butalbital 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | 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 µM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 35 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
kinase-safety-class ACVR2A,ACVR2B,AXL,BRAF,CAMK2D,CDK5,CDK9,DYRK1B,EIF2AK3,ERBB2,GRK2,ITK,MAP3K21,MAPK7,NTRK2,PDK1,PDK2,PRKDC,STK33,TEK 20
kinase-selectivity-class GRK2,PDK1 2
pfas-class PFAS structural alert (1 = True, 0 = False) 0

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 302.32 16.00 158 5593 144900 90477796
Death 156.18 16.00 167 5584 456384 90166312
Toxicity to various agents 110.15 16.00 112 5639 287734 90334962
Cholecystitis chronic 57.06 16.00 22 5729 9804 90612892
Drug abuse 50.88 16.00 42 5709 82305 90540391
Cardio-respiratory arrest 44.95 16.00 35 5716 63105 90559591
Migraine 39.09 16.00 54 5697 190338 90432358
Peritoneal perforation 33.46 16.00 6 5745 126 90622570
Poisoning 29.91 16.00 16 5735 15201 90607495
Headache 27.72 16.00 118 5633 862628 89760068
Injection site necrosis 23.18 16.00 7 5744 1494 90621202
Tracheitis 21.92 16.00 6 5745 904 90621792
Emotional distress 21.18 16.00 18 5733 36644 90586052
Breast cyst 20.98 16.00 7 5744 2060 90620636
Respiratory arrest 20.57 16.00 17 5734 33294 90589402
Gallbladder disorder 18.64 16.00 13 5738 19790 90602906
Product complaint 17.94 16.00 11 5740 13489 90609207
Depression 17.34 16.00 50 5701 300551 90322145
Hypercoagulation 16.60 16.00 6 5745 2236 90620460
Ventricular hyperkinesia 16.55 16.00 3 5748 67 90622629
Intentional product misuse 16.28 16.00 24 5727 89580 90533116

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 72.50 29.36 59 616 471126 42149534
Cardio-respiratory arrest 42.60 29.36 20 655 58616 42562044
Drug abuse 31.70 29.36 20 655 104751 42515909
Completed suicide 30.65 29.36 19 656 96446 42524214

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
Completed suicide 359.05 20.53 179 4165 242202 110342753
Death 267.55 20.53 219 4125 698650 109886305
Toxicity to various agents 149.05 20.53 134 4210 480421 110104534
Cardio-respiratory arrest 86.92 20.53 55 4289 115781 110469174
Drug abuse 72.17 20.53 58 4286 177353 110407602
Cholecystitis chronic 52.18 20.53 18 4326 9482 110575473
Migraine 36.31 20.53 39 4305 171613 110413342
Peritoneal perforation 34.44 20.53 6 4338 175 110584780
Emotional distress 30.39 20.53 20 4324 44827 110540128
Poisoning 30.06 20.53 17 4327 29088 110555867
Respiratory arrest 25.67 20.53 20 4324 58279 110526676
Injection site necrosis 25.37 20.53 7 4337 1759 110583196
Gallbladder disorder 23.67 20.53 13 4331 21016 110563939
Headache 22.67 20.53 81 4263 882296 109702659
Intentional overdose 21.08 20.53 26 4318 132475 110452480
Off label use 21 20.53 17 4327 1500168 109084787
Tracheitis 20.99 20.53 6 4338 1715 110583240

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
FDA CS M0002177 Barbiturates
FDA EPC N0000175693 Barbiturate
CHEBI has role CHEBI:35480 analgesic
CHEBI has role CHEBI:35717 sedative

Drug Use | Suggest Off label Use Form| |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




🐶 Veterinary Drug Use

None

🐶 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
C004470 MESH_SUPPLEMENTAL_RECORD_UI
7138 IUPHAR_LIGAND_ID
7 INN_ID
KHS0AZ4JVK UNII
4311 MMSL
72849 MMSL
d03061 MMSL
387563005 SNOMEDCT_US
96196008 SNOMEDCT_US
4018107 VANDF
001423 NDDF

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
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
Butalbital, Acetaminophen, and Caffeine HUMAN PRESCRIPTION DRUG LABEL 3 0143-0170 CAPSULE 50 mg ORAL ANDA 26 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 28 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, 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 and acetaminophen HUMAN PRESCRIPTION DRUG LABEL 2 0603-2540 TABLET 50 mg ORAL ANDA 25 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, aspirin, and caffeine HUMAN PRESCRIPTION DRUG LABEL 3 0781-2270 CAPSULE 50 mg ORAL ANDA 25 sections
Butalbital, Acetaminophen, and Caffeine HUMAN PRESCRIPTION DRUG LABEL 3 0904-6938 TABLET 50 mg ORAL ANDA 28 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
Butalbital, Acetaminophen and Caffeine Human Prescription Drug Label 3 13107-075 CAPSULE 50 mg ORAL ANDA 24 sections
BUTALBITAL, ACETAMINOPHEN AND CAFFEINE HUMAN PRESCRIPTION DRUG LABEL 3 13925-535 CAPSULE 50 mg ORAL ANDA 14 sections
BUTALBITAL, ACETAMINOPHEN AND CAFFEINE HUMAN PRESCRIPTION DRUG LABEL 3 13925-536 CAPSULE 50 mg ORAL ANDA 14 sections
ACETAMINOPHEN, BUTALBITAL AND CAFFEINE HUMAN PRESCRIPTION DRUG LABEL 3 16590-022 TABLET 50 mg ORAL ANDA 13 sections
BUTALBITAL, ACETAMINOPHEN AND CAFFEINEPLUS HUMAN PRESCRIPTION DRUG LABEL 3 16590-581 TABLET 50 mg ORAL ANDA 21 sections
BUTALBITAL, ASPIRIN, AND CAFFEINE HUMAN PRESCRIPTION DRUG LABEL 3 16590-911 CAPSULE 50 mg ORAL NDA authorized generic 27 sections