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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL27
CHEMBL27
Compound Name PROPRANOLOL
ChEMBL Synonyms RAPRANOL SR | PROPRANOLOL HYDROCHLORIDE | INDERAL LA | DUPROMEX | AVLOCARDYL | Inderide-80/25 | SLOPROLOL | SLO-BLOK | PROPANIX-40 | PROPANIX-160 | INNOPRAN XL | Inderal | PROPANIX LA | PROPRANOLOL | BEDRANOL S.R. | SLO-PRO | ANGILOL | APSOLOL | AY 64043 | HALF BETA-PROGRANE MR | HALF PROPANIX LA | HALF-BETADUR CR | PROPATARD LA | PROPRANOLOL HYDROCHLORIDE INTENSOL | INDERAL | BEDRANOL | HALF-BEPRANE CR | PROPANIX-160 SR | PROPANIX-80 | Inderide-40/25 | Tesnol | Sagittol | SYPROL | ICI 45520 | HALF-INDERAL LA | CARDINOL | PROPANIX-10 | PROBETA LA | INNOPRAN | HEMANGEOL | HALF PROPATARD LA | LOPRANOL LA | LEDERPRONOL | BETADUR CR | BETA-PROGRANE MR | BERKOLOL
Max Phase 4 (Approved)
Trade Names BEDRANOL S.R. | INDERAL | PROPANIX LA | INNOPRAN XL | PROPANIX-160 | PROPANIX-40 | SLO-BLOK | SLOPROLOL | AVLOCARDYL | DUPROMEX | INDERAL LA | PROPRANOLOL HYDROCHLORIDE | RAPRANOL SR | SLO-PRO | ANGILOL | APSOLOL | HALF BETA-PROGRANE MR | HALF PROPANIX LA | HALF-BETADUR CR | PROPATARD LA | PROPRANOLOL HYDROCHLORIDE INTENSOL | BEDRANOL | HALF-BEPRANE CR | PROPANIX-160 SR | PROPANIX-80 | BERKOLOL | BETA-PROGRANE MR | BETADUR CR | LEDERPRONOL | LOPRANOL LA | HALF PROPATARD LA | HEMANGEOL | INNOPRAN | PROBETA LA | PROPANIX-10 | CARDINOL | HALF-INDERAL LA | SYPROL | Sagittol | Tesnol
Molecular Formula C16H21NO2

Additional synonyms for CHEMBL27 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CC(C)NCC(O)COc1cccc2ccccc12
Standard InChI InChI=1S/C16H21NO2/c1-12(2)17-10-14(18)11-19-16-9-5-7-13-6-3 ...
Download InChI
Standard InChI Key AQHHHDLHHXJYJD-UHFFFAOYSA-N

Sources

  • British National Formulary
  • Curated Drug Metabolism Pathways
  • DrugMatrix
  • Open TG-GATEs
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL27

Molecule Features

CHEMBL27 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Racemic Mixture Prodrug:N Oral:Y Parenteral:Y Topical:N Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Beta-1 adrenergic receptor antagonist Beta-1 adrenergic receptor DailyMed
Beta-2 adrenergic receptor antagonist Beta-2 adrenergic receptor DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Breast NeoplasmsD001943EFO:0000305breast carcinoma2ClinicalTrials
Depressive DisorderD003866EFO:0003761unipolar depression1ClinicalTrials
Diabetes Mellitus, Type 1D003922EFO:0001359type I diabetes mellitus2ClinicalTrials
Diabetic RetinopathyD003930EFO:0003770diabetic retinopathy1ClinicalTrials
HemangiomaD006391EFO:1000635hemangioma3ClinicalTrials
Kidney DiseasesD007674EFO:0003086kidney disease1ClinicalTrials
Sleep Apnea, ObstructiveD020181EFO:0003918obstructive sleep apnea2ClinicalTrials
AscitesD001201HP:0001541Ascites3ClinicalTrials
Colorectal NeoplasmsD015179EFO:0004142colorectal neoplasm3ClinicalTrials
ClinicalTrials
DystociaD004420EFO:1000911dystocia2ClinicalTrials
FibromyalgiaD005356EFO:0005687fibromyalgia1ClinicalTrials
Pulmonary Disease, Chronic ObstructiveD029424EFO:0000341chronic obstructive pulmonary disease1ClinicalTrials
Diabetes Mellitus, Type 2D003924EFO:0001360type II diabetes mellitus1ClinicalTrials
AnxietyD001007EFO:0005230anxiety3ClinicalTrials
Marfan SyndromeD008382Orphanet:558Marfan syndrome2ClinicalTrials
Migraine without AuraD020326EFO:0005296migraine without aura2ClinicalTrials
Stress Disorders, Post-TraumaticD013313EFO:0001358post-traumatic stress disorder3ClinicalTrials
ClinicalTrials
Anemia, Sickle CellD000755Orphanet:232Sickle cell anemia2ClinicalTrials
Wounds and InjuriesD014947EFO:0000546injury2ClinicalTrials
Movement DisordersD009069EFO:0004280movement disorder2ClinicalTrials
Prostatic NeoplasmsD011471EFO:0001663prostate carcinoma2ClinicalTrials
LymphedemaD008209Orphanet:79383Lymphedema2ClinicalTrials
Migraine with AuraD020325EFO:0005295migraine with aura2ClinicalTrials
Multiple MyelomaD009101EFO:0001378multiple myeloma2ClinicalTrials
PainD010146EFO:0003843pain2ClinicalTrials
Panic DisorderD016584EFO:0004262panic disorder2ClinicalTrials
Cardiovascular DiseasesD002318EFO:0000319cardiovascular disease4ATC
Cocaine-Related DisordersD019970EFO:0002610cocaine dependence2ClinicalTrials
ClinicalTrials
HemangiosarcomaD006394EFO:0003968angiosarcoma1ClinicalTrials
Hypertension, PortalD006975EFO:0000666portal hypertension3ClinicalTrials
MelanomaD008545EFO:0000756melanoma2ClinicalTrials
Migraine DisordersD008881EFO:0003821migraine disorder3ClinicalTrials
ClinicalTrials
MelanomaD008545EFO:0000389cutaneous melanoma2ClinicalTrials
AsthmaD001249EFO:0000270asthma2ClinicalTrials
Carcinoma, Renal CellD002292EFO:0000681renal cell carcinoma2ClinicalTrials
Child Development Disorders, PervasiveD002659EFO:0003756autism spectrum disorder0ClinicalTrials
Hypotension, OrthostaticD007024EFO:0005252orthostatic hypotension0ClinicalTrials
Memory DisordersD008569EFO:0001072memory impairment1ClinicalTrials
Smoking CessationD016540EFO:0004319smoking cessation3ClinicalTrials
StrokeD020521EFO:0000712stroke2ClinicalTrials
Substance-Related DisordersD019966EFO:0003890drug dependence2ClinicalTrials
Carcinoma, HepatocellularD006528EFO:0000182hepatocellular carcinoma2ClinicalTrials
HypertensionD006973EFO:0000537hypertension4ClinicalTrials
ClinicalTrials
DailyMed
DailyMed
Liver CirrhosisD008103EFO:0001422cirrhosis of liver3ClinicalTrials
ClinicalTrials
NeoplasmsD009369EFO:0000311cancer1ClinicalTrials
OsteoporosisD010024EFO:0003882osteoporosis0ClinicalTrials
Retinopathy of PrematurityD012178EFO:1001158retinopathy of prematurity2ClinicalTrials
SarcomaD012509EFO:1001968soft tissue sarcoma2ClinicalTrials

Clinical Data

ClinicalTrials.gov PROPRANOLOL
The Cochrane Collaboration PROPRANOLOL

Metabolites for CHEMBL27

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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 CHEMBL27. 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
CHEMBL213 Beta-1 adrenergic receptor Homo sapiens 1.000
CHEMBL210 Beta-2 adrenergic receptor Homo sapiens 1.000
CHEMBL3373 Beta-2 adrenergic receptor Bos taurus 1.000
CHEMBL246 Beta-3 adrenergic receptor Homo sapiens 1.000
CHEMBL3252 Beta-1 adrenergic receptor Rattus norvegicus 1.000
CHEMBL1878 Calcium sensing receptor Homo sapiens 1.000
CHEMBL4302 P-glycoprotein 1 Homo sapiens 0.998
CHEMBL5414 Beta-2 adrenergic receptor Cavia porcellus 0.966
CHEMBL289 Cytochrome P450 2D6 Homo sapiens 0.943
CHEMBL228 Serotonin transporter Homo sapiens 0.920
CHEMBL214 Serotonin 1a (5-HT1a) receptor Homo sapiens 0.891
CHEMBL3247 HMG-CoA reductase Rattus norvegicus 0.763
CHEMBL3459 Serotonin 1b (5-HT1b) receptor Rattus norvegicus 0.459
CHEMBL4361 Induced myeloid leukemia cell differentiation protein Mcl-1 Homo sapiens 0.203
CHEMBL1075138 Tyrosyl-DNA phosphodiesterase 1 Homo sapiens 0.201



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL3373 Beta-2 adrenergic receptor Bos taurus 1.000
CHEMBL213 Beta-1 adrenergic receptor Homo sapiens 1.000
CHEMBL210 Beta-2 adrenergic receptor Homo sapiens 1.000
CHEMBL3252 Beta-1 adrenergic receptor Rattus norvegicus 1.000
CHEMBL246 Beta-3 adrenergic receptor Homo sapiens 1.000
CHEMBL2289 Beta-2 adrenergic receptor Canis lupus familiaris 1.000
CHEMBL1878 Calcium sensing receptor Homo sapiens 1.000
CHEMBL4302 P-glycoprotein 1 Homo sapiens 0.990
CHEMBL3251 Nuclear factor NF-kappa-B p105 subunit Homo sapiens 0.970
CHEMBL5414 Beta-2 adrenergic receptor Cavia porcellus 0.969
CHEMBL3459 Serotonin 1b (5-HT1b) receptor Rattus norvegicus 0.945
CHEMBL214 Serotonin 1a (5-HT1a) receptor Homo sapiens 0.881
CHEMBL228 Serotonin transporter Homo sapiens 0.843
CHEMBL289 Cytochrome P450 2D6 Homo sapiens 0.829
CHEMBL3247 HMG-CoA reductase Rattus norvegicus 0.713
CHEMBL3815 Squalene synthetase Rattus norvegicus 0.629

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
259.4 259.1572 2.58 6 41.49 BASE


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


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
13.84 9.5 2.9 .79 2 19 0.84

Structural Alerts

There are 1 structural alerts for CHEMBL27. To view alerts please click here.

Compound Cross References

ATC C - CARDIOVASCULAR SYSTEM
C07 - BETA BLOCKING AGENTS
C07A - BETA BLOCKING AGENTS
C07AA - Beta blocking agents, non-selective
C07AA05 - propranolol

ChemSpider ChemSpider:AQHHHDLHHXJYJD-UHFFFAOYSA-N
DailyMed propranolol hydrochloride
PubChem SID: 124881056 SID: 26751802 SID: 26755283 SID: 50104497 SID: 90341556
Wikipedia Propranolol

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL27



ACToR 525-66-6 13013-17-7
BindingDB 25761
Brenda 66047 3905 45500 5606
ChEBI 8499
DrugBank DB00571
DrugCentral 2303
eMolecules 735071
EPA CompTox Dashboard DTXSID6023525
Guide to Pharmacology 564
Human Metabolome Database HMDB0001849
IBM Patent System E8CE792491FBFDE504024008C3A8AF91
KEGG Ligand C07407
LINCS LSM-4329
Mcule MCULE-7804628650
Metabolights MTBLC8499
MolPort MolPort-001-794-623
Nikkaji J6.653B
PharmGKB PA451145
PubChem 4946
PubChem: Thomson Pharma 14823711
SureChEMBL SCHEMBL3955

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