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primidone C12H14N2O2 structure – Flashcards

Flashcard maker : Noel Macdonald

Contents

Experimental Melting Point:
Experimental Solubility:
Predicted Melting Point:
Appearance:
Target Organs:
Drug Status:
Compound Source:
Bio Activity:
Retention Index (Kovats):
Retention Index (Normal Alkane):
Retention Index (Linear):

Molecular Formula	C₁₂H₁₄N₂O₂
Average mass	218.252 Da
Density	1.1±0.1 g/cm³
Boiling Point	520.7±50.0 °C at 760 mmHg
Flash Point	228.2±30.3 °C
Molar Refractivity	59.1±0.3 cm³
Polarizability	23.4±0.5 10^-24cm³
Surface Tension	38.5±3.0 dyne/cm
Molar Volume	191.7±3.0 cm³

Experimental data
Predicted – ACD/Labs
Predicted – EPISuite
Predicted – ChemAxon
Predicted – Mcule

Experimental Physico-chemical Properties

Experimental Melting Point:

281 °C TCI P1906

281.5 °C Jean-Claude Bradley Open Melting Point Dataset 17047, 17328, 21614

281 °C Jean-Claude Bradley Open Melting Point Dataset 8982

281-2820 °C LabNetwork LN00196100

Experimental Solubility:

10 mM in H2O (free soluble) MedChem Express HY-B0339

-2.64 Egon Willighagen http://dx.doi.org/10.1021/ci050282s

DMSO 44 mg/mL; Water <1 mg/mL MedChem Express HY-B0339

Soluble to 100 mM in DMSO Tocris Bioscience 0830, 830

Predicted Physico-chemical Properties
- Predicted Melting Point:
  
  281 °C TCI
  
  281 °C TCI P1906

Miscellaneous

Appearance:

WHITE POWDER NIH Clinical Collection
[SMR000058501]
Target Organs:

AChR antagonist;GABAR;GluR antagonist;Sodium Channel inhibitor TargetMol T0024
Drug Status:

approved BIONET-Key Organics KS-5217
Compound Source:

synthetic Microsource
[01500501]

Bio Activity:

Anticonvulsant. Tocris Bioscience 0830, 830

GABA Receptor MedChem Express HY-B0339

GABAA and A-rho Receptors Tocris Bioscience 830

Ion Channels Tocris Bioscience 830

Ligand-gated Ion Channels Tocris Bioscience 830

Membrane Tranporter/Ion Channel MedChem Express HY-B0339

Membrane Tranporter/Ion Channel; Neuronal Signaling; MedChem Express HY-B0339

Membrane Transporter/Ion Channel; Neuroscience TargetMol T0024

Neuronal AChR;GABAR;Glutamate receptor 2;Sodium channel TargetMol T0024

Potentiates GABAA receptor function Tocris Bioscience 0830, 830

Primidone is an anticonvulsant of the pyrimidinedione class. MedChem Express

Primidone is an anticonvulsant of the pyrimidinedione class.; Target: GABA Receptor; Primidone is an anticonvulsant of the pyrimidinedione class, the active metabolites of which, phenobarbital (minor) and phenylethylmalonamide (PEMA) (major), are also anticonvulsants. MedChem Express HY-B0339

Primidone is an anticonvulsant of the pyrimidinedione class.;Target: GABA ReceptorPrimidone is an anticonvulsant of the pyrimidinedione class, the active metabolites of which, phenobarbital (minor) and phenylethylmalonamide (PEMA) (major), are also anticonvulsants. It is believed to work via interactions with voltage-gated sodium channels which inhibit high-frequency repetitive firing of action potentials [1]. The effect of primidone in essential tremor is not mediated by PEMA.[76] The major metabolite, phenobarbital, is also a potent anticonvulsant in its own right and likely contributes to primidone’s effects in many forms of epilepsy [2]. Primidone and the other enzyme-inducing anticonvulsants can cut the half-life of antipyrine roughly in half (6.2 ? 1.9 h vs. 11.2 ? 4.2 h), and increases the clearance rate by almost 70%. Phenobarbital reduces the half-life to 4.8 ? 1.3 and increases the clearance by almost 109% [3]. MedChem Express HY-B0339

Gas Chromatography

Retention Index (Kovats):

1854 (estimated with error: 83) NIST Spectra mainlib_244337, replib_335106, replib_113833, replib_246244, replib_312906

2239 (Program type: Isothermal; Col… (show more) umn class: Standard non-polar; Column diameter: 0.53 mm; Column length: 30 m; Column type: Capillary; Start T: 275 C; CAS no: 125337; Active phase: DB-1; Carrier gas: N2; Phase thickness: 1.5 um; Data type: Kovats RI; Authors: Japp, M.; Gill, R.; Osselton, M.D., Comparison of drug retention indices determined on packed, wide bore capillary and narrow bore capillary columns, J. Forensic Sci., 32(6), 1987, 1574-1586.) NIST Spectra nist ri

2242 (Program type: Isothermal; Col… (show more) umn class: Standard non-polar; Column diameter: 0.22 mm; Column length: 25 m; Column type: Capillary; Start T: 275 C; CAS no: 125337; Active phase: BP-1; Carrier gas: N2; Phase thickness: 0.25 um; Data type: Kovats RI; Authors: Japp, M.; Gill, R.; Osselton, M.D., Comparison of drug retention indices determined on packed, wide bore capillary and narrow bore capillary columns, J. Forensic Sci., 32(6), 1987, 1574-1586.) NIST Spectra nist ri

2243 (Program type: Isothermal; Col… (show more) umn class: Standard non-polar; Column diameter: 0.20 mm; Column length: 25 m; Column type: Capillary; Start T: 250 C; CAS no: 125337; Active phase: SPB-1; Carrier gas: He; Data type: Kovats RI; Authors: Lora-Tamayo, C.; Rams, M.A.; Chacon, J.M.R., Gas Chromatographic Data for 187 Nitrogen- or Phosphorus-Containing Drugs and Metabolites of Toxicological Interest Analysed on Methyl Silicone Capillary Columns, J. Chromatogr., 374, 1986, 73-85.) NIST Spectra nist ri

2202 (Program type: Ramp; Column cl… (show more) ass: Standard non-polar; Column diameter: 0.49 mm; Column length: 25 m; Column type: Capillary; Heat rate: 8 K/min; Start T: 100 C; End T: 275 C; End time: 15 min; Start time: 2 min; CAS no: 125337; Active phase: SE-30; Phase thickness: 1.14 um; Data type: Kovats RI; Authors: Schepers, P.; Wijsbeek, J.; Franke, J.P.; de Zeeuw, R.A., Applicability of capillary gas chromatography to substance identification in toxicology by means of retention indices, J. Forensic Sci., 27(1), 1982, 49-60.) NIST Spectra nist ri

2254 (Program type: Isothermal; Col… (show more) umn class: Semi-standard non-polar; Column diameter: 0.25 mm; Column length: 15 m; Column type: Capillary; Start T: 220 C; CAS no: 125337; Active phase: DB-5; Carrier gas: He; Phase thickness: 0.2 um; Data type: Kovats RI; Authors: Phillips, A.M.; Logan, B.K.; Stafford, D.T., Further applications for capillary gas chromatography in routine quantitative toxicological analyses, J. Hi. Res. Chromatogr., 13, 1990, 754-758.) NIST Spectra nist ri

Retention Index (Normal Alkane):

2244.7 (Program type: Ramp; Column cl… (show more) ass: Standard non-polar; Column diameter: 0.75 mm; Column length: 30 m; Column type: Capillary; Heat rate: 8 K/min; Start T: 155 C; End T: 290 C; End time: 10 min; Start time: 4 min; CAS no: 125337; Active phase: SPB-1; Carrier gas: He; Phase thickness: 10 um; Data type: Normal alkane RI; Authors: Coudore, F.; Alazard, J.-M.; Paire, M.; Andraud, G.; Lavarenne, J., Rapid toxicological screening of barbiturates in plasma by wide-bore capillary gas chromatography and nitrogen-phosphorus detection, J. Anal. Toxicol., 17, 1993, 109-113.) NIST Spectra nist ri

2227.2 (Program type: Ramp; Column cl… (show more) ass: Standard non-polar; Column diameter: 0.32 mm; Column length: 12 m; Column type: Capillary; Heat rate: 10 K/min; Start T: 40 C; End T: 290 C; Start time: 1 min; CAS no: 125337; Active phase: SE-30; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Neill, G.P.; Davies, N.W.; McLean, S., Automated screening procedure using gas chromatography-mass spectrometry for identification of drugs after their extraction from biological samples, J. Chromatogr., 565, 1991, 207-224.) NIST Spectra nist ri

2200 (Program type: Ramp; Column cl… (show more) ass: Standard non-polar; Column length: 2 m; Column type: Packed; Heat rate: 2.5 K/min; Start T: 120 C; End T: 200 C; CAS no: 125337; Active phase: SE-30; Substrate: Gas Chrom P; Data type: Normal alkane RI; Authors: Marozzi, E.; Gambaro, V.; Saligari, E.; Mariani, R.; Lodi, F., Use of the retention index in gas chromatographic studies of drugs, J. Anal. Toxicol., 6, 1982, 185-192.) NIST Spectra nist ri

2225 (Program type: Ramp; Column cl… (show more) ass: Standard non-polar; Column length: 2 m; Column type: Packed; Heat rate: 2.5 K/min; Start T: 120 C; End T: 200 C; CAS no: 125337; Active phase: OV-1; Substrate: Gas Chrom P; Data type: Normal alkane RI; Authors: Marozzi, E.; Gambaro, V.; Saligari, E.; Mariani, R.; Lodi, F., Use of the retention index in gas chromatographic studies of drugs, J. Anal. Toxicol., 6, 1982, 185-192.) NIST Spectra nist ri

2247 (Program type: Ramp; Column cl… (show more) ass: Standard non-polar; Column type: Other; CAS no: 125337; Active phase: Methyl Silicone; Data type: Normal alkane RI; Authors: Ardrey, R.E.; Moffat, A.C., Gas-liquid chromatographic retention indices of 1318 substances of toxicological interest on SE-30 or OV-1 stationary phase, J. Chromatogr., 220, 1981, 195-252.) NIST Spectra nist ri

2248.7 (Program type: Ramp; Column cl… (show more) ass: Standard non-polar; Column length: 2 m; Column type: Packed; Heat rate: 10 K/min; Start T: 220 C; End T: 270 C; CAS no: 125337; Active phase: OV-101; Substrate: Chromosorb (100-120 mesh); Data type: Normal alkane RI; Authors: Cailleux, A.; Turcant, A.; Premel-Cabic, A.; Allain, P., Identification and Quantitation of Neutral and Basic Drugs in Blood By Gas Chromatography and Mass Spectrometry, J. Chromatogr. Sci., 19, 1981, 163-176.) NIST Spectra nist ri

2253.3 (Program type: Complex; Column… (show more) class: Semi-standard non-polar; Column diameter: 0.32 mm; Column length: 25 m; Column type: Capillary; Description: 70 0C (0.7 min) ^ 20 0C/min -; 140 0C ^ 10 0C/min -; 280 0C (4 min); CAS no: 125337; Active phase: NB-54; Carrier gas: He; Phase thickness: 0.10 um; Data type: Normal alkane RI; Authors: Ojanpera, I.; Rasanen, I.; Vuori, E., Automated quantitative screening for acidic and neutral drugs in whole blood by dual-column capillary gas chromatography, J. Anal. Toxicol., 15, 1991, 204-208.) NIST Spectra nist ri

Retention Index (Linear):

2250 (Program type: Ramp; Column cl… (show more) ass: Standard non-polar; Column length: 1.8 m; Column type: Packed; Heat rate: 8 K/min; Start T: 130 C; End T: 290 C; End time: 8 min; Start time: 2 min; CAS no: 125337; Active phase: SE-30; Carrier gas: N2; Substrate: Chromosorb W; Data type: Linear RI; Authors: Perrigo, B.J.; Peel, H.W., The use of retention indices and temperature-programmed gas chromatography in analytical toxicology, J. Chromatogr. Sci., 19, 1981, 219-226.) NIST Spectra nist ri

Predicted data is generated using the ACD/Labs Percepta Platform – PhysChem Module

Density:	1.1±0.1 g/cm³
Boiling Point:	520.7±50.0 °C at 760 mmHg
Vapour Pressure:	0.0±1.4 mmHg at 25°C
Enthalpy of Vaporization:	79.4±3.0 kJ/mol
Flash Point:	228.2±30.3 °C
Index of Refraction:	1.529
Molar Refractivity:	59.1±0.3 cm³
#H bond acceptors:	4
#H bond donors:	2
#Freely Rotating Bonds:	2
#Rule of 5 Violations:	0

ACD/LogP:	0.40
ACD/LogD (pH 5.5):	0.61
ACD/BCF (pH 5.5):	1.71
ACD/KOC (pH 5.5):	51.05
ACD/LogD (pH 7.4):	0.61
ACD/BCF (pH 7.4):	1.71
ACD/KOC (pH 7.4):	51.05
Polar Surface Area:	58 Å²
Polarizability:	23.4±0.5 10^-24cm³
Surface Tension:	38.5±3.0 dyne/cm
Molar Volume:	191.7±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) = 0.73
 Log Kow (Exper. database match) = 0.91
 Exper. Ref: Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
 Boiling Pt (deg C): 463.54 (Adapted Stein & Brown method)
 Melting Pt (deg C): 195.57 (Mean or Weighted MP)
 VP(mm Hg,25 deg C): 3.3E-010 (Modified Grain method)
 MP (exp database): 281.5 deg C
 Subcooled liquid VP: 2.26E-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): 5874
 log Kow used: 0.91 (expkow database)
 no-melting pt equation used
 Water Sol (Exper. database match) = 500 mg/L (22 deg C)
 Exper. Ref: YALKOWSKY,SH & DANNENFELSER,RM (1992)

 Water Sol Estimate from Fragments:
 Wat Sol (v1.01 est) = 2.4468e+005 mg/L
 Wat Sol (Exper. database match) = 500.00
 Exper. Ref: YALKOWSKY,SH & DANNENFELSER,RM (1992)

 ECOSAR Class Program (ECOSAR v0.99h):
 Class(es) found:
 Neutral Organics

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
 Bond Method : 1.94E-010 atm-m3/mole
 Group Method: Incomplete
 Henrys LC [VP/WSol estimate using EPI values]: 1.613E-014 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
 Log Kow used: 0.91 (exp database)
 Log Kaw used: -8.101 (HenryWin est)
 Log Koa (KOAWIN v1.10 estimate): 9.011
 Log Koa (experimental database): None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
 Biowin1 (Linear Model) : 1.0081
 Biowin2 (Non-Linear Model) : 0.9954
 Expert Survey Biodegradation Results:
 Biowin3 (Ultimate Survey Model): 2.4183 (weeks-months)
 Biowin4 (Primary Survey Model) : 3.7952 (days )
 MITI Biodegradation Probability:
 Biowin5 (MITI Linear Model) : 0.4943
 Biowin6 (MITI Non-Linear Model): 0.4211
 Anaerobic Biodegradation Probability:
 Biowin7 (Anaerobic Linear Model): -1.0665
 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): 3.01E-005 Pa (2.26E-007 mm Hg)
 Log Koa (Koawin est ): 9.011
 Kp (particle/gas partition coef. (m3/ug)):
 Mackay model : 0.0996 
 Octanol/air (Koa) model: 0.000252 
 Fraction sorbed to airborne particulates (phi):
 Junge-Pankow model : 0.782 
 Mackay model : 0.888 
 Octanol/air (Koa) model: 0.0197 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
 Hydroxyl Radicals Reaction:
 OVERALL OH Rate Constant = 34.8062 E-12 cm3/molecule-sec
 Half-Life = 0.307 Days (12-hr day; 1.5E6 OH/cm3)
 Half-Life = 3.688 Hrs
 Ozone Reaction:
 No Ozone Reaction Estimation
 Fraction sorbed to airborne particulates (phi): 0.835 (Junge,Mackay)
 Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
 Koc : 715.4
 Log Koc: 2.855 

 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 = 0.500 (BCF = 3.162)
 log Kow used: 0.91 (expkow database)

 Volatilization from Water:
 Henry LC: 1.94E-010 atm-m3/mole (estimated by Bond SAR Method)
 Half-Life from Model River: 4.459E+006 hours (1.858E+005 days)
 Half-Life from Model Lake : 4.864E+007 hours (2.027E+006 days)

 Removal In Wastewater Treatment:
 Total removal: 1.88 percent
 Total biodegradation: 0.09 percent
 Total sludge adsorption: 1.79 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 0.102 7.38 1000 
 Water 43 900 1000 
 Soil 56.8 1.8e+003 1000 
 Sediment 0.0892 8.1e+003 0 
 Persistence Time: 920 hr

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primidone C12H14N2O2 structure – Flashcards

Experimental Melting Point:

Experimental Solubility:

Predicted Melting Point:

Appearance:

Target Organs:

Drug Status:

Compound Source:

Bio Activity:

Retention Index (Kovats):

Retention Index (Normal Alkane):

Retention Index (Linear):

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