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

Stem definitionDrug idCAS RN
diazepam derivatives 399 1812-30-2

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • bromazepam
  • durazanil
One of the BENZODIAZEPINES that is used in the treatment of ANXIETY DISORDERS.
  • Molecular weight: 316.16
  • Formula: C14H10BrN3O
  • CLOGP: 1.70
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 1
  • TPSA: 54.35
  • ALOGS: -3.90
  • ROTB: 1

Drug dosage:

DoseUnitRoute
10 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.17 mg/mL Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 1.36 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 84 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.85 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 0.51 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.48 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 21 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Jan. 1, 1974 YEAR INTRODUCED

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
Coma 631.87 14.78 344 18348 61439 53268935
Drug abuse 599.34 14.78 339 18353 65187 53265187
Sopor 428.76 14.78 188 18504 20896 53309478
Suicide attempt 312.95 14.78 215 18477 57953 53272421
Poisoning deliberate 291.24 14.78 111 18581 8602 53321772
Intentional overdose 273.99 14.78 210 18482 66995 53263379
Toxicity to various agents 216.07 14.78 321 18371 219277 53111097
Somnolence 179.06 14.78 255 18437 167479 53162895
Bradypnoea 170.38 14.78 58 18634 3239 53327135
Hypotension 164.61 14.78 308 18384 253768 53076606
Overdose 158.69 14.78 192 18500 107544 53222830
Mydriasis 155.45 14.78 77 18615 11249 53319125
Electrocardiogram QT prolonged 125.63 14.78 125 18567 56278 53274096
Altered state of consciousness 115.31 14.78 84 18608 24752 53305622
Bradycardia 115.07 14.78 133 18559 70923 53259451
Drug interaction 113.19 14.78 242 18450 219087 53111287
Intentional self-injury 111.71 14.78 83 18609 25201 53305173
Hepatocellular injury 103.36 14.78 85 18607 29901 53300473
Hypothermia 93.97 14.78 58 18634 12998 53317376
Drug dependence 91.54 14.78 69 18623 21403 53308971
Confusional state 87.41 14.78 203 18489 194018 53136356
Prescription form tampering 86.92 14.78 24 18668 657 53329717
Hyponatraemia 86.00 14.78 144 18548 108463 53221911
Miosis 85.52 14.78 44 18648 6958 53323416
Rheumatoid arthritis 81.50 14.78 8 18684 314523 53015851
Pain 80.44 14.78 54 18638 588344 52742030
Parkinsonism 80.43 14.78 46 18646 8967 53321407
Drug use disorder 79.57 14.78 33 18659 3186 53327188
Bradyphrenia 78.37 14.78 41 18651 6709 53323665
Poisoning 76.24 14.78 52 18640 13798 53316576
Persecutory delusion 71.31 14.78 29 18663 2663 53327711
Coma scale abnormal 67.49 14.78 34 18658 5144 53325230
Drug ineffective 67.23 14.78 115 18577 817130 52513244
Toxic epidermal necrolysis 65.38 14.78 59 18633 23491 53306883
Toxic skin eruption 64.53 14.78 46 18646 13093 53317281
Hypokalaemia 63.48 14.78 118 18574 96399 53233975
Fall 61.28 14.78 268 18424 358172 52972202
Psychomotor hyperactivity 60.59 14.78 40 18652 10056 53320318
Cor pulmonale acute 60.56 14.78 16 18676 369 53330005
Abdominal discomfort 58.89 14.78 5 18687 221057 53109317
Electrocardiogram QRS complex prolonged 58.57 14.78 32 18660 5710 53324664
Agitation 57.80 14.78 86 18606 58540 53271834
Respiratory acidosis 55.38 14.78 32 18660 6356 53324018
Joint swelling 53.45 14.78 9 18683 234629 53095745
Rhabdomyolysis 53.03 14.78 71 18621 43852 53286522
Livedo reticularis 50.35 14.78 22 18670 2415 53327959
Nasopharyngitis 49.48 14.78 5 18687 192290 53138084
Drug hypersensitivity 48.94 14.78 16 18676 265226 53065148
Sinus tachycardia 46.55 14.78 49 18643 23523 53306851
Peripheral swelling 44.58 14.78 9 18683 206099 53124275
Vasoplegia syndrome 41.99 14.78 16 18676 1236 53329138
Acute kidney injury 41.91 14.78 188 18504 253680 53076694
Respiratory depression 41.41 14.78 35 18657 12771 53317603
Loss of consciousness 41.38 14.78 110 18582 114102 53216272
Cardiogenic shock 41.22 14.78 40 18652 17442 53312932
Fatigue 41.11 14.78 126 18566 730380 52599994
Rash 41.08 14.78 58 18634 446133 52884241
Drug intolerance 40.43 14.78 11 18681 205482 53124892
Product dose omission issue 40.14 14.78 9 18683 191611 53138763
Dermatitis exfoliative 39.26 14.78 25 18667 5911 53324463
Serotonin syndrome 38.68 14.78 47 18645 26359 53304015
Thymus disorder 38.42 14.78 10 18682 217 53330157
Hyperthermia 37.54 14.78 28 18664 8541 53321833
Sinusitis 37.20 14.78 7 18685 168557 53161817
Headache 36.67 14.78 84 18608 536737 52793637
Vertigo 36.13 14.78 68 18624 56013 53274361
Hypoglycaemia 36.11 14.78 70 18622 58943 53271431
Metabolic acidosis 36.07 14.78 58 18634 42184 53288190
Postmortem blood drug level abnormal 36.03 14.78 10 18682 279 53330095
Arthropathy 35.55 14.78 4 18688 141449 53188925
Electrocardiogram QRS complex shortened 35.25 14.78 11 18681 465 53329909
Cross sensitivity reaction 34.11 14.78 16 18676 2071 53328303
Treatment failure 33.91 14.78 3 18689 128400 53201974
Depressed level of consciousness 33.83 14.78 65 18627 54363 53276011
Psychiatric decompensation 33.79 14.78 14 18678 1348 53329026
Salivary hypersecretion 33.38 14.78 24 18668 6919 53323455
Pneumonia aspiration 33.34 14.78 50 18642 34251 53296123
Housebound 33.07 14.78 9 18683 233 53330141
Bradykinesia 33.01 14.78 20 18672 4333 53326041
Swelling 32.73 14.78 13 18679 191092 53139282
Alopecia 32.64 14.78 21 18671 234562 53095812
Drug reaction with eosinophilia and systemic symptoms 32.15 14.78 48 18644 32752 53297622
Ventricular dyskinesia 31.55 14.78 8 18684 156 53330218
Alcohol abuse 31.21 14.78 15 18677 2049 53328325
Hepatitis toxic 30.64 14.78 17 18675 3124 53327250
Therapeutic product effect decreased 30.48 14.78 4 18688 125651 53204723
Tremor 30.35 14.78 105 18587 125631 53204743
Bundle branch block right 29.98 14.78 20 18672 5113 53325261
Nausea 29.96 14.78 150 18542 755941 52574433
Eosinophilia 29.67 14.78 37 18655 21298 53309076
Infusion related reaction 29.47 14.78 9 18683 155948 53174426
Arrhythmia 29.37 14.78 49 18643 36730 53293644
Drug level increased 29.34 14.78 36 18656 20385 53309989
Contraindicated product administered 29.15 14.78 6 18686 135623 53194751
Hyperthyroidism 29.12 14.78 29 18663 13044 53317330
Prevertebral soft tissue swelling of cervical space 28.58 14.78 6 18686 48 53330326
Wrong rate 28.36 14.78 6 18686 50 53330324
Psychomotor retardation 28.32 14.78 17 18675 3621 53326753
Intentional product misuse 28.29 14.78 57 18635 49335 53281039
Eczema eyelids 28.24 14.78 7 18685 124 53330250
Hepatitis acute 28.07 14.78 24 18668 8892 53321482
Inappropriate antidiuretic hormone secretion 27.61 14.78 30 18662 14921 53315453
Arthralgia 27.49 14.78 72 18620 439711 52890663
Asphyxia 27.46 14.78 20 18672 5881 53324493
Disorientation 26.95 14.78 49 18643 39310 53291064
Fear of weight gain 26.75 14.78 5 18687 20 53330354
Cholestasis 26.71 14.78 41 18651 28654 53301720
Extrapyramidal disorder 26.68 14.78 27 18665 12375 53317999
Hyperchloraemia 26.66 14.78 10 18682 740 53329634
Sinus bradycardia 26.45 14.78 29 18663 14572 53315802
Systemic lupus erythematosus 26.03 14.78 6 18686 125408 53204966
Growth disorder 26.00 14.78 5 18687 24 53330350
White blood cell count decreased 25.75 14.78 6 18686 124469 53205905
Leukocytosis 25.39 14.78 37 18655 24697 53305677
Pain in extremity 25.26 14.78 38 18654 285012 53045362
Lactic acidosis 25.03 14.78 46 18646 37207 53293167
Cholinergic syndrome 24.60 14.78 8 18684 387 53329987
Eczema 24.57 14.78 36 18656 24146 53306228
Cardiorenal syndrome 24.20 14.78 9 18683 650 53329724
Cholecystitis 23.74 14.78 28 18664 15218 53315156
Mucosal erosion 23.42 14.78 11 18681 1428 53328946
Circulatory collapse 23.35 14.78 34 18658 22680 53307694
Cutaneous T-cell lymphoma 23.34 14.78 11 18681 1438 53328936
Myoglobin blood increased 23.12 14.78 11 18681 1469 53328905
Patella fracture 23.01 14.78 12 18680 1950 53328424
Nystagmus 22.67 14.78 18 18674 6018 53324356
Pneumonia 22.26 14.78 71 18621 407098 52923276
Hypotonia 22.10 14.78 21 18671 8920 53321454
Antipsychotic drug level increased 21.92 14.78 14 18678 3325 53327049
Tonic convulsion 21.87 14.78 10 18682 1221 53329153
Ventricular tachycardia 21.87 14.78 29 18663 17733 53312641
Restlessness 21.86 14.78 37 18655 28050 53302324
Suicidal ideation 21.61 14.78 58 18634 60453 53269921
Hypercapnic coma 21.56 14.78 6 18686 169 53330205
Dermatitis exfoliative generalised 21.49 14.78 14 18678 3441 53326933
Nasal mucosal erosion 21.47 14.78 5 18687 67 53330307
Haemolytic anaemia 21.14 14.78 22 18670 10417 53319957
Stress cardiomyopathy 20.95 14.78 20 18672 8542 53321832
Haemodynamic instability 20.89 14.78 20 18672 8574 53321800
Platelet count decreased 20.85 14.78 6 18686 108093 53222281
Chemical submission 20.57 14.78 6 18686 201 53330173
Multiple organ dysfunction syndrome 20.52 14.78 54 18638 55623 53274751
Muscle rigidity 20.45 14.78 22 18670 10819 53319555
Torsade de pointes 20.44 14.78 24 18668 12981 53317393
Substance abuse 20.39 14.78 15 18677 4479 53325895
Rash maculo-papular 20.32 14.78 37 18655 29712 53300662
Blood gases abnormal 20.31 14.78 8 18684 676 53329698
Phlebitis 20.19 14.78 17 18675 6170 53324204
Epilepsy 20.13 14.78 34 18658 25733 53304641
Generalised anxiety disorder 19.99 14.78 11 18681 1989 53328385
General physical health deterioration 19.98 14.78 103 18589 146839 53183535
Violence-related symptom 19.67 14.78 7 18685 446 53329928
Lower respiratory tract infection 19.60 14.78 4 18688 90977 53239397
Drug-induced liver injury 19.51 14.78 36 18656 29197 53301177
Atrioventricular block first degree 19.38 14.78 17 18675 6518 53323856
Chronic fatigue syndrome 19.37 14.78 9 18683 1140 53329234
Delirium 19.33 14.78 44 18648 41385 53288989
Major depression 19.10 14.78 18 18674 7564 53322810
Discomfort 18.97 14.78 5 18687 95467 53234907
Disturbance in attention 18.88 14.78 39 18653 34344 53296030
Cerebral haematoma 18.88 14.78 13 18679 3501 53326873
Purpura 18.70 14.78 21 18671 10832 53319542
Psychomotor skills impaired 18.56 14.78 11 18681 2288 53328086
Autoimmune haemolytic anaemia 18.23 14.78 14 18678 4457 53325917
Colitis 18.15 14.78 43 18649 41509 53288865
Haemoglobin decreased 18.13 14.78 13 18679 137294 53193080
Drug screen false positive 18.08 14.78 8 18684 905 53329469
Occupational dermatitis 17.99 14.78 4 18688 43 53330331
Therapeutic product effect incomplete 17.87 14.78 5 18687 91779 53238595
Acute pulmonary oedema 17.81 14.78 18 18674 8237 53322137
Rash scarlatiniform 17.76 14.78 5 18687 147 53330227
Urinary retention 17.69 14.78 34 18658 28432 53301942
Occupational exposure to product 17.50 14.78 10 18682 1945 53328429
Right ventricular dilatation 17.49 14.78 8 18684 977 53329397
Status epilepticus 17.49 14.78 24 18668 15160 53315214
Cardiac output decreased 17.42 14.78 8 18684 987 53329387
Pyramidal tract syndrome 17.28 14.78 6 18686 355 53330019
Long QT syndrome 17.25 14.78 12 18680 3284 53327090
Infection 17.21 14.78 21 18671 172184 53158190
Apallic syndrome 17.07 14.78 7 18685 656 53329718
Conduction disorder 17.03 14.78 9 18683 1503 53328871
Tachycardia 16.96 14.78 79 18613 108133 53222241
Cough 16.83 14.78 41 18651 256852 53073522
Chest discomfort 16.70 14.78 7 18685 99688 53230686
Contusion 16.67 14.78 9 18683 110723 53219651
Drop attacks 16.23 14.78 7 18685 744 53329630
Injection site pain 15.96 14.78 10 18682 113381 53216993
Cerebellar stroke 15.94 14.78 5 18687 215 53330159
Hallucination, auditory 15.71 14.78 20 18672 11753 53318621
Respiratory disorder 15.67 14.78 36 18656 34061 53296313
Hypoosmolar state 15.59 14.78 5 18687 231 53330143
Hospitalisation 15.55 14.78 3 18689 71009 53259365
Mixed liver injury 15.35 14.78 12 18680 3921 53326453
Cell death 15.32 14.78 10 18682 2465 53327909
Head injury 15.01 14.78 30 18662 25803 53304571
Electrolyte imbalance 14.86 14.78 25 18667 18859 53311515
Oropharyngeal pain 14.79 14.78 5 18687 81263 53249111

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
Coma 356.65 18.07 203 10417 42409 32460497
Poisoning deliberate 285.83 18.07 99 10521 6276 32496630
Drug abuse 267.49 18.07 216 10404 80027 32422879
Toxicity to various agents 175.98 18.07 251 10369 177790 32325116
Intentional overdose 140.41 18.07 113 10507 41488 32461418
Drug dependence 117.85 18.07 81 10539 23403 32479503
Somnolence 112.13 18.07 153 10467 103644 32399262
Sopor 111.72 18.07 61 10559 11688 32491218
Miosis 87.78 18.07 47 10573 8657 32494249
Suicide attempt 85.02 18.07 82 10538 38162 32464744
Drug use disorder 74.76 18.07 32 10588 3589 32499317
Visceral congestion 74.74 18.07 20 10600 522 32502384
Altered state of consciousness 64.24 18.07 55 10565 21942 32480964
Overdose 56.96 18.07 102 10518 86975 32415931
Substance abuse 56.96 18.07 33 10587 7074 32495832
Lactic acidosis 56.55 18.07 62 10558 33474 32469432
Intentional product misuse 54.56 18.07 63 10557 35988 32466918
Pneumonia aspiration 54.20 18.07 67 10553 41089 32461817
Mydriasis 51.84 18.07 30 10590 6416 32496490
Oral discharge 49.06 18.07 11 10609 133 32502773
Drug ineffective 48.64 18.07 33 10587 383444 32119462
Depressed level of consciousness 48.25 18.07 63 10557 40784 32462122
Prescription form tampering 46.46 18.07 14 10606 565 32502341
Confusional state 44.98 18.07 125 10495 142990 32359916
Asphyxia 44.87 18.07 26 10594 5574 32497332
Vertigo 41.11 18.07 45 10575 24238 32478668
Hypothermia 39.55 18.07 30 10590 10073 32492833
Cluster headache 39.25 18.07 12 10608 509 32502397
Housebound 38.91 18.07 10 10610 222 32502684
Bradypnoea 38.60 18.07 18 10602 2468 32500438
Mucosal dryness 37.32 18.07 14 10606 1113 32501793
Disturbance in attention 36.75 18.07 42 10578 23711 32479195
Vascular stenosis 36.39 18.07 9 10611 170 32502736
Lichenoid keratosis 36.13 18.07 17 10603 2379 32500527
Hyperthermia 35.82 18.07 29 10591 10699 32492207
Laryngeal dyspnoea 34.79 18.07 8 10612 109 32502797
Withdrawal syndrome 34.74 18.07 30 10590 12092 32490814
Brief psychotic disorder with marked stressors 34.55 18.07 9 10611 211 32502695
Brain oedema 33.01 18.07 30 10590 12930 32489976
Pneumonia 32.65 18.07 41 10579 355211 32147695
Acute pulmonary oedema 32.56 18.07 24 10596 7717 32495189
Bradycardia 31.37 18.07 71 10549 71491 32431415
Haematocrit increased 31.26 18.07 14 10606 1749 32501157
Left atrial dilatation 30.45 18.07 14 10606 1858 32501048
Amyotrophy 30.27 18.07 10 10610 546 32502360
Hepatocellular injury 29.80 18.07 39 10581 25279 32477627
Hypovolaemia 29.65 18.07 24 10596 8853 32494053
Bradyphrenia 28.11 18.07 18 10602 4611 32498295
Behaviour disorder 26.86 18.07 16 10604 3608 32499298
Kounis syndrome 26.74 18.07 13 10607 1955 32500951
Loss of consciousness 26.68 18.07 73 10547 82634 32420272
Parotid gland haemorrhage 26.19 18.07 5 10615 25 32502881
Wrong drug 26.15 18.07 6 10614 81 32502825
Anal haemorrhage 25.86 18.07 13 10607 2100 32500806
Cerebrovascular stenosis 24.43 18.07 6 10614 110 32502796
Agitation 24.20 18.07 56 10564 57180 32445726
Incorrect product administration duration 24.08 18.07 16 10604 4362 32498544
Ureteric haemorrhage 23.94 18.07 6 10614 120 32502786
Intentional self-injury 23.94 18.07 26 10594 13874 32489032
Congestive hepatopathy 23.93 18.07 12 10608 1928 32500978
Haemoglobin increased 23.87 18.07 14 10606 3068 32499838
Psychomotor skills impaired 23.79 18.07 13 10607 2490 32500416
Poisoning 23.03 18.07 23 10597 11135 32491771
Systolic hypertension 22.82 18.07 7 10613 300 32502606
Angiopathy 22.73 18.07 15 10605 4042 32498864
Acute kidney injury 22.37 18.07 168 10452 293300 32209606
Inappropriate antidiuretic hormone secretion 21.54 18.07 23 10597 12040 32490866
Squamous cell carcinoma 21.53 18.07 22 10598 10946 32491960
Respiratory depression 21.52 18.07 24 10596 13187 32489719
Victim of crime 21.18 18.07 7 10613 383 32502523
Tremor 20.73 18.07 66 10554 81211 32421695
Cognitive disorder 20.41 18.07 33 10587 25861 32477045
Vascular encephalopathy 19.12 18.07 5 10615 119 32502787
Drug diversion 18.68 18.07 8 10612 897 32502009
Restlessness 18.65 18.07 31 10589 24850 32478056
Fatigue 18.64 18.07 56 10564 350645 32152261
Sinus bradycardia 18.54 18.07 22 10598 12916 32489990

Pharmacologic Action:

SourceCodeDescription
ATC N05BA08 NERVOUS SYSTEM
PSYCHOLEPTICS
ANXIOLYTICS
Benzodiazepine derivatives
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 D018377 Neurotransmitter Agents
MeSH PA D011619 Psychotropic Drugs
MeSH PA D014149 Tranquilizing Agents

Drug Use (View source of the data)

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 11.29 acidic
pKa2 3.26 Basic
pKa3 2.58 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-1/beta-2/gamma-2 Ion channel WOMBAT-PK

External reference:

IDSource
N0000166922 NUI
D01245 KEGG_DRUG
C0006213 UMLSCUI
CHEBI:31302 CHEBI
CHEMBL277062 ChEMBL_ID
DB01558 DRUGBANK_ID
D001960 MESH_DESCRIPTOR_UI
2441 PUBCHEM_CID
2692 INN_ID
X015L14V0O UNII
1749 RXNORM
11834 MMSL
003512 NDDF
387571009 SNOMEDCT_US
96234002 SNOMEDCT_US

Pharmaceutical products:

None