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

Stem definitionDrug idCAS RN
2630 1420-55-9

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • thiethylperazine
  • ethylthioperazine
  • thiethylperazine malate
  • thiethylperazine maleate
  • thiethylperazine dimalate
A dopamine antagonist that is particularly useful in treating the nausea and vomiting associated with anesthesia, mildly emetic cancer chemotherapy agents, radiation therapy, and toxins. This piperazine phenothiazine does not prevent vertigo or motion sickness. (From AMA Drug Evaluations Annual, 1994, p457)
  • Molecular weight: 399.62
  • Formula: C22H29N3S2
  • CLOGP: 4.75
  • LIPINSKI: 0
  • HAC: 3
  • HDO: 0
  • TPSA: 9.72
  • ALOGS: -4.91
  • ROTB: 6

  • Status: OFM

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

Drug dosage:

DoseUnitRoute
13 mg O
13 mg P
13 mg R

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.83 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD

Approvals:

DateAgencyCompanyOrphan
July 18, 1961 FDA NOVARTIS

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

Pharmacologic Action:

SourceCodeDescription
ATC R06AD03 RESPIRATORY SYSTEM
ANTIHISTAMINES FOR SYSTEMIC USE
ANTIHISTAMINES FOR SYSTEMIC USE
Phenothiazine derivatives
MeSH PA D000932 Antiemetics
MeSH PA D002491 Central Nervous System Agents
MeSH PA D015259 Dopamine Agents
MeSH PA D018492 Dopamine Antagonists
MeSH PA D005765 Gastrointestinal Agents
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018373 Peripheral Nervous System Agents
CHEBI has role CHEBI:37930 phenothiazine antipsychotic drug
CHEBI has role CHEBI:37956 histamine antagonist
CHEBI has role CHEBI:48876 muscarinic antagonist
CHEBI has role CHEBI:48279 serotonergic antagonist
CHEBI has role CHEBI:48561 dopaminergic antagonist
CHEBI has role CHEBI:50919 antiemetic

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Nausea and vomiting indication 16932000
Vomiting indication 422400008
Nausea indication 422587007

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.74 Basic
pKa2 4.74 Basic
pKa3 3.2 Basic

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
D(2) dopamine receptor GPCR ANTAGONIST Ki 8.70 WOMBAT-PK CHEMBL
Sigma non-opioid intracellular receptor 1 Membrane receptor Ki 7.15 WOMBAT-PK
Muscarinic acetylcholine receptor M5 GPCR WOMBAT-PK
Muscarinic acetylcholine receptor M4 GPCR WOMBAT-PK
Muscarinic acetylcholine receptor M3 GPCR WOMBAT-PK
Muscarinic acetylcholine receptor M2 GPCR WOMBAT-PK
Muscarinic acetylcholine receptor M1 GPCR WOMBAT-PK
Histamine H1 receptor GPCR Ki 7.60 WOMBAT-PK
D(3) dopamine receptor GPCR Ki 8.70 WOMBAT-PK
Alpha-1A adrenergic receptor GPCR Ki 8.70 WOMBAT-PK
5-hydroxytryptamine receptor 2C GPCR Ki 7 WOMBAT-PK
5-hydroxytryptamine receptor 2B GPCR Ki 7 WOMBAT-PK
5-hydroxytryptamine receptor 2A GPCR Ki 7 WOMBAT-PK
5-hydroxytryptamine receptor 1A GPCR Ki 6.15 WOMBAT-PK
D(1A) dopamine receptor GPCR Ki 6.30 WOMBAT-PK
FAD-linked sulfhydryl oxidase ALR Enzyme AC50 5.96 CHEMBL
Pleiotropic ABC efflux transporter of multiple drugs Transporter IC50 5.64 CHEMBL

External reference:

IDSource
4019943 VUID
N0000148028 NUI
C0039865 UMLSCUI
D02354 KEGG_DRUG
36218003 SNOMEDCT_US
4019943 VANDF
10471 RXNORM
372719002 SNOMEDCT_US
5567 MMSL
d00857 MMSL
004595 NDDF
8ETK1WAF6R UNII
1034 INN_ID
CHEMBL1378 ChEMBL_ID
DB00372 DRUGBANK_ID
52239-63-1 SECONDARY_CAS_RN
CHEBI:9544 CHEBI
CHEMBL1201074 ChEMBL_ID
D013847 MESH_DESCRIPTOR_UI
CHEMBL2359670 ChEMBL_ID
CHEMBL3989478 ChEMBL_ID
5440 PUBCHEM_CID
7306 IUPHAR_LIGAND_ID

Pharmaceutical products:

None