oxybutynin Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
spasmolytics with a papaverine-like action 2028 5633-20-5

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • oxybutynin hydrochloride
  • oxybutynin
  • oxybutynin chloride
  • oxytrol
  • ditropan
  • kentera
  • oxybutynin HCl
Oxybutynin acts as a competitive antagonist of acetylcholine at post-ganglionic muscarinic receptors, resulting in relaxation of bladder smooth muscle. Oxybutynin is a racemic (50:50) mixture of R- and S-isomers. Antimuscarinic activity resides predominantly in the R-isomer. The R-isomer of oxybutynin shows greater selectivity for the M1 and M3 muscarinic subtypes (predominant in bladder detrusor muscle and parotid gland) compared to the M2 subtype (predominant in cardiac tissue).
  • Molecular weight: 357.49
  • Formula: C22H31NO3
  • CLOGP: 4.69
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 1
  • TPSA: 49.77
  • ALOGS: -4.55
  • ROTB: 10

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
15 mg O
3.90 mg TD

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.80 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0.50 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.93 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 6 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.85 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 5.10 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.00 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 7.20 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
July 16, 1975 FDA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug ineffective 267.95 32.67 123 837 101501 2255624
Application site erythema 252.43 32.67 46 914 1234 2355891
Dry mouth 209.77 32.67 55 905 8198 2348927
Completed suicide 202.98 32.67 66 894 20968 2336157
Drug hypersensitivity 155.06 32.67 67 893 46576 2310549
Application site pruritus 143.45 32.67 27 933 859 2356266
Product adhesion issue 140.13 32.67 28 932 1224 2355901
Application site rash 94.70 32.67 18 942 601 2356524
Pruritus 86.73 32.67 44 916 43296 2313829
Confusional state 77.21 32.67 34 926 24310 2332815
Urinary retention 76.56 32.67 21 939 3646 2353479
Toxicity to various agents 73.54 32.67 36 924 32718 2324407
Cardio-respiratory arrest 65.23 32.67 23 937 9123 2348002
Hyponatraemia 63.79 32.67 25 935 13300 2343825
Fall 61.24 32.67 36 924 47063 2310062
Hallucination 56.22 32.67 20 940 8128 2348997
Constipation 55.20 32.67 26 934 21603 2335522
Skin irritation 53.72 32.67 13 947 1372 2355753
Pollakiuria 53.61 32.67 16 944 3740 2353385
Respiratory arrest 53.60 32.67 18 942 6160 2350965
Erythema 51.47 32.67 26 934 25133 2331992
Product administered at inappropriate site 50.73 32.67 11 949 712 2356413
Somnolence 50.18 32.67 25 935 23460 2333665
Application site irritation 49.20 32.67 10 950 472 2356653
Rash 48.70 32.67 34 926 59524 2297601
Hallucination, visual 48.25 32.67 14 946 2965 2354160
Therapeutic product effect decreased 47.26 32.67 19 941 10770 2346355
Application site vesicles 44.48 32.67 9 951 415 2356710
Product complaint 42.45 32.67 14 946 4524 2352601
Overdose 41.93 32.67 21 939 19886 2337239
Hypertension 41.03 32.67 23 937 27338 2329787
Product quality issue 40.38 32.67 17 943 10812 2346313
Poisoning 40.17 32.67 12 948 2808 2354317
Dizziness 39.95 32.67 30 930 58635 2298490
Cerebral atrophy 38.56 32.67 9 951 812 2356313
Vision blurred 38.50 32.67 18 942 14650 2342475
Urinary incontinence 35.37 32.67 12 948 4221 2352904
Porphyria acute 35.30 32.67 6 954 104 2357021
Cardiac arrest 35.14 32.67 17 943 14913 2342212

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Completed suicide 245.10 38.66 70 463 16242 1730006
Dry mouth 167.98 38.66 39 494 3874 1742374
Confusional state 140.51 38.66 49 484 21229 1725019
Urinary retention 92.90 38.66 26 507 5369 1740879
Constipation 70.37 38.66 27 506 14973 1731275
Toxicity to various agents 59.09 38.66 29 504 29112 1717136
Muscle spasticity 54.31 38.66 13 520 1436 1744812
Agitation 45.06 38.66 18 515 11008 1735240
Vision blurred 42.38 38.66 16 517 8407 1737841
Hepatitis acute 40.55 38.66 10 523 1247 1745001

Pharmacologic Action:

SourceCodeDescription
ATC G04BD04 GENITO URINARY SYSTEM AND SEX HORMONES
UROLOGICALS
UROLOGICALS
Drugs for urinary frequency and incontinence
MeSH PA D018678 Cholinergic Agents
MeSH PA D018680 Cholinergic Antagonists
MeSH PA D018727 Muscarinic Antagonists
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D010276 Parasympatholytics
MeSH PA D018373 Peripheral Nervous System Agents
CHEBI has role CHEBI:50370 parasympatholytic
CHEBI has role CHEBI:53784 antispasmodic drug
CHEBI has role CHEBI:51371 muscle relaxant
CHEBI has role CHEBI:36333 local anaesthetic
CHEBI has role CHEBI:48876 muscarinic antagonist
FDA EPC N0000175700 Cholinergic Muscarinic Antagonist
FDA MoA N0000000125 Cholinergic Muscarinic Antagonists
MeSH PA D064804 Urological Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Urgent desire to urinate indication 75088002
Urge incontinence of urine indication 87557004
Bladder muscle dysfunction - overactive indication 236633002
Neurogenic bladder indication 398064005
Increased Urinary Frequency indication
Sinus tachycardia contraindication 11092001
Severe chronic ulcerative colitis contraindication 14311001
Toxic megacolon contraindication 28536002 DOID:1770
Atony of colon contraindication 29479008
Hyperthyroidism contraindication 34486009 DOID:7998
Hypertensive disorder contraindication 38341003 DOID:10763
Conduction disorder of the heart contraindication 44808001
Chronic heart failure contraindication 48447003
Paralytic ileus contraindication 55525008 DOID:8442
Ulcerative colitis contraindication 64766004 DOID:8577
Hiatal hernia contraindication 84089009 DOID:12642
Kidney disease contraindication 90708001 DOID:557
Myasthenia gravis contraindication 91637004 DOID:437
Gastrointestinal obstruction contraindication 126765001
Gastroesophageal reflux disease contraindication 235595009 DOID:8534
Disease of liver contraindication 235856003 DOID:409
Bladder outflow obstruction contraindication 236645006
Benign prostatic hyperplasia contraindication 266569009
Retention of urine contraindication 267064002
Drowsy contraindication 271782001
Gastric retention contraindication 307227006
Angle-closure glaucoma contraindication 392291006 DOID:13550
Disorder of coronary artery contraindication 414024009
Gastrointestinal hypomotility contraindication 421807004

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 7.67 Basic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
3.9MG/24HR OXYTROL ALLERGAN N021351 Feb. 26, 2003 RX FILM, EXTENDED RELEASE TRANSDERMAL 6743441 April 26, 2020 TREATMENT OF PATIENTS WITH AN OVERACTIVE BLADDER WITH SYMPTOMS OF URINARY FREQUENCY, URGENCY, OR URGE INCONTINENCE
3.9MG/24HR OXYTROL ALLERGAN N021351 Feb. 26, 2003 RX FILM, EXTENDED RELEASE TRANSDERMAL 7081249 April 26, 2020 TREATMENT OF PATIENTS WITH AN OVERACTIVE BLADDER WITH SYMPTOMS OF URINARY FREQUENCY, URGENCY, OR URGE INCONTINENCE
3.9MG/24HR OXYTROL ALLERGAN N021351 Feb. 26, 2003 RX FILM, EXTENDED RELEASE TRANSDERMAL 7081250 April 26, 2020 TREATMENT OF PATIENTS WITH AN OVERACTIVE BLADDER WITH SYMPTOMS OF URINARY FREQUENCY, URGENCY, OR URGE INCONTINENCE
3.9MG/24HR OXYTROL ALLERGAN N021351 Feb. 26, 2003 RX FILM, EXTENDED RELEASE TRANSDERMAL 7081251 April 26, 2020 TREATMENT OF PATIENTS WITH AN OVERACTIVE BLADDER WITH SYMPTOMS OF URINARY FREQUENCY, URGENCY, OR URGE INCONTINENCE
3.9MG/24HR OXYTROL ALLERGAN N021351 Feb. 26, 2003 RX FILM, EXTENDED RELEASE TRANSDERMAL 7081252 April 26, 2020 TREATMENT OF PATIENTS WITH AN OVERACTIVE BLADDER WITH SYMPTOMS OF URINARY FREQUENCY, URGENCY, OR URGE INCONTINENCE
3.9MG/24HR OXYTROL ALLERGAN N021351 Feb. 26, 2003 RX FILM, EXTENDED RELEASE TRANSDERMAL 7179483 April 26, 2020 TREATMENT OF PATIENTS WITH AN OVERACTIVE BLADDER WITH SYMPTOMS OF URINARY FREQUENCY, URGENCY, OR URGE INCONTINENCE
10% (100MG/PACKET) GELNIQUE ALLERGAN N022204 Jan. 27, 2009 RX GEL TRANSDERMAL 10272061 April 26, 2020 TREATMENT OF PATIENTS WITH AN OVERACTIVE BLADDER WITH SYMPTOMS OF URINARY FREQUENCY, URGENCY OR URGE INCONTINENCE
10% (100MG/PACKET) GELNIQUE ALLERGAN N022204 Jan. 27, 2009 RX GEL TRANSDERMAL 7029694 April 26, 2020 TREATMENT OF PATIENTS WITH AN OVERACTIVE BLADDER WITH SYMPTOMS OF URINARY FREQUENCY, URGENCY, OR URGE INCONTINENCE
10% (100MG/PACKET) GELNIQUE ALLERGAN N022204 Jan. 27, 2009 RX GEL TRANSDERMAL 7179483 April 26, 2020 TREATMENT OF PATIENTS WITH AN OVERACTIVE BLADDER WITH SYMPTOMS OF URINARY FREQUENCY, URGENCY, OR URGE INCONTINENCE
10% (100MG/PACKET) GELNIQUE ALLERGAN N022204 Jan. 27, 2009 RX GEL TRANSDERMAL 8241662 April 26, 2020 TREATMENT OF PATIENTS WITH AN OVERACTIVE BLADDER WITH SYMPTOMS OF URINARY FREQUENCY, URGENCY, OR URGE INCONTINENCE
3.9MG/24HR OXYTROL FOR WOMEN ALLERGAN N202211 Jan. 25, 2013 OTC FILM, EXTENDED RELEASE TRANSDERMAL 6743441 April 26, 2020 TREATMENT OF PATIENTS WITH AN OVERACTIVE BLADDER
3.9MG/24HR OXYTROL FOR WOMEN ALLERGAN N202211 Jan. 25, 2013 OTC FILM, EXTENDED RELEASE TRANSDERMAL 7081249 April 26, 2020 TREATMENT OF PATIENTS WITH AN OVERACTIVE BLADDER
3.9MG/24HR OXYTROL FOR WOMEN ALLERGAN N202211 Jan. 25, 2013 OTC FILM, EXTENDED RELEASE TRANSDERMAL 7081250 April 26, 2020 TREATMENT OF PATIENTS WITH AN OVERACTIVE BLADDER
3.9MG/24HR OXYTROL FOR WOMEN ALLERGAN N202211 Jan. 25, 2013 OTC FILM, EXTENDED RELEASE TRANSDERMAL 7081251 April 26, 2020 TREATMENT OF PATIENTS WITH AN OVERACTIVE BLADDER
3.9MG/24HR OXYTROL FOR WOMEN ALLERGAN N202211 Jan. 25, 2013 OTC FILM, EXTENDED RELEASE TRANSDERMAL 7081252 April 26, 2020 TREATMENT OF PATIENTS WITH AN OVERACTIVE BLADDER
3.9MG/24HR OXYTROL FOR WOMEN ALLERGAN N202211 Jan. 25, 2013 OTC FILM, EXTENDED RELEASE TRANSDERMAL 7179483 April 26, 2020 TREATMENT OF PATIENTS WITH AN OVERACTIVE BLADDER
3% GELNIQUE 3% ALLERGAN N202513 Dec. 7, 2011 DISCN GEL, METERED TRANSDERMAL 7029694 April 26, 2020 TREATMENT OF PATIENTS WITH AN OVERACTIVE BLADDER WITH SYMPTOMS OF URINARY FREQUENCY, URGENCY, OR URGE INCONTINENCE
3% GELNIQUE 3% ALLERGAN N202513 Dec. 7, 2011 DISCN GEL, METERED TRANSDERMAL 7179483 April 26, 2020 TREATMENT OF PATIENTS WITH AN OVERACTIVE BLADDER WITH SYMPTOMS OF URINARY FREQUENCY, URGENCY, OR URGE INCONTINENCE
3% GELNIQUE 3% ALLERGAN N202513 Dec. 7, 2011 DISCN GEL, METERED TRANSDERMAL 8241662 April 26, 2020 TREATMENT OF PATIENTS WITH AN OVERACTIVE BLADDER WITH SYMPTOMS OF URINARY FREQUENCY, URGENCY, OR URGE INCONTINENCE
10% (100MG/PACKET) GELNIQUE ALLERGAN N022204 Jan. 27, 2009 RX GEL TRANSDERMAL 10449173 Nov. 6, 2029 TREATMENT OF PATIENTS WITH AN OVERACTIVE BLADDER WITH SYMPTOMS OF URINARY FREQUENCY, URGENCY, OR URGE INCONTINENCE WITH A SINGLE UNIT DOSE OF 10% OXYBUTYNIN CHLORIDE GEL
10% (100MG/PACKET) GELNIQUE ALLERGAN N022204 Jan. 27, 2009 RX GEL TRANSDERMAL 9259388 Nov. 6, 2029 TREATMENT OF OVERACTIVE BLADDER BY APPLICATION OF OXYBUTYNIN CHLORIDE GEL TO SKIN
10% (100MG/PACKET) GELNIQUE ALLERGAN N022204 Jan. 27, 2009 RX GEL TRANSDERMAL 8920392 March 26, 2031 TREATMENT OF OVERACTIVE BLADDER BY APPLICATION OF OXYBUTYNIN CHLORIDE GEL TO SKIN

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Muscarinic acetylcholine receptor M1 GPCR ANTAGONIST Ki 9 CHEMBL DRUG LABEL
Muscarinic acetylcholine receptor M3 GPCR ANTAGONIST Ki 9.11 CHEMBL DRUG LABEL
5-hydroxytryptamine receptor 2B GPCR Ki 6.30 DRUG MATRIX
D(3) dopamine receptor GPCR Ki 6.84 DRUG MATRIX
Sodium-dependent dopamine transporter Transporter Ki 7.17 DRUG MATRIX
Cytochrome P450 2C19 Enzyme IC50 6.22 DRUG MATRIX
Muscarinic acetylcholine receptor M2 GPCR ANTAGONIST Ki 8.09 CHEMBL
Muscarinic acetylcholine receptor M4 GPCR Ki 8.44 CHEMBL
Sigma non-opioid intracellular receptor 1 Membrane receptor Ki 7.99 DRUG MATRIX
Muscarinic acetylcholine receptor M5 GPCR Ki 7.85 CHEMBL
Sodium-dependent noradrenaline transporter Transporter Ki 5.59 DRUG MATRIX
Membrane-associated progesterone receptor component 1 Membrane receptor Ki 6.09 DRUG MATRIX
Muscarinic acetylcholine receptor M1 GPCR Ki 8.23 CHEMBL
Muscarinic acetylcholine receptor M3 GPCR Ki 9.02 CHEMBL
Muscarinic acetylcholine receptor M2 GPCR Ki 8.16 CHEMBL

External reference:

IDSource
4018815 VUID
N0000147118 NUI
C0134394 UMLSCUI
D00465 KEGG_DRUG
35768004 SNOMEDCT_US
4019869 VANDF
28244 MMSL
d00328 MMSL
32675 RXNORM
372717000 SNOMEDCT_US
004715 NDDF
CHEMBL1133 ChEMBL_ID
CHEMBL1231 ChEMBL_ID
DB01062 DRUGBANK_ID
K9P6MC7092 UNII
1354 INN_ID
1508-65-2 SECONDARY_CAS_RN
CHEBI:7856 CHEBI
4634 PUBCHEM_CID
359 IUPHAR_LIGAND_ID
C005419 MESH_SUPPLEMENTAL_RECORD_UI

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
GELNIQUE HUMAN PRESCRIPTION DRUG LABEL 1 0023-5812 GEL 100 mg TRANSDERMAL NDA 17 sections
GELNIQUE HUMAN PRESCRIPTION DRUG LABEL 1 0023-5861 GEL 100 mg TRANSDERMAL NDA 17 sections
OXYTROL HUMAN PRESCRIPTION DRUG LABEL 1 0023-6153 PATCH 3.90 mg TRANSDERMAL NDA 18 sections
Oxytrol for Women HUMAN OTC DRUG LABEL 1 0023-9637 PATCH 3.90 mg TRANSDERMAL NDA 8 sections
OXYBUTYNIN CHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 0093-5206 TABLET, EXTENDED RELEASE 5 mg ORAL ANDA 17 sections
OXYBUTYNIN CHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 0093-5207 TABLET, EXTENDED RELEASE 10 mg ORAL ANDA 17 sections
OXYBUTYNIN CHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 0093-5208 TABLET, EXTENDED RELEASE 15 mg ORAL ANDA 17 sections
OXYBUTYNIN CHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 0121-0671 SYRUP 5 mg ORAL ANDA 12 sections
OXYBUTYNIN CHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 0179-0187 TABLET, EXTENDED RELEASE 10 mg ORAL ANDA 17 sections
Oxybutynin Chloride HUMAN PRESCRIPTION DRUG LABEL 1 0603-4975 TABLET 5 mg ORAL ANDA 15 sections
Oxybutynin Chloride HUMAN PRESCRIPTION DRUG LABEL 1 0615-3512 TABLET 5 mg ORAL ANDA 13 sections
oxybutynin chloride HUMAN PRESCRIPTION DRUG LABEL 1 0615-7521 TABLET, EXTENDED RELEASE 15 mg ORAL NDA 12 sections
oxybutynin HUMAN PRESCRIPTION DRUG LABEL 1 0615-8219 TABLET, FILM COATED, EXTENDED RELEASE 5 mg ORAL ANDA 17 sections
Oxybutynin HUMAN PRESCRIPTION DRUG LABEL 1 0615-8220 TABLET, FILM COATED, EXTENDED RELEASE 10 mg ORAL ANDA 17 sections
Oxybutynin Chloride HUMAN PRESCRIPTION DRUG LABEL 1 0832-0038 TABLET 5 mg ORAL ANDA 14 sections
Oxybutynin Chloride HUMAN PRESCRIPTION DRUG LABEL 1 0904-2821 TABLET 5 mg ORAL ANDA 14 sections
Oxybutynin Chloride HUMAN PRESCRIPTION DRUG LABEL 1 0904-6570 TABLET, EXTENDED RELEASE 5 mg ORAL ANDA 16 sections
Oxybutynin Chloride HUMAN PRESCRIPTION DRUG LABEL 1 10135-609 TABLET, EXTENDED RELEASE 5 mg ORAL ANDA 17 sections
Oxybutynin Chloride HUMAN PRESCRIPTION DRUG LABEL 1 10135-610 TABLET, EXTENDED RELEASE 10 mg ORAL ANDA 17 sections
Oxybutynin Chloride HUMAN PRESCRIPTION DRUG LABEL 1 10135-611 TABLET, EXTENDED RELEASE 15 mg ORAL ANDA 17 sections
Oxybutynin Chloride HUMAN PRESCRIPTION DRUG LABEL 1 10135-640 TABLET 5 mg ORAL ANDA 14 sections
Oxybutynin Chloride HUMAN PRESCRIPTION DRUG LABEL 1 10147-0761 TABLET, EXTENDED RELEASE 5 mg ORAL NDA 17 sections
Oxybutynin Chloride HUMAN PRESCRIPTION DRUG LABEL 1 10147-0771 TABLET, EXTENDED RELEASE 10 mg ORAL NDA 17 sections
Oxybutynin Chloride HUMAN PRESCRIPTION DRUG LABEL 1 10544-518 TABLET 5 mg ORAL ANDA 15 sections
Oxybutynin Chloride HUMAN PRESCRIPTION DRUG LABEL 1 10544-559 TABLET 5 mg ORAL ANDA 14 sections
Oxybutynin Chloride HUMAN PRESCRIPTION DRUG LABEL 1 10702-201 TABLET 5 mg ORAL ANDA 13 sections
Oxybutynin Chloride HUMAN PRESCRIPTION DRUG LABEL 1 14539-653 TABLET 5 mg ORAL ANDA 13 sections
oxybutynin chloride HUMAN PRESCRIPTION DRUG LABEL 1 16729-317 TABLET, EXTENDED RELEASE 5 mg ORAL ANDA 17 sections
oxybutynin chloride HUMAN PRESCRIPTION DRUG LABEL 1 16729-318 TABLET, EXTENDED RELEASE 10 mg ORAL ANDA 17 sections
oxybutynin chloride HUMAN PRESCRIPTION DRUG LABEL 1 16729-319 TABLET, EXTENDED RELEASE 15 mg ORAL ANDA 17 sections