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    Chemistry

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    Also known as: Restoril, Hydroxydiazepam, Methyloxazepam, Levanxol, Oxydiazepam, Levanxene
    Molecular Formula
    C16H13ClN2O2
    Molecular Weight
    300.74  g/mol
    InChI Key
    SEQDDYPDSLOBDC-UHFFFAOYSA-N
    FDA UNII
    CHB1QD2QSS
    Temazepam
    A benzodiazepine that acts as a GAMMA-AMINOBUTYRIC ACID modulator and anti-anxiety agent.
    Temazepam is a Benzodiazepine.
    1 2D Structure

    Temazepam

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    7-chloro-3-hydroxy-1-methyl-5-phenyl-3H-1,4-benzodiazepin-2-one
    2.1.2 InChI
    InChI=1S/C16H13ClN2O2/c1-19-13-8-7-11(17)9-12(13)14(18-15(20)16(19)21)10-5-3-2-4-6-10/h2-9,15,20H,1H3
    2.1.3 InChI Key
    SEQDDYPDSLOBDC-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CN1C2=C(C=C(C=C2)Cl)C(=NC(C1=O)O)C3=CC=CC=C3
    2.2 Other Identifiers
    2.2.1 UNII
    CHB1QD2QSS
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 3 Hydroxydiazepam

    2. 3-hydroxydiazepam

    3. Apo Temazepam

    4. Apo-temazepam

    5. Dasuen

    6. Euhypnos

    7. Gen Temazepam

    8. Gen-temazepam

    9. Hydroxydiazepam

    10. Levanxol

    11. Methyloxazepam

    12. Nocturne

    13. Norkotral Tema

    14. Normison

    15. Normitab

    16. Nortem

    17. Novo Temazepam

    18. Novo-temazepam

    19. Nu Temazepam

    20. Nu-temazepam

    21. Oxydiazepam

    22. Planum

    23. Pms Temazepam

    24. Pms-temazepam

    25. Pronervon T

    26. Remestan

    27. Restoril

    28. Ro 5 5345

    29. Ro-5-5345

    30. Ro55345

    31. Sah 47 603

    32. Sah 47-603

    33. Sah 47603

    34. Signopam

    35. Tema, Norkotral

    36. Temaze

    37. Temazep Von Ct

    38. Temtabs

    39. Tenox

    40. Von Ct, Temazep

    41. Wy 3917

    42. Wy-3917

    43. Wy3917

    2.3.2 Depositor-Supplied Synonyms

    1. Restoril

    2. Hydroxydiazepam

    3. Methyloxazepam

    4. Levanxol

    5. Oxydiazepam

    6. Levanxene

    7. Crisonar

    8. Euhypnos

    9. Signopam

    10. 846-50-4

    11. N-methyloxazepam

    12. Mabertin

    13. Normison

    14. Remestan

    15. Planum

    16. 3-hydroxydiazepam

    17. Cerepax

    18. Euipnos

    19. Temaz

    20. Tenox

    21. Wy-3917

    22. Temazepamum

    23. Er 115

    24. (rs)-temazepam

    25. Ro 5-5345

    26. Wy 3917

    27. Temazepam, Pharmaceutical Grade

    28. K-3917

    29. Temazepam Civ

    30. 2h-1,4-benzodiazepin-2-one, 7-chloro-1,3-dihydro-3-hydroxy-1-methyl-5-phenyl-

    31. Nsc 246303

    32. 7-chloro-3-hydroxy-1-methyl-5-phenyl-3h-1,4-benzodiazepin-2-one

    33. Chb1qd2qss

    34. Nocturne

    35. Normitab

    36. Temtabs

    37. Dasuen

    38. Nortem

    39. Norkotral Tema

    40. Nsc-246303

    41. Temazep Von Ct

    42. Pronervon T

    43. 1,3-dihydro-7-chloro-3-hydroxy-1-methyl-5-phenyl-2h-1,4-benzodiazepin-2-one

    44. Chebi:9435

    45. Nomapam

    46. Temador

    47. Lenal

    48. Uvamin Retard

    49. Neodorm Sp

    50. 7-chloro-3-hydroxy-1-methyl-5-phenyl-1,3-dihydro-2h-1,4-benzodiazepin-2-one

    51. Ncgc00159440-02

    52. Gelthix

    53. Levanzene

    54. Perdorm

    55. Dsstox_cid_1309

    56. Dsstox_rid_76071

    57. Dsstox_gsid_21309

    58. Temazepamum [inn-latin]

    59. Strazepam

    60. 7-chloro-3-hydroxy-1-methyl-5-phenyl-2,3-dihydro-1h-1,4-benzodiazepin-2-one

    61. Restoril (tn)

    62. Cas-846-50-4

    63. Ccris 1954

    64. Temazepam (usp/inn)

    65. K3917

    66. Unii-chb1qd2qss

    67. Einecs 212-688-1

    68. Brn 0759300

    69. Dea No. 2925

    70. Temazepam [usan:usp:inn:ban]

    71. Diazepam, 3-hydroxy

    72. (+/-)-temazepam

    73. Wy 2917

    74. Temazepam [inn]

    75. Temazepam [mi]

    76. Temazepam [iarc]

    77. Temazepam [usan]

    78. Temazepam [vandf]

    79. Chembl967

    80. Temazepam [mart.]

    81. Temazepam [who-dd]

    82. Schembl29463

    83. 5-25-02-00242 (beilstein Handbook Reference)

    84. Mls003899242

    85. Divk1c_000989

    86. Temazepam, Analytical Standard

    87. Gtpl7300

    88. Temazepam [orange Book]

    89. Temazepam Civ [usp-rs]

    90. Dtxsid8021309

    91. Temazepam [ep Monograph]

    92. Hms503e19

    93. Kbio1_000989

    94. Temazepam [usp Monograph]

    95. Ninds_000989

    96. Temazepam 1.0 Mg/ml In Methanol

    97. Tox21_111670

    98. Tox21_200044

    99. Bdbm50408032

    100. Nsc246303

    101. Ccg-213642

    102. Db00231

    103. Ro-5-5354

    104. Idi1_000989

    105. Ncgc00159440-03

    106. Ncgc00257598-01

    107. Smr000238146

    108. Wln: T67 Gnv Jn Ihj Cg G1 Iq Kr

    109. C07125

    110. D00370

    111. Ab01563160_01

    112. Q414796

    113. Temazepam, British Pharmacopoeia (bp) Reference Standard

    114. 2h-1, 7-chloro-1,3-dihydro-3-hydroxy-1-methyl-5-phenyl-

    115. Temazepam, United States Pharmacopeia (usp) Reference Standard

    116. Temazepam; T8275_sigma; Divk1c_000989; Ninds_000989

    117. 1-methyl-7-chloro-3-hydroxy-5-phenyl-1,3-dihydro-2h-1,4-benzodiazepine-2-one

    118. 2h-1,4-benzodiazepin-2-one, 1,3-dihydro-7-chloro-3-hydroxy-1-methyl-5-phenyl-

    119. 3-hydroxy-1,3-dihydro-1-methyl-7-chloro-5-phenyl-2h-1,4-benzodiazepin-2-one

    120. 7-chloro-3-hydroxy-1-methyl-5-phenyl-1,3-dihydro-2h-1,4-benzodiazepin-2-one #

    121. 7-chloro-3-hydroxy-1-methyl-5-phenyl-1,3-dihydro-2h-benzo[e][1,4]diazepin-2-one

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

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 300.74 g/mol
    Molecular Formula C16H13ClN2O2
    XLogP32.2
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count1
    Exact Mass300.0665554 g/mol
    Monoisotopic Mass300.0665554 g/mol
    Topological Polar Surface Area52.9 Ų
    Heavy Atom Count21
    Formal Charge0
    Complexity434
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 4  
    Drug NameRestoril
    PubMed HealthTemazepam (By mouth)
    Drug ClassesAntianxiety, Hypnotic
    Drug LabelRestoril (temazepam) is a benzodiazepine hypnotic agent. The chemical name is 7-chloro-1,3-dihydro-3-hydroxy-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one, and the structural formula is: Temazepam is a white, crystalline substance, very slightly so...
    Active IngredientTemazepam
    Dosage FormCapsule
    RouteOral
    Strength22.5mg; 7.5mg; 30mg; 15mg
    Market StatusPrescription
    CompanyMallinckrodt

    2 of 4  
    Drug NameTemazepam
    PubMed HealthTemazepam (By mouth)
    Drug ClassesAntianxiety, Hypnotic
    Drug LabelDESCRIPTIONTemazepam is a benzodiazepine hypnotic agent. The chemical name is 7-chloro1,3-dihydro-3-hydroxy-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one, and the structural formula is:C16H13ClN2O2...
    Active IngredientTemazepam
    Dosage FormCapsule
    RouteOral
    Strength22.5mg; 7.5mg; 30mg; 15mg
    Market StatusPrescription
    CompanySandoz; Novel Labs; Actavis Elizabeth; Mutual Pharm; Mylan

    3 of 4  
    Drug NameRestoril
    PubMed HealthTemazepam (By mouth)
    Drug ClassesAntianxiety, Hypnotic
    Drug LabelRestoril (temazepam) is a benzodiazepine hypnotic agent. The chemical name is 7-chloro-1,3-dihydro-3-hydroxy-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one, and the structural formula is: Temazepam is a white, crystalline substance, very slightly so...
    Active IngredientTemazepam
    Dosage FormCapsule
    RouteOral
    Strength22.5mg; 7.5mg; 30mg; 15mg
    Market StatusPrescription
    CompanyMallinckrodt

    4 of 4  
    Drug NameTemazepam
    PubMed HealthTemazepam (By mouth)
    Drug ClassesAntianxiety, Hypnotic
    Drug LabelDESCRIPTIONTemazepam is a benzodiazepine hypnotic agent. The chemical name is 7-chloro1,3-dihydro-3-hydroxy-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one, and the structural formula is:C16H13ClN2O2...
    Active IngredientTemazepam
    Dosage FormCapsule
    RouteOral
    Strength22.5mg; 7.5mg; 30mg; 15mg
    Market StatusPrescription
    CompanySandoz; Novel Labs; Actavis Elizabeth; Mutual Pharm; Mylan

    4.2 Drug Indication

    Temazepam is specifically indicated only for the short-term management of insomnia,. Furthermore, such management is generally predominantly associated with the symptomatic relief of transient and short-term insomnia characterized by difficulty in falling asleep, frequent nocturnal awakenings and/or early morning awakenings. In particular, the official prescribing information for temazepam typically specifies that the instructions issued for dispensed prescriptions of the medication should indicate specifically that patients are only expected to use the therapy for short periods of time - usually 7-10 days in general. Subsequently, treatment with temazepam should usually not exceed 7 to 10 consecutive days and nor should it be prescribed in quantities exceeding a one-month supply. Some regional prescribing information also notes that temazepam may be used for premedication prior to minor surgery or other related procedures.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Temazepam is a benzodiazepine used as a hypnotic agent in the management of insomnia. Temazepam produces CNS depression at limbic, thalamic, and hypothalamic levels of the CNS. Temazepam increases the affinity of the neurotransmitter gamma-aminobutyric acid (GABA) for GABA receptors by binding to benzodiazepine receptors. Results are sedation, hypnosis, skeletal muscle relaxation, anticonvulsant activity, and anxiolytic action. In sleep laboratory studies, the effect of temazepam was compared to placebo during a two week period. The studies demonstrated a linear dose-response improvement in total sleep time and sleep latency with substantial drug-placebo differences apparent for total sleep time and for sleep latency at higher doses of temazepam. Regardless, REM sleep was ultimately unchanged but slow wave sleep was decreased. Moreover, a transient syndrome, known as "rebound insomnia", wherein the symptoms that led to treatment with temazepam in the first place recur in an enhanced form, may happen on withdrawal of temazepam treatment. The possibility of this occurrence is in part why long term use of temazepam is not recommended due to worries over tolerance and dependence wherein patients' bodies become physiologically accustomed to the regular presence and pharmacological effect of higher and higher doses of the benzodiazepine used. The duration of hypnotic effect and the profile of unwanted adverse effects may be influenced by the distribution and elimination half-lives of the administered temazepam and any active metabolites that may be formed. When such half-lives are long, the drug or its metabolite(s) may accumulate during periods of nightly administration and be associated with impairments of cognitive and motor performance during waking hours. Conversely, if half-lives are short, the drug and metabolites would be cleared before the next dose is ingested, and carry-over effects related to sedation or CNS depression should be minimal or not present at all. However, during nightly use and for an extended period, pharmacodynamic tolerance or adaptation to some effects of benzodiazepine hypnotics may develop - which may also contribute to the possibility of 'rebound insomnia'. Consequently, if the drug has a very short elimination half-life, it is possible that a relative deficiency (for example, in relation to benzodiazepine GABA(a) receptor sites) may occur at some point in the interval between each night's use. This sequence of events may account for certain clinical findings reported happening after several weeks of nightly use of rapidly eliminated benzodiazepine hypnotics, including increased wakefulness during the last third of the night and the appearance of increased daytime anxiety.

    5.2 MeSH Pharmacological Classification

    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.)

    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.)

    Hypnotics and Sedatives

    Drugs used to induce drowsiness or sleep or to reduce psychological excitement or anxiety. (See all compounds classified as Hypnotics and Sedatives.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    TEMAZEPAM
    5.3.2 FDA UNII
    CHB1QD2QSS
    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

    N05CD07 - Temazepam

    5.5 Absorption, Distribution and Excretion

    Absorption

    Studies demonstrate that between 90 to 100% of an orally administered temazepam dose is absorbed, making the medication very well absorbed. The oral administration of 15 to 45 mg temazepam resulted in rapid absorption with significant blood levels achieved in 30 minutes and peak levels at 2-3 hours. In particular, direct studies following the oral ingestion of 30 mg of temazepam revealed measurable plasma concentrations were obtained 10-20 minutes after dosing with peak plasma levels ranging between 666-982 ng/mL (with a mean of 865 ng/mL) presenting approximately 1.2-1.6 hours (with a mean of 1.5 hours) after the dosing. Finally, a dose-proportional relationship was established for the area under the plasma concentration/time curve over the 15 to 30 mg dose range.

    Route of Elimination

    Following a single dose, 80-90% of the dose appears in the urine, predominantly as the O-conjugate metabolite, and 3-13% of the dose appears in the faeces. Less than 2% of the dose is excreted unchanged or as N-desmethyltemazepam in the urine.

    Volume of Distribution

    The volume of distribution documented for temazepam is 1.3-1.5 L/kg body weight - and in particular, 43-68 L/kg for the unbound fraction.

    Clearance

    Studies regarding the clearance of temazepam have recorded the values of 1.03 ml/min/kg and 31 ml/min/kg for the clearance of total temazepam and the clearance of unbound temazepam, respectively.

    5.6 Metabolism/Metabolites

    First-pass metabolism of temazepam is minimal at approximately 5-8% of an administered dose. Nevertheless, temazepam is principally metabolized in the liver where most of the unchanged drug is directly conjugated to glucuronide and excreted in the urine. In particular, the primary metabolite present in the blood is the O-conjugate of temazepam. Less than 5% of the drug is demethylated to oxazepam and subsequently eliminated as the glucuronide. Regardless, the glucuronides of temazepam have no demonstrable CNS activity and it is believed that no active metabolites are formed in general. Since temazepam mainly undergoes Phase II conjugation reactions, it is proposed that it is devoid of CYP450 interactions.

    Temazepam is a known human metabolite of diazepam.

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

    5.7 Biological Half-Life

    The terminal half-life determined for temazepam is recorded as being between 3.5-18 hours, with a mean of 9 hours.

    5.8 Mechanism of Action

    Gamma-Aminobutyric acid (GABA) is considered the principal inhibitory neurotransmitter in the human body. When GABA binds to GABA(a) receptors found in neuron synapses, chloride ions are conducted across neuron cell membranes via an ion channel in the receptors. With enough chloride ions conducted, the local, associated neuron membrane potentials are hyperpolarized - making it more difficult or less likely for action potentials to fire, ultimately resulting in less excitation of the neurons. Subsequently, benzodiazepines like temazepam can bind to benzodiazepine receptors that are components of various varieties of GABA(a) receptors. This binding acts to enhance the effects of GABA by increasing GABA affinity for the GABA(a) receptor, which ultimately enhances GABA ligand binding at the receptors. This enhanced ligand binding of the inhibitory neurotransmitter GABA to the receptors increases the aforementioned chloride ion conduction (perhaps reportedly via an increase in the frequency of the chloride channel opening), resulting in a hyperpolarized cell membrane that prevents further excitation of the associated neuron cells. Combined with the notion that such benzodiazepine receptor associated GABA(a) receptors exist both peripherally and in the CNS, this activity consequently facilitates various effects like sedation, hypnosis, skeletal muscle relaxation, anticonvulsant activity, and anxiolytic action.

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    25-Jun-2021
    25-Jun-2024
    KGS
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    Average Price (USD/KGS)

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    DOSAGE - CAPSULE;ORAL - 15MG

    USFDA APPLICATION NUMBER - 18163

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