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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL1098
CHEMBL1098
Compound Name BUPIVACAINE
ChEMBL Synonyms Bupivacaine Hydrochloride Kit | Bupivacaine HCl | Marcaine HCl | Anekain | Bupivacaine | WIN-11318 | SKY-0402 | Marcaine | Exparel | Sensorcaine | LAC-43
Max Phase 4 (Approved)
Trade Names Exparel | Anekain | Bupivacaine HCl | Sensorcaine | Marcaine HCl | Marcaine | Bupivacaine Hydrochloride Kit
Molecular Formula C18H28N2O

Additional synonyms for CHEMBL1098 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CCCCN1CCCCC1C(=O)Nc2c(C)cccc2C
Standard InChI InChI=1S/C18H28N2O/c1-4-5-12-20-13-7-6-11-16(20)18(21)19-17- ...
Download InChI
Standard InChI Key LEBVLXFERQHONN-UHFFFAOYSA-N

Mechanism of Action

Mechanism of Action ChEMBL Target References
Sodium channel protein type IV alpha subunit blocker Sodium channel protein type IV alpha subunit PubMed PubMed

Indications for CHEMBL1098

MESH Heading MESH ID EFO ID EFO Term Max phase for indication
BREAST NEOPLASMSD001943EFO:0000305BREAST CARCINOMA3
FRACTURES, BONED050723EFO:0003931BONE FRACTURE3
HERNIA, INGUINALD006552HP:0000023INGUINAL HERNIA4
HYPOTENSIOND007022EFO:0005251HYPOTENSION2
INFLAMMATIOND007249MP:0001845INFLAMMATION2
OSTEOARTHRITISD010003EFO:0002506OSTEOARTHRITIS4
PAIND010146EFO:0003843PAIN4
WOUNDS AND INJURIESD014947EFO:0000546INJURY3

Molecule Features

CHEMBL1098 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Racemic Mixture Prodrug:N Oral:N Parenteral:Y Topical:N Black Box:Y Availability Type:Prescription-only

Clinical Data

Number of clinical trials registered at clinicaltrials.gov
Number of reviews at The Cochrane Collaboration
Number of entries at British National Formulary

Structural Alerts

There are no structural alerts for CHEMBL1098

Alternate Forms of Compound in ChEMBL


CHEMBL1098

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 CHEMBL1098. 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
CHEMBL6141 Acyl-CoA:cholesterol acyltransferase Oryctolagus cuniculus 0.992

10uM


ChEMBL_ID Target Name Organism Score
CHEMBL6141 Acyl-CoA:cholesterol acyltransferase Oryctolagus cuniculus 0.991
CHEMBL253 Cannabinoid CB2 receptor Homo sapiens 0.244

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
288.4 288.2202 4.31 5 32.34 ACID


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
2 1 0 3 1 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
1.62 - 2.28 2.88 1 21 0.88

Compound Cross References

ATC N - NERVOUS SYSTEM
N01 - ANESTHETICS
N01B - ANESTHETICS, LOCAL
N01BB - Amides
N01BB01 - bupivacaine

N - NERVOUS SYSTEM
N01 - ANESTHETICS
N01B - ANESTHETICS, LOCAL
N01BB - Amides
N01BB51 - bupivacaine, combinations

ChemSpider ChemSpider:LEBVLXFERQHONN-UHFFFAOYSA-N
DailyMed bupivacaine bupivacaine hydrochloride
PubChem SID: 160644527
Wikipedia Bupivacaine

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL1098



ACToR 38396-39-3 15233-43-9 2180-92-9
BindingDB 50350790
ChEBI 77431
DrugBank DB00297
eMolecules 901488
EPA CompTox Dashboard DTXSID2022703
Guide to Pharmacology 2397
Human Metabolome Database HMDB14442
IBM Patent System 32F45F6858C9E1B3A5B9C6B026BC6CA5
KEGG Ligand C07529
LINCS LSM-4301
Mcule MCULE-2286784276
Nikkaji J7.351B
PharmGKB PA135057240
PubChem 2474
PubChem: Thomson Pharma 14897927
SureChEMBL SCHEMBL25438

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