chlordiazepoxide ๐Ÿถ Veterinary Use | 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 ยตM/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 218.08 23.17 43 3023 2031 63483925
Drug abuse 126.06 23.17 64 3002 72454 63413502
Bradyphrenia 91.80 23.17 27 3039 6953 63479003
Hyperreflexia 91.60 23.17 26 3040 5908 63480048
Thalamic infarction 81.78 23.17 15 3051 477 63485479
Drug interaction 76.42 23.17 73 2993 229058 63256898
Toxicity to various agents 69.90 23.17 72 2994 247178 63238778
Sopor 58.12 23.17 26 3040 22138 63463818
Intentional product misuse 57.28 23.17 36 3030 60881 63425075
Drug withdrawal syndrome 50.06 23.17 25 3041 27169 63458787
Disorientation 49.27 23.17 28 3038 39424 63446532
Clonus 48.33 23.17 15 3051 4621 63481335
Apraxia 47.10 23.17 12 3054 1809 63484147
Completed suicide 43.93 23.17 44 3022 145629 63340327
Perseveration 43.23 23.17 8 3058 267 63485689
Dyskinesia 38.04 23.17 22 3044 31980 63453976
Slow response to stimuli 37.83 23.17 9 3057 1023 63484933
Confusional state 37.01 23.17 51 3015 236329 63249627
Muscle twitching 33.03 23.17 17 3049 19651 63466305
Derailment 31.87 23.17 5 3061 60 63485896
Overdose 31.47 23.17 33 3033 115045 63370911
Abdominal tenderness 29.40 23.17 12 3054 8154 63477802
Abnormal behaviour 28.89 23.17 16 3050 21410 63464546
Accidental overdose 27.63 23.17 16 3050 23293 63462663
Myoclonus 27.47 23.17 14 3052 15854 63470102
Disturbance in attention 27.21 23.17 19 3047 38170 63447786
Psychomotor retardation 26.07 23.17 9 3057 3861 63482095
Cognitive disorder 24.86 23.17 21 3045 55794 63430162
Serotonin syndrome 24.57 23.17 16 3050 28666 63457290
Drug dependence 24.32 23.17 15 3051 24468 63461488

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 192.31 28.70 98 1836 98998 34855999
Toxicity to various agents 180.06 28.70 120 1814 200242 34754755
Ventricular tachyarrhythmia 103.94 28.70 18 1916 356 34954641
Delusion of replacement 61.60 28.70 10 1924 131 34954866
Shoshin beriberi 44.41 28.70 7 1927 75 34954922
Overdose 44.10 28.70 38 1896 91021 34863976
Completed suicide 37.76 28.70 36 1898 98132 34856865
Tracheobronchitis 31.54 28.70 8 1926 1033 34953964

FDA Adverse Event Reporting System (Geriatric)

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 300.75 22.61 156 4248 162535 79577449
Cerebral venous thrombosis 200.09 22.61 43 4361 2710 79737274
Toxicity to various agents 199.85 22.61 173 4231 421367 79318617
Hyperreflexia 83.32 22.61 27 4377 8358 79731626
Bradyphrenia 77.01 22.61 27 4377 10613 79729371
Completed suicide 74.21 22.61 79 4325 245688 79494296
Intentional product misuse 72.69 22.61 52 4352 95113 79644871
Sopor 70.37 22.61 35 4369 32975 79707009
Thalamic infarction 65.15 22.61 15 4389 1292 79738692
Delusion of replacement 59.79 22.61 10 4394 159 79739825
Drug interaction 59.30 22.61 92 4312 415091 79324893
Drug withdrawal syndrome 57.29 22.61 31 4373 34687 79705297
Disorientation 56.59 22.61 38 4366 62738 79677246
Overdose 49.93 22.61 56 4348 184150 79555834
Shoshin beriberi 44.41 22.61 7 4397 75 79739909
Clonus 40.63 22.61 15 4389 6825 79733159
Apraxia 40.11 22.61 12 4392 2855 79737129
Perseveration 39.23 22.61 8 4396 389 79739595
Cardio-respiratory arrest 38.30 22.61 38 4366 108472 79631512
Confusional state 37.88 22.61 65 4339 317932 79422052
Alcoholism 37.02 22.61 12 4392 3711 79736273
Agoraphobia 36.23 22.61 8 4396 570 79739414
Withdrawal syndrome 33.56 22.61 20 4384 26834 79713150
Accidental overdose 33.37 22.61 23 4381 39558 79700426
Abnormal behaviour 32.69 22.61 22 4382 36399 79703585
Slow response to stimuli 31.54 22.61 9 4395 1816 79738168
Delirium 30.52 22.61 30 4374 84597 79655387
Derailment 29.92 22.61 5 4399 79 79739905
Muscle twitching 29.79 22.61 18 4386 24746 79715238
Dyskinesia 28.60 22.61 22 4382 44751 79695233
Dementia 27.30 22.61 17 4387 24642 79715342
Poisoning 26.92 22.61 17 4387 25255 79714729
Tracheobronchitis 26.20 22.61 8 4396 2038 79737946
Respiratory arrest 25.74 22.61 23 4381 57527 79682457
Abdominal tenderness 24.85 22.61 12 4392 10582 79729402

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC N05BA02 NERVOUS SYSTEM
PSYCHOLEPTICS
ANXIOLYTICS
Benzodiazepine derivatives
FDA CS M0002356 Benzodiazepines
CHEBI has role CHEBI:35474 anti-anxiety agents
CHEBI has role CHEBI:35717 hypnotics
CHEBI has role CHEBI:60807 anaesthestic adjuvant
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 | Suggest Off label Use Form| |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




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

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
203173 RXNORM
4017808 VANDF
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
3903 MMSL
4409 MMSL
4410 MMSL
d00189 MMSL
001454 NDDF
001455 NDDF
372866006 SNOMEDCT_US
40601003 SNOMEDCT_US
82746003 SNOMEDCT_US
4017780 VANDF

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Librax HUMAN PRESCRIPTION DRUG LABEL 2 0187-4100 CAPSULE 5 mg ORAL NDA 18 sections
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 25 sections
Chlordiazepoxide and Amitriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 0378-0211 TABLET, FILM COATED 5 mg ORAL ANDA 25 sections
Chlordiazepoxide and Amitriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 0378-0211 TABLET, FILM COATED 5 mg ORAL ANDA 25 sections
Chlordiazepoxide and Amitriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 0378-0277 TABLET, FILM COATED 10 mg ORAL ANDA 25 sections
Chlordiazepoxide and Amitriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 0378-0277 TABLET, FILM COATED 10 mg ORAL ANDA 25 sections
Chlordiazepoxide and Amitriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 0378-0277 TABLET, FILM COATED 10 mg ORAL ANDA 25 sections
Chlordiazepoxide Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0555-0033 CAPSULE 10 mg ORAL ANDA 18 sections
Chlordiazepoxide Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0555-0033 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 0555-0158 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 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 and Clidinium Bromide HUMAN PRESCRIPTION DRUG LABEL 2 11534-197 CAPSULE 5 mg ORAL ANDA 19 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 and Amitriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 42571-302 TABLET 12.50 mg ORAL ANDA 24 sections
Chlordiazepoxide and Amitriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 42571-302 TABLET 12.50 mg ORAL ANDA 24 sections
Chlordiazepoxide and Amitriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 42571-303 TABLET 25 mg ORAL ANDA 24 sections
Chlordiazepoxide and Amitriptyline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 2 42571-303 TABLET 25 mg ORAL ANDA 24 sections
CHLORDIAZEPOXIDE HCL AND CLIDINIUM BROMIDE HUMAN PRESCRIPTION DRUG LABEL 2 42571-381 CAPSULE 5 mg ORAL ANDA 22 sections
CHLORDIAZEPOXIDE HCL AND CLIDINIUM BROMIDE HUMAN PRESCRIPTION DRUG LABEL 2 42571-381 CAPSULE 5 mg ORAL ANDA 22 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