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

Stem definitionDrug idCAS RN
hypnotics, barbituric acid derivatives 2633 76-75-5

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • pentothal
  • thiopental sodium
  • thiopental
  • thiomebumal
  • thionembutal
  • pentothiobarbital
A barbiturate that is administered intravenously for the induction of general anesthesia or for the production of complete anesthesia of short duration.
  • Molecular weight: 242.34
  • Formula: C11H18N2O2S
  • CLOGP: 2.98
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 2
  • TPSA: 58.20
  • ALOGS: -3.78
  • ROTB: 4

  • Status: OFM

  • 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
S (Water solubility) 50 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0.50 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 20.63 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution) 1.20 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 8.20 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.14 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 2 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
None FDA ABBOTT

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
Status epilepticus 198.31 37.80 61 3068 15123 53330814
Diabetes insipidus 134.17 37.80 31 3098 2560 53343377
Renal ischaemia 119.46 37.80 22 3107 586 53345351
Exposure during pregnancy 114.65 37.80 78 3051 124782 53221155
Breast cancer recurrent 109.90 37.80 29 3100 4136 53341801
PCO2 increased 109.50 37.80 23 3106 1220 53344717
Foetal death 107.06 37.80 34 3095 9313 53336624
Cardiac arrest 106.68 37.80 67 3062 93600 53252337
PO2 increased 99.00 37.80 20 3109 874 53345063
Blood pH decreased 92.35 37.80 23 3106 2607 53343330
Oxygen saturation abnormal 90.41 37.80 23 3106 2839 53343098
Blood bicarbonate decreased 84.76 37.80 22 3107 2940 53342997
Hypotension 76.94 37.80 84 3045 253992 53091945
Left ventricular dysfunction 74.02 37.80 27 3102 11210 53334727
Maternal exposure during pregnancy 64.43 37.80 61 3068 155578 53190359
Blood magnesium decreased 58.33 37.80 23 3106 11791 53334146
Seizure 57.89 37.80 53 3076 129456 53216481
Encephalopathy 48.61 37.80 29 3100 36779 53309158
Electroencephalogram abnormal 48.31 37.80 15 3114 3806 53342131
Blood calcium decreased 46.92 37.80 23 3106 19771 53326166
Multiple-drug resistance 46.44 37.80 14 3115 3221 53342716
Anaesthetic complication 43.95 37.80 12 3117 1942 53343995
Renal impairment 42.96 37.80 37 3092 83281 53262656
Bronchospasm 41.48 37.80 20 3109 16578 53329359
Maternal exposure during delivery 40.84 37.80 10 3119 1055 53344882
Intensive care unit acquired weakness 38.90 37.80 9 3120 745 53345192
Anaphylactic reaction 38.67 37.80 30 3099 58296 53287641

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
Status epilepticus 141.69 37.66 46 2119 11960 32499401
Intensive care unit acquired weakness 89.48 37.66 19 2146 934 32510427
Hyperthermia malignant 61.14 37.66 16 2149 1943 32509418
Hepatitis fulminant 57.56 37.66 18 2147 4125 32507236
Propofol infusion syndrome 57.03 37.66 13 2152 887 32510474
Drug ineffective 48.61 37.66 89 2076 383388 32127973
Metabolic acidosis 45.01 37.66 30 2135 40669 32470692

Pharmacologic Action:

SourceCodeDescription
ATC N01AF03 NERVOUS SYSTEM
ANESTHETICS
ANESTHETICS, GENERAL
Barbiturates, plain
ATC N05CA19 NERVOUS SYSTEM
PSYCHOLEPTICS
HYPNOTICS AND SEDATIVES
Barbiturates, plain
MeSH PA D018757 GABA Modulators
MeSH PA D000777 Anesthetics
MeSH PA D018686 Anesthetics, Intravenous
MeSH PA D000927 Anticonvulsants
MeSH PA D002491 Central Nervous System Agents
MeSH PA D002492 Central Nervous System Depressants
MeSH PA D018682 GABA Agents
MeSH PA D006993 Hypnotics and Sedatives
MeSH PA D018377 Neurotransmitter Agents
CHEBI has role CHEBI:38877 i.v.-Anaesthetika
CHEBI has role CHEBI:35623 antiepileptic
CHEBI has role CHEBI:35703 Xenobiotic
CHEBI has role CHEBI:35717 sedatives
CHEBI has role CHEBI:78298 environmental contaminants
CHEBI has role CHEBI:88188 allergenic drug

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
General anesthesia indication 50697003
Benign intracranial hypertension indication 68267002 DOID:11459
Epilepsy indication 84757009 DOID:1826
Narcoanalysis indication 302683009
Cerebral ischemia off-label use 287731003
Hypoxia of brain off-label use 389088001
Chronic disease of respiratory system contraindication 17097001
Shock contraindication 27942005
Myxedema contraindication 43153006 DOID:11634
Uremia contraindication 44730006 DOID:4676
Low blood pressure contraindication 45007003
Variegate porphyria contraindication 58275005 DOID:4346
Kidney disease contraindication 90708001 DOID:557
Myasthenia gravis contraindication 91637004 DOID:437
Acute disease of cardiovascular system contraindication 128487001
Asthma contraindication 195967001 DOID:2841
Acute intermittent porphyria contraindication 234422006 DOID:3890
Disease of liver contraindication 235856003 DOID:409
Anemia contraindication 271737000 DOID:2355
Primary adrenocortical insufficiency contraindication 373662000

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 7.46 acidic
pKa2 11.46 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 POSITIVE ALLOSTERIC MODULATOR WOMBAT-PK CHEMBL
GABA-A receptor; anion channel Ion channel IC50 4.53 CHEMBL
Potassium voltage-gated channel subfamily C member 4 Ion channel GATING INHIBITOR IC50 4 IUPHAR

External reference:

IDSource
4018713 VUID
N0000179744 NUI
D00714 KEGG_DRUG
71-73-8 SECONDARY_CAS_RN
4018713 VANDF
4019945 VANDF
C0039925 UMLSCUI
CHEBI:102166 CHEBI
EDP PDB_CHEM_ID
CHEMBL441 ChEMBL_ID
DB00599 DRUGBANK_ID
CHEMBL738 ChEMBL_ID
D013874 MESH_DESCRIPTOR_UI
3000715 PUBCHEM_CID
2579 IUPHAR_LIGAND_ID
433 INN_ID
JI8Z5M7NA3 UNII
10493 RXNORM
2118 MMSL
2227 MMSL
5570 MMSL
d00388 MMSL
001398 NDDF
004578 NDDF
349829005 SNOMEDCT_US
387448009 SNOMEDCT_US
412605006 SNOMEDCT_US

Pharmaceutical products:

None