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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2021-09-14 14:58:38 UTC
HMDB IDHMDB0015195
Secondary Accession Numbers
  • HMDB15195
Metabolite Identification
Common NameOxybutynin
DescriptionOxybutynin, also known as ditropan or kentera, 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. Based on a literature review a significant number of articles have been published on Oxybutynin.
Structure
Data?1582753269
Synonyms
ValueSource
DitropanChEBI
KenteraChEBI
OxibutininaChEBI
OxybutynineChEBI
OxybutyninumChEBI
AnturolKegg
OxytrolKegg
4-(diethylamino)-2-Butynyl alpha-phenylcyclohexaneglycolic acid esterChEBI, HMDB
4-diethylamino-2-Butinyl alpha-cyclohexylmandelatChEBI, HMDB
4-diethylamino-2-Butynyl alpha-phenylcyclohexaneglycolateChEBI, HMDB
Benzeneacetic acid, alpha-cyclohexyl-alpha-hydroxy-, 4-(diethylamino)-2-butynyl esterChEBI, HMDB
Cyclohexaneglycolic acid, alpha-phenyl-, 4-(diethylamino)-2-butynyl esterChEBI, HMDB
4-(diethylamino)-2-Butynyl a-phenylcyclohexaneglycolate esterGenerator, HMDB
4-(diethylamino)-2-Butynyl a-phenylcyclohexaneglycolic acid esterGenerator, HMDB
4-(diethylamino)-2-Butynyl alpha-phenylcyclohexaneglycolate esterGenerator, HMDB
4-(diethylamino)-2-Butynyl α-phenylcyclohexaneglycolate esterGenerator, HMDB
4-(diethylamino)-2-Butynyl α-phenylcyclohexaneglycolic acid esterGenerator, HMDB
4-diethylamino-2-Butinyl a-cyclohexylmandelatGenerator, HMDB
4-diethylamino-2-Butinyl α-cyclohexylmandelatGenerator, HMDB
4-diethylamino-2-Butynyl a-phenylcyclohexaneglycolateGenerator, HMDB
4-diethylamino-2-Butynyl a-phenylcyclohexaneglycolic acidGenerator, HMDB
4-diethylamino-2-Butynyl alpha-phenylcyclohexaneglycolic acidGenerator, HMDB
4-diethylamino-2-Butynyl α-phenylcyclohexaneglycolateGenerator, HMDB
4-diethylamino-2-Butynyl α-phenylcyclohexaneglycolic acidGenerator, HMDB
Benzeneacetate, a-cyclohexyl-a-hydroxy-, 4-(diethylamino)-2-butynyl esterGenerator, HMDB
Benzeneacetate, alpha-cyclohexyl-alpha-hydroxy-, 4-(diethylamino)-2-butynyl esterGenerator, HMDB
Benzeneacetate, α-cyclohexyl-α-hydroxy-, 4-(diethylamino)-2-butynyl esterGenerator, HMDB
Benzeneacetic acid, a-cyclohexyl-a-hydroxy-, 4-(diethylamino)-2-butynyl esterGenerator, HMDB
Benzeneacetic acid, α-cyclohexyl-α-hydroxy-, 4-(diethylamino)-2-butynyl esterGenerator, HMDB
Cyclohexaneglycolate, a-phenyl-, 4-(diethylamino)-2-butynyl esterGenerator, HMDB
Cyclohexaneglycolate, alpha-phenyl-, 4-(diethylamino)-2-butynyl esterGenerator, HMDB
Cyclohexaneglycolate, α-phenyl-, 4-(diethylamino)-2-butynyl esterGenerator, HMDB
Cyclohexaneglycolic acid, a-phenyl-, 4-(diethylamino)-2-butynyl esterGenerator, HMDB
Cyclohexaneglycolic acid, α-phenyl-, 4-(diethylamino)-2-butynyl esterGenerator, HMDB
OxibutyninumHMDB
OxybutininHMDB
Oxybutynin baseHMDB
Oxybutynin chlorideHMDB, MeSH
Oxybutynin hydrochlorideHMDB, MeSH
Oxybutynin topical gelHMDB
Transdermal patchHMDB
Oxyb abzMeSH, HMDB
OxybugammaMeSH, HMDB
Oxybutin holstenMeSH, HMDB
RenamelMeSH, HMDB
RyolMeSH, HMDB
TavorMeSH, HMDB
GelniqueMeSH, HMDB
4-(diethylamino)-2-Butynyl-alpha-cyclohexyl-alpha-hydroxybenzeneacetateMeSH, HMDB
apo-OxybutyninMeSH, HMDB
ContiminMeSH, HMDB
DridaseMeSH, HMDB
DriptaneMeSH, HMDB
OxybutonMeSH, HMDB
Oxybutynin alMeSH, HMDB
Oxybutynin hexalMeSH, HMDB
Oxybutynin-ratiopharmMeSH, HMDB
OxymedinMeSH, HMDB
SpasytMeSH, HMDB
ZaturMeSH, HMDB
CystonormMeSH, HMDB
CystrinMeSH, HMDB
DresplanMeSH, HMDB
novo-OxybutyninMeSH, HMDB
Nu-oxybutynMeSH, HMDB
Oxybutynin azuMeSH, HMDB
Oxybutynin heumannMeSH, HMDB
PMS-OxybutyninMeSH, HMDB
Spasmex oxybutyninMeSH, HMDB
4-(diethylamino)-2-Butynyl-alpha-phenylcyclohexaneglycolateMeSH, HMDB
Gen-oxybutyninMeSH, HMDB
Oxybutynin stadaMeSH, HMDB
Oxybutynin-purenMeSH, HMDB
PollakisuMeSH, HMDB
Oxybutynin von CTMeSH, HMDB
Chemical FormulaC22H31NO3
Average Molecular Weight357.4864
Monoisotopic Molecular Weight357.230393863
IUPAC Name4-(diethylamino)but-2-yn-1-yl 2-cyclohexyl-2-hydroxy-2-phenylacetate
Traditional Nameoxybutynin
CAS Registry Number5633-20-5
SMILES
CCN(CC)CC#CCOC(=O)C(O)(C1CCCCC1)C1=CC=CC=C1
InChI Identifier
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
InChI KeyXIQVNETUBQGFHX-UHFFFAOYSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Monocyclic benzene moiety
  • Tertiary alcohol
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Aromatic alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point129 - 130 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.01 g/LNot Available
LogP4.3Not Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.01 g/LALOGPS
logP10(4.36) g/LALOGPS
logP10(4.44) g/LChemAxon
logS10(-4.6) g/LALOGPS
pKa (Strongest Acidic)11.53ChemAxon
pKa (Strongest Basic)8.77ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.77 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity105.26 m³·mol⁻¹ChemAxon
Polarizability41.25 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+186.26531661259
DarkChem[M-H]-185.07431661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Oxybutynin,1TMS,#1CCN(CC)CC#CCOC(=O)C(O[Si](C)(C)C)(C1=CC=CC=C1)C1CCCCC12592.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Oxybutynin,1TBDMS,#1CCN(CC)CC#CCOC(=O)C(O[Si](C)(C)C(C)(C)C)(C1=CC=CC=C1)C1CCCCC12827.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01062 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01062 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01062
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4473
KEGG Compound IDC07360
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOxybutynin
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID7856
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Tupker RA, Harmsze AM, Deneer VH: Oxybutynin therapy for generalized hyperhidrosis. Arch Dermatol. 2006 Aug;142(8):1065-6. [PubMed:16924061 ]
  2. Mijnhout GS, Kloosterman H, Simsek S, Strack van Schijndel RJ, Netelenbos JC: Oxybutynin: dry days for patients with hyperhidrosis. Neth J Med. 2006 Oct;64(9):326-8. [PubMed:17057269 ]
  3. Schollhammer M, Misery L: Treatment of hyperhidrosis with oxybutynin. Arch Dermatol. 2007 Apr;143(4):544-5. [PubMed:17438194 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. 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. [PubMed:9825837 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular weight:
57108.065
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular weight:
55824.275
References
  1. 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. [PubMed:15601807 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific 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
Gene Name:
CHRM3
Uniprot ID:
P20309
Molecular weight:
66127.4
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. 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. [PubMed:17016423 ]
  3. Baldwin CM, Keating GM: Transdermal oxybutynin. Drugs. 2009;69(3):327-37. doi: 10.2165/00003495-200969030-00008. [PubMed:19275276 ]
  4. 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. [PubMed:19446545 ]
  5. 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. [PubMed:20590605 ]
  6. 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. [PubMed:17222678 ]
  7. 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. [PubMed:16406943 ]
  8. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific 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
Gene Name:
CHRM1
Uniprot ID:
P11229
Molecular weight:
51420.4
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. 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. [PubMed:17016423 ]
  3. 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. [PubMed:20590605 ]
  4. 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. [PubMed:17222678 ]
  5. 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. [PubMed:16406943 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific 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
Gene Name:
CHRM2
Uniprot ID:
P08172
Molecular weight:
51714.6
References
  1. Dmochowski R: Improving the tolerability of anticholinergic agents in the treatment of overactive bladder. Drug Saf. 2005;28(7):583-600. [PubMed:15963006 ]
  2. 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. [PubMed:16188951 ]
  3. 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. [PubMed:19446545 ]
  4. 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. [PubMed:20590605 ]
  5. 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. [PubMed:17222678 ]