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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:54:55 UTC
Update Date2019-07-23 06:35:23 UTC
HMDB IDHMDB0042029
Secondary Accession Numbers
  • HMDB42029
Metabolite Identification
Common NameTetrazepam
DescriptionAllergic reactions can develop to tetrazepam and it is considered to be a potential allergen. Drug rash and drug-induced eosinophilia with systemic symptoms is a known complication of tetrazepam exposure. These hypersensitive allergic reactions can be of the delayed type. Drowsiness is a common side effect of tetrazepam. A reduction in muscle force can occur. Myasthenia gravis, a condition characterised by severe muscle weakness is another potential adverse effect from tetrazepam. Cardiovascular and respiratory adverse effects can occur with tetrazepam similar to other benzodiazepines. Prolonged use, as with all benzodiazepines, should be avoided, as tolerance occurs and there is a risk of benzodiazepine dependence and a benzodiazepine withdrawal syndrome after stopping or reducing dosage. Tetrazepam (is marketed under the following brand names, Clinoxan, Epsipam, Myolastan, Musaril, Relaxam and Spasmorelax) is a benzodiazepine derivative with anticonvulsant, anxiolytic, hypnotic and muscle relaxant properties. It is used mainly in Austria, France, Belgium, Germany and Spain to treat muscle spasm, anxiety disorders such as panic attacks, or more rarely to treat depression, premenstrual syndrome or agoraphobia. Tetrazepam has relatively little sedative effect at low doses while still producing useful muscle relaxation and anxiety relief. Tetrazepam is an unusual benzodiazepine in its molecular structure as it has cyclohexenyl group which has substituted the typical 5-phenyl moiety seen in other benzodiazepines. Tetrazepam, is rapidly absorbed after oral administration, within 45 mins and reaches peak plasma levels in less than 2 hours. It is classed as an intermediate acting benzodiazepine with an elimination half-life of approximately 15 hours. It is primarily metabolised to the inactive metabolites 3-hydroxy-tetrazepam and norhydroxytetrazepam. The pharmacological effects of tetrazepam are significantly less potent when compared against diazepam, in animal studies. Tetrazepam is a benzodiazepine site agonist and binds unselectively to type 1 and type 2 benzodiazepine site types as well as to peripheral benzodiazepine receptors. The muscle relaxant properties of tetrazepam are most likely due to a reduction of calcium influx. Small amounts of diazepam as well as the active metabolites of diazepam are produced from metabolism of tetrazepam. The metabolism of tetrazepam has led to false accusations of prisoners prescribed tetrazepam of taking illicit diazepam; this can lead to increased prison sentences for prisoners. Tetrazepam, like other benzodiazepines is a drug which is very frequently used in overdoses. These overdoses are often mixed overdoses, i.e. a mixture of other benzodiazepines or other drug classes with tetrazepam.
Structure
Data?1563863723
Synonyms
ValueSource
MyolastanKegg
ClinoxanHMDB
MusarilHMDB
Lichtenstein brand OF tetrazepamHMDB
MobifortonHMDB
MusapamHMDB
TetramduraHMDB
Tetrazep 1a pharmaHMDB
1a Brand OF tetrazepamHMDB
AbZ brand OF tetrazepamHMDB
Gry brand OF tetrazepamHMDB
Krewel brand OF tetrazepamHMDB
MTW-TetrazepamHMDB
PanosHMDB
Tetra-saarHMDB
MTW Brand OF tetrazepamHMDB
Merck dura brand OF tetrazepamHMDB
Sanofi synthelabo brand OF tetrazepamHMDB
TethexalHMDB
TetrarelaxHMDB
Tetrazep abzHMDB
Mibe brand OF tetrazepamHMDB
Fornet brand OF tetrazepamHMDB
Hexal brand OF tetrazepamHMDB
MIP brand OF tetrazepamHMDB
MyospasmalHMDB
RilexHMDB
TAD brand OF tetrazepamHMDB
CT-Arzneimittel brand OF tetrazepamHMDB
Tetrazep von CTHMDB
Chemical FormulaC16H17ClN2O
Average Molecular Weight288.772
Monoisotopic Molecular Weight288.102940883
IUPAC Name7-chloro-5-(cyclohex-1-en-1-yl)-1-methyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one
Traditional Nametetrazepam
CAS Registry Number10379-14-3
SMILES
CN1C2=C(C=C(Cl)C=C2)C(=NCC1=O)C1=CCCCC1
InChI Identifier
InChI=1S/C16H17ClN2O/c1-19-14-8-7-12(17)9-13(14)16(18-10-15(19)20)11-5-3-2-4-6-11/h5,7-9H,2-4,6,10H2,1H3
InChI KeyIQWYAQCHYZHJOS-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1,4-benzodiazepines. These are organic compounds containing a benzene ring fused to a 1,4-azepine.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzodiazepines
Sub Class1,4-benzodiazepines
Direct Parent1,4-benzodiazepines
Alternative Parents
Substituents
  • 1,4-benzodiazepine
  • Alpha-amino acid or derivatives
  • Aryl chloride
  • Aryl halide
  • Benzenoid
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Ketimine
  • Lactam
  • Carboxylic acid derivative
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organochloride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Imine
  • Organic nitrogen compound
  • Organic oxide
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point144 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP3.20Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.042 g/LALOGPS
logP3.53ALOGPS
logP3.14ChemAxon
logS-3.8ALOGPS
pKa (Strongest Basic)3.24ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area32.67 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity81.72 m³·mol⁻¹ChemAxon
Polarizability30.78 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06z9-0190000000-e89bbe3f5be5dd2d8ef6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-000i-0090000000-648ea07cfb54da221938Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-000i-0090000000-6fa6feb988c28cea9701Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-000i-0190000000-133e43f99f45b667ff8dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0fc0-1690000000-9b2cabcfe30f022505faSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-005a-2940000000-160b387e0e158e114ad3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-003s-1920000000-afce32e992dcf0ffa799Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-481bd9921daf23c25723Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1090000000-1da96f135036ef7911ebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-9330000000-4698b4ebfdf65cd11c90Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-13675d06f8c473dd2019Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-0b2235e8dd6ef6442946Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9430000000-ec79a12e3355732a7950Spectrum
MSMass Spectrum (Electron Ionization)splash10-0udr-2690000000-03229b9979372af89a08Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB13324
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID23551
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTetrazepam
METLIN IDNot Available
PubChem Compound25215
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available