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    Chemistry

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    Also known as: 29975-16-4, Prosom, Eurodin, Nuctalon, Julodin, Esilgan
    Molecular Formula
    C16H11ClN4
    Molecular Weight
    294.74  g/mol
    InChI Key
    CDCHDCWJMGXXRH-UHFFFAOYSA-N
    FDA UNII
    36S3EQV54C
    Estazolam
    A benzodiazepine with anticonvulsant, hypnotic, and muscle relaxant properties. It has been shown in some cases to be more potent than DIAZEPAM or NITRAZEPAM.
    Estazolam is a Benzodiazepine.
    1 2D Structure

    Estazolam

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    8-chloro-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine
    2.1.2 InChI
    InChI=1S/C16H11ClN4/c17-12-6-7-14-13(8-12)16(11-4-2-1-3-5-11)18-9-15-20-19-10-21(14)15/h1-8,10H,9H2
    2.1.3 InChI Key
    CDCHDCWJMGXXRH-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1C2=NN=CN2C3=C(C=C(C=C3)Cl)C(=N1)C4=CC=CC=C4
    2.2 Other Identifiers
    2.2.1 UNII
    36S3EQV54C
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. D-40ta

    2. D40ta

    3. Nuctalon

    4. Prosom

    5. Tasedan

    2.3.2 Depositor-Supplied Synonyms

    1. 29975-16-4

    2. Prosom

    3. Eurodin

    4. Nuctalon

    5. Julodin

    6. Esilgan

    7. D 40ta

    8. 8-chloro-6-phenyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine

    9. Estazolamum

    10. D-40ta

    11. Abbott-47631

    12. 8-chloro-6-phenyl-4h-s-triazolo(4,3-a)(1,4)benzodiazepine

    13. Estazolam Civ

    14. Nsc 290818

    15. U 33737

    16. Nsc-290818

    17. 36s3eqv54c

    18. Chebi:4858

    19. 4h-(1,2,4)triazolo(4,3-a)(1,4)benzodiazepine, 8-chloro-6-phenyl-

    20. 53180-72-6

    21. Ncgc00168250-01

    22. 8-chloro-6-phenyl-4h-2,3,5,10b-tetraaza-benzo[e]azulene

    23. 8-chloro-6-phenyl-4h-s-triazolo[4,3-a][1,4]benzodiazepine

    24. Nemurel

    25. Somnatrol

    26. Cannoc

    27. 4h-s-triazolo(4,3-a)(1,4)benzodiazepine, 8-chloro-6-phenyl-

    28. 4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine, 8-chloro-6-phenyl-

    29. Abbott 47631

    30. Estazolamum [inn-latin]

    31. Estazolam [usan:inn:jan]

    32. Prosom (tn)

    33. Ccris 1955

    34. Einecs 249-982-4

    35. Brn 1220868

    36. Unii-36s3eqv54c

    37. 8-chloro-6-phenyl-4h-(1,2,4)triazolo(4,3-a)(1,4)benzodiazepine

    38. Dea No. 2756

    39. 8-chloro-6-phenyl-4h-(1,2,4)triazolo-(4,3-a)(1,4)benzodiazepine

    40. 8-chloro-6-phenyl-4h-s-triazolo(4,3-a)(1,4)benzodiazepine (iupac)

    41. Estazolam [inn]

    42. Estazolam [jan]

    43. Estazolam [mi]

    44. Estazolam [iarc]

    45. Estazolam [usan]

    46. Dsstox_cid_572

    47. Estazolam [vandf]

    48. Estazolam [mart.]

    49. Estazolam [who-dd]

    50. Dsstox_rid_75665

    51. Dsstox_gsid_20572

    52. Schembl28766

    53. Mls003899222

    54. Bidd:gt0481

    55. Estazolam (jp17/usp/inn)

    56. Chembl285674

    57. Gtpl7550

    58. Zinc1370

    59. Estazolam [orange Book]

    60. Estazolam Civ [usp-rs]

    61. Dtxsid5020572

    62. Cdchdcwjmgxxrh-uhfffaoysa-

    63. Estazolam [usp Monograph]

    64. Estazolam 0.1 Mg/ml In Methanol

    65. Estazolam 1.0 Mg/ml In Methanol

    66. Bcp13317

    67. Tox21_112609

    68. Nsc290818

    69. Akos005064373

    70. Ab07556

    71. Db01215

    72. Smr000238168

    73. Cas-29975-16-4

    74. Wln: T B576 Bn Dnn Hn Ghj Ir& Lg

    75. C06981

    76. D00311

    77. 975e164

    78. A820132

    79. Q-201071

    80. Q3045264

    81. 8-chloro-6-phenyl-4h-s-triazolo[4,4]benzodiazepine

    82. 4h-s-triazolo[4,4]benzodiazepine, 8-chloro-6-phenyl-

    83. Estazolam Solution, Drug Standard, 100 Mug/l In Methanol

    84. 8-chloro-6-phenyl-4h-s-triazolo [4,3-a][1,4] Benzodiazepine

    85. 8-chloro-6-phenyl-4h-s-triazolo-[4,3-a][1,4]benzodiazepine

    86. Estazolam, United States Pharmacopeia (usp) Reference Standard

    87. 4h-[1,4]triazolo[4,3-a][1,4]benzodiazepine, 8-chloro-6-phenyl-

    88. 8-chloro-6-phenyl-4h-[1,4]triazolo[4,3-a][1,4]benzodiazepine

    89. 8-chloro-6-phenyl-4h-benzo[f][1,2,4]triazolo[4,3-a][1,4]diazepine

    90. Estazolam Solution, 1.0 Mg/ml In Methanol, Ampule Of 1 Ml, Certified Reference Material

    91. 12-chloro-9-phenyl-2,4,5,8-tetraazatricyclo[8.4.0.0?,?]tetradeca-1(14),3,5,8,10,12-hexaene

    92. 12-chloro-9-phenyl-2,4,5,8-tetraazatricyclo[8.4.0.0^{2,6}]tetradeca-1(10),3,5,8,11,13-hexaene

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 294.74 g/mol
    Molecular Formula C16H11ClN4
    XLogP31.7
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count1
    Exact Mass294.0672241 g/mol
    Monoisotopic Mass294.0672241 g/mol
    Topological Polar Surface Area43.1 Ų
    Heavy Atom Count21
    Formal Charge0
    Complexity407
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameEstazolam
    PubMed HealthEstazolam (By mouth)
    Drug ClassesHypnotic
    Drug LabelEstazolam, a triazolobenzodiazepine derivative, is an oral hypnotic agent. Estazolam occurs as a fine, white, odorless powder that is soluble in alcohol and practically insoluble in water. The chemical name for estazolam is 8-chloro-6-phenyl-4H-s-tri...
    Active IngredientEstazolam
    Dosage FormTablet
    RouteOral
    Strength2mg; 1mg
    Market StatusPrescription
    CompanyWatson Labs; Teva; Par Pharm

    2 of 2  
    Drug NameEstazolam
    PubMed HealthEstazolam (By mouth)
    Drug ClassesHypnotic
    Drug LabelEstazolam, a triazolobenzodiazepine derivative, is an oral hypnotic agent. Estazolam occurs as a fine, white, odorless powder that is soluble in alcohol and practically insoluble in water. The chemical name for estazolam is 8-chloro-6-phenyl-4H-s-tri...
    Active IngredientEstazolam
    Dosage FormTablet
    RouteOral
    Strength2mg; 1mg
    Market StatusPrescription
    CompanyWatson Labs; Teva; Par Pharm

    4.2 Drug Indication

    For the short-term management of insomnia characterized by difficulty in falling asleep, frequent nocturnal awakenings, and/or early morning awakenings.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Estazolam, a triazolobenzodiazepine derivative, is an oral hypnotic agent with anticonvulsant, hypnotic, and muscle relaxant properties. It has been shown in some cases to be more potent than diazepam or nitrazepam.

    5.2 MeSH Pharmacological Classification

    Anticonvulsants

    Drugs used to prevent SEIZURES or reduce their severity. (See all compounds classified as Anticonvulsants.)

    Anti-Anxiety Agents

    Agents that alleviate ANXIETY, tension, and ANXIETY DISORDERS, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions. ADRENERGIC BETA-ANTAGONISTS are commonly used in the symptomatic treatment of anxiety but are not included here. (See all compounds classified as Anti-Anxiety Agents.)

    GABA Modulators

    Substances that do not act as agonists or antagonists but do affect the GAMMA-AMINOBUTYRIC ACID receptor-ionophore complex. GABA-A receptors (RECEPTORS, GABA-A) appear to have at least three allosteric sites at which modulators act: a site at which BENZODIAZEPINES act by increasing the opening frequency of GAMMA-AMINOBUTYRIC ACID-activated chloride channels; a site at which BARBITURATES act to prolong the duration of channel opening; and a site at which some steroids may act. GENERAL ANESTHETICS probably act at least partly by potentiating GABAergic responses, but they are not included here. (See all compounds classified as GABA Modulators.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    ESTAZOLAM
    5.3.2 FDA UNII
    36S3EQV54C
    5.3.3 Pharmacological Classes
    Benzodiazepines [CS]; Benzodiazepine [EPC]
    5.4 ATC Code

    N - Nervous system

    N05 - Psycholeptics

    N05C - Hypnotics and sedatives

    N05CD - Benzodiazepine derivatives

    N05CD04 - Estazolam

    5.5 Absorption, Distribution and Excretion

    Absorption

    Tablets have been found to be equivalent in absorption to an orally administered solution of estazolam. In healthy subjects who received up to three times the recommended dose, peak estazolam plasma concentrations occurred within two hours after dosing (range 0.5 to 6.0 hours) and were proportional to the administered dose, suggesting linear pharmacokinetics over the dosage range tested.

    Route of Elimination

    Estazolam is extensively metabolized. The elimination of the parent drug takes place via hepatic metabolism of estazolam to hydroxylated and other metabolites that are eliminated largely in the urine both free and conjugated. Less than 5% of a 2 mg dose of estazolam was excreted unchanged in the urine, with only 4% of the dose appearing in the feces. Radiolabel mass balance studies indicate that the main route of excretion is via the kidneys. After 5 days, 87% of the administered radioactivity was excreted in human urine. Less than 4% of the dose was excreted unchanged.

    5.6 Metabolism/Metabolites

    Extensively metabolized in the liver. In vitro studies with human liver microsomes indicate that the biotransformation of estazolam to the major circulating metabolite 4-hydroxy-estazolam is mediated by cytochrome P450 3A (CYP3A).

    Estazolam has known human metabolites that include 4-hydroxyestazolam.

    S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

    5.7 Biological Half-Life

    The range of estimates for the mean elimination half-life of estazolam varies from 10 to 24 hours.

    5.8 Mechanism of Action

    Benzodiazepines bind nonspecifically to benzodiazepine receptors, which affects affects muscle relaxation, anticonvulsant activity, motor coordination, and memory. As benzodiazepine receptors are thought to be coupled to gamma-aminobutyric acid-A (GABAA) receptors, this enhances the effects GABA by increasing GABA affinity for the GABA receptor. Binding of the inhibitory neurotransmitter GABA to the site opens the chloride channel, resulting in a hyperpolarized cell membrane that prevents further excitation of the cell.

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