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Mexazolam

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Name

Mexazolam

EINECS N/A
CAS No. 31868-18-5 Density 1.44 g/cm3
PSA 41.57000 LogP 3.94320
Solubility N/A Melting Point 172-175°
Formula C18H16 Cl2 N2 O2 Boiling Point 522.2 °C at 760 mmHg
Molecular Weight 363.243 Flash Point 269.6 °C
Transport Information N/A Appearance N/A
Safety Moderately toxic by intraperitoneal and subcutaneous routes. Mildly toxic by ingestion. When heated to decomposition it emits toxic fumes of Cl and NOx. Risk Codes N/A
Molecular Structure Molecular Structure of 31868-18-5 (mexazolam) Hazard Symbols N/A
Synonyms

CS 386;Melex; Mexazolam

Article Data 5

Mexazolam Synthetic route

6168-72-5

2-Amino-1-propanol

5504-92-7

2-(2-bromo-acetylamino)-5,2'-dichloro-benzophenone

31868-18-5

mexazolam

Conditions
ConditionsYield
(i) CH2Cl2, (ii) AcOH, EtOH; Multistep reaction;

7-Chloro-5-(2-chloro-phenyl)-4-(2-hydroxy-1-methyl-ethyl)-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-4-ium

31868-18-5

mexazolam

Conditions
ConditionsYield
With borate buffer (pH=8-10.5) In ethanol; water Equilibrium constant; Mechanism; variation of pH and buffers.;
In ethanol; water at 25℃; Rate constant;
31868-18-5

mexazolam

74-88-4

methyl iodide

32711-03-8

10-chloro-11b-(2-chloro-phenyl)-3,7-dimethyl-2,3,7,11b-hexahydro-benzo[f]oxazolo[3,2-e][1,4]diazepin-6-one

Conditions
ConditionsYield
(i) NaOMe, MeOH, (ii) /BRN= 969135/, DMF; Multistep reaction;
31868-18-5

mexazolam

7-Chloro-5-(2-chloro-phenyl)-4-(2-hydroxy-1-methyl-ethyl)-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-4-ium

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water Equilibrium constant; Mechanism; variation of pH and buffers.;
In ethanol; water at 25℃; Rate constant;

Mexazolam Chemical Properties

Molecule structure of Mexazolam (CAS NO.31868-18-5) :

IUPAC Name: 10-chloro-11b-(2-chlorophenyl)-3-methyl-2,3,5,7-tetrahydro-[1,3]oxazolo[3,2-d][1,4]benzodiazepin-6-one 
Molecular Weight: 363.23784 g/mol
Molecular Formula: C18H16Cl2N2O2 
Density: 1.44 g/cm3 
Boiling Point: 522.2 °C at 760 mmHg 
Flash Point: 269.6 °C
Index of Refraction: 1.675
Molar Refractivity: 94.18 cm3
Molar Volume: 250.5 cm3
Polarizability: 37.33*10-24 cm3
Surface Tension: 62.9 dyne/cm
Enthalpy of Vaporization: 79.56 kJ/mol
Vapour Pressure: 5.29E-11 mmHg at 25 °C
XLogP3-AA: 3.7
H-Bond Donor: 1
H-Bond Acceptor: 3
Rotatable Bond Count: 1
Tautomer Count: 2
Exact Mass: 362.058883
MonoIsotopic Mass: 362.058883
Topological Polar Surface Area: 41.6
Heavy Atom Count: 24
Complexity: 505
Canonical SMILES: CC1COC2(N1CC(=O)NC3=C2C=C(C=C3)Cl)C4=CC=CC=C4Cl
InChI: InChI=1S/C18H16Cl2N2O2/c1-11-10-24-18(13-4-2-3-5-15(13)20)14-8-12(19)6-7-16(14)21-17(23)9-22(11)18/h2-8,11H,9-10H2,1H3,(H,21,23)
InChIKey: ANUCDXCTICZJRH-UHFFFAOYSA-N

Mexazolam Toxicity Data With Reference

1.    

orl-rat LD50:4500 mg/kg

    SKKNAJ    Sankyo Kenkyusho Nempo. Annual Report of Sankyo Research Laboratories 30 (1978),175.
2.    

ipr-rat LD50:4000 mg/kg

    SKKNAJ    Sankyo Kenkyusho Nempo. Annual Report of Sankyo Research Laboratories 30 (1978),175.
3.    

scu-rat LD50:4000 mg/kg

    SKKNAJ    Sankyo Kenkyusho Nempo. Annual Report of Sankyo Research Laboratories 30 (1978),175.
4.    

orl-mus LD50:4571 mg/kg

    SKKNAJ    Sankyo Kenkyusho Nempo. Annual Report of Sankyo Research Laboratories 30 (1978),175.
5.    

ipr-mus LD50:6000 mg/kg

    SKKNAJ    Sankyo Kenkyusho Nempo. Annual Report of Sankyo Research Laboratories 30 (1978),175.
6.    

scu-mus LD50:6000 mg/kg

    SKKNAJ    Sankyo Kenkyusho Nempo. Annual Report of Sankyo Research Laboratories 30 (1978),175.

Mexazolam Safety Profile

Moderately toxic by intraperitoneal and subcutaneous routes. Mildly toxic by ingestion. When heated to decomposition it emits toxic fumes of Cl and NOx.

Mexazolam Specification

Mexazolam (CAS NO.31868-18-5) is also called 10-Chloro-11b-(o-chlorophenyl)-2,3,7,11b-tetrahydro-3-methyloxazolo(3,2-d)(1,4)benzodiazepin-6(5H)-one ; BRN 1091849 ; CS 386 ; Melex ; Mexazolamum ; Mexazolamum [INN-Latin] ; UNII-S5969B6237 ; Oxazolo(3,2-d)(1,4)benzodiazepin-6(5H)-one, 10-chloro-11b-(2-chlorophenyl)-2,3,7,11b-tetrahydro-3-methyl- . Mexazolam (CAS NO.31868-18-5) (marketed under brand name Melex and Sedoxil) is a drug which is a benzodiazepine derivative. Atorvastatin administration along with mexazolam results in a reduced elimination rate of mexazolam. Mexazolam has been trialed for anxiety and was found to be effective in alleviating anxiety at one week follow-up, however, after three weeks of therapy mexazolam had lost its therapeutic anxiolytic properties becoming no more effective than placebo, presumably due to benzodiazepine tolerance. Mexazolam is metabolised via thee CYP3A4 pathway. HMG-CoA reductase inhibitors including simvastatin, simvastatin acid, lovastatin, fluvastatin, atorvastatin and cerivastatin inhibit the metabolism of mexazolam. Pravastatin, an HMG-CoA reductase inhibitor however, does not inhibit mexazolam metabolism.

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