shibukawa A, Ishizawa N, Kimura T, Sakamoto Y, Ogita K, Matsuo Y, Kuroda Y, Matayatsu C, Nakagawa T, Wainer IW: Plasma protein binding study of oxybutynin by high-performance frontal analysis. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Feb 25;768(1):177-88. [Article]
- Shibukaw A, Yoshikawa Y, Kimura T, Kuroda Y, Nakagawa T, Wainer IW: Binding study of desethyloxybutynin using high-performance frontal analysis method. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Feb 25;768(1):189-97. [Article]
Drug created at June 13, 2005 13:24 / Updated at October 07, 2024 17:54