ChemSpider 2D Image | Zolmitriptan | C16H21N3O2

Zolmitriptan

  • Molecular FormulaC16H21N3O2
  • Average mass287.357 Da
  • Monoisotopic mass287.163391 Da
  • ChemSpider ID54844

  • defined stereocentres - 1 of 1 defined stereocentres

More details:

Featured data source
The Merck Index Online

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

(4S)-4-((3-(2-(Dimethylamino)ethyl)-1H-indol-5-yl)methyl)-2-oxazolidinone
(4S)-4-({3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl}methyl)-1,3-oxazolidin-2-on [German] [ACD/IUPAC Name]
(4S)-4-({3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl}methyl)-1,3-oxazolidin-2-one [ACD/IUPAC Name]
(4S)-4-({3-[2-(Diméthylamino)éthyl]-1H-indol-5-yl}méthyl)-1,3-oxazolidin-2-one [French] [ACD/IUPAC Name]
(S)-4-((3-(2-(Dimethylamino)ethyl)indol-5-yl)methyl)-2-oxazolidinone
(S)-N,N-Dimethyl-2-[5-(2-oxo-1,3-oxazolidin-4-ylmethyl)-1H-indol-3-yl]ethylamine
139264-17-8 [RN]
2FS66TH3YW
2-Oxazolidinone, 4-[[3-[2-(dimethylamino)ethyl]-1H-indol-5-yl]methyl]-, (4S)- [ACD/Index Name]
311C90
More...

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

7408 [DBID]
LS-100559 [DBID]
SPBio_000656 [DBID]
Spectrum2_000728 [DBID]
  • Experimental Physico-chemical Properties

    • Experimental Solubility:

      10 mM in DMSO MedChem Express HY-B0229
      DMSO 58 mg/mL (201 mM); Water <1 mg/mL (<1 mM) MedChem Express HY-B0229
      Soluble in DMSO (100mM) or ethanol (100mM) Hello Bio HB1801
      Soluble to 100 mM in DMSO and to 100 mM in ethanol Tocris Bioscience 4657
  • Miscellaneous

    • Toxicity:

      Organic Compound; Amine; Ether; Ester; Drug; Vasoconstrictor Agent; Anti-Inflammatory Agent; Anti-Migraine Agent; Selective Serotonin Agonist; Serotonin Agonist; Serotonin Antagonist; Metabolite; Synthetic Compound; Serotonin 5-HT1 Receptor Agonist; Serotonin Receptor Agonist Toxin, Toxin-Target Database T3D2748

    • Safety:

      N02CC03 Wikidata Q218820

    • Chemical Class:

      A member of the class of tryptamines that is N,N-dimethyltryptamine in which the hydrogen at position 5 of the indole ring has been replaced by a [(4S)-2-oxo-1,3-oxazolidin-4-yl]methyl group. A seroto nin 5-HT1 B and D receptor agonist, it is used for the treatment of migraine. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:10124, CHEBI:10124

    • Bio Activity:

      5-HT Receptor MedChem Express HY-B0229
      5-HT Receptors Tocris Bioscience 4657
      5-HT1 Receptors Tocris Bioscience 4657
      7-TM Receptors Tocris Bioscience 4657
      GPCR/G protein MedChem Express HY-B0229
      GPCR/G protein; Neuronal Signaling; MedChem Express HY-B0229
      Potent 5-HT<sub>1B/</sub><sub>1D/</sub><sub>1F</sub> agonist Hello Bio HB1801
      Potent 5-HT<sub>1B/</sub><sub>1D/</sub><sub>1F</sub> agonist (K<sub>i</sub> values are 0.63, 5.01 and 63.09 nM for h5-HT<sub>1D</sub>, h5-HT<sub>1B</sub> and h5-HT<sub>1F</sub> receptors respectively). Hello Bio HB1801
      Potent 5-HT1B/1D/1F agonist Tocris Bioscience 4657
      Potent 5-HT1B/1D/1F agonist (Ki values are 0.63, 5.01 and 63.09 nM for h5-HT1D, h5-HT1B and h5-HT1F receptors respectively). Inhibits trigeminal nerve stimulation-mediated neurogenic plasma protein ex travasation in guinea pigs; blocks long excitatory postsynaptic potentials (EPSPs) in a rat model of spinal cord injury. Tocris Bioscience 4657
      Potent 5-HT1B/1D/1F agonist (Ki values are 0.63, 5.01 and 63.09 nM for h5-HT1D, h5-HT1B and h5-HT1F receptors respectively). Inhibits trigeminal nerve stimulation-mediated neurogenic plasma protein extravasation in guinea pigs; blocks long excitatory postsynaptic potentials (EPSPs) in a rat model of spinal cord injury. Tocris Bioscience 4657
      Receptors & Transporters/G protein coupled receptors/5-HT/5-HT<sub>1</sub>/5-HT<sub>1B</sub> Hello Bio HB1801
      Receptors & Transporters/G protein coupled receptors/5-HT/5-HT<sub>1</sub>/5-HT<sub>1D</sub> Hello Bio HB1801
      Receptors & Transporters/G protein coupled receptors/5-HT/5-HT<sub>1</sub>/5-HT<sub>1F</sub> Hello Bio HB1801
      Type/Biochemicals & small molecules/Agonists & activators Hello Bio HB1801
      Zolmitriptan, a selective serotonin receptor agonist, is used to treat migraine attacks with or without aura and cluster headaches. MedChem Express
      Zolmitriptan, a selective serotonin receptor agonist, is used to treat migraine attacks with or without aura and cluster headaches.; Target: serotonin receptor agonist; Zolmitriptan is a selective serotonin receptor agonist of the 1B and 1D subtypes. MedChem Express HY-B0229
      Zolmitriptan, a selective serotonin receptor agonist, is used to treat migraine attacks with or without aura and cluster headaches.;Target: serotonin receptor agonistZolmitriptan is a selective serotonin receptor agonist of the 1B and 1D subtypes. It is a triptan, used in the acute treatment of migraine attacks with or without aura and cluster headaches. Zolmitriptan is available as a swallowable tablet, an oral disintegrating tablet, and a nasal spray, in doses of 2.5 and 5 mg. People who get migraines from aspartame should not use the disintegrating tablet (Zomig ZMT), which contains aspartame. According to a study of healthy volunteers, food intake seems to have no significant effect on the effectiveness of Zolmitriptan in both men and women.Zolmitriptan should not be given to patients with ischemic heart disease (angina pectoris, history of myocardial infarction, or documented silent ischemia) or to patients who have symptoms or findings consistent with ischemic heart disease MedChem Express HY-B0229

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

Density: 1.2±0.1 g/cm3
Boiling Point: 563.3±38.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.5 mmHg at 25°C
Enthalpy of Vaporization: 84.7±3.0 kJ/mol
Flash Point: 294.5±26.8 °C
Index of Refraction: 1.620
Molar Refractivity: 82.9±0.3 cm3
#H bond acceptors: 5
#H bond donors: 2
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 0
ACD/LogP: 1.64
ACD/LogD (pH 5.5): -0.66
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): 0.44
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 5.38
Polar Surface Area: 57 Å2
Polarizability: 32.9±0.5 10-24cm3
Surface Tension: 53.0±3.0 dyne/cm
Molar Volume: 236.1±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) =  1.92

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  476.72  (Adapted Stein & Brown method)
    Melting Pt (deg C):  201.72  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.44E-009  (Modified Grain method)
    Subcooled liquid VP: 1.06E-007 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):  3402
       log Kow used: 1.92 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  433.57 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Aliphatic Amines
       Esters

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   4.90E-016  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.600E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.92  (KowWin est)
  Log Kaw used:  -13.698  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  15.618
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.5944
   Biowin2 (Non-Linear Model)     :   0.2439
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.1129  (months      )
   Biowin4 (Primary Survey Model) :   3.2017  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.2672
   Biowin6 (MITI Non-Linear Model):   0.0046
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.0778
 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):  1.41E-005 Pa (1.06E-007 mm Hg)
  Log Koa (Koawin est  ): 15.618
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.212 
       Octanol/air (Koa) model:  1.02E+003 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.885 
       Mackay model           :  0.944 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 301.8286 E-12 cm3/molecule-sec
      Half-Life =     0.035 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    25.515 Min
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.915 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  3.017E+004
      Log Koc:  4.480 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
    Rate constants can NOT be estimated for this structure!

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.778 (BCF = 5.992)
       log Kow used: 1.92 (estimated)

 Volatilization from Water:
    Henry LC:  4.9E-016 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 2.025E+012  hours   (8.44E+010 days)
    Half-Life from Model Lake :  2.21E+013  hours   (9.207E+011 days)

 Removal In Wastewater Treatment:
    Total removal:               2.18  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     2.08  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       4.47e-008       0.851        1000       
   Water     24.9            1.44e+003    1000       
   Soil      75              2.88e+003    1000       
   Sediment  0.0899          1.3e+004     0          
     Persistence Time: 1.82e+003 hr

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