phenobarbital Indications/Contra | FAERs-F | FAERs-M | Orange Bk | 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

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 1 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 24 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 9.30 ┬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) 0.54 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 0.06 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.49 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 99 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Jan. 1, 1912 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
Drug reaction with eosinophilia and systemic symptoms 444.42 66.78 93 848 5425 2351719
Toxicity to various agents 350.55 66.78 110 831 32644 2324500
Drug ineffective 270.47 66.78 123 818 101501 2255643
Drug hypersensitivity 218.81 66.78 85 856 46558 2310586
Seizure 206.48 66.78 69 872 24397 2332747
Completed suicide 183.95 66.78 61 880 20973 2336171
Status epilepticus 171.20 66.78 37 904 2441 2354703
Hypotension 129.93 66.78 53 888 32383 2324761
Pyrexia 110.24 66.78 55 886 53653 2303491
Maternal exposure during pregnancy 105.57 66.78 37 904 14826 2342318
Epilepsy 104.21 66.78 28 913 4611 2352533
Drug resistance 99.17 66.78 24 917 2600 2354544
Laryngeal stenosis 90.81 66.78 13 928 68 2357076
Cytomegalovirus hepatitis 89.59 66.78 13 928 76 2357068
Developmental glaucoma 87.92 66.78 11 930 14 2357130
Intra-abdominal pressure increased 85.55 66.78 11 930 20 2357124
Pneumatosis 82.00 66.78 12 929 75 2357069
Exposure during pregnancy 79.97 66.78 35 906 25184 2331960
Coma 77.67 66.78 26 915 9030 2348114
Overdose 77.60 66.78 32 909 19875 2337269
Abortion spontaneous 74.88 66.78 28 913 13417 2343727
Necrosis ischaemic 73.71 66.78 11 930 80 2357064
Nystagmus 72.66 66.78 16 925 1139 2356005
Off label use 70.79 66.78 46 895 73552 2283592
Toxic epidermal necrolysis 70.64 66.78 19 922 3125 2354019
Ataxia 70.10 66.78 18 923 2474 2354670
Eosinophilia 66.97 66.78 18 923 2952 2354192

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 ineffective 341.93 60.81 136 608 63665 1682372
Seizure 321.59 60.81 98 646 20343 1725694
Toxicity to various agents 311.49 60.81 104 640 29037 1717000
Drug reaction with eosinophilia and systemic symptoms 243.83 60.81 59 685 5011 1741026
Completed suicide 199.94 60.81 65 679 16247 1729790
Multiple-drug resistance 143.96 60.81 24 720 286 1745751
Status epilepticus 124.94 60.81 29 715 2017 1744020
Drug resistance 111.78 60.81 29 715 3201 1742836
Overdose 98.91 60.81 39 705 16662 1729375
Drug abuse 77.53 60.81 31 713 13658 1732379
Sedation 77.44 60.81 22 722 3395 1742642
Hyperammonaemia 64.20 60.81 15 729 1063 1744974
Rash maculo-papular 62.58 60.81 19 725 3684 1742353
Urine copper increased 62.33 60.81 8 736 9 1746028

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 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
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
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
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:11335
Bronchitis contraindication 32398004 DOID:6132
Dehydration contraindication 34095006
Hyperthyroidism contraindication 34486009 DOID:7998
Depressive disorder contraindication 35489007
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
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:0050847
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:557
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
Sleep automatism contraindication 247962006
Raynaud's phenomenon contraindication 266261006
Benign prostatic hyperplasia contraindication 266569009
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
Myocardial infarction in recovery phase contraindication 418044006
Porphyria contraindication 418470004
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
4017422 VUID
N0000145810 NUI
C0031412 UMLSCUI
D00506 KEGG_DRUG
51073002 SNOMEDCT_US
4017422 VANDF
2390 MMSL
8134 RXNORM
373505007 SNOMEDCT_US
5272 MMSL
001406 NDDF
d00340 MMSL
4763 PUBCHEM_CID
CHEBI:8069 CHEBI
CHEMBL40 ChEMBL_ID
CHEMBL149972 ChEMBL_ID
SW9M9BB5K3 UNII
4172 INN_ID
57-30-7 SECONDARY_CAS_RN
DB01174 DRUGBANK_ID
D010634 MESH_DESCRIPTOR_UI
2804 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Phenobarbital HUMAN PRESCRIPTION DRUG LABEL 1 0121-0531 SOLUTION 20 mg ORAL unapproved drug other 12 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
Phenobarbital HUMAN PRESCRIPTION DRUG LABEL 1 0143-1495 TABLET 15 mg ORAL UNAPPROVED DRUG OTHER 12 sections
Phenobarbital HUMAN PRESCRIPTION DRUG LABEL 1 0143-1500 TABLET 30 mg ORAL UNAPPROVED DRUG OTHER 12 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 13517-107 ELIXIR 20 mg ORAL unapproved drug other 14 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
Phenobarbital HUMAN PRESCRIPTION DRUG LABEL 1 13517-755 TABLET 15 mg ORAL unapproved drug other 12 sections
Phenobarbital HUMAN PRESCRIPTION DRUG LABEL 1 13517-756 TABLET 30 mg ORAL unapproved drug other 12 sections
Phenobarbital HUMAN PRESCRIPTION DRUG LABEL 1 13517-757 TABLET 60 mg ORAL unapproved drug other 12 sections
Phenobarbital HUMAN PRESCRIPTION DRUG LABEL 1 13517-758 TABLET 100 mg ORAL unapproved drug other 12 sections
Phenobarbital HUMAN PRESCRIPTION DRUG LABEL 1 16571-330 LIQUID 20 mg ORAL UNAPPROVED DRUG OTHER 13 sections