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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL13280
CHEMBL13280
Compound Name FLUNITRAZEPAM
ChEMBL Synonyms FLUNITRAZEPAM | RO 5-4200 | ROHYPNOL
Max Phase 4 (Approved)
Withdrawn Yes
Trade Names ROHYPNOL
Molecular Formula C16H12FN3O3

Additional synonyms for CHEMBL13280 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CN1C(=O)CN=C(c2ccccc2F)c3cc(ccc13)[N+](=O)[O-]
Standard InChI InChI=1S/C16H12FN3O3/c1-19-14-7-6-10(20(22)23)8-12(14)16(18- ...
Download InChI
Standard InChI Key PPTYJKAXVCCBDU-UHFFFAOYSA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification
  • Withdrawn Drugs

Alternate Forms of Compound in ChEMBL


CHEMBL13280

Molecule Features

CHEMBL13280 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First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:N Parenteral:N Topical:N Black Box:N Availability Type:Withdrawn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 1996
Country France; unapproved in United States
Reason Abuse
Class Misuse

Mechanism of Action

Mechanism of Action ChEMBL Target References
GABA-A receptor; anion channel positive allosteric modulator GABA-A receptor; anion channel Other PubMed PubMed PubMed

Clinical Data

ClinicalTrials.gov FLUNITRAZEPAM
The Cochrane Collaboration FLUNITRAZEPAM

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 CHEMBL13280. 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
CHEMBL1962 GABA receptor alpha-1 subunit Homo sapiens 1.000
CHEMBL250 Platelet activating factor receptor Homo sapiens 1.000
CHEMBL3577 Aldehyde dehydrogenase 1A1 Homo sapiens 0.995
CHEMBL3198 Acetylcholinesterase Mus musculus 0.932
CHEMBL1075138 Tyrosyl-DNA phosphodiesterase 1 Homo sapiens 0.846
CHEMBL2871 Cholecystokinin A receptor Rattus norvegicus 0.789
CHEMBL6110 Thioredoxin glutathione reductase Schistosoma mansoni 0.778
CHEMBL3464 Nitric oxide synthase, inducible Mus musculus 0.693
CHEMBL4191 Monoglyceride lipase Homo sapiens 0.686
CHEMBL5514 Huntingtin Homo sapiens 0.671
CHEMBL1855 Gonadotropin-releasing hormone receptor Homo sapiens 0.616
CHEMBL1293231 Nuclear receptor ROR-gamma Mus musculus 0.603
CHEMBL2392 DNA polymerase beta Homo sapiens 0.586
CHEMBL2608 Lysosomal alpha-glucosidase Homo sapiens 0.469
CHEMBL2949 Cyclooxygenase-1 Ovis aries 0.455
CHEMBL2026 Beta-lactamase AmpC Escherichia coli K-12 0.415
CHEMBL1287622 Lethal(3)malignant brain tumor-like protein 1 Homo sapiens 0.391
CHEMBL4552 Peripheral-type benzodiazepine receptor Rattus norvegicus 0.346
CHEMBL1293224 Microtubule-associated protein tau Homo sapiens 0.277



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL1962 GABA receptor alpha-1 subunit Homo sapiens 1.000
CHEMBL250 Platelet activating factor receptor Homo sapiens 0.999
CHEMBL4796 Beta-chymotrypsin Homo sapiens 0.982
CHEMBL3577 Aldehyde dehydrogenase 1A1 Homo sapiens 0.943
CHEMBL1075138 Tyrosyl-DNA phosphodiesterase 1 Homo sapiens 0.885
CHEMBL5514 Huntingtin Homo sapiens 0.694
CHEMBL4143 Calpain 2 Sus scrofa 0.672
CHEMBL2830 Voltage-gated L-type calcium channel alpha-1C subunit Oryctolagus cuniculus 0.666
CHEMBL1075189 Pyruvate kinase isozymes M1/M2 Homo sapiens 0.636
CHEMBL1293224 Microtubule-associated protein tau Homo sapiens 0.629
CHEMBL6110 Thioredoxin glutathione reductase Schistosoma mansoni 0.582
CHEMBL6113 Phosphoethanolamine/phosphocholine phosphatase Homo sapiens 0.482
CHEMBL1287622 Lethal(3)malignant brain tumor-like protein 1 Homo sapiens 0.477
CHEMBL3026 GABA receptor alpha-3 subunit Homo sapiens 0.439
CHEMBL1293231 Nuclear receptor ROR-gamma Mus musculus 0.365
CHEMBL3622 Cytochrome P450 2C19 Homo sapiens 0.219
CHEMBL5804 Toll-like receptor 9 Homo sapiens 0.211
CHEMBL1293266 Nucleotide-binding oligomerization domain-containing protein 2 Homo sapiens 0.209

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
313.3 313.0863 2.55 2 75.81 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
4 0 0 6 0 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
- 1.68 2.13 2.13 2 23 0.63

Structural Alerts

There are 5 structural alerts for CHEMBL13280. To view alerts please click here.

Compound Cross References

ATC N - NERVOUS SYSTEM
N05 - PSYCHOLEPTICS
N05C - HYPNOTICS AND SEDATIVES
N05CD - Benzodiazepine derivatives
N05CD03 - flunitrazepam

ChemSpider ChemSpider:PPTYJKAXVCCBDU-UHFFFAOYSA-N
Wikipedia Flunitrazepam

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL13280



ACToR 1622-62-4
BindingDB 25878
Brenda 6165 110933
ChEBI 31622
DrugBank DB01544
DrugCentral 1202
eMolecules 538506
EPA CompTox Dashboard DTXSID7023065
FDA SRS 620X0222FQ
Guide to Pharmacology 4193 4360
Human Metabolome Database HMDB0015510
IBM Patent System 76573577644AED5D1A64190D27368D49 849441ED887B546E15052DE76A5BD588
NMRShiftDB 20233880
PharmGKB PA164781320
PubChem 3380
PubChem: Thomson Pharma 15494069
SureChEMBL SCHEMBL44169
ZINC ZINC000003812994

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