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 188.26 39.89 59 2998 13920 46669085
Diabetes insipidus 141.60 39.89 32 3025 2142 46680863
Renal ischaemia 123.58 39.89 23 3034 580 46682425
PCO2 increased 112.44 39.89 24 3033 1230 46681775
Exposure during pregnancy 109.80 39.89 75 2982 108137 46574868
Breast cancer recurrent 108.55 39.89 29 3028 3882 46679123
Foetal death 105.62 39.89 34 3023 8709 46674296
PO2 increased 102.76 39.89 21 3036 869 46682136
Cardiac arrest 99.67 39.89 66 2991 90333 46592672
Blood pH decreased 94.78 39.89 24 3033 2603 46680402
Oxygen saturation abnormal 93.97 39.89 24 3033 2694 46680311
Blood bicarbonate decreased 87.72 39.89 23 3034 2862 46680143
Maternal exposure during pregnancy 83.03 39.89 62 2995 102487 46580518
Left ventricular dysfunction 77.25 39.89 28 3029 10227 46672778
Hypotension 77.18 39.89 85 2972 232504 46450501
Blood magnesium decreased 57.48 39.89 23 3034 10969 46672036
Seizure 53.34 39.89 52 3005 123002 46560003
Blood calcium decreased 52.76 39.89 24 3033 15649 46667356
Electroencephalogram abnormal 51.10 39.89 16 3041 3738 46679267
Encephalopathy 50.72 39.89 30 3027 33559 46649446
Renal impairment 47.20 39.89 39 3018 74333 46608672
Anaesthetic complication 43.51 39.89 12 3045 1805 46681200
Bronchospasm 40.44 39.89 20 3037 15687 46667318

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 125.09 34.44 41 1944 11031 29939462
Intensive care unit acquired weakness 68.50 34.44 15 1970 857 29949636
Hyperthermia malignant 62.27 34.44 16 1969 1818 29948675
Propofol infusion syndrome 57.60 34.44 13 1972 853 29949640
Hepatitis fulminant 46.08 34.44 15 1970 3926 29946567
Metabolic acidosis 42.49 34.44 28 1957 37433 29913060

Pharmacologic Action:

SourceCodeDescription
ATC N01AF03 NERVOUS SYSTEM
ANESTHETICS
ANESTHETICS, GENERAL
Barbiturates, plain
ATC N05CA19 NERVOUS SYSTEM
PSYCHOLEPTICS
HYPNOTICS AND SEDATIVES
Barbiturates, plain
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 D018757 GABA Modulators
MeSH PA D006993 Hypnotics and Sedatives
MeSH PA D018377 Neurotransmitter Agents
CHEBI has role CHEBI:38877 intravenous anesthetics
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 Unclassified 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
C0600350 UMLSCUI
CHEBI:102166 CHEBI
EDP PDB_CHEM_ID
CHEMBL738 ChEMBL_ID
CHEMBL441 ChEMBL_ID
D013874 MESH_DESCRIPTOR_UI
DB00599 DRUGBANK_ID
433 INN_ID
JI8Z5M7NULL3 UNII
3000715 PUBCHEM_CID
2579 IUPHAR_LIGAND_ID
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