chlordiazepoxide Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
diazepam derivatives 594 58-25-3

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • chlordiazepoxide
  • chlordiazepoxide hydrochloride
  • chloridazepoxide
  • methaminodiazepoxide
  • chlordiazepoxid
  • chlorodiazepoxide
  • chlordiazepoxide HCl
An anxiolytic benzodiazepine derivative with anticonvulsant, sedative, and amnesic properties. It has also been used in the symptomatic treatment of alcohol withdrawal.
  • Molecular weight: 299.76
  • Formula: C16H14ClN3O
  • CLOGP: 3.79
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 1
  • TPSA: 53.14
  • ALOGS: -4.18
  • ROTB: 1

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
30 mg O
50 mg P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 2 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0.50 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 14.30 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 99 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.25 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 0.37 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.06 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 8.30 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Feb. 24, 1960 FDA VALEANT PHARM INTL

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Cerebral venous thrombosis 183.02 18.69 43 5109 2301 53341613
Completed suicide 134.15 18.69 109 5043 138092 53205822
Drug abuse 122.23 18.69 77 5075 65449 53278465
Hyperreflexia 75.85 18.69 26 5126 5454 53338460
Bradyphrenia 74.26 18.69 27 5125 6723 53337191
Toxicity to various agents 73.79 18.69 98 5054 219500 53124414
Thalamic infarction 69.83 18.69 15 5137 531 53343383
Poisoning 64.73 18.69 30 5122 13820 53330094
Intentional product misuse 54.27 18.69 42 5110 49350 53294564
Sopor 47.49 18.69 28 5124 21056 53322858
Drug withdrawal syndrome 47.38 18.69 31 5121 27991 53315923
Drug interaction 42.58 18.69 76 5076 219253 53124661
Disorientation 42.21 18.69 33 5119 39326 53304588
Clonus 39.27 18.69 15 5137 4276 53339638
Apraxia 39.15 18.69 12 5140 1766 53342148
Perseveration 37.75 18.69 8 5144 265 53343649
Morbid thoughts 36.27 18.69 9 5143 605 53343309
Overdose 34.41 18.69 47 5105 107689 53236225
Slow response to stimuli 32.29 18.69 9 5143 950 53342964
Derailment 27.97 18.69 5 5147 66 53343848
Confusional state 27.53 18.69 59 5093 194162 53149752
Abdominal tenderness 27.50 18.69 14 5138 7893 53336021
Disturbance in attention 26.83 18.69 24 5128 34359 53309555
Dyskinesia 24.41 18.69 22 5130 31811 53312103
Respiratory arrest 23.42 18.69 22 5130 33518 53310396
Abnormal behaviour 22.71 18.69 18 5134 21848 53322066
Muscle twitching 22.59 18.69 16 5136 16410 53327504
Cognitive disorder 21.49 18.69 24 5128 44754 53299160
Alcoholism 21.14 18.69 8 5144 2223 53341691
Torsade de pointes 21.03 18.69 14 5138 12991 53330923
Cardio-respiratory arrest 20.84 18.69 27 5125 58731 53285183
Psychomotor retardation 20.55 18.69 9 5143 3629 53340285
Cardiac arrest 20.13 18.69 34 5118 93633 53250281
Hepatitis alcoholic 19.70 18.69 4 5148 107 53343807

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug abuse 199.42 21.82 108 2645 80135 32430638
Toxicity to various agents 139.74 21.82 117 2636 177924 32332849
Ventricular tachyarrhythmia 99.40 21.82 18 2735 296 32510477
Completed suicide 83.12 21.82 66 2687 92451 32418322
Overdose 67.40 21.82 57 2696 87020 32423753
Delusion of replacement 62.94 21.82 11 2742 146 32510627
Shoshin beriberi 41.60 21.82 7 2746 73 32510700
Poisoning 36.05 21.82 18 2735 11140 32499633
Cardio-respiratory arrest 35.92 21.82 33 2720 55956 32454817
Accidental death 26.19 21.82 9 2744 2168 32508605
Exposure via ingestion 25.49 21.82 9 2744 2348 32508425
Alcoholism 25.30 21.82 10 2743 3562 32507211
Alcohol poisoning 22.57 21.82 9 2744 3280 32507493

Pharmacologic Action:

SourceCodeDescription
ATC N05BA02 NERVOUS SYSTEM
PSYCHOLEPTICS
ANXIOLYTICS
Benzodiazepine derivatives
FDA CS M0002356 Benzodiazepines
CHEBI has role CHEBI:35474 minor tranquilisers
CHEBI has role CHEBI:35717 sedatives
CHEBI has role CHEBI:60807 anaesthesia adjuvants
MeSH PA D000759 Adjuvants, Anesthesia
MeSH PA D014151 Anti-Anxiety Agents
MeSH PA D002491 Central Nervous System Agents
MeSH PA D002492 Central Nervous System Depressants
MeSH PA D018682 GABA Agents
MeSH PA D018757 GABA Modulators
MeSH PA D006993 Hypnotics and Sedatives
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D011619 Psychotropic Drugs
MeSH PA D014149 Tranquilizing Agents
FDA EPC N0000175694 Benzodiazepine

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Alcohol withdrawal delirium indication 8635005
Irritable bowel syndrome indication 10743008 DOID:9778
Peptic ulcer indication 13200003 DOID:750
Anxiety indication 48694002
General anesthesia indication 50697003
Severe anxiety (panic) indication 80583007
Alcohol withdrawal syndrome indication 191480000
Mixed anxiety and depressive disorder indication 231504006
Local anesthesia indication 386761002
Preoperative Anxiety indication
Pre-Op Apprehension indication
Anxiety associated with Menopause indication
Panic disorder off-label use 371631005 DOID:594
Tension-type headache off-label use 398057008
Brain damage contraindication 2470005
Hyperlipoproteinemia contraindication 3744001 DOID:1168
Hypocalcemia contraindication 5291005
Tachyarrhythmia contraindication 6285003
Suicidal thoughts contraindication 6471006
Urinary tract obstruction contraindication 7163005 DOID:5200
Alcoholism contraindication 7200002
Sinus tachycardia contraindication 11092001
Hypercholesterolemia contraindication 13644009
Severe chronic ulcerative colitis contraindication 14311001
Disorder of lung contraindication 19829001 DOID:850
Myocardial infarction contraindication 22298006 DOID:5844
Glaucoma contraindication 23986001 DOID:1686
Alcohol intoxication contraindication 25702006
Shock contraindication 27942005
Toxic megacolon contraindication 28536002 DOID:1770
Orthostatic hypotension contraindication 28651003
Atony of colon contraindication 29479008
Torsades de pointes contraindication 31722008
Hyperthyroidism contraindication 34486009 DOID:7998
Depressive disorder contraindication 35489007
Chloasma contraindication 36209000
Migraine contraindication 37796009 DOID:6364
Hypertensive disorder contraindication 38341003 DOID:10763
Disorder of gallbladder contraindication 39621005 DOID:0060262
Hypothyroidism contraindication 40930008 DOID:1459
Complete trisomy 21 syndrome contraindication 41040004 DOID:14250
Body fluid retention contraindication 43498006
Hyperactive behavior contraindication 44548000
Conduction disorder of the heart contraindication 44808001
Achalasia of esophagus contraindication 45564002 DOID:9164
Thrombosis of retinal vein contraindication 46085004
Humoral hypercalcemia of malignancy contraindication 47709007
Chronic heart failure contraindication 48447003
Dementia contraindication 52448006
Hepatic porphyria contraindication 55056006 DOID:3133
Systemic lupus erythematosus contraindication 55464009 DOID:9074
Paralytic ileus contraindication 55525008 DOID:8442
Peptic reflux disease contraindication 57643001
Thrombophlebitis contraindication 64156001 DOID:3875
Ulcerative colitis contraindication 64766004 DOID:8577
Intermenstrual bleeding - irregular contraindication 64996003
Drug AND/OR toxin-induced diarrhea contraindication 65979008
Substance abuse contraindication 66214007
Psychotic disorder contraindication 69322001
Diabetes mellitus contraindication 73211009 DOID:9351
Sleep apnea contraindication 73430006 DOID:0050847
Spastic paralysis contraindication 78403003
Disturbance of salivary secretion contraindication 78948009
Chronic idiopathic constipation contraindication 82934008
Hiatal hernia contraindication 84089009 DOID:12642
Open-angle glaucoma contraindication 84494001 DOID:1067
Epilepsy contraindication 84757009 DOID:1826
Breast lump contraindication 89164003
Kidney disease contraindication 90708001 DOID:557
Myasthenia gravis contraindication 91637004 DOID:437
Uterine leiomyoma contraindication 95315005 DOID:13223
Prolonged QT interval contraindication 111975006
Hypoalbuminemia contraindication 119247004
Gastrointestinal obstruction contraindication 126765001
Deep venous thrombosis contraindication 128053003
Endometriosis contraindication 129103003
Autonomic dysreflexia contraindication 129618003
Bleeding contraindication 131148009
Mammography abnormal contraindication 168750009
Bipolar affective disorder, current episode manic contraindication 191618007
Asthma contraindication 195967001 DOID:2841
Cerebrovascular accident contraindication 230690007
Myocardial dysfunction contraindication 233928007
Pulmonary thromboembolism contraindication 233935004
Thrombophilia contraindication 234467004 DOID:2452
Disease of liver contraindication 235856003 DOID:409
Bladder outflow obstruction contraindication 236645006
Pyloric obstruction contraindication 244815007
Endometrial carcinoma contraindication 254878006 DOID:2871
Benign prostatic hyperplasia contraindication 266569009
Retention of urine contraindication 267064002
Syncope contraindication 271594007
Chorea contraindication 271700006
Drowsy contraindication 271782001
Pregnancy, function contraindication 289908002
Hypertriglyceridemia contraindication 302870006
Functional visual loss contraindication 313165001
Severe chronic obstructive pulmonary disease contraindication 313299006
Malignant tumor of ovary contraindication 363443007 DOID:2394
Thromboembolic disorder contraindication 371039008
Angle-closure glaucoma contraindication 392291006 DOID:13550
Cardiovascular event risk contraindication 395112001
Gastric ulcer contraindication 397825006 DOID:10808
Breastfeeding (mother) contraindication 413712001
Chronic lung disease contraindication 413839001
Disorder of coronary artery contraindication 414024009
Obesity contraindication 414916001 DOID:9970
Estrogen receptor positive tumor contraindication 416053008
Myocardial infarction in recovery phase contraindication 418044006
Porphyria contraindication 418470004
Family history of malignant neoplasm of breast contraindication 429740004
Congenital long QT syndrome contraindication 442917000
Hypertensive urgency contraindication 443482000
Carcinoma of female breast contraindication 447782002
Smokes tobacco daily contraindication 449868002

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 4.79 Basic
pKa2 4.13 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
GABA-A receptor alpha-2/beta-3/gamma-2 Ion channel POSITIVE ALLOSTERIC MODULATOR Ki 6.34 WOMBAT-PK CHEMBL
GABA-A receptor alpha-3/beta-3/gamma-2 Ion channel POSITIVE ALLOSTERIC MODULATOR Ki 6.56 WOMBAT-PK CHEMBL
GABA-A receptor alpha-5/beta-3/gamma-2 Ion channel POSITIVE ALLOSTERIC MODULATOR Ki 6.50 WOMBAT-PK CHEMBL
GABA-A receptor alpha-1/beta-2/gamma-2 Ion channel POSITIVE ALLOSTERIC MODULATOR Ki 6.25 WOMBAT-PK CHEMBL
GABA-A receptor alpha-1/beta-3/gamma-2 Ion channel Ki 6.25 CHEMBL
Cholecystokinin receptor GPCR IC50 4 CHEMBL
Histamine H1 receptor GPCR Ki 6.68 DRUG MATRIX
Thyrotropin-releasing hormone receptor GPCR Ki 6.54 WOMBAT-PK
Thyrotropin-releasing hormone receptor GPCR ANTAGONIST Ki 4.82 IUPHAR
Cholinesterase Enzyme Ki 6.52 CHEMBL
Thyrotropin-releasing hormone receptor GPCR ANTAGONIST Ki 4.70 IUPHAR
GABA-A receptor; anion channel Ion channel IC50 6.70 CHEMBL
GABA-A receptor; anion channel Ion channel IC50 6.10 CHEMBL
Cholecystokinin receptor GPCR IC50 4 CHEMBL
Acetylcholinesterase Enzyme Ki 4.30 CHEMBL
Translocator protein Membrane receptor Ki 6.36 CHEMBL

External reference:

IDSource
4017780 VUID
N0000146141 NUI
D00267 KEGG_DRUG
438-41-5 SECONDARY_CAS_RN
C0008188 UMLSCUI
CHEBI:3611 CHEBI
CHEMBL451 ChEMBL_ID
DB00475 DRUGBANK_ID
CHEMBL1200703 ChEMBL_ID
D002707 MESH_DESCRIPTOR_UI
2712 PUBCHEM_CID
3370 IUPHAR_LIGAND_ID
1049 INN_ID
6RZ6XEZ3CR UNII
203173 RXNORM
3903 MMSL
4409 MMSL
4410 MMSL
d00189 MMSL
001454 NDDF
001455 NDDF
372866006 SNOMEDCT_US
40601003 SNOMEDCT_US
82746003 SNOMEDCT_US
4017780 VANDF
4017808 VANDF

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Librax HUMAN PRESCRIPTION DRUG LABEL 2 0187-4100 CAPSULE 5 mg ORAL NDA 18 sections
Not applicable HUMAN PRESCRIPTION DRUG LABEL 2 0276-0500 CAPSULE 5 mg ORAL ANDA 19 sections
Chlordiazepoxide and Amitriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 0378-0211 TABLET, FILM COATED 5 mg ORAL ANDA 24 sections
Chlordiazepoxide and Amitriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 0378-0277 TABLET, FILM COATED 10 mg ORAL ANDA 24 sections
Chlordiazepoxide Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0555-0033 CAPSULE 10 mg ORAL ANDA 18 sections
Chlordiazepoxide Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0555-0158 CAPSULE 5 mg ORAL ANDA 18 sections
Chlordiazepoxide Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0555-0159 CAPSULE 25 mg ORAL ANDA 18 sections
Chlordiazepoxide Hydrochloride and Clidinium Bromide HUMAN PRESCRIPTION DRUG LABEL 2 10135-622 CAPSULE 5 mg ORAL UNAPPROVED DRUG OTHER 17 sections
Chlordiazepoxide Hydrochloride and Clidinium Bromide HUMAN PRESCRIPTION DRUG LABEL 2 11534-197 CAPSULE 5 mg ORAL ANDA 19 sections
Chlordiazepoxide Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 17856-0164 CAPSULE 25 mg ORAL ANDA 19 sections
chlordiazepoxide hydrochloride and clidinium bromide HUMAN PRESCRIPTION DRUG LABEL 2 23155-808 CAPSULE 5 mg ORAL ANDA 19 sections
Chlordiazepoxide Hydrochloride and Clidinium Bromide HUMAN PRESCRIPTION DRUG LABEL 2 42494-409 CAPSULE 5 mg ORAL NDA authorized generic 20 sections
Chlordiazepoxide Hydrochloride and Clidinium Bromide HUMAN PRESCRIPTION DRUG LABEL 2 42582-300 CAPSULE 5 mg ORAL UNAPPROVED DRUG OTHER 18 sections
Chlordiazepoxide Hydrochloride and Clidinium Bromide HUMAN PRESCRIPTION DRUG LABEL 2 42582-301 CAPSULE 5 mg ORAL UNAPPROVED DRUG OTHER 18 sections
CHLORDIAZEPOXIDE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 42806-561 CAPSULE, GELATIN COATED 5 mg ORAL ANDA 21 sections
CHLORDIAZEPOXIDE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 42806-562 CAPSULE, GELATIN COATED 10 mg ORAL ANDA 21 sections
CHLORDIAZEPOXIDE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 42806-563 CAPSULE, GELATIN COATED 25 mg ORAL ANDA 21 sections
CHLORDIAZEPOXIDE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 42806-564 CAPSULE, GELATIN COATED 5 mg ORAL ANDA 20 sections
CHLORDIAZEPOXIDE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 42806-565 CAPSULE, GELATIN COATED 10 mg ORAL ANDA 20 sections
CHLORDIAZEPOXIDE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 42806-566 CAPSULE, GELATIN COATED 25 mg ORAL ANDA 20 sections
Chlordiazepoxide Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 43063-046 CAPSULE 25 mg ORAL ANDA 19 sections
Chlordiazepoxide Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 43353-699 CAPSULE, GELATIN COATED 25 mg ORAL ANDA 14 sections
Chlordiazepoxide Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 43353-969 CAPSULE, GELATIN COATED 10 mg ORAL ANDA 14 sections
Chlordiazepoxide Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 43547-251 CAPSULE, GELATIN COATED 5 mg ORAL ANDA 18 sections
Chlordiazepoxide Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 43547-252 CAPSULE, GELATIN COATED 10 mg ORAL ANDA 18 sections
Chlordiazepoxide Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 43547-253 CAPSULE, GELATIN COATED 25 mg ORAL ANDA 18 sections
Chlordiazepoxide Hydrochloride and Clidinium Bromide HUMAN PRESCRIPTION DRUG LABEL 2 43598-706 CAPSULE 5 mg ORAL ANDA 15 sections
Chlordiazepoxide Hydrochloride/Clidinium Bromide HUMAN PRESCRIPTION DRUG LABEL 2 50090-0131 CAPSULE 5 mg ORAL Unapproved drug other 19 sections
Chlordiazepoxide Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50090-0328 CAPSULE 25 mg ORAL ANDA 19 sections
Chlordiazepoxide Hydrochloride and Clidinium Bromide HUMAN PRESCRIPTION DRUG LABEL 2 50090-1528 CAPSULE 5 mg ORAL NDA authorized generic 18 sections