InChI=1/C17H13ClN4/c1-11-20-21-16-10-19-17(12-5-3-2-4-6-12)14-9-13(18)7-8-15(14)22(11)16/h2-9H,10H2,1H3

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Inherent Properties, Identifiers and References

ChemSpider ID:	2034
Empirical Formula:	C₁₇H₁₃ClN₄
Molecular Weight:	308.7649
Nominal Mass:	308 Da
Average Mass:	308.7649 Da
Monoisotopic Mass:	308.082874 Da

Systematic Name:

8-chloro-1-methyl-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine

SMILES:

Clc3cc2\C(=N/Cc1nnc(n1c2cc3)C)c4ccccc4 Copy

InChI:

InChI=1/C17H13ClN4/c1-11-20-21-16-10-19-17(12-5-3-2-4-6-12)14-9-13(18)7-8-15(14)22(11)16/h2-9H,10H2,1H3 Copy

InChIKey:

VREFGVBLTWBCJP-UHFFFAOYAT

Std. InChI:

InChI=1S/C17H13ClN4/c1-11-20-21-16-10-19-17(12-5-3-2-4-6-12)14-9-13(18)7-8-15(14)22(11)16/h2-9H,10H2,1H3 Copy

Std. InChIKey:

VREFGVBLTWBCJP-UHFFFAOYSA-N

LicenseWikipedia Article(s)

Patents

Articles

QSAR World - Datasets - GG - Plasma Binding

Kenneth E. Thummel and Danny D. Shen. Percentage Binding in Plasma , "Goodman & Gilman's The Pharmacological Basis of Therapeutics", 10/e, Ed. by Joel G. Hardman, Lee E. Limbird and Alfred Goodman Gilman, McGraw-Hill, pp. 1917-2023

'Bound in Plasma' (%) values have been taken from the Table A-II-1 given in Appendix II of the above mentioned reference. Users are requested to go through the comments associated with these values, which have been given as footnotes in the table. Only drugs that had 'Bound in Plasma' values indicated for them have been provided in the files here. Structures (and values) for Clavulanate (22), Heparin (Extensive), Lithium (0), Mycophenolate (MPA: 97.5), Prednisolone (90-95 (<200 ng/ml), ~70(>1 microgm/ml)) and Rapacuronium (50-88) have not been provided here. In all, 280 drugs and their 'Bound in Plasma' values (%) are given in the files here.

QSAR World - Datasets - GG - Peak Time

Kenneth E. Thummel and Danny D. Shen. Peak Time , "Goodman & Gilman's The Pharmacological Basis of Therapeutics", 10/e, Ed. by Joel G. Hardman, Lee E. Limbird and Alfred Goodman Gilman, McGraw-Hill, pp. 1917-2023

'Peak-Time' values have been taken from the Table A-II-1 given in Appendix II of the above mentioned reference. These are in hours unless otherwise indicated. Users are requested to go through the comments associated with these values, which have been given as footnotes in the table. Only drugs that had 'Peak-Time' values indicated for them have been provided in the files here. Structures (and values) for Clavulanate (1.3), Enoxaparin (3), Epoetin Alfa (SC: 18, IP:12), Etanercept (SC-SD:72(48-96)), Filgrastim (4-5.8), Heparin (3), Interferon Alfa (IM:3.8,SC:7.3), Interferon Beta (SC:1-8), Lithium (IR:0.5-3, SR:2-6), Mycophenolate (MPA: 1.1-2.2), Prednisolone (1.5+-0.5), Sargramostim (A,SC: 1-3, C,SC:1.5-4) and Streptokinase (0.9+-0.21) have not been provided here. In all, 270 drugs and their 'Peak-Time' values are given in the files here.

QSAR World - Datasets - GG - Urinary Excretion

Kenneth E. Thummel and Danny D. Shen. Urinary Excretion , "Goodman & Gilman's The Pharmacological Basis of Therapeutics", 10/e, Ed. by Joel G. Hardman, Lee E. Limbird and Alfred Goodman Gilman, McGraw-Hill, pp. 1917-2023

Urinary Excretion (%) values have been taken from the Table A-II-1 given in Appendix II of the above mentioned reference. Users are requested to go through the comments associated with these values, which have been given as footnotes in the table. Only drugs that had Urinary Excretion values indicated for them have been provided in the files here. Structures (and values) for Alteplase (t-PA) (Low), Clavulanate (43+-14), Enoxaparin (43), Epoetin alfa (<3), Etanercept (Negligible), Heparin (Negligible), Lithium (95+-15), Mycophenolate (MPA: <1), Prednisolone (26+-9), Rapacuronium (6-22) and Streptokinase (0) have not been provided here. In all, 297 drugs and their Urinary Excretion values (%) are given in the files here.

QSAR World - Datasets - GG - Volume of Distribution

Kenneth E. Thummel and Danny D. Shen. Volume of Distribution , "Goodman & Gilman's The Pharmacological Basis of Therapeutics", 10/e, Ed. by Joel G. Hardman, Lee E. Limbird and Alfred Goodman Gilman, McGraw-Hill, pp. 1917-2023

'Volume of Distribution' values have been taken from the Table A-II-1 given in Appendix II of the above mentioned reference. These are in liters/kg units unless otherwise indicated. Users are requested to go through the comments associated with these values, which have been given as footnotes in the table. Only drugs that had 'Volume of Distribution' values indicated for them have been provided in the files here. Structures (and values) for Alteplase (t-PA) (0.10+-0.01), Clavulanate (0.21+-0.05), Enoxaparin (0.12+-0.04), Epoetin Alfa (0.033+-0.013 (0.033-0.075)), Etanercept (0.11), Filgrastim (0.15), Heparin (0.058+-0.11) +- 0.1), Infliximab (0.043). Interferon Alfa (0.40+-0.19), Interferon Beta (2.9+-1.8), Lithium (0.66+-0.16), Mycophenolate (MPA: 3.6+-4), Prednisolone (0.42+-0.11), Rapacuronium (0.2-0.5), Sargramostim (A: -, C:2(0.4-18) liters/(m.m)) and Streptokinase (0.08+-0.04) have not been provided here. In all, 284 drugs and their 'Volume of Distribution' values are given in the files here.

QSAR World - Datasets - GG - Peak Concentration

Kenneth E. Thummel and Danny D. Shen. Peak Concentration , "Goodman & Gilman's The Pharmacological Basis of Therapeutics", 10/e, Ed. by Joel G. Hardman, Lee E. Limbird and Alfred Goodman Gilman, McGraw-Hill, pp. 1917-2023

'Peak-Concentrations' values have been taken from the Table A-II-1 given in Appendix II of the above mentioned reference. The units are indicated along with the values. Users are requested to go through the comments associated with these values, which have been given as footnotes in the table. Structures (and values) for Alteplase (t-PA) (973+-133 ng/ml), Clavulanate (2.8 micro g/ml), Enoxaparin (ACLM: 145+-45 ng/ml, BCLM: 414+-87 ng/ml), Epoetin Alfa (SC: 176+-75 U/l, IP: 375+-123 U/l), Etanercept (IV:2.32 micro-g/ml, SC-SD:1.2 micro-g/ml, SC-MD 3 micro-g/ml), Filgrastim (SC: 4 and 49 ng/ml), Heparin (70+-39 ng/ml), Infliximab (118 micro-g/ml), Interferon Alfa (IV: ~13 ng/ml, IM: 2.0 (1.5-2.6) ng/ml, SC: 1.7 (1.2-2.3) ng/ml), Interferon Beta (IV: 1491+-659 IU/ml, SC: 40+-20 IU/ml), Lithium (IR: 1-2 mM, SR: 0.7-1.2 mM), Mycophenolate (MPA: 8-19 micro-g/ml), Prednisolone (458+-150 ng/ml), Rapacuronium (6-20 micro-g/ml), Sargramostim (A, IV: 5ng/ml, A, SC: 1.5 ng/ml, C, IV: 100 ng/ml, C, SC: 10 ng/ml) and Streptokinase (188+-58 IU/ml) have not been provided here. In all, 304 drugs and their 'Peak-Concentration' values are given in the files here.

QSAR World - Datasets - GG - Clearance

Kenneth E. Thummel and Danny D. Shen. Clearance , "Goodman & Gilman's The Pharmacological Basis of Therapeutics", 10/e, Ed. by Joel G. Hardman, Lee E. Limbird and Alfred Goodman Gilman, McGraw-Hill, pp. 1917-2023

'Clearance' values have been taken from the Table A-II-1 given in Appendix II of the above mentioned reference. These are in (ml/min/kg) units unless otherwise indicated. Users are requested to go through the comments associated with these values, which have been given as footnotes in the table. Only drugs that had 'Clearance' values indicated for them have been provided in the files here. Structures (and values) for Alteplase (t-PA) (10+-4), Clavulanate (3.6+-1.0), Enoxaparin (0.3+-0.1), Epoetin Alfa (0.047+-0.017 (0.047-0.092)), Etanercept (0.02), Filgrastim (0.5-0.7), Heparin (1/(0.65 + 0/0.008D) +- 0.1), Interferon Alfa (2.8+-0.6), Interferon Beta (13+-5), Lithium (0.35+-0.11), Mycophenolate (MM: 120-163, MPA: 2.5+-0.4), Prednisolone (1.0+-0.16), Rapacuronium (7-11), Sargramostim (A: 420 ml/min/(m.m), C:49(15-118) ml/min/(m.m)) and Streptokinase (1.7+-0.7) have not been provided here. In all, 301 drugs and their 'Clearance' values are given in the files here.

QSAR World - Datasets - GG - Oral Availability

Kenneth E. Thummel and Danny D. Shen. Percentage Oral Availability , "Goodman & Gilman's The Pharmacological Basis of Therapeutics", 10/e, Ed. by Joel G. Hardman, Lee E. Limbird and Alfred Goodman Gilman, McGraw-Hill, pp. 1917-2023

Availability (Oral) % have been taken from the Table A-II-1 given in Appendix II of the above mentioned reference. Users are requested to go through the comments associated with these values, which have been given as footnotes in the table. Only drugs that had Availability values indicated for them have been provided in the files here. Structures (and values) for Clavulanate (75+-21), Enoxaparin (SC: 92), Epoetin alfa (SC: 22 (11-36), IP: 3 (1-7)), Etanercept (SC: 58), Filgrastim (SC: 49+-9), Interferon alfa (IM: 80-83, SC: 90), Interferon beta (SC: 51+-17), Lithium (100), Mycophenolate (MM: ~0, MPA: 94) and Prednisolone (82+-13) have not been provided here. In all, 242 drugs and their Availability (Oral) % are given in the files here.

Daniel F. Veber, Stephen R. Johnson, Hung-Yuan Cheng, Brian R. Smith, Keith W. Ward, and Kenneth D. Kopple. Molecular Properties That Influence the Oral Bioavailability of Drug Candidates , J. Med. Chem. 2002, 45(12), 2615-2623

[DOI: 10.1021/jm020017n]

275 drugs and their human oral bioavalability values have been given in the supplementary material of the paper. These values have in turn been taken from Goodman & Gilman's The Pharmacological Basis of Therapeutics, VIII and X Editions. The datasets are available from the QSAR World pages: http://www.qsarworld.com/qsar-datasets-veber.php

Zhao YH, Abraham MH, Le J, Hersey A, Luscombe CN, Beck G, Sherborne B, and Cooper I. Rate-limited Steps of Human Oral Absorption and QSAR Studies , Pharm Res., 2002, 19(10), 1446-57

QSAR World - Datasets - Zhao

Franco Lombardo, R. Scott Obach, Marina Y. Shalaeva, and Feng Gao. Prediction of Human Volume of Distribution Values for Neutral and Basic Drugs. 2. Extended Data Set and Leave-Class-Out Statistics , J. Med. Chem., 2004, 47(5), 1242-1250

[DOI: 10.1021/jm030408h]

In all, 120 compounds, their VDss (volume-of-distribution in steady-state) Fu (fraction unbound in human plasma) values have been given. The same have been provided here in .sdf and .txt files.

Skelton Kelly H, Nemeroff Charles B, Owens Michael J. Spontaneous withdrawal from the triazolobenzodiazepine alprazolam increases cortical corticotropin-releasing factor mRNA expression. , The Journal of neuroscience : the official journal of the Society for Neuroscience, Oct 2004

[PubMed: 15496666]

Kauppila Tiina J.. Rapid analysis of metabolites and drugs of abuse from urine samples by desorption electrospray ionization-mass spectrometry , The Analyst, 2007

[DOI: 10.1039/b703524a]

Wikipedia Aricle About Xanax

Identifiers

Names and Synonyms
Database ID(s)

Edit

Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Redirected by Users, Redirect Approved by Experts

4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine, 8-chloro-1-methyl-6-phenyl-

8-Chlor-1-methyl-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin

8-Chloro-1-methyl-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine

8-chloro-1-méthyl-6-phényl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazépine

Alprax

Alprazolam [Wiki]

Alprazolam (JP15/USP)

Alprazolam [USAN:BAN:INN:JAN]

Alprazolamum [INN-Latin]

Anxyl

More...

Edit

Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Redirected by Users, Redirect Approved by Experts

U-31889

ZINC00000903

611026_ALDRICH

A6551_SIGMA

A8800_SIGMA

AP-1002

AZ-002

BRN 1223125

C06817

CHEBI:2611

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AddDescription

Predicted Properties

Pred. Prop. (ACD/Labs)
Pred. Prop. (EPISuite)
NMRShiftDB
Exptl. Prop.

ACD/LogP:	2.50	# of Rule of 5 Violations:	0
ACD/LogD (pH 5.5):	2.5	ACD/LogD (pH 7.4):	2.5
ACD/BCF (pH 5.5):	46.67	ACD/BCF (pH 7.4):	46.71
ACD/KOC (pH 5.5):	544.74	ACD/KOC (pH 7.4):	545.23
#H bond acceptors:	4	#H bond donors:	0
#Freely Rotating Bonds:	1	Polar Surface Area:	43.07 Å²
Index of Refraction:	1.71	Molar Refractivity:	88.22 cm³
Molar Volume:	225.5 cm³	Polarizability:	34.97 10^-24cm³
Surface Tension:	52.1 dyne/cm	Density:	1.36 g/cm³
Flash Point:	261.6 °C	Enthalpy of Vaporization:	77.94 kJ/mol
Boiling Point:	509 °C at 760 mmHg	Vapour Pressure:	1.77E-10 mmHg at 25°C

                    
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  3.87
    Log Kow (Exper. database match) =  2.12
       Exper. Ref:  BioByte (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  441.81  (Adapted Stein & Brown method)
    Melting Pt (deg C):  185.42  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.65E-008  (Modified Grain method)
    Subcooled liquid VP: 7.84E-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):  13.1
       log Kow used: 2.12 (expkow database)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.15855 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   9.77E-012  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  5.117E-010 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.12  (exp database)
  Log Kaw used:  -9.399  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  11.519
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.6009
   Biowin2 (Non-Linear Model)     :   0.2660
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.2574  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.1733  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.1488
   Biowin6 (MITI Non-Linear Model):   0.0042
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.4906
 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):  0.000105 Pa (7.84E-007 mm Hg)
  Log Koa (Koawin est  ): 11.519
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0287 
       Octanol/air (Koa) model:  0.0811 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.509 
       Mackay model           :  0.697 
       Octanol/air (Koa) model:  0.866 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =   7.6246 E-12 cm3/molecule-sec
      Half-Life =     1.403 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    16.834 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.603 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  2.151E+006
      Log Koc:  6.333 

 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 = 0.932 (BCF = 8.559)
       log Kow used: 2.12 (expkow database)

 Volatilization from Water:
    Henry LC:  9.77E-012 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.053E+008  hours   (4.388E+006 days)
    Half-Life from Model Lake : 1.149E+009  hours   (4.786E+007 days)

 Removal In Wastewater Treatment:
    Total removal:               2.37  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     2.27  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       0.000217        33.7         1000       
   Water     21              900          1000       
   Soil      78.9            1.8e+003     1000       
   Sediment  0.094           8.1e+003     0          
     Persistence Time: 1.48e+003 hr

User Data

miscellaneous

Applications: Tranquilliser;

No description available

Bio-Activity: Benzodiazepine receptor agonist

No description available

Medical Subject Headings Classification

SimBioSys LASSO

RSC Databases