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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL597
CHEMBL597
Compound Name PHENTOLAMINE
ChEMBL Synonyms REGITINE HYDROCHLORIDE | PHENTOLAMINE MESYLATE | PHENTOLAMINE MESILATE | REGITINE | ROGITINE | ORAVERSE | PHENTOLAMINE | PHENTOLAMINE HYDROCHLORIDE | PHENTOLAMINE METHANESULFONATE
Max Phase 4 (Approved)
Trade Names ORAVERSE | ROGITINE | PHENTOLAMINE MESYLATE | REGITINE HYDROCHLORIDE | REGITINE
Molecular Formula C17H19N3O

Additional synonyms for CHEMBL597 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES Cc1ccc(cc1)N(CC2=NCCN2)c3cccc(O)c3
Standard InChI InChI=1S/C17H19N3O/c1-13-5-7-14(8-6-13)20(12-17-18-9-10-19-1 ...
Download InChI
Standard InChI Key MRBDMNSDAVCSSF-UHFFFAOYSA-N

Sources

  • British National Formulary
  • DrugMatrix
  • Gene Expression Atlas Compounds
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL597

Molecule Features

CHEMBL597 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:N Parenteral:Y Topical:N Black Box:N Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Adrenergic receptor alpha antagonist Adrenergic receptor alpha DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Cardiovascular DiseasesD002318EFO:0000319cardiovascular disease4ClinicalTrials
ATC
Prostatic NeoplasmsD011471EFO:0001663prostate carcinoma2ClinicalTrials

Clinical Data

ClinicalTrials.gov PHENTOLAMINE
The Cochrane Collaboration PHENTOLAMINE

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 CHEMBL597. 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
CHEMBL4744 Alpha-2a adrenergic receptor Bos taurus 1.000
CHEMBL3923 Nischarin Homo sapiens 1.000
CHEMBL5857 Trace amine-associated receptor 1 Homo sapiens 1.000
CHEMBL270 Mu opioid receptor Rattus norvegicus 0.957
CHEMBL1287622 Lethal(3)malignant brain tumor-like protein 1 Homo sapiens 0.703
CHEMBL2026 Beta-lactamase AmpC Escherichia coli K-12 0.583
CHEMBL1963 Thyroid stimulating hormone receptor Homo sapiens 0.546
CHEMBL1293237 Bloom syndrome protein Homo sapiens 0.440
CHEMBL5162 Neuropeptide S receptor Homo sapiens 0.421
CHEMBL3622 Cytochrome P450 2C19 Homo sapiens 0.405
CHEMBL242 Estrogen receptor beta Homo sapiens 0.321
CHEMBL2608 Lysosomal alpha-glucosidase Homo sapiens 0.279
CHEMBL3358 Monoamine oxidase A Rattus norvegicus 0.236
CHEMBL2392 DNA polymerase beta Homo sapiens 0.217
CHEMBL2789 Estradiol 17-beta-dehydrogenase 2 Homo sapiens 0.214
CHEMBL5514 Huntingtin Homo sapiens 0.209
CHEMBL206 Estrogen receptor alpha Homo sapiens 0.208



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL4744 Alpha-2a adrenergic receptor Bos taurus 1.000
CHEMBL3923 Nischarin Homo sapiens 1.000
CHEMBL5221 Nischarin Rattus norvegicus 0.994
CHEMBL270 Mu opioid receptor Rattus norvegicus 0.943
CHEMBL5857 Trace amine-associated receptor 1 Homo sapiens 0.883
CHEMBL206 Estrogen receptor alpha Homo sapiens 0.527
CHEMBL2608 Lysosomal alpha-glucosidase Homo sapiens 0.458
CHEMBL2026 Beta-lactamase AmpC Escherichia coli K-12 0.366
CHEMBL242 Estrogen receptor beta Homo sapiens 0.346
CHEMBL1287622 Lethal(3)malignant brain tumor-like protein 1 Homo sapiens 0.334
CHEMBL1293231 Nuclear receptor ROR-gamma Mus musculus 0.226

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
281.4 281.1528 2.84 4 47.86 BASE


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
4 2 0 4 2 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
9.52 10.31 4.08 2.13 2 21 0.91

Structural Alerts

There are no structural alerts for CHEMBL597

Compound Cross References

ATC V - VARIOUS
V03 - ALL OTHER THERAPEUTIC PRODUCTS
V03A - ALL OTHER THERAPEUTIC PRODUCTS
V03AB - Antidotes
V03AB36 - phentolamine

C - CARDIOVASCULAR SYSTEM
C04 - PERIPHERAL VASODILATORS
C04A - PERIPHERAL VASODILATORS
C04AB - Imidazoline derivatives
C04AB01 - phentolamine

ChemSpider ChemSpider:MRBDMNSDAVCSSF-UHFFFAOYSA-N
DailyMed phentolamine mesylate
PubChem SID: 104171285 SID: 11112200 SID: 124882050 SID: 124882053 SID: 144203915 SID: 170464866 SID: 26751465 SID: 26751466 SID: 26751467 SID: 50085867 SID: 50100389 SID: 50100390 SID: 50103967 SID: 860967 SID: 90341742
Wikipedia Phentolamine

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL597



ACToR 50-60-2
Atlas phentolamine
BindingDB 31046
Brenda 116403
ChEBI 8081
ChemicalBook CB6665216
DrugBank DB00692
DrugCentral 2142
eMolecules 975745 31790003
EPA CompTox Dashboard DTXSID4023462
FDA SRS Z468598HBV
Guide to Pharmacology 502
Human Metabolome Database HMDB0014830
IBM Patent System 2294EEFBE5DFBF2D855E5ED8F25B40A0
LINCS LSM-4022
Mcule MCULE-3004652227
MolPort MolPort-001-783-569 MolPort-000-771-097
Nikkaji J4.105J
PharmGKB PA450926
PubChem 5775 4920903
PubChem: Thomson Pharma 14848762
SureChEMBL SCHEMBL5653
ZINC ZINC000000020251

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