Chlordiazepoxide (CHEM002206)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (18)XML
Record Information
Version1.0
Creation Date2009-07-21 20:27:00 UTC
Update Date2026-03-25 19:15:05 UTC
Accession NumberCHEM002206
Identification
Common NameChlordiazepoxide
ClassSmall Molecule
DescriptionChlordiazepoxide is only found in individuals that have used or taken this drug. It is an anxiolytic benzodiazepine derivative with anticonvulsant, sedative, and amnesic properties. It has also been used in the symptomatic treatment of alcohol withdrawal. Chlordiazepoxide binds to stereospecific benzodiazepine (BZD) binding sites on GABA (A) receptor complexes at several sites within the central nervous system, including the limbic system and reticular formation. This results in an increased binding of the inhibitory neurotransmitter GABA to the GABA(A) receptor.BZDs, therefore, enhance GABA-mediated chloride influx through GABA receptor channels, causing membrane hyperpolarization. The net neuro-inhibitory effects result in the observed sedative, hypnotic, anxiolytic, and muscle relaxant properties.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • Suspected Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Adjuvant, Anesthesia
  • Amine
  • Anti-Anxiety Agent
  • Benzodiazepine
  • Drug
  • GABA Modulator
  • Hypnotic and Sedative
  • Metabolite
  • Organic Compound
  • Organochloride
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
7-Chloro-2-methylamino-5-phenyl-3H-1,4-benzodiazepin-4-oxideChEBI
CDPChEBI
Chlordiazepoxide baseChEBI
ChlordiazepoxidumChEBI
ClopoxideChEBI
HelogaphenChEBI
LibritabsChEBI
MethaminodiazepoxideChEBI
MultumChEBI
RisolidChEBI
SilibrinChEBI
TropiumChEBI
Chemical FormulaC16H14ClN3O
Average Molecular Mass299.755 g/mol
Monoisotopic Mass299.083 g/mol
CAS Registry Number58-25-3
IUPAC Name7-chloro-2-(methylamino)-5-phenyl-3H-1,4λ⁵-benzodiazepin-4-one
Traditional Namemultum
SMILESCNC1=NC2=C(C=C(Cl)C=C2)C(C2=CC=CC=C2)=N(=O)C1
InChI IdentifierInChI=1S/C16H14ClN3O/c1-18-15-10-20(21)16(11-5-3-2-4-6-11)13-9-12(17)7-8-14(13)19-15/h2-9H,10H2,1H3,(H,18,19)
InChI KeyANTSCNMPPGJYLG-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
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • Imidolactam
  • Nitrone
  • Azacycle
  • Carboxylic acid amidine
  • Allyl-type 1,3-dipolar organic compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Amidine
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organic nitrogen compound
  • Organic zwitterion
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point236-236.5°C
Boiling PointNot Available
Solubility2000 mg/L
Predicted Properties
PropertyValueSource
Water Solubility0.02 g/LALOGPS
logP2.01ALOGPS
logP3.05ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)18.52ChemAxon
pKa (Strongest Basic)6.43ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area53.14 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity87.34 m³·mol⁻¹ChemAxon
Polarizability30.97 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0udi-0079000000-a3045f81d776a5127fe9Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-5590000000-a20477457b7e9f8a22eaSpectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0udi-0079000000-a3045f81d776a5127fe9Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-5590000000-a20477457b7e9f8a22eaSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ce9-3190000000-fd85fc0a63c0f6fa743aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0090000000-a293b353926a16c4d11aSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-004i-2590000000-965415c5fb9e79098c6dSpectrum
LC-MS/MSLC-MS/MS Spectrum - -1V, Positivesplash10-001i-0090000000-c7b6568f60df163a9045Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-145539550957c8a47ff2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-2039000000-5d3fa4444adf37869d3aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-23b22bc4629e93465c34Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-cae96ea0a93acd325b0aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-1090000000-e599edf7db7a647524e4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-9030000000-ed7b2614fcfebabd55dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-20c277fa4f0e38cb4802Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0029000000-72801e1fa9da3f451f42Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02tc-1290000000-0b39e76350bab6708551Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-d48fa0574ae5210c8c30Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kb-2090000000-459de3a61617176e7e3bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gc0-9010000000-5ae42ebf2246e4f7b539Spectrum
Toxicity Profile
Route of ExposureOral
Mechanism of ToxicityChlordiazepoxide binds to stereospecific benzodiazepine (BZD) binding sites on GABA (A) receptor complexes at several sites within the central nervous system, including the limbic system and reticular formation. This results in an increased binding of the inhibitory neurotransmitter GABA to the GABA(A) receptor.BZDs, therefore, enhance GABA-mediated chloride influx through GABA receptor channels, causing membrane hyperpolarization. The net neuro-inhibitory effects result in the observed sedative, hypnotic, anxiolytic, and muscle relaxant properties.
MetabolismHepatic. Route of Elimination: Chlordiazepoxide is excreted in the urine, with 1% to 2% unchanged and 3% to 6% as conjugate. Half Life: 24-48 hours
Toxicity ValuesLD50: 537 mg/kg (Oral, Rat) (1)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the management of anxiety disorders or for the short-term relief of symptoms of anxiety, withdrawal symptoms of acute alcoholism, and preoperative apprehension and anxiety.
Minimum Risk LevelNot Available
Health EffectsThey cause slurred speech, disorientation and "drunken" behavior. They are physically and psychologically addictive.
SymptomsSigns of overdose include respiratory depression, muscle weakness, somnolence (general depressed activity).
TreatmentGeneral supportive measures should be employed, along with immediate gastric lavage. Intravenous fluids should be administered and an adequate airway maintained. Hypotension may be combated by the use of Levophed (norepinephrine) or Aramine (metaraminol). Flumazenil, a specific benzodiazepine-receptor antagonist, is indicated for the complete or partial reversal of the sedative effects of benzodiazepines and may be used in situations when an overdose with a benzodiazepine is known or suspected. (8)
Concentrations
Not Available
DrugBank IDDB00475
HMDB IDHMDB0014618
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkChlordiazepoxide
Chemspider ID10248513
ChEBI ID3611
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Sternbach, L.H.; US. Patent 2,893,992; July 7,1959; assigned to Hoffmann-LaRoche, Inc.

MSDSLink
General References
1. Earley JV, Fryer RI, Ning RY: Quinazolines and 1,4-benzodiazepines. LXXXIX: Haptens useful in benzodiazepine immunoassay development. J Pharm Sci. 1979 Jul;68(7):845-50.
2. Olive G, Dreux C: [Pharmacologic bases of use of benzodiazepines in pereinatal medicine]. Arch Fr Pediatr. 1977 Jan;34(1):74-89.
3. Oishi R, Nishibori M, Itoh Y, Saeki K: Diazepam-induced decrease in histamine turnover in mouse brain. Eur J Pharmacol. 1986 May 27;124(3):337-42.
4. Vozeh S: [Pharmacokinetic of benzodiazepines in old age]. Schweiz Med Wochenschr. 1981 Nov 21;111(47):1789-93.
5. Skerritt JH, Johnston GA: Enhancement of GABA binding by benzodiazepines and related anxiolytics. Eur J Pharmacol. 1983 May 6;89(3-4):193-8.
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=17049372
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=19643124
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=9632243