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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL495
CHEMBL495
Compound Name ALPROSTADIL
ChEMBL Synonyms VITAROS | VIRIDAL 5 | PGE1 | PROSTIN VR PEDIATRIC | VIRIDAL DUO | CAVERJECT | PROSTIN | EDEX | PROSTAGLANDIN E1 | VIRIDAL 10 | VIRIDAL 20 | ALPROSTADIL | PROSTIN VR | CAVERJECT IMPULSE | U-10,136
Max Phase 4 (Approved)
Trade Names CAVERJECT | CAVERJECT IMPULSE | VIRIDAL 10 | PROSTIN VR PEDIATRIC | VITAROS | EDEX | ALPROSTADIL | PROSTIN VR | PROSTIN | VIRIDAL 20 | VIRIDAL 5 | VIRIDAL DUO
Molecular Formula C20H34O5

Additional synonyms for CHEMBL495 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)O
Standard InChI InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(1 ...
Download InChI
Standard InChI Key GMVPRGQOIOIIMI-DWKJAMRDSA-N

Sources

  • British National Formulary
  • Orange Book
  • Patent Bioactivity Data
  • 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


CHEMBL495

Molecule Features

CHEMBL495 compound icon
Drug Type:Natural Product-derived Rule of Five:Y First In Class:N Chirality:Single Stereoisomer Prodrug:N Oral:N Parenteral:Y Topical:Y Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Prostanoid EP1 receptor agonist Prostanoid EP1 receptor FDA ISBN
Prostanoid EP2 receptor agonist Prostanoid EP2 receptor FDA ISBN

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Peripheral Vascular DiseasesD016491EFO:0003875peripheral vascular disease2ClinicalTrials
Prostatic NeoplasmsD011471EFO:0001663prostate carcinoma2ClinicalTrials
Cardiovascular DiseasesD002318EFO:0000319cardiovascular disease4ATC
ClinicalTrials
Arteriosclerosis ObliteransD001162EFO:1000820arteriosclerosis obliterans2ClinicalTrials
Macular DegenerationD008268EFO:0001365age-related macular degeneration3ClinicalTrials
Respiratory Distress Syndrome, AdultD012128EFO:1000637acute respiratory distress syndrome2ClinicalTrials
Erectile DysfunctionD007172EFO:0004234erectile dysfunction2ClinicalTrials
Heart FailureD006333EFO:0003144heart failure3ClinicalTrials
Sexual Dysfunction, PhysiologicalD012735EFO:0004714sexual dysfunction2ClinicalTrials

Clinical Data

ClinicalTrials.gov ALPROSTADIL
The Cochrane Collaboration ALPROSTADIL

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 CHEMBL495. 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
CHEMBL2181 Prostanoid EP1 receptor Mus musculus 1.000
CHEMBL2488 Prostanoid EP2 receptor Mus musculus 1.000
CHEMBL2489 Prostanoid EP4 receptor Mus musculus 1.000
CHEMBL4336 Prostanoid EP3 receptor Mus musculus 1.000
CHEMBL1987 Prostanoid FP receptor Homo sapiens 1.000
CHEMBL1881 Prostanoid EP2 receptor Homo sapiens 1.000
CHEMBL1836 Prostanoid EP4 receptor Homo sapiens 1.000
CHEMBL4086 Prostanoid EP4 receptor Rattus norvegicus 1.000
CHEMBL1995 Prostanoid IP receptor Homo sapiens 1.000
CHEMBL4909 Prostanoid EP2 receptor Rattus norvegicus 1.000
CHEMBL1811 Prostanoid EP1 receptor Homo sapiens 1.000
CHEMBL2069 Thromboxane A2 receptor Homo sapiens 1.000
CHEMBL3911 Leukotriene B4 receptor 1 Homo sapiens 0.999
CHEMBL3310 Histone deacetylase 11 Homo sapiens 0.989
CHEMBL5103 Histone deacetylase 10 Homo sapiens 0.955
CHEMBL2878 Histone deacetylase 6 Mus musculus 0.777
CHEMBL2966 Adenosine deaminase Bos taurus 0.411
CHEMBL3114 Sucrase-isomaltase Rattus norvegicus 0.259
CHEMBL2179 Beta-glucocerebrosidase Homo sapiens 0.206



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL2181 Prostanoid EP1 receptor Mus musculus 1.000
CHEMBL2488 Prostanoid EP2 receptor Mus musculus 1.000
CHEMBL1995 Prostanoid IP receptor Homo sapiens 1.000
CHEMBL4086 Prostanoid EP4 receptor Rattus norvegicus 1.000
CHEMBL1836 Prostanoid EP4 receptor Homo sapiens 1.000
CHEMBL1881 Prostanoid EP2 receptor Homo sapiens 1.000
CHEMBL1987 Prostanoid FP receptor Homo sapiens 1.000
CHEMBL2489 Prostanoid EP4 receptor Mus musculus 1.000
CHEMBL4336 Prostanoid EP3 receptor Mus musculus 1.000
CHEMBL1811 Prostanoid EP1 receptor Homo sapiens 1.000
CHEMBL4909 Prostanoid EP2 receptor Rattus norvegicus 1.000
CHEMBL2069 Thromboxane A2 receptor Homo sapiens 1.000
CHEMBL3710 Prostanoid EP3 receptor Homo sapiens 1.000
CHEMBL3156 Thromboxane A2 receptor Rattus norvegicus 1.000
CHEMBL3911 Leukotriene B4 receptor 1 Homo sapiens 1.000
CHEMBL402 HMG-CoA reductase Homo sapiens 1.000
CHEMBL3310 Histone deacetylase 11 Homo sapiens 0.994
CHEMBL1628461 Oxoeicosanoid receptor 1 Homo sapiens 0.992
CHEMBL3775 Dual specificity phosphatase Cdc25A Homo sapiens 0.968
CHEMBL5103 Histone deacetylase 10 Homo sapiens 0.962

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
354.5 354.2406 3.48 13 94.83 ACID


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
4 3 0 5 3 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
4.77 - 2.75 .16 0 25 0.35

Structural Alerts

There are 7 structural alerts for CHEMBL495. To view alerts please click here.

Compound Cross References

ATC G - GENITO URINARY SYSTEM AND SEX HORMONES
G04 - UROLOGICALS
G04B - UROLOGICALS
G04BE - Drugs used in erectile dysfunction
G04BE01 - alprostadil

C - CARDIOVASCULAR SYSTEM
C01 - CARDIAC THERAPY
C01E - OTHER CARDIAC PREPARATIONS
C01EA - Prostaglandins
C01EA01 - alprostadil

ChemSpider ChemSpider:GMVPRGQOIOIIMI-DWKJAMRDSA-N
DailyMed alprostadil
PubChem SID: 144204033 SID: 49681576
Wikipedia Prostaglandin_E1

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL495



ACToR 745-65-3 119314-69-1
BindingDB 50101853
Brenda 1654 33678 154395 90230 153410
ChEBI 15544
ChemicalBook CB6141459
DrugCentral 138
eMolecules 29541183 531173
EPA CompTox Dashboard DTXSID9022578
FDA SRS F5TD010360
Guide to Pharmacology 1882
Human Metabolome Database HMDB0001442
KEGG Ligand C04741
LINCS LSM-42979
LipidMaps LMFA03010134
Metabolights MTBLC15544
MolPort MolPort-003-939-183
NIH Clinical Collection SAM001246840
Nikkaji J3.319G
PDBe XPG
PubChem 5280723
PubChem: Drugs of the Future 12013405
PubChem: Thomson Pharma 14901056 14901054
Selleck Alprostadil(Caverject)
SureChEMBL SCHEMBL33317
ZINC ZINC000003813088

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