ChemSpider 2D Image | oxybutynin | C22H31NO3

oxybutynin

  • Molecular FormulaC22H31NO3
  • Average mass357.486 Da
  • Monoisotopic mass357.230408 Da
  • ChemSpider ID4473

More details:

Featured data source
The Merck Index Online

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

oxybutynin [INN] [USAN] [Wiki]
4-(Diethylamino)-2-butin-1-yl-cyclohexyl(hydroxy)phenylacetat [German] [ACD/IUPAC Name]
4-(Diethylamino)-2-butyn-1-yl cyclohexyl(hydroxy)phenylacetate [ACD/IUPAC Name]
4-(Diethylamino)but-2-in-1-ylcyclohexyl(hydroxy)phenylacetat
4-(diethylamino)but-2-yn-1-yl 2-cyclohexyl-2-hydroxy-2-phenylacetate
4-(Diethylamino)but-2-yn-1-yl cyclohexyl(hydroxy)phenylacetate
4-Diethylamino-2-butynyl phenyl cyclohexylglycolate
5633-20-5 [RN]
a-Cyclohexyl-a-hydroxybenzene acetic acid 4-(diethylamino)-2-butynyl ester
a-Phenylcyclohexaneglycolic acid 4-(diethylamino)-2-butynyl ester
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

39EY4NVB8T [DBID]
5BRQ29UUB7 [DBID]
C07360 [DBID]
CCRIS 1923 [DBID]
D00465 [DBID]
HSDB 3270 [DBID]
K9P6MC7092 [DBID]
Prestwick0_000287 [DBID]
Prestwick1_000287 [DBID]
SPBio_002413 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Safety:

      G04BD04 Wikidata Q1060922

    • Target Organs:

      AChR antagonist TargetMol T1049L

    • Chemical Class:

      A carboxylic ester resulting from the formal condensation of the carboxy group of cyclohexyl(hydroxy)phenylacetic acid with the hydroxy group of 4-(diethylamino)but-2-yn-1-ol. ChEBI CHEBI:144551
      A racemate comprising equimolar amounts of (R)-oxybutynin and esoxybutynin. An antispasmodic used for the treatment of overactive bladder. ChEBI CHEBI:7856

    • Bio Activity:

      GPCR/G protein; Neuronal Signaling; MedChem Express HY-B0267
      mAChR MedChem Express HY-B0267
      Muscarinic AChR TargetMol T1049L
      Neuroscience TargetMol T1049L
      Oxybutynin is an anticholinergic medication used to relieve urinary and bladder difficulties. MedChem Express
      Oxybutynin is an anticholinergic medication used to relieve urinary and bladder difficulties.;Target: mAChROxybutynin is an anticholinergic medication used to relieve urinary and bladder difficulties, including frequent urination and inability to control urination (urge incontinence), by decreasing muscle spasms of the bladder. Oxybutynin competitively antagonizes the M1, M2, and M3 subtypes of the muscarinic acetylcholine receptor. It also has direct spasmolytic effects on bladder smooth muscle as a calcium antagonist and local anesthetic, but at concentrations far above those used clinically. Oxybutynin is available orally in generic formulation or as the brand-names Ditropan, Lyrinel XL, or Ditrospam, as a transdermal patch under the brand name Oxytrol, and as a topical gel under the brand name Gelnique. Oxybutynin is also a possible treatment of hyperhidrosis (hyper-active sweating) [1-3]. MedChem Express HY-B0267
  • Gas Chromatography

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.1±0.1 g/cm3
Boiling Point: 494.4±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.3 mmHg at 25°C
Enthalpy of Vaporization: 80.2±3.0 kJ/mol
Flash Point: 252.8±28.7 °C
Index of Refraction: 1.546
Molar Refractivity: 103.1±0.3 cm3
#H bond acceptors: 4
#H bond donors: 1
#Freely Rotating Bonds: 10
#Rule of 5 Violations: 1
ACD/LogP: 5.19
ACD/LogD (pH 5.5): 2.04
ACD/BCF (pH 5.5): 4.97
ACD/KOC (pH 5.5): 20.25
ACD/LogD (pH 7.4): 3.72
ACD/BCF (pH 7.4): 242.20
ACD/KOC (pH 7.4): 985.82
Polar Surface Area: 50 Å2
Polarizability: 40.9±0.5 10-24cm3
Surface Tension: 45.6±3.0 dyne/cm
Molar Volume: 325.7±3.0 cm3

Predicted data is generated using the US Environmental Protection Agency�s EPISuite™ 

                        
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  3.96

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  445.87  (Adapted Stein & Brown method)
    Melting Pt (deg C):  185.84  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.69E-010  (Modified Grain method)
    Subcooled liquid VP: 8.09E-009 mm Hg (25 deg C, Mod-Grain method)

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  23.51
       log Kow used: 3.96 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  97.576 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Esters
       Benzyl Alcohols
       Propargyl Amines

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   6.80E-010  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.381E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.96  (KowWin est)
  Log Kaw used:  -7.556  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  11.516
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.4904
   Biowin2 (Non-Linear Model)     :   0.4662
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.1044  (months      )
   Biowin4 (Primary Survey Model) :   3.1244  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.3258
   Biowin6 (MITI Non-Linear Model):   0.0848
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.2759
 Ready Biodegradability Prediction:   NO

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  1.08E-006 Pa (8.09E-009 mm Hg)
  Log Koa (Koawin est  ): 11.516
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  2.78 
       Octanol/air (Koa) model:  0.0805 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.99 
       Mackay model           :  0.996 
       Octanol/air (Koa) model:  0.866 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 143.5417 E-12 cm3/molecule-sec
      Half-Life =     0.075 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.894 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     0.003000 E-17 cm3/molecule-sec
      Half-Life =   382.000 Days (at 7E11 mol/cm3)
   Fraction sorbed to airborne particulates (phi): 0.993 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1.364E+004
      Log Koc:  4.135 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  1.028E-002  L/mol-sec
  Kb Half-Life at pH 8:       2.135  years  
  Kb Half-Life at pH 7:      21.355  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 2.351 (BCF = 224.2)
       log Kow used: 3.96 (estimated)

 Volatilization from Water:
    Henry LC:  6.8E-010 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.628E+006  hours   (6.783E+004 days)
    Half-Life from Model Lake : 1.776E+007  hours   (7.4E+005 days)

 Removal In Wastewater Treatment:
    Total removal:              28.27  percent
    Total biodegradation:        0.31  percent
    Total sludge adsorption:    27.96  percent
    Total to Air:                0.00  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       0.0406          1.79         1000       
   Water     12.6            1.44e+003    1000       
   Soil      84              2.88e+003    1000       
   Sediment  3.42            1.3e+004     0          
     Persistence Time: 1.81e+003 hr

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