butalbital ๐Ÿถ Veterinary Use | 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 ยตM/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 204.42 15.52 152 6136 131737 50467099
Death 135.38 15.52 183 6105 325196 50273640
Toxicity to various agents 72.49 15.52 109 6179 212390 50386446
Migraine 55.55 15.52 57 6231 75223 50523613
Cholecystitis chronic 46.14 15.52 23 6265 9646 50589190
Drug abuse 36.52 15.52 41 6247 59805 50539031
Peritoneal perforation 29.71 15.52 6 6282 120 50598716
Poisoning 27.77 15.52 18 6270 12411 50586425
Cardio-respiratory arrest 26.38 15.52 33 6255 53859 50544977
Breast cyst 22.04 15.52 8 6280 1536 50597300
Product complaint 21.75 15.52 15 6273 11451 50587385
Headache 20.64 15.52 120 6168 506415 50092421
Drug abuser 20.55 15.52 9 6279 2819 50596017
Injection site necrosis 19.91 15.52 7 6281 1226 50597610
Emotional distress 19.85 15.52 21 6267 28642 50570194
Injury 19.37 15.52 27 6261 48898 50549938
Tracheitis 18.82 15.52 6 6282 778 50598058
Depression 18.80 15.52 54 6234 165369 50433467
Off label use 18.57 15.52 19 6269 474407 50124429
Hypoaesthesia 17.94 15.52 45 6243 127212 50471624
Intentional product misuse 17.33 15.52 25 6263 46709 50552127
Dependence 17.06 15.52 7 6281 1868 50596968
Gallbladder disorder 16.73 15.52 15 6273 16727 50582109
Anxiety 16.47 15.52 54 6234 177552 50421284
Ventricular hyperkinesia 15.67 15.52 3 6285 45 50598791

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
Death 86.39 27.39 76 845 342008 29231598
Cardio-respiratory arrest 40.48 27.39 23 898 50578 29523028

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
Death 258.00 17.61 251 5002 482454 64011025
Completed suicide 227.37 17.61 169 5084 224245 64269234
Toxicity to various agents 88.46 17.61 127 5126 363386 64130093
Cardio-respiratory arrest 61.11 17.61 56 5197 98337 64395142
Migraine 49.65 17.61 41 5212 62636 64430843
Cholecystitis chronic 43.04 17.61 19 5234 9268 64484211
Drug abuse 42.35 17.61 53 5200 132321 64361158
Peritoneal perforation 30.24 17.61 6 5247 170 64493309
Poisoning 27.78 17.61 19 5234 21860 64471619
Emotional distress 25.29 17.61 22 5231 36016 64457463
Injection site necrosis 22.32 17.61 7 5246 1318 64492161
Injury 22.14 17.61 25 5228 55967 64437512
Headache 21.07 17.61 92 5161 529375 63964104
Drug abuser 20.99 17.61 10 5243 5798 64487681
Gallbladder disorder 19.77 17.61 14 5239 17016 64476463
Off label use 19.43 17.61 14 5239 632792 63860687
Dependence 18.98 17.61 7 5246 2148 64491331
Intentional product misuse 18.54 17.61 26 5227 72269 64421210
Tracheitis 18.38 17.61 6 5247 1284 64492195
Anxiety 17.74 17.61 46 5207 202603 64290876

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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

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




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 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
19860 RXNORM
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
4311 MMSL
72849 MMSL
d03061 MMSL
001423 NDDF
387563005 SNOMEDCT_US
96196008 SNOMEDCT_US
4018107 VANDF

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
Butalbital, Acetaminophen, Caffeine and Codeine Phosphate HUMAN PRESCRIPTION DRUG LABEL 4 0054-0650 CAPSULE 50 mg ORAL ANDA 33 sections
Butalbital, Acetaminophen, Caffeine and Codeine Phosphate HUMAN PRESCRIPTION DRUG LABEL 4 0054-3000 CAPSULE 50 mg ORAL ANDA 33 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 38 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 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