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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL2105458
CHEMBL2105458
Compound Name THENALIDINE
ChEMBL Synonyms THENALIDINE
Max Phase 4 (Approved)
Withdrawn Yes
Trade Names
Molecular Formula C17H22N2S

Additional synonyms for CHEMBL2105458 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CN1CCC(CC1)N(Cc2cccs2)c3ccccc3
Standard InChI InChI=1S/C17H22N2S/c1-18-11-9-16(10-12-18)19(14-17-8-5-13-20 ...
Download InChI
Standard InChI Key KLOHYVOVXOUKQI-UHFFFAOYSA-N

Sources

  • PubChem BioAssays
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification
  • Withdrawn Drugs

Alternate Forms of Compound in ChEMBL


CHEMBL2105458

Molecule Features

CHEMBL2105458 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:N Parenteral:N Topical:N Black Box:N Availability Type:Withdrawn

Withdrawal Information

Year 1960
Country United States
Reason Agranulocytosis
Class Hematological toxicity

Mechanism of Action

Mechanism of Action ChEMBL Target References
Histamine H1 receptor antagonist Histamine H1 receptor PubMed PubMed PubMed PubMed

Clinical Data

ClinicalTrials.gov THENALIDINE
The Cochrane Collaboration THENALIDINE

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL2105458. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL3568 Nitric-oxide synthase, brain Homo sapiens 1.000
CHEMBL245 Muscarinic acetylcholine receptor M3 Homo sapiens 0.998
CHEMBL216 Muscarinic acetylcholine receptor M1 Homo sapiens 0.995
CHEMBL4481 Nitric oxide synthase, inducible Homo sapiens 0.897
CHEMBL231 Histamine H1 receptor Homo sapiens 0.687
CHEMBL211 Muscarinic acetylcholine receptor M2 Homo sapiens 0.426
CHEMBL289 Cytochrome P450 2D6 Homo sapiens 0.376



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL3568 Nitric-oxide synthase, brain Homo sapiens 1.000
CHEMBL4481 Nitric oxide synthase, inducible Homo sapiens 1.000
CHEMBL245 Muscarinic acetylcholine receptor M3 Homo sapiens 0.997
CHEMBL4803 Nitric-oxide synthase, endothelial Homo sapiens 0.993
CHEMBL216 Muscarinic acetylcholine receptor M1 Homo sapiens 0.968
CHEMBL289 Cytochrome P450 2D6 Homo sapiens 0.755
CHEMBL211 Muscarinic acetylcholine receptor M2 Homo sapiens 0.555
CHEMBL1850 Dopamine D5 receptor Homo sapiens 0.258

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
286.4 286.1504 3.85 4 6.48 BASE


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
3 0 0 2 0 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
- 8.78 2.9 1.64 2 20 0.84

Structural Alerts

There are no structural alerts for CHEMBL2105458

Compound Cross References

ATC R - RESPIRATORY SYSTEM
R06 - ANTIHISTAMINES FOR SYSTEMIC USE
R06A - ANTIHISTAMINES FOR SYSTEMIC USE
R06AX - Other antihistamines for systemic use
R06AX53 - thenalidine, combinations

R - RESPIRATORY SYSTEM
R06 - ANTIHISTAMINES FOR SYSTEMIC USE
R06A - ANTIHISTAMINES FOR SYSTEMIC USE
R06AX - Other antihistamines for systemic use
R06AX03 - thenalidine

D - DERMATOLOGICALS
D04 - ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC.
D04A - ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC.
D04AA - Antihistamines for topical use
D04AA03 - thenalidine

ChemSpider ChemSpider:KLOHYVOVXOUKQI-UHFFFAOYSA-N
PubChem SID: 144206868

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL2105458



ACToR 86-12-4
ChEBI 135187
DrugBank DB04826
DrugCentral 2617
EPA CompTox Dashboard DTXSID1048835
FDA SRS 6U94N2D00F
IBM Patent System 431DA5E1A599F0F977674E6E79AF367A
Nikkaji J4.932H
PubChem 27901
PubChem: Thomson Pharma 16888620
SureChEMBL SCHEMBL29498
ZINC ZINC000000002146

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/KLOHYVOVXOUKQI-UHFFFAOYSA-N spacer
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