Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C15H10BrClN2O |
| Molecular Weight | 349.61 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
ClC1=CC=CC=C1C2=NCC(=O)NC3=C2C=C(Br)C=C3
InChI
InChIKey=CGMJQQJSWIRRRL-UHFFFAOYSA-N
InChI=1S/C15H10BrClN2O/c16-9-5-6-13-11(7-9)15(18-8-14(20)19-13)10-3-1-2-4-12(10)17/h1-7H,8H2,(H,19,20)
| Molecular Formula | C15H10BrClN2O |
| Molecular Weight | 349.61 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: Description was created based on several sources, including https://extrapharmacy.ru/pdf/Phenazepam.pdf http://www.valentapharm.com/eng/phenazepam/
Curator's Comment: Description was created based on several sources, including https://extrapharmacy.ru/pdf/Phenazepam.pdf http://www.valentapharm.com/eng/phenazepam/
Phenazepam belongs to the 1,4-benzodiazepines, the same family of medicines to which diazepam, oxazepam and temazepam belong. Phenazepam was first synthesized and developed in 1975 in the former Soviet Union where it became one of the most prescribed benzodiazepines since 1978 to treat sleep disorder, anxiety, alcohol use disorder and epilepsy. Phenazepam has not been licensed elsewhere in the world. The actions of phenazepam are mediated by the GABAA-receptor and reversed by the selective benzodiazepine antagonist flumazenil. In vitro, phenazepam and its metabolite 3-hydroxyphenazepam potentiate GABA responses with EC50-values of 6.1 nM and 10.3 nM, respectively, comparable to the value of 13.5 nM for diazepam. In vivo, phenazepam induces pronounced myorelaxation in the rotarod test with an ED50-value of 2.48 (1.65-3.72) mg/kg, and at 10 mg/kg it decreases punished responding in the conflict test (conflict between drinking motivation and painful electrical stimuli). Phenazepam increases the duration of sleep induced by hexanal several fold and is in this respect superior to diazepam. Both phenazepam and 3-hydroxyphenazepam are full GABAA receptor agonists.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2109244 |
6.1 nM [EC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Fenazepam Approved UseFenazepam is used in various neurotic, neurosis-like, psychopathic, psychopathy-like and other conditions, accompanied by anxiety, fear, increased irritability, stress, mood swings, reactive psychoses, senesthopathic-hypochondriac syndrome (including cases resistant to other anxiolytics), vegetative and sleep disorders, anxiety and mental stress prophylaxis.
As anticonvulsant medication in temporal lobe and myoclonic epilepsy.
Fenazepam is used in neurology for management of hyperkinesis and tic disorders, muscular rigidity, vegetative dysfunction. Launch Date1978 |
|||
| Primary | Fenazepam Approved UseFenazepam is used in various neurotic, neurosis-like, psychopathic, psychopathy-like and other conditions, accompanied by anxiety, fear, increased irritability, stress, mood swings, reactive psychoses, senesthopathic-hypochondriac syndrome (including cases resistant to other anxiolytics), vegetative and sleep disorders, anxiety and mental stress prophylaxis.
As anticonvulsant medication in temporal lobe and myoclonic epilepsy.
Fenazepam is used in neurology for management of hyperkinesis and tic disorders, muscular rigidity, vegetative dysfunction. Launch Date1978 |
|||
| Primary | Fenazepam Approved UseFenazepam is used in various neurotic, neurosis-like, psychopathic, psychopathy-like and other conditions, accompanied by anxiety, fear, increased irritability, stress, mood swings, reactive psychoses, senesthopathic-hypochondriac syndrome (including cases resistant to other anxiolytics), vegetative and sleep disorders, anxiety and mental stress prophylaxis.
As anticonvulsant medication in temporal lobe and myoclonic epilepsy.
Fenazepam is used in neurology for management of hyperkinesis and tic disorders, muscular rigidity, vegetative dysfunction. Launch Date1978 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
0.024 μg/mL |
3 mg single, oral dose: 3 mg route of administration: Oral experiment type: SINGLE co-administered: |
PHENAZEPAM blood | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
0.038 μg/mL |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
PHENAZEPAM blood | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
112 μg × min/mL |
3 mg single, oral dose: 3 mg route of administration: Oral experiment type: SINGLE co-administered: |
PHENAZEPAM blood | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
208 μg × min/mL |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
PHENAZEPAM blood | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
60 h |
3 mg single, oral dose: 3 mg route of administration: Oral experiment type: SINGLE co-administered: |
PHENAZEPAM blood | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
60 h |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
PHENAZEPAM blood | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
14.9 h |
2 mg single, intravenous dose: 2 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
PHENAZEPAM unknown | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
15.6 h |
2 mg single, intramuscular dose: 2 mg route of administration: Intramuscular experiment type: SINGLE co-administered: |
PHENAZEPAM unknown | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
103 h |
3 mg single, oral dose: 3 mg route of administration: Oral experiment type: SINGLE co-administered: |
PHENAZEPAM unknown | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.7% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29582576/ |
PHENAZEPAM plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: FEMALE / MALE food status: UNKNOWN |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Fatality involving the ingestion of phenazepam and poppy seed tea. | 2010-10 |
|
| β-Polymorph of phenazepam: a powder study. | 2010-09-25 |
|
| [Pharmacologic correction of psycho-emotional status of patients with thyroid nodules in the preoperative period]. | 2010 |
|
| Tenoten in the therapy of patients with moderate cognitive impairment. | 2009-08 |
|
| The use of tenoten and tenoten (pediatric formulation) as a drug for premedication in adults and children during outpatients dentist visit. | 2009-08 |
|
| [Therapeutic effect and pharmacokinetics of transdermal phenazepam preparation in patients with different anxiety disorders]. | 2009-05-16 |
|
| [Abuse of phenazepam--new phenomenon in Sweden. Benzodiazepine derivative from Russia caused severe intoxication]. | 2009-04-09 |
|
| [Predictors of the efficacy of methods for psychocorrection in patients with irritable bowel syndrome and constipation]. | 2008-12-17 |
|
| Direct analysis of illicit drugs by desorption atmospheric pressure photoionization. | 2008-04 |
|
| [Discriminative stimulus properties of phenazepam and lorazepam: specificity and role of GABA A receptors]. | 2008-03-28 |
|
| Study of bipathic effect of phenazepam. | 2007-10 |
|
| [Effect of caffeine and phenazepam on the quantitative parameters of the EEG and ultraslow electrical processes in the brain]. | 2007-07-11 |
|
| [Application of extraction freezing for analysis of 1,4-benzodiazepines in urine]. | 2007-05-25 |
|
| [A comparative study of the development of drug differentiation between mexidol and phenazepam]. | 2005-11-10 |
|
| Free radical oxidation in rat brain during chronic stress and pharmacological regulation of this process. | 2005-10 |
|
| [Preoperative psychopharmacological correction in women with focal breast diseases]. | 2005-08-04 |
|
| [Thanatogenesis in poisoning with psychopharmaceuticals]. | 2005-05-11 |
|
| [Methodological bases of early psychosocial rehabilitation of poststroke patients in neurological hospital]. | 2005 |
|
| [Stress-induced alteration of the antiaggressive effect of anxiolytics]. | 2004-10-27 |
|
| [Experimental pharmacokinetics of phenazepam during transdermal administration of the therapeutic phenaperkuten system]. | 2004-06-11 |
|
| [Characteristics of clinical and pharmacological efficacy of tranquilizers and antidepressants in patients with ischemic heart disease and type A behavior]. | 2004 |
|
| Effect of lauric acid on transdermal penetration of phenazepam in vivo. | 2003-12 |
|
| [The influence of pharmacologically active substances of different classes at ultra low doses on lipid peroxidation in brain cell membranes and activity of acetylcholinesterase in vivo and in vitro]. | 2003-07-29 |
|
| [Effects of psychotropic drugs of different classes injected in super small doses]. | 2003-07-29 |
|
| [Screening method for compounds acting at super low concentrations]. | 2003-07-29 |
|
| [Clinical picture and treatment of agoraphobia with panic disorder]. | 2003-06 |
|
| The influence of anticonvulsant and antioxidant drugs on nitric oxide level and lipid peroxidation in the rat brain during penthylenetetrazole-induced epileptiform model seizures. | 2003-05 |
|
| [Effect of naloxone on the activity of Cl(-)-activated Mg(2+)-ATPase from plasma membrane fraction of the common bream brain (Abramis brama L.) in the presence of GABAa-ergic substances]. | 2003-04-26 |
|
| [Pharmacokinetics and efficacy of phenazepam after transdermal and enteral administration in rats]. | 2003-04-10 |
|
| Psychotropic activity of the antialcohol preparation Proproten-100. | 2003-01 |
|
| Phenazepam in therapeutic and ultralow doses in vitro modulates the content of lipid peroxidation products and acetylcholinesterase activity in membrane fraction from mouse brain. | 2003-01 |
|
| Pharmacological activity of phenazepam and flunitrazepam in ultralow doses. | 2003-01 |
|
| Effects of phenazepam in ultralow doses on bioelectric activity of the brain and behavior of rats in various models of anxiety. | 2003-01 |
|
| [Effect of phenazepam metabolite, 2-amino-5-bromo-2'-chlorobenzophenone, on glycine and glutamate NMDA receptors of rat hippocampal pyramidal neurones]. | 2003 |
|
| Biokinetics of transdermal 3-hydroxyphenazepam. | 2002-09 |
|
| Effect of activators and blockers of ligand-regulated ion channels on the activity of the Cl-stimulated Mg2+-ATPase of the plasma membrane fraction from bream (Abramis brama L.) brain. | 2002-02 |
|
| [Is it possible to predict individual stress resistance by evaluating low dose benzodiazepine effect in modeled emotional stress]. | 2001-09-11 |
|
| [Using computer sound cards in electrophysiological data processing]. | 2001-09-08 |
|
| [Predicting individual reactions to emotional stress and benzodiazepine tranquilizers]. | 2001-09-08 |
|
| Modulation of GABAA receptor-mediated currents by phenazepam and its metabolites. | 2001-07 |
|
| [Pharmacological analysis of memory disorders of different origins]. | 1989-06 |
|
| Effect of nicergoline on learning and memory. | 1988-07 |
Patents
Sample Use Guides
Rx dosage: 0.5 mg 2-3 times daily (10 mg daily maximum)
Recreational dose: 0.5 – 2.0 mg (online user states 1 mg phenazepam = 5 mg diazepam in effect)
Route of Administration:
Oral
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:39:18 GMT 2025
by
admin
on
Mon Mar 31 18:39:18 GMT 2025
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| Record UNII |
3DSB43090Z
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| Record Status |
Validated (UNII)
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WIKIPEDIA |
Designer-drugs-Phenazepam
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NCI_THESAURUS |
C1012
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PHENAZEPAM
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100000079408
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3DSB43090Z
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SUB14828MIG
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51753-57-2
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C98139
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DTXSID00199685
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SALT/SOLVATE -> PARENT |
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METABOLITE ACTIVE -> PARENT |
in rat and mouse
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METABOLITE -> PARENT |
PLASMA; URINE
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ACTIVE MOIETY |
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| Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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| Tmax | PHARMACOKINETIC |
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| Volume of Distribution | PHARMACOKINETIC |
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| Biological Half-life | PHARMACOKINETIC |
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