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 214.89 22.72 43 2876 1828 50600377
Drug abuse 95.64 22.72 53 2866 59793 50542412
Hyperreflexia 90.84 22.72 26 2893 5092 50597113
Bradyphrenia 90.44 22.72 27 2892 6125 50596080
Thalamic infarction 80.56 22.72 15 2904 432 50601773
Drug interaction 72.13 22.72 72 2847 199549 50402656
Sopor 56.41 22.72 26 2893 19853 50582352
Toxicity to various agents 47.95 22.72 60 2859 212439 50389766
Drug withdrawal syndrome 47.78 22.72 25 2894 25056 50577149
Disorientation 47.41 22.72 28 2891 35456 50566749
Clonus 47.25 22.72 15 2904 4160 50598045
Apraxia 46.95 22.72 12 2907 1533 50600672
Intentional product misuse 42.71 22.72 29 2890 46705 50555500
Perseveration 42.17 22.72 8 2911 255 50601950
Completed suicide 39.30 22.72 43 2876 131846 50470359
Confusional state 37.97 22.72 50 2869 185878 50416327
Slow response to stimuli 37.78 22.72 9 2910 860 50601345
Dyskinesia 37.24 22.72 22 2897 27839 50574366
Muscle twitching 34.08 22.72 17 2902 15414 50586791
Derailment 31.56 22.72 5 2914 53 50602152
Overdose 28.79 22.72 32 2887 99695 50502510
Abdominal tenderness 28.67 22.72 12 2907 7268 50594937
Disturbance in attention 27.64 22.72 19 2900 31167 50571038
Abnormal behaviour 27.52 22.72 16 2903 19642 50582563
Cognitive disorder 25.92 22.72 21 2898 44102 50558103
Psychomotor retardation 25.60 22.72 9 2910 3409 50598796
Serotonin syndrome 24.15 22.72 16 2903 24697 50577508
Myoclonus 23.55 22.72 13 2906 14457 50587748
Product use in unapproved indication 23.36 22.72 31 2888 115788 50486417
Body temperature increased 22.95 22.72 17 2902 31324 50570881

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 165.97 29.30 81 1452 79802 29493192
Ventricular tachyarrhythmia 109.21 29.30 18 1515 280 29572714
Toxicity to various agents 101.01 29.30 78 1455 173583 29399411
Delusion of replacement 63.14 29.30 10 1523 119 29572875
Overdose 46.36 29.30 36 1497 79783 29493211
Shoshin beriberi 45.40 29.30 7 1526 69 29572925
Completed suicide 32.53 29.30 31 1502 90215 29482779
Hypoglycaemia 30.63 29.30 23 1510 48323 29524671

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 237.14 22.94 128 3758 132246 64362600
Cerebral venous thrombosis 201.54 22.94 43 3843 2398 64492448
Toxicity to various agents 116.01 22.94 125 3761 363388 64131458
Hyperreflexia 85.26 22.94 27 3859 7121 64487725
Bradyphrenia 77.98 22.94 27 3859 9379 64485467
Sopor 68.08 22.94 34 3852 29627 64465219
Thalamic infarction 66.26 22.94 15 3871 1097 64493749
Completed suicide 64.08 22.94 73 3813 224341 64270505
Delusion of replacement 59.78 22.94 10 3876 145 64494701
Disorientation 57.65 22.94 38 3848 55790 64439056
Drug interaction 51.57 22.94 84 3802 361999 64132847
Overdose 47.33 22.94 53 3833 159513 64335333
Intentional product misuse 44.52 22.94 36 3850 72259 64422587
Shoshin beriberi 44.34 22.94 7 3879 69 64494777
Drug withdrawal syndrome 44.19 22.94 26 3860 31265 64463581
Clonus 41.11 22.94 15 3871 6052 64488794
Apraxia 40.73 22.94 12 3874 2483 64492363
Perseveration 38.84 22.94 8 3878 374 64494472
Alcoholism 37.01 22.94 12 3874 3405 64491441
Agoraphobia 35.98 22.94 8 3878 539 64494307
Cardio-respiratory arrest 34.98 22.94 36 3850 98357 64396489
Muscle twitching 32.78 22.94 18 3868 18980 64475866
Abnormal behaviour 32.55 22.94 22 3864 33600 64461246
Confusional state 32.33 22.94 57 3829 261087 64233759
Slow response to stimuli 32.13 22.94 9 3877 1556 64493290
Derailment 29.99 22.94 5 3881 71 64494775
Dyskinesia 29.41 22.94 22 3864 39366 64455480
Dementia 28.64 22.94 17 3869 20749 64474097
Delirium 25.82 22.94 26 3860 69168 64425678
Abdominal tenderness 25.22 22.94 12 3874 9393 64485453
Cognitive disorder 24.89 22.94 23 3863 55064 64439782
Withdrawal syndrome 24.25 22.94 16 3870 23476 64471370

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 (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
4017780 VANDF
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

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 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 42571-303 TABLET 25 mg ORAL ANDA 24 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 42806-562 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 42806-563 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 42806-564 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 42806-565 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 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 43063-046 CAPSULE 25 mg ORAL ANDA 19 sections