phenobarbital Indications/Contra | FAERs | Orange Book | BioActivity |

Stem definitionDrug idCAS RN
hypnotics, barbituric acid derivatives 2134 50-06-6

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • phenobarbitone
  • phenobarbital
  • adonal
  • dormiral
  • versomnal
  • neurobarb
  • phenaemal
  • sedophen
  • phenobarbital sodium
A barbituric acid derivative that acts as a nonselective central nervous system depressant. It potentiates GAMMA-AMINOBUTYRIC ACID action on GABA-A RECEPTORS, and modulates chloride currents through receptor channels. It also inhibits glutamate induced depolarizations.
  • Molecular weight: 232.24
  • Formula: C12H12N2O3
  • CLOGP: 1.37
  • LIPINSKI: 0
  • HAC: 5
  • HDO: 2
  • TPSA: 75.27
  • ALOGS: -2.93
  • ROTB: 2

Drug dosage:

DoseUnitRoute
0.10 g O
0.10 g P

Approvals:

DateAgencyCompanyOrphan
Jan. 1, 1912 YEAR INTRODUCED

FDA Adverse Event Reporting System

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
Toxicity to various agents 494.27 51.10 157 1138 46897 3337667
Drug reaction with eosinophilia and systemic symptoms 466.79 51.10 104 1191 7791 3376773
Drug ineffective 409.51 51.10 173 1122 115917 3268647
Seizure 342.14 51.10 115 1180 40285 3344279
Completed suicide 252.40 51.10 86 1209 31028 3353536
Status epilepticus 249.26 51.10 54 1241 3481 3381083
Drug hypersensitivity 192.42 51.10 73 1222 35607 3348957
Overdose 174.05 51.10 67 1228 33911 3350653
Epilepsy 118.25 51.10 34 1261 6911 3377653
Coma 118.24 51.10 39 1256 12513 3372051
Foetal exposure during pregnancy 110.05 51.10 39 1256 15512 3369052
Condition aggravated 108.50 51.10 50 1245 39183 3345381
Ataxia 101.55 51.10 27 1268 4105 3380459
Pyrexia 91.89 51.10 57 1238 81058 3303506
Urine copper increased 87.09 51.10 11 1284 15 3384549
Porphyrins stool increased 85.14 51.10 10 1285 3 3384561
Cardio-respiratory arrest 80.66 51.10 31 1264 15409 3369155
Suicide attempt 79.87 51.10 31 1264 15816 3368748
Hypotension 77.58 51.10 43 1252 49471 3335093
Intentional overdose 77.50 51.10 30 1265 15195 3369369
Maternal exposure during pregnancy 77.31 51.10 27 1268 10244 3374320
Urine delta aminolevulinate increased 76.40 51.10 9 1286 3 3384561
Exposure during pregnancy 72.53 51.10 34 1261 27529 3357035
Eosinophilia 70.29 51.10 21 1274 4852 3379712
Nystagmus 68.76 51.10 17 1278 1930 3382634
Drug abuse 65.41 51.10 28 1267 18302 3366262
Cognitive disorder 64.26 51.10 22 1273 7852 3376712
Generalised tonic-clonic seizure 63.81 51.10 22 1273 8020 3376544
Stillbirth 61.96 51.10 15 1280 1560 3383004
Hyperammonaemia 61.22 51.10 15 1280 1640 3382924
Off label use 61.08 51.10 38 1257 53939 3330625
Rash maculo-papular 58.23 51.10 19 1276 5848 3378716
Drug interaction 58.17 51.10 35 1260 46777 3337787
Hypotonia 57.59 51.10 16 1279 2855 3381709
Sudden unexplained death in epilepsy 56.56 51.10 10 1285 217 3384347
Hyperammonaemic encephalopathy 53.29 51.10 11 1284 552 3384012
Death 52.34 51.10 53 1242 152271 3232293
Coma blister 51.24 51.10 7 1288 23 3384541

Pharmacologic Action:

SourceCodeDescription
ATC N03AA02 NERVOUS SYSTEM
ANTIEPILEPTICS
ANTIEPILEPTICS
Barbiturates and derivatives
CHEBI has role CHEBI:35623 anticonvulsant
CHEBI has role CHEBI:35717 sedative
CHEBI has role CHEBI:88188 drug allergen
MeSH PA D000927 Anticonvulsants
MeSH PA D002491 Central Nervous System Agents
MeSH PA D002492 Central Nervous System Depressants
MeSH PA D065695 Cytochrome P-450 CYP2B6 Inducers
MeSH PA D065701 Cytochrome P-450 CYP3A Inducers
MeSH PA D018683 Excitatory Amino Acid Agents
MeSH PA D018691 Excitatory Amino Acid Antagonists
MeSH PA D018682 GABA Agents
MeSH PA D018757 GABA Modulators
MeSH PA D006993 Hypnotics and Sedatives
MeSH PA D065606 Metabolic Side Effects of Drugs and Substances
MeSH PA D018377 Neurotransmitter Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Migraine indication 37796009 DOID:6364
Tonic-clonic seizure indication 54200006
Epilepsy indication 84757009 DOID:1826
Bipolar disorder in remission indication 85248005
Vascular headache indication 128187005
Cluster headache syndrome indication 193031009
Lennox-Gastaut syndrome indication 230418006
Tonic-clonic epilepsy indication 352818000 DOID:7725
Epilepsy characterized by intractable complex partial seizures indication 442481002
Simple partial seizure indication 117891000119100
Cluster Headache Prevention indication
Hyperbilirubinemia off-label use 14783006 DOID:2741
Postmenopausal osteoporosis off-label use 102447009
Seizure disorder off-label use 128613002 DOID:1826
Bipolar affective disorder, current episode depression off-label use 191627008 DOID:3312
Status epilepticus off-label use 230456007 DOID:1824
Neuropathic pain off-label use 247398009
Rapid Cycling Bipolar Affective Disorder off-label use
Brain damage contraindication 2470005
Necrotizing enterocolitis in fetus OR newborn contraindication 2707005 DOID:8677
Goiter contraindication 3716002 DOID:12176
Gastritis contraindication 4556007 DOID:4029
Osteomalacia contraindication 4598005 DOID:10573
Tachyarrhythmia contraindication 6285003
Suicidal thoughts contraindication 6471006
Urinary tract obstruction contraindication 7163005 DOID:5200
Alcoholism contraindication 7200002
Hyperammonemia contraindication 9360008
Peptic ulcer contraindication 13200003 DOID:750
Chronic obstructive lung disease contraindication 13645005 DOID:3083
Hepatic encephalopathy contraindication 13920009 DOID:13413
Hyperkalemia contraindication 14140009
Disorder of thyroid gland contraindication 14304000 DOID:50
Severe chronic ulcerative colitis contraindication 14311001
Disorder of autonomic nervous system contraindication 15241006
Agranulocytosis contraindication 17182001 DOID:12987
Pulmonary edema contraindication 19242006 DOID:11396
Hashimoto thyroiditis contraindication 21983002 DOID:7188
Myocardial infarction contraindication 22298006 DOID:5844
Glaucoma contraindication 23986001 DOID:1686
Acute tuberculosis contraindication 25629007
Alcohol intoxication contraindication 25702006
Shock contraindication 27942005
Toxic megacolon contraindication 28536002 DOID:1770
Atony of colon contraindication 29479008
Lymphadenopathy contraindication 30746006
Sarcoidosis contraindication 31541009 DOID:13404
Bronchitis contraindication 32398004 DOID:6132
Dehydration contraindication 34095006
Hyperthyroidism contraindication 34486009 DOID:7998
Depressive disorder contraindication 35489007 DOID:2848
Acute hepatitis contraindication 37871000
Hypertensive disorder contraindication 38341003 DOID:10763
Hypovolemic shock contraindication 39419009
Gastrointestinal ulcer contraindication 40845000
Hypothyroidism contraindication 40930008 DOID:1459
Complete trisomy 21 syndrome contraindication 41040004 DOID:14250
Third trimester pregnancy contraindication 41587001
Hyperactive behavior contraindication 44548000
Conduction disorder of the heart contraindication 44808001
Low blood pressure contraindication 45007003
Achalasia of esophagus contraindication 45564002 DOID:9164
Chronic heart failure contraindication 48447003
Retroperitoneal fibrosis contraindication 49120005
Disorder of cardiovascular system contraindication 49601007 DOID:1287
Fibrosis of lung contraindication 51615001 DOID:3770
Vitamin K deficiency contraindication 52675005 DOID:11249
Nasal polyp contraindication 52756005
Megaloblastic anemia contraindication 53165003 DOID:13382
Systemic lupus erythematosus contraindication 55464009 DOID:9074
Paralytic ileus contraindication 55525008 DOID:8442
Heart disease contraindication 56265001 DOID:114
Peptic reflux disease contraindication 57643001 DOID:13976
Multiple organ failure contraindication 57653000
Acute nephropathy contraindication 58574008
Hepatic failure contraindication 59927004
Diarrhea contraindication 62315008
Thrombophlebitis contraindication 64156001 DOID:3875
Ulcerative colitis contraindication 64766004 DOID:8577
Poisoning by phenobarbital contraindication 64921004
Drug AND/OR toxin-induced diarrhea contraindication 65979008
Substance abuse contraindication 66214007
Hypercalcemia contraindication 66931009 DOID:12678
Hyperparathyroidism contraindication 66999008 DOID:13543
Psychotic disorder contraindication 69322001
Poisoning by acetaminophen contraindication 70273001
Agoraphobia contraindication 70691001 DOID:593
Incontinence of feces contraindication 72042002
Hepatic coma contraindication 72836002 DOID:12550
Diabetes mellitus contraindication 73211009 DOID:9351
Sleep apnea contraindication 73430006 DOID:0050848
Factor II deficiency contraindication 73975000
Reye's syndrome contraindication 74351001 DOID:14525
Appendicitis contraindication 74400008 DOID:8337
Gastrointestinal hemorrhage contraindication 74474003
Thrombotic thrombocytopenic purpura contraindication 78129009 DOID:10772
Spastic paralysis contraindication 78403003
Disturbance of salivary secretion contraindication 78948009
Hyperglycemia contraindication 80394007 DOID:4195
Cor pulmonale contraindication 83291003 DOID:8515
Hiatal hernia contraindication 84089009 DOID:12642
Leukopenia contraindication 84828003 DOID:615
Gout contraindication 90560007 DOID:13189
Kidney disease contraindication 90708001 DOID:2527
Hemophilia contraindication 90935002
Myasthenia gravis contraindication 91637004 DOID:437
Kidney stone contraindication 95570007
Dermatitis herpetiformis contraindication 111196000 DOID:8505
Anemia due to enzyme deficiency contraindication 111577008
Gastrointestinal obstruction contraindication 126765001
Pancytopenia contraindication 127034005 DOID:12450
von Willebrand disorder contraindication 128105004 DOID:12531
Autonomic dysreflexia contraindication 129618003
Bleeding contraindication 131148009
Cystic fibrosis contraindication 190905008 DOID:1485
Obsessive-compulsive disorder contraindication 191736004 DOID:10933
Insomnia contraindication 193462001
Angina pectoris contraindication 194828000
Impaired renal function disorder contraindication 197663003
Osteolysis contraindication 203522001
Non-infective meningitis contraindication 230155003
Myocardial dysfunction contraindication 233928007
Peripheral ischemia contraindication 233958001
Gastroesophageal reflux disease contraindication 235595009 DOID:8534
Disease of liver contraindication 235856003 DOID:409
Bladder outflow obstruction contraindication 236645006
Sepsis syndrome contraindication 238150007
Hypocomplementemic urticarial vasculitis contraindication 239945009
Pyloric obstruction contraindication 244815007 DOID:3122
Sleep automatism contraindication 247962006
Raynaud's phenomenon contraindication 266261006
Benign prostatic hyperplasia contraindication 266569009 DOID:2883
Dyspnea contraindication 267036007
Retention of urine contraindication 267064002
Anemia contraindication 271737000 DOID:2355
Continuous fever contraindication 271751000
Drowsy contraindication 271782001
Cerebral ischemia contraindication 287731003
Pregnancy, function contraindication 289908002
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Neutropenic disorder contraindication 303011007 DOID:1227
Aplastic anemia contraindication 306058006 DOID:12449
Osteopenia contraindication 312894000
Panic disorder contraindication 371631005 DOID:594
Smoking cessation assistance contraindication 384742004
Angle-closure glaucoma contraindication 392291006 DOID:13550
Gastric ulcer contraindication 397825006 DOID:10808
Peripheral vascular disease contraindication 400047006
Respiratory insufficiency contraindication 409623005
Breastfeeding (mother) contraindication 413712001
Chronic lung disease contraindication 413839001
Chronic myocardial ischemia contraindication 413844008 DOID:3393
Disorder of coronary artery contraindication 414024009
Myocardial ischemia contraindication 414795007 DOID:3393
Granulocytopenic disorder contraindication 417672002 DOID:12987
Myocardial infarction in recovery phase contraindication 418044006
Porphyria contraindication 418470004 DOID:13268
Fever greater than 100.4 Fahrenheit contraindication 426000000
Hyperplasia of gingiva contraindication 441798003
Fibrosis of pleura contraindication 442110002
Acute erosive gastritis contraindication 444926003
Smokes tobacco daily contraindication 449868002
Acute exacerbation of asthma contraindication 708038006
Severe Hypoxemia contraindication
Severe Pruritus contraindication
HLA-B 1502 Positive Status contraindication
Ergot Alkaloid Toxicity contraindication
Theophylline Toxicity contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 7.56 acidic
pKa2 9.25 acidic

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
Nuclear receptor subfamily 1 group I member 2 Nuclear hormone receptor WOMBAT-PK
Nuclear receptor subfamily 1 group I member 3 Nuclear hormone receptor WOMBAT-PK
Sodium channel alpha subunits; brain (Types I, II, III) Ion channel IC50 5.60 CHEMBL

External reference:

IDSource
2804 IUPHAR_LIGAND_ID
4017422 VUID
N0000145810 NUI
C0031412 UMLSCUI
D00506 KEGG_DRUG
CHEMBL40 ChEMBL_ID
4763 PUBCHEM_CID
4017422 VANDF
2390 MMSL
8134 RXNORM
373505007 SNOMEDCT_US
51073002 SNOMEDCT_US
5272 MMSL
N0000005893 NDFRT
N0000145810 NDFRT
001406 NDDF
d00340 MMSL
CHEMBL149972 ChEMBL_ID
CHEBI:8069 CHEBI
DB01174 DRUGBANK_ID
D010634 MESH_DESCRIPTOR_UI
SW9M9BB5K3 UNII
4172 INN_ID
57-30-7 SECONDARY_CAS_RN

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Belladonna Alkaloids with Phenobarbital HUMAN PRESCRIPTION DRUG LABEL 4 0143-1140 TABLET 16.20 mg ORAL UNAPPROVED DRUG OTHER 11 sections
Phenobarbital HUMAN PRESCRIPTION DRUG LABEL 1 0143-1445 TABLET 15 mg ORAL UNAPPROVED DRUG OTHER 12 sections
Phenobarbital HUMAN PRESCRIPTION DRUG LABEL 1 0143-1450 TABLET 30 mg ORAL UNAPPROVED DRUG OTHER 12 sections
Phenobarbital HUMAN PRESCRIPTION DRUG LABEL 1 0143-1455 TABLET 60 mg ORAL UNAPPROVED DRUG OTHER 12 sections
Phenobarbital HUMAN PRESCRIPTION DRUG LABEL 1 0143-1458 TABLET 100 mg ORAL UNAPPROVED DRUG OTHER 12 sections
DONNATAL HUMAN PRESCRIPTION DRUG LABEL 4 0179-0088 ELIXIR 16.20 mg ORAL unapproved drug other 12 sections
Donnatal HUMAN PRESCRIPTION DRUG LABEL 4 0179-0132 TABLET 16.20 mg ORAL unapproved drug other 15 sections
Belladonna Alkaloids with Phenobartbital HUMAN PRESCRIPTION DRUG LABEL 4 0440-7183 TABLET 16.20 mg ORAL UNAPPROVED DRUG OTHER 10 sections
Phenobarbital HUMAN PRESCRIPTION DRUG LABEL 1 0463-6145 TABLET 30 mg ORAL UNAPPROVED DRUG OTHER 12 sections
Phenobarbital HUMAN PRESCRIPTION DRUG LABEL 1 0463-6151 TABLET 60 mg ORAL UNAPPROVED DRUG OTHER 12 sections
Phenobarbital HUMAN PRESCRIPTION DRUG LABEL 1 0463-6160 TABLET 15 mg ORAL UNAPPROVED DRUG OTHER 12 sections
Phenobarbital HUMAN PRESCRIPTION DRUG LABEL 1 0463-6170 TABLET 100 mg ORAL UNAPPROVED DRUG OTHER 12 sections
Phenobarbital HUMAN PRESCRIPTION DRUG LABEL 1 0603-1508 ELIXIR 20 mg ORAL UNAPPROVED DRUG OTHER 13 sections
Phenobarbital HUMAN PRESCRIPTION DRUG LABEL 1 0603-5165 TABLET 16.20 mg ORAL UNAPPROVED DRUG OTHER 13 sections
Phenobarbital HUMAN PRESCRIPTION DRUG LABEL 1 0603-5166 TABLET 32.40 mg ORAL UNAPPROVED DRUG OTHER 13 sections
Phenobarbital HUMAN PRESCRIPTION DRUG LABEL 1 0603-5167 TABLET 64.80 mg ORAL UNAPPROVED DRUG OTHER 13 sections
Phenobarbital HUMAN PRESCRIPTION DRUG LABEL 1 0603-5168 TABLET 97.20 mg ORAL UNAPPROVED DRUG OTHER 13 sections
Phenobarbital Sodium HUMAN PRESCRIPTION DRUG LABEL 1 0641-0476 INJECTION 65 mg INTRAMUSCULAR UNAPPROVED DRUG OTHER 12 sections
Phenobarbital Sodium HUMAN PRESCRIPTION DRUG LABEL 1 0641-0477 INJECTION 130 mg INTRAMUSCULAR UNAPPROVED DRUG OTHER 12 sections
Phenobarbital HUMAN PRESCRIPTION DRUG LABEL 1 0904-6575 TABLET 32.40 mg ORAL Unapproved drug other 13 sections
Phenobarbital HUMAN PRESCRIPTION DRUG LABEL 1 13517-110 TABLET 16.20 mg ORAL unapproved drug other 13 sections
Phenobarbital HUMAN PRESCRIPTION DRUG LABEL 1 13517-111 TABLET 32.40 mg ORAL unapproved drug other 13 sections
Phenobarbital HUMAN PRESCRIPTION DRUG LABEL 1 13517-112 TABLET 64.80 mg ORAL unapproved drug other 13 sections
Phenobarbital HUMAN PRESCRIPTION DRUG LABEL 1 13517-113 TABLET 97.20 mg ORAL unapproved drug other 13 sections
Belladonna Alkaloids with Phenobartbital HUMAN PRESCRIPTION DRUG LABEL 4 15338-600 TABLET 16.20 mg ORAL Unapproved drug other 12 sections
Phenobarbital HUMAN PRESCRIPTION DRUG LABEL 1 16571-330 LIQUID 20 mg ORAL UNAPPROVED DRUG OTHER 13 sections
Donnatal HUMAN PRESCRIPTION DRUG LABEL 4 17856-0423 ELIXIR 16.20 mg ORAL unapproved drug other 12 sections
Phenobarbital HUMAN PRESCRIPTION DRUG LABEL 1 17856-1508 ELIXIR 20 mg ORAL UNAPPROVED DRUG OTHER 12 sections
RE-PB HYOS ELIXIR HUMAN PRESCRIPTION DRUG LABEL 4 21695-594 ELIXIR 16.20 mg ORAL Unapproved drug other 11 sections
Belladonna Alkaloids with Phenobartbital HUMAN PRESCRIPTION DRUG LABEL 4 21695-890 TABLET 16.20 mg ORAL Unapproved drug other 12 sections