oxybutynin indications/contra

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

Drug dosage:

DoseUnitRoute
15 mg O
3.90 mg TD

Approvals:

DateAgencyCompanyOrphan
July 16, 1975 FDA

FDA Adverse Event Reporting System

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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
Dry mouth 344.63 33.78 84 1147 9738 3374890
Completed suicide 252.83 33.78 85 1146 31029 3353599
Drug ineffective 239.52 33.78 118 1113 115972 3268656
Application site erythema 225.77 33.78 45 1186 2022 3382606
Drug hypersensitivity 149.45 33.78 60 1171 35620 3349008
Urinary retention 144.26 33.78 40 1191 7532 3377096
Confusional state 142.38 33.78 59 1172 37939 3346689
Product adhesion issue 127.25 33.78 27 1204 1643 3382985
Application site pruritus 125.00 33.78 26 1205 1436 3383192
Constipation 122.62 33.78 50 1181 30762 3353866
Application site rash 90.55 33.78 19 1212 1092 3383536
Pruritus 87.69 33.78 45 1186 46788 3337840
Psychotic disorder 78.91 33.78 26 1205 8708 3375920
Toxicity to various agents 78.87 33.78 42 1189 47012 3337616
Muscle spasticity 78.41 33.78 20 1211 2716 3381912
Product quality issue 75.19 33.78 34 1197 26701 3357927
Agitation 68.15 33.78 29 1202 19677 3364951
Fall 67.48 33.78 41 1190 58842 3325786
Hallucination 64.56 33.78 25 1206 13315 3371313
Cognitive disorder 61.43 33.78 21 1210 7853 3376775
Dizziness 60.00 33.78 42 1189 76470 3308158
Drug effect decreased 59.94 33.78 23 1208 11946 3372682
Pollakiuria 56.48 33.78 18 1213 5412 3379216
Urinary incontinence 54.67 33.78 18 1213 5994 3378634
Delirium 53.61 33.78 20 1211 9608 3375020
Vision blurred 52.13 33.78 24 1207 19565 3365063
Skin irritation 51.34 33.78 13 1218 1710 3382918
Urinary tract infection 49.67 33.78 27 1204 31301 3353327
Product administered at inappropriate site 46.26 33.78 11 1220 1114 3383514
Somnolence 46.23 33.78 26 1205 32178 3352450

Pharmacologic Action:

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SourceCodeDescription
ATC G04BD04 GENITO URINARY SYSTEM AND SEX HORMONES
UROLOGICALS
UROLOGICALS
Drugs for urinary frequency and incontinence
FDA EPC N0000175700 Cholinergic Muscarinic Antagonist
FDA MoA N0000000125 Cholinergic Muscarinic Antagonists
MeSH PA D001337 Autonomic Agents
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
MeSH PA D064804 Urological 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:48876 muscarinic antagonist

Drug Use (View source of the data)

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DiseaseRelationSNOMED_IDDOID
Urgent desire to urinate indication 75088002
Urge incontinence of urine indication 87557004
Bladder muscle dysfunction - overactive indication 236633002
Neurogenic bladder indication 398064005 DOID:12143
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:2527
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 DOID:2883
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

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Dissociation levelDissociation constantType (acidic/basic)
pKa1 7.67 Basic

Orange Book patent data (new drug applications)

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Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
3.9MG/24HR OXYTROL ALLERGAN SALES LLC 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 SALES LLC 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 SALES LLC 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 SALES LLC 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 SALES LLC 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 SALES LLC 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 SALES LLC 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 SALES LLC 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 SALES LLC 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 SALES LLC 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 SALES LLC 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 SALES LLC 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 SALES LLC 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 SALES LLC 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 SALES LLC N202211 Jan. 25, 2013 OTC FILM, EXTENDED RELEASE TRANSDERMAL 7179483 April 26, 2020 TREATMENT OF PATIENTS WITH AN OVERACTIVE BLADDER
3% GELNIQUE 3% ALLERGAN SALES LLC 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 SALES LLC 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 SALES LLC 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 SALES LLC 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 SALES LLC 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:

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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:

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IDSource
359 IUPHAR_LIGAND_ID
4018815 VUID
N0000147118 NUI
C0134394 UMLSCUI
D00465 KEGG_DRUG
DB01062 DRUGBANK_ID
4019869 VANDF
N0000179206 NDFRT
N0000147954 NDFRT
28244 MMSL
d00328 MMSL
32675 RXNORM
35768004 SNOMEDCT_US
372717000 SNOMEDCT_US
004715 NDDF
CHEMBL1133 ChEMBL_ID
CHEMBL1231 ChEMBL_ID
4634 PUBCHEM_CID
C005419 MESH_SUPPLEMENTAL_RECORD_UI
K9P6MC7092 UNII
1354 INN_ID
1508-65-2 SECONDARY_CAS_RN
CHEBI:7856 CHEBI

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
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
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 0378-6605 TABLET, FILM COATED, EXTENDED RELEASE 5 mg ORAL ANDA 16 sections
Oxybutynin Chloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-6610 TABLET, FILM COATED, EXTENDED RELEASE 10 mg ORAL ANDA 16 sections
Oxybutynin Chloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-6615 TABLET, FILM COATED, EXTENDED RELEASE 15 mg ORAL ANDA 16 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 0615-7519 TABLET, FILM COATED, EXTENDED RELEASE 5 mg ORAL ANDA 17 sections
Oxybutynin Chloride HUMAN PRESCRIPTION DRUG LABEL 1 0615-7520 TABLET, FILM COATED, EXTENDED RELEASE 10 mg ORAL ANDA 17 sections
oxybutynin chloride HUMAN PRESCRIPTION DRUG LABEL 1 0615-7521 TABLET, EXTENDED RELEASE 15 mg ORAL NDA 12 sections
Oxybutynin Chloride HUMAN PRESCRIPTION DRUG LABEL 1 0832-0038 TABLET 5 mg ORAL ANDA 13 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 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 10147-0781 TABLET, EXTENDED RELEASE 15 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 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