General Information of Drug (ID: DMUTYR2)

Drug Name
Epoprostenol
Synonyms
Epoprostanol; Epoprostenolum; Flolan; PGX; Prostacyclin; Prostacycline; Prostacyclins; Vasocyclin; ProstaglandinI; Prostaglandin X; Prostaglandins X; PGI2; Prostacyclin I2; Prostaglandin I2; TRY 200; Epoprostenol (TN); Epoprostenol [USAN:INN]; Epoprostenolum [INN-Latin]; PG-I2; PGI(sub 2); Prostaglandin I(2); Try-200; U 53,217; U-53217; Epoprostenol (USAN/INN); KB-IV-24; (5E)-5-[(3aR,4R,5R,6aS)-5-hydroxy-4-[(E,3R)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-ylidene]pentanoic acid; (5Z)-5-[(3aR,4R,5R,6aS)-5-hydroxy-4-[(E,3S)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-ylidene]pentanoic acid; (5Z)-5-[(4R,5R)-5-hydroxy-4-[(E,3S)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-ylidene]pentanoic acid; (5Z,13E)-(15S)-6,9alpha-Epoxy-11alpha,15-dihydroxyprosta-5,13-dienoate; (5Z,13E,15S)-6,9alpha-epoxy-11alpha,15-dihydroxyprosta-5,13-dienoic acid; (5Z,9alpha,11alpha,13E,15S)-11,15-dihydroxy-6,9-epoxyprosta-5,13-dien-1-oic acid; (5Z,9alpha,11alpha,13E,15S)-6,9-epoxy-11,15-dihydroxyprosta-5,13-dien-1-oic acid; (Z)-(3aR,4R,5R,6aS)-Hexahydro-5-hydroxy-4-((E)-(3S)-3-hydroxy-1-octenyl)-2H-cyclopenta(b)furan-delta(sup 2,delta)-valeric acid; 5-[(3aR,4R,5R,6aS)-5-hydroxy-4-[(3S)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-ylidene]pentanoic acid; 5-[(3aR,4R,5R,6aS)-5-hydroxy-4-[(E,3S)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-ylidene]pentanoic acid; 5-[5-hydroxy-4-(3-hydroxyoct-1-enyl)-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-ylidene]pentanoic acid; 6,9-alpha-Epoxy-11-alpha,15(S)-dihydroxyprosta-5(Z),13(E)-dien-1-oic acid
Indication
Disease Entry ICD 11 Status REF
Allergic rhinitis CA08.0 Approved [1]
Common cold CA00 Approved [1]
Cough MD12 Approved [1]
Pulmonary hypertension BB01 Approved [2]
Rhinitis FA20 Approved [1]
Therapeutic Class
Antihypertensive Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 352.5
Logarithm of the Partition Coefficient (xlogp) 2.9
Rotatable Bond Count (rotbonds) 10
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 5
ADMET Property
Half-life
The concentration or amount of drug in body reduced by one-half in less than 6 minutes [3]
Metabolism
The drug is metabolized via spontaneous degradation []
Vd
The volume of distribution (Vd) of drug is 0.357 L/kg []
Chemical Identifiers
Formula
C20H32O5
IUPAC Name
(5Z)-5-[(3aR,4R,5R,6aS)-5-hydroxy-4-[(E,3S)-3-hydroxyoct-1-enyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-ylidene]pentanoic acid
Canonical SMILES
CCCCC[C@@H](/C=C/[C@H]1[C@@H](C[C@H]2[C@@H]1C/C(=C/CCCC(=O)O)/O2)O)O
InChI
InChI=1S/C20H32O5/c1-2-3-4-7-14(21)10-11-16-17-12-15(8-5-6-9-20(23)24)25-19(17)13-18(16)22/h8,10-11,14,16-19,21-22H,2-7,9,12-13H2,1H3,(H,23,24)/b11-10+,15-8-/t14-,16+,17+,18+,19-/m0/s1
InChIKey
KAQKFAOMNZTLHT-OZUDYXHBSA-N
Cross-matching ID
PubChem CID
5282411
ChEBI ID
CHEBI:15552
CAS Number
35121-78-9
DrugBank ID
DB01240
TTD ID
D0V0IX
INTEDE ID
DR0593
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Prostacyclin receptor (PTGIR) TTOFYT1 PI2R_HUMAN Agonist [4]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 2C9 (CYP2C9)
Main DME
DE5IED8 CP2C9_HUMAN Substrate [5]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
C-C motif chemokine 2 (CCL2) OTAD2HEL CCL2_HUMAN Gene/Protein Processing [6]
Interleukin-1 alpha (IL1A) OTPSGILV IL1A_HUMAN Regulation of Drug Effects [7]
Mitogen-activated protein kinase 1 (MAPK1) OTH85PI5 MK01_HUMAN Gene/Protein Processing [8]
Mitogen-activated protein kinase 3 (MAPK3) OTCYKGKO MK03_HUMAN Gene/Protein Processing [8]
Peroxisome proliferator-activated receptor gamma coactivator 1-alpha (PPARGC1A) OTHCDQ22 PRGC1_HUMAN Gene/Protein Processing [9]
Platelet-derived growth factor subunit A (PDGFA) OTCMZ0W8 PDGFA_HUMAN Regulation of Drug Effects [8]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Allergic rhinitis
ICD Disease Classification CA08.0
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Prostacyclin receptor (PTGIR) DTT PTGIR 7.12E-02 -0.13 -0.33
Cytochrome P450 2C9 (CYP2C9) DME CYP2C9 2.25E-03 -4.98E-01 -6.49E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Epoprostenol (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Trastuzumab Emtansine DMU1LXS Moderate Increased risk of bleeding by the combination of Epoprostenol and Trastuzumab Emtansine. Breast cancer [2C60-2C6Y] [10]
Levomilnacipran DMV26S8 Moderate Increased risk of bleeding by the combination of Epoprostenol and Levomilnacipran. Chronic pain [MG30] [11]
Regorafenib DMHSY1I Major Increased risk of bleeding by the combination of Epoprostenol and Regorafenib. Colorectal cancer [2B91] [12]
Ardeparin DMYRX8B Major Increased risk of bleeding by the combination of Epoprostenol and Ardeparin. Coronary thrombosis [BA43] [13]
Danaparoid DM6CLBN Major Increased risk of bleeding by the combination of Epoprostenol and Danaparoid. Deep vein thrombosis [BD71] [13]
Rivaroxaban DMQMBZ1 Major Increased risk of bleeding by the combination of Epoprostenol and Rivaroxaban. Deep vein thrombosis [BD71] [14]
Vilazodone DM4LECQ Moderate Increased risk of bleeding by the combination of Epoprostenol and Vilazodone. Depression [6A70-6A7Z] [11]
Vortioxetine DM6F1PU Moderate Increased risk of bleeding by the combination of Epoprostenol and Vortioxetine. Depression [6A70-6A7Z] [11]
Isocarboxazid DMAF1NB Moderate Additive hypotensive effects by the combination of Epoprostenol and Isocarboxazid. Depression [6A70-6A7Z] [15]
Milnacipran DMBFE74 Moderate Increased risk of bleeding by the combination of Epoprostenol and Milnacipran. Depression [6A70-6A7Z] [11]
Desvenlafaxine DMHD4PE Moderate Increased risk of bleeding by the combination of Epoprostenol and Desvenlafaxine. Depression [6A70-6A7Z] [11]
Clomipramine DMINRKW Moderate Increased risk of bleeding by the combination of Epoprostenol and Clomipramine. Depression [6A70-6A7Z] [11]
Heme DMGC287 Moderate Increased risk of bleeding by the combination of Epoprostenol and Heme. Discovery agent [N.A.] [16]
Apigenin DMI3491 Minor Increased risk of bleeding by the combination of Epoprostenol and Apigenin. Discovery agent [N.A.] [17]
Avapritinib DMK2GZX Major Increased risk of bleeding by the combination of Epoprostenol and Avapritinib. Gastrointestinal stromal tumour [2B5B] [12]
Acalabrutinib DM7GCVW Major Increased risk of bleeding by the combination of Epoprostenol and Acalabrutinib. Mature B-cell lymphoma [2A85] [18]
Ibrutinib DMHZCPO Major Increased risk of bleeding by the combination of Epoprostenol and Ibrutinib. Mature B-cell lymphoma [2A85] [19]
Ponatinib DMYGJQO Major Increased risk of bleeding by the combination of Epoprostenol and Ponatinib. Mature B-cell lymphoma [2A85] [20]
Panobinostat DM58WKG Major Increased risk of bleeding by the combination of Epoprostenol and Panobinostat. Multiple myeloma [2A83] [21]
Ozanimod DMT6AM2 Moderate Additive hypotensive effects by the combination of Epoprostenol and Ozanimod. Multiple sclerosis [8A40] [15]
Dasatinib DMJV2EK Major Increased risk of bleeding by the combination of Epoprostenol and Dasatinib. Myeloproliferative neoplasm [2A20] [22]
Omacetaxine mepesuccinate DMPU2WX Major Increased risk of bleeding by the combination of Epoprostenol and Omacetaxine mepesuccinate. Myeloproliferative neoplasm [2A20] [23]
Prasugrel DM7MT6E Moderate Increased risk of bleeding by the combination of Epoprostenol and Prasugrel. Myocardial infarction [BA41-BA43] [10]
Vorapaxar DMA16BR Moderate Increased risk of bleeding by the combination of Epoprostenol and Vorapaxar. Myocardial infarction [BA41-BA43] [10]
Nepafenac DMYK490 Moderate Increased risk of bleeding by the combination of Epoprostenol and Nepafenac. Osteoarthritis [FA00-FA05] [24]
MK-4827 DMLYGH4 Moderate Increased risk of bleeding by the combination of Epoprostenol and MK-4827. Ovarian cancer [2C73] [12]
Safinamide DM0YWJC Moderate Additive hypotensive effects by the combination of Epoprostenol and Safinamide. Parkinsonism [8A00] [15]
Rasagiline DM3WKQ4 Moderate Additive hypotensive effects by the combination of Epoprostenol and Rasagiline. Parkinsonism [8A00] [15]
Choline salicylate DM8P137 Moderate Increased risk of bleeding by the combination of Epoprostenol and Choline salicylate. Postoperative inflammation [1A00-CA43] [10]
Salsalate DM13P4C Moderate Increased risk of bleeding by the combination of Epoprostenol and Salsalate. Rheumatoid arthritis [FA20] [10]
Plicamycin DM7C8YV Moderate Increased risk of bleeding by the combination of Epoprostenol and Plicamycin. Testicular cancer [2C80] [10]
Caplacizumab DMPUKA7 Moderate Increased risk of bleeding by the combination of Epoprostenol and Caplacizumab. Thrombocytopenia [3B64] [10]
Apixaban DM89JLN Major Increased risk of bleeding by the combination of Epoprostenol and Apixaban. Thrombosis [DB61-GB90] [12]
Cangrelor DM8JRH0 Moderate Increased risk of bleeding by the combination of Epoprostenol and Cangrelor. Thrombosis [DB61-GB90] [10]
Brilinta DMBR01X Moderate Increased risk of bleeding by the combination of Epoprostenol and Brilinta. Thrombosis [DB61-GB90] [12]
Cabozantinib DMIYDT4 Major Increased risk of bleeding by the combination of Epoprostenol and Cabozantinib. Thyroid cancer [2D10] [25]
Betrixaban DM2C4RF Major Increased risk of bleeding by the combination of Epoprostenol and Betrixaban. Venous thromboembolism [BD72] [26]
⏷ Show the Full List of 37 DDI Information of This Drug

References

1 Epoprostenol FDA Label
2 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 1915).
3 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4 Novel signaling pathways promote a paracrine wave of prostacyclin-induced vascular smooth muscle differentiation. J Mol Cell Cardiol. 2009 May;46(5):682-94.
5 Cytochrome P4502C9-derived epoxyeicosatrienoic acids induce the expression of cyclooxygenase-2 in endothelial cells. Arterioscler Thromb Vasc Biol. 2005 Feb;25(2):321-6.
6 Soluble CD40 ligand in pulmonary arterial hypertension: possible pathogenic role of the interaction between platelets and endothelial cells. Circulation. 2004 Aug 24;110(8):999-1005. doi: 10.1161/01.CIR.0000139859.68513.FC. Epub 2004 Aug 9.
7 Effects of PCB126 and 17beta-oestradiol on endothelium-derived vasoactive factors in human endothelial cells. Toxicology. 2011 Jul 11;285(1-2):46-56.
8 Celecoxib induces hepatic stellate cell apoptosis through inhibition of Akt activation and suppresses hepatic fibrosis in rats. Gut. 2009 Nov;58(11):1517-27. doi: 10.1136/gut.2008.157420. Epub 2009 Feb 6.
9 A cardiac-specific robotized cellular assay identified families of human ligands as inducers of PGC-1 expression and mitochondrial biogenesis. PLoS One. 2012;7(10):e46753. doi: 10.1371/journal.pone.0046753. Epub 2012 Oct 3.
10 Product Information. Flolan (epoprostenol). Glaxo Wellcome, Research Triangle Park, NC.
11 Alderman CP, Moritz CK, Ben-Tovim DI "Abnormal platelet aggregation associated with fluoxetine therapy." Ann Pharmacother 26 (1992): 1517-9. [PMID: 1482806]
12 Cerner Multum, Inc. "UK Summary of Product Characteristics.".
13 Price AJ, Frcpath DO "Is there a clinical interaction between low molecular weight heparin and non-steroidal analgesics after total hip replacement?" Ann R Coll Surg Engl 77 (1995): 395. [PMID: 7486773]
14 Product Information. Xarelto (rivaroxaban). Bayer Inc, Toronto, IA.
15 Ban TA "Drug interactions with psychoactive drugs." Dis Nerv Syst 36 (1975): 164-6. [PMID: 1116424]
16 Product Information. Panhematin (hemin). Recordati Rare Diseases Inc, Lebanon, NJ.
17 Heck AM, DeWitt BA, Lukes AL "Potential interactions between alternative therapies and warfarin." Am J Health Syst Pharm 57 (2000): 1221-7 quiz 1228-30. [PMID: 10902065]
18 Product Information. Calquence (acalabrutinib). Astra-Zeneca Pharmaceuticals, Wilmington, DE.
19 Agencia Espaola de Medicamentos y Productos Sanitarios Healthcare "Centro de informacion online de medicamentos de la AEMPS - CIMA.".
20 Product Information. Iclusig (ponatinib). Ariad Pharmaceuticals Inc, Cambridge, MA.
21 Cerner Multum, Inc. "Australian Product Information.".
22 Product Information. Sprycel (dasatinib). Bristol-Myers Squibb, Princeton, NJ.
23 Product Information. Brukinsa (zanubrutinib). BeiGene USA, Inc, San Mateo, CA.
24 Product Information. Acular (ketorolac). Allergan Inc, Irvine, CA.
25 Product Information. Cometriq (cabozantinib). Exelixis Inc, S San Francisco, CA.
26 Product Information. Bevyxxa (betrixaban). Portola Pharmaceuticals, South San Francisco, CA.