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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL288470
CHEMBL288470
Compound Name AMINOPYRINE
ChEMBL Synonyms AMINOPYRINE | AMINOPHENAZONE CYCLAMATE | AMINOPHENAZONE | AMIDOPYRINE
Max Phase 4 (Approved)
Withdrawn Yes
Trade Names
Molecular Formula C13H17N3O

Additional synonyms for CHEMBL288470 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CN(C)C1=C(C)N(C)N(C1=O)c2ccccc2
Standard InChI InChI=1S/C13H17N3O/c1-10-12(14(2)3)13(17)16(15(10)4)11-8-6-5 ...
Download InChI
Standard InChI Key RMMXTBMQSGEXHJ-UHFFFAOYSA-N

Sources

  • AstraZeneca Deposited Data
  • PubChem BioAssays
  • Scientific Literature
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification
  • Withdrawn Drugs

Alternate Forms of Compound in ChEMBL


CHEMBL288470

Molecule Features

CHEMBL288470 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:Unknown

Withdrawal Information

Year 1970
Country United Kingdom; United States; Germany; France
Reason Agranulocytosis
Class Hematological toxicity

Mechanism of Action

Mechanism of Action ChEMBL Target References
Unknown Not Available PubMed PubMed PubMed PubMed PubMed

Clinical Data

ClinicalTrials.gov AMINOPYRINE
The Cochrane Collaboration AMINOPYRINE

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 CHEMBL288470. 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
CHEMBL1250375 NADPH oxidase 4 Homo sapiens 0.936

10uM


ChEMBL_ID Target Name Organism Score
CHEMBL1250375 NADPH oxidase 4 Homo sapiens 0.914
CHEMBL2608 Lysosomal alpha-glucosidase Homo sapiens 0.395
CHEMBL2026 Beta-lactamase AmpC Escherichia coli K-12 0.318

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
231.3 231.1372 1.55 2 30.17 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
4 0 0 4 0 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
- 4.5 .85 .85 2 17 0.78

Structural Alerts

There are no structural alerts for CHEMBL288470

Compound Cross References

ATC N - NERVOUS SYSTEM
N02 - ANALGESICS
N02B - OTHER ANALGESICS AND ANTIPYRETICS
N02BB - Pyrazolones
N02BB53 - aminophenazone, combinations excl. psycholeptics

N - NERVOUS SYSTEM
N02 - ANALGESICS
N02B - OTHER ANALGESICS AND ANTIPYRETICS
N02BB - Pyrazolones
N02BB73 - aminophenazone, combinations with psycholeptics

N - NERVOUS SYSTEM
N02 - ANALGESICS
N02B - OTHER ANALGESICS AND ANTIPYRETICS
N02BB - Pyrazolones
N02BB03 - aminophenazone

ChemSpider ChemSpider:RMMXTBMQSGEXHJ-UHFFFAOYSA-N
PubChem SID: 104171274 SID: 11112141 SID: 144203884 SID: 144208742 SID: 144213147 SID: 170465863 SID: 17389912 SID: 56463351
Wikipedia Aminophenazone

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL288470



ACToR 58-15-1 144574-10-7
BindingDB 74258
Brenda 148192 135962
ChEBI 160246
ChemicalBook CB1476086
DrugBank DB01424
DrugCentral 171
eMolecules 537453
EPA CompTox Dashboard DTXSID7020504
FDA SRS 01704YP3MO
Human Metabolome Database HMDB0015493
IBM Patent System 321B26FD00C3B6CCB5C4AE0DBBA8811D
KEGG Ligand C07539
LINCS LSM-20000
Mcule MCULE-1554715918
MolPort MolPort-001-783-069
Nikkaji J2.331K
PharmGKB PA164748135
PubChem 6009
PubChem: Thomson Pharma 15019234
Selleck amidopyrine
SureChEMBL SCHEMBL26293
ZINC ZINC000000057115

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