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

Stem definitionDrug idCAS RN
hypnotics, barbituric acid derivatives 441 77-26-9

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • alisobumal
  • allylbarbital
  • allylbarbitone
  • allylisobutylbarbital
  • allylisobutylbarbituric acid
  • butalbarbital
  • isobutylallylbarbituric acid
  • itobarbital
  • butalbital
management of butalbital withdrawal can be simplified by using a phenobarbital-loading protocol; RN given refers to parent cpd
  • Molecular weight: 224.26
  • Formula: C11H16N2O3
  • CLOGP: 1.63
  • LIPINSKI: 0
  • HAC: 5
  • HDO: 2
  • TPSA: 75.27
  • ALOGS: -2
  • ROTB: 4

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

None

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 3.60 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 22.30 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 85 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
May 4, 1976 FDA ACTAVIS LABS UT INC

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
Completed suicide 345.52 12.31 345 17275 145575 46522867
Migraine 234.10 12.31 201 17419 69825 46598617
Toxicity to various agents 138.42 12.31 269 17351 211497 46456945
Headache 99.33 12.31 399 17221 477953 46190489
Drug abuse 72.91 12.31 104 17516 63304 46605138
Poisoning 44.29 12.31 39 17581 13955 46654487
Rheumatoid arthritis 39.08 12.31 21 17599 240194 46428248
Death 37.89 12.31 236 17384 335312 46333130
Product physical issue 34.23 12.31 22 17598 4905 46663537
Cardio-respiratory arrest 31.81 12.31 70 17550 59799 46608643
Pain 31.61 12.31 296 17324 476652 46191790
Respiratory arrest 29.72 12.31 49 17571 33767 46634675
Cholecystitis chronic 26.89 12.31 26 17594 10473 46657969
Depression 26.76 12.31 131 17489 169973 46498469
Injury 26.30 12.31 54 17566 43973 46624469
Feeling abnormal 26.25 12.31 105 17515 124955 46543487
Anxiety 24.37 12.31 134 17486 181823 46486619
Hypoaesthesia 23.52 12.31 98 17522 118771 46549671
Multiple sclerosis relapse 23.22 12.31 50 17570 42075 46626367
Peritoneal perforation 22.89 12.31 6 17614 124 46668318
Anion gap 22.47 12.31 10 17610 1063 46667379
Medication overuse headache 22.45 12.31 8 17612 474 46667968
Breast cyst 22.14 12.31 11 17609 1498 46666944
Intentional product misuse 21.61 12.31 52 17568 47076 46621366
Emotional distress 21.16 12.31 40 17580 30667 46637775
Neutropenia 19.86 12.31 15 17605 143189 46525253
Product dose omission issue 19.24 12.31 119 17501 168401 46500041
Metabolic acidosis 19.09 12.31 44 17576 38736 46629706
Insomnia 17.92 12.31 115 17505 164809 46503633
Road traffic accident 17.76 12.31 32 17588 23659 46644783
Overdose 17.07 12.31 80 17540 101899 46566543
Febrile neutropenia 15.77 12.31 8 17612 94619 46573823
Hereditary angioedema 14.77 12.31 14 17606 5502 46662940
Drug withdrawal syndrome 14.51 12.31 32 17588 27352 46641090
Gallbladder disorder 13.58 12.31 24 17596 17474 46650968
Hyponatraemia 13.56 12.31 11 17609 101321 46567121
Sepsis 13.48 12.31 19 17601 135995 46532447
Suicidal ideation 13.17 12.31 49 17571 56333 46612109
Therapeutic response unexpected 12.88 12.31 22 17598 15594 46652848
Neck pain 12.87 12.31 48 17572 55258 46613184
Acute kidney injury 12.70 12.31 46 17574 235809 46432633
Treatment failure 12.59 12.31 10 17610 93077 46575365
Tracheitis 12.52 12.31 6 17614 756 46667686
Illness 12.51 12.31 19 17601 12205 46656237
Ventricular hyperkinesia 12.35 12.31 3 17617 45 46668397
Pyroglutamate increased 12.31 12.31 5 17615 424 46668018

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
Completed suicide 65.82 19.67 66 3123 99426 29849863
Toxicity to various agents 59.49 19.67 83 3106 177100 29772189
Migraine 57.96 19.67 28 3161 12846 29936443
Cardio-respiratory arrest 55.32 19.67 47 3142 57259 29892030
Drug abuse 49.78 19.67 52 3137 82020 29867269
Death 34.33 19.67 99 3090 357184 29592105
Headache 26.25 19.67 59 3130 182247 29767042
Anion gap 20.89 19.67 6 3183 640 29948649

Pharmacologic Action:

SourceCodeDescription
FDA CS M0002177 Barbiturates
FDA EPC N0000175693 Barbiturate
CHEBI has role CHEBI:35717 sedatives

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Tension-type headache indication 398057008
Migraine off-label use 37796009 DOID:6364
Necrotizing enterocolitis in fetus OR newborn contraindication 2707005
Suicidal thoughts contraindication 6471006
Dependent drug abuse contraindication 6525002
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
Chronic disease of respiratory system contraindication 17097001
Mood swings contraindication 18963009
Inflammatory bowel disease contraindication 24526004 DOID:0050589
Depressive disorder contraindication 35489007
Hypertensive disorder contraindication 38341003 DOID:10763
Disorder of gallbladder contraindication 39621005 DOID:0060262
Gastrointestinal ulcer contraindication 40845000
Hypothyroidism contraindication 40930008 DOID:1459
Hyperactive behavior contraindication 44548000
Conduction disorder of the heart contraindication 44808001
Low blood pressure contraindication 45007003
Bradycardia contraindication 48867003
Vitamin K deficiency contraindication 52675005 DOID:11249
Nasal polyp contraindication 52756005
Acute nephropathy contraindication 58574008
Hepatic failure contraindication 59927004
Drug AND/OR toxin-induced diarrhea contraindication 65979008
Substance abuse contraindication 66214007
Benign intracranial hypertension contraindication 68267002 DOID:11459
Poisoning by acetaminophen contraindication 70273001
Agoraphobia contraindication 70691001 DOID:593
Hepatic coma contraindication 72836002 DOID:12550
Sleep apnea contraindication 73430006 DOID:0050847
Factor II deficiency contraindication 73975000
Reye's syndrome contraindication 74351001 DOID:14525
Gastrointestinal hemorrhage contraindication 74474003
Urethral stricture contraindication 76618002
Thrombotic thrombocytopenic purpura contraindication 78129009 DOID:10772
Decreased respiratory function contraindication 80954004
Injury of head contraindication 82271004
Epilepsy contraindication 84757009 DOID:1826
Gout contraindication 90560007 DOID:13189
Kidney disease contraindication 90708001 DOID:557
Hemophilia contraindication 90935002
Anemia due to enzyme deficiency contraindication 111577008
Acute abdominal pain contraindication 116290004
Procedure on urinary system contraindication 118677009
von Willebrand disorder contraindication 128105004 DOID:12531
Seizure disorder contraindication 128613002
Obsessive-compulsive disorder contraindication 191736004 DOID:10933
Insomnia contraindication 193462001
Impaired renal function disorder contraindication 197663003
Disease of liver contraindication 235856003 DOID:409
Sleep automatism contraindication 247962006
Benign prostatic hyperplasia contraindication 266569009
Anemia contraindication 271737000 DOID:2355
Pregnancy, function contraindication 289908002
Lesion of brain contraindication 301766008
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Neutropenic disorder contraindication 303011007 DOID:1227
Panic disorder contraindication 371631005 DOID:594
Primary adrenocortical insufficiency contraindication 373662000
Operation on gastrointestinal tract contraindication 386621005
Pseudomembranous enterocolitis contraindication 397683000
Respiratory insufficiency contraindication 409623005
Breastfeeding (mother) contraindication 413712001
Myocardial ischemia contraindication 414795007 DOID:3393
Myocardial infarction in recovery phase contraindication 418044006
Central nervous system depression contraindication 418072004
Porphyria contraindication 418470004
Ultrarapid metabolizer due to cytochrome p450 CYP2D6 variant contraindication 422681000
Dysfunction of sphincter of Oddi contraindication 430887001
Acute erosive gastritis contraindication 444926003
Acute exacerbation of asthma contraindication 708038006

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 7.65 acidic
pKa2 9.34 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-3/gamma-2 Ion channel POSITIVE ALLOSTERIC MODULATOR WOMBAT-PK CHEMBL

External reference:

IDSource
4018107 VUID
N0000179058 NUI
D03182 KEGG_DRUG
4018107 VANDF
C0054234 UMLSCUI
CHEBI:102524 CHEBI
CHEMBL454 ChEMBL_ID
DB00241 DRUGBANK_ID
2481 PUBCHEM_CID
7 INN_ID
C004470 MESH_SUPPLEMENTAL_RECORD_UI
7138 IUPHAR_LIGAND_ID
KHS0AZ4JVK UNII
19860 RXNORM
4311 MMSL
72849 MMSL
d03061 MMSL
001423 NDDF
387563005 SNOMEDCT_US
96196008 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Fiorinal with Codeine HUMAN PRESCRIPTION DRUG LABEL 4 0023-6010 CAPSULE 50 mg ORAL NDA 36 sections
Fiorinal HUMAN PRESCRIPTION DRUG LABEL 3 0023-6146 CAPSULE 50 mg ORAL NDA 23 sections
BUPAP HUMAN PRESCRIPTION DRUG LABEL 2 0095-3000 TABLET 50 mg ORAL ANDA 25 sections
Butalbital, Acetaminophen, and Caffeine HUMAN PRESCRIPTION DRUG LABEL 3 0143-0170 CAPSULE 50 mg ORAL ANDA 26 sections
Butalbital, Aspirin, Caffeine and Codeine Phosphate HUMAN PRESCRIPTION DRUG LABEL 4 0527-1312 CAPSULE 50 mg ORAL ANDA 25 sections
Butalbital, aspirin, and caffeine HUMAN PRESCRIPTION DRUG LABEL 3 0527-1552 CAPSULE 50 mg ORAL ANDA 25 sections
Butalbital, Acetaminophen, and Caffeine HUMAN PRESCRIPTION DRUG LABEL 3 0527-1695 TABLET 50 mg ORAL ANDA 27 sections
butalbital, acetaminophen and caffeine HUMAN PRESCRIPTION DRUG LABEL 3 0527-4094 CAPSULE 50 mg ORAL ANDA 27 sections
Butalbital, Acetaminophen, and Caffeine HUMAN PRESCRIPTION DRUG LABEL 3 0527-4095 CAPSULE 50 mg ORAL ANDA 27 sections
Butalbital, Acetaminophen, and Caffeine HUMAN PRESCRIPTION DRUG LABEL 3 0591-2640 CAPSULE 50 mg ORAL ANDA 25 sections
Butalbital, Acetaminophen, Caffeine, and Codeine Phosphate HUMAN PRESCRIPTION DRUG LABEL 4 0591-2641 CAPSULE 50 mg ORAL ANDA 27 sections
Butalbital, Aspirin, and Caffeine HUMAN PRESCRIPTION DRUG LABEL 3 0591-3219 CAPSULE 50 mg ORAL NDA authorized generic 24 sections
Butalbital, Acetaminophen, Caffeine, and Codeine Phosphate HUMAN PRESCRIPTION DRUG LABEL 4 0591-3220 CAPSULE 50 mg ORAL NDA AUTHORIZED GENERIC 32 sections
Butalbital, Acetaminophen, and Caffeine HUMAN PRESCRIPTION DRUG LABEL 3 0591-3369 TABLET 50 mg ORAL ANDA 27 sections
Butalbital, Aspirin, Caffeine and Codeine Phosphate HUMAN PRESCRIPTION DRUG LABEL 4 0591-3546 CAPSULE 50 mg ORAL NDA authorized generic 36 sections
butalbital and acetaminophen HUMAN PRESCRIPTION DRUG LABEL 2 0603-2540 TABLET 50 mg ORAL ANDA 25 sections
Butalbital, Acetaminophen and Caffeine HUMAN PRESCRIPTION DRUG LABEL 3 0603-2544 TABLET 50 mg ORAL ANDA 27 sections
Butalbital, Acetaminophen, Caffeine, and Codeine Phosphate HUMAN PRESCRIPTION DRUG LABEL 4 0603-2553 CAPSULE 50 mg ORAL ANDA 35 sections
Ascomp with Codeine HUMAN PRESCRIPTION DRUG LABEL 4 0722-6094 CAPSULE 50 mg ORAL ANDA 33 sections
Butalbital, Acetaminophen, Caffeine, and Codeine Phosphate HUMAN PRESCRIPTION DRUG LABEL 4 0722-6670 CAPSULE 50 mg ORAL ANDA 32 sections
Butalbital, Acetaminophen, Caffeine, and Codeine Phosphate HUMAN PRESCRIPTION DRUG LABEL 4 0722-7028 CAPSULE 50 mg ORAL ANDA 32 sections
Butalbital, Acetaminophen, and Caffeine HUMAN PRESCRIPTION DRUG LABEL 3 0722-7029 CAPSULE 50 mg ORAL ANDA 27 sections
Butalbital and Acetaminophen HUMAN PRESCRIPTION DRUG LABEL 2 0722-7075 TABLET 50 mg ORAL ANDA 25 sections
Butalbital, Acetaminophen, and Caffeine HUMAN PRESCRIPTION DRUG LABEL 3 0722-7320 TABLET 50 mg ORAL ANDA 26 sections
Butalbital, Acetaminophen and Caffeine HUMAN PRESCRIPTION DRUG LABEL 3 0904-6538 TABLET 50 mg ORAL ANDA 25 sections
Butalbital, Acetaminophen, and Caffeine HUMAN PRESCRIPTION DRUG LABEL 3 0904-6938 TABLET 50 mg ORAL ANDA 27 sections
Butalbital, Acetaminophen and Caffeine HUMAN PRESCRIPTION DRUG LABEL 3 10135-628 CAPSULE 50 mg ORAL ANDA 25 sections
Butalbital, Acetaminophen and Caffeine HUMAN PRESCRIPTION DRUG LABEL 3 10702-253 TABLET 50 mg ORAL ANDA 26 sections
BUTALBITAL, ACETAMINOPHEN AND CAFFEINE HUMAN PRESCRIPTION DRUG LABEL 3 11534-187 CAPSULE 50 mg ORAL ANDA 27 sections
Tencon HUMAN PRESCRIPTION DRUG LABEL 2 11584-0030 TABLET 50 mg ORAL ANDA 28 sections