Identification
- Generic Name
- Beraprost
- DrugBank Accession Number
- DB05229
- Background
Beraprost is a synthetic analogue of prostacyclin, under clinical trials for the treatment of pulmonary hypertension. It is also being studied for use in avoiding reperfusion injury.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Beraprost (DB05229)
- Weight
- Average: 398.499
Monoisotopic: 398.209324066 - Chemical Formula
- C24H30O5
- Synonyms
- Beraprost
- Beraprostum
- External IDs
- MDL 201229
- MDL-201229
- ML 1229
- ML-1229
Pharmacology
- Indication
For the treatment of pulmonary hypertension.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Symptomatic treatment of Cystic fibrosis (cf) •••••••••••• ••••••• •••••• Symptomatic treatment of Pain •••••••••••• ••••••• •••••• Symptomatic treatment of Ulcers •••••••••••• ••••••• •••••• Symptomatic treatment of Sensations of cold •••••••••••• ••••••• •••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Beraprost is a stable, orally active prostacyclin analogue with vasodilatory, antiplatelet and cytoprotective effects. Beraprost is generally well tolerated and appears to be an effective agent in the treatment of patients with Buerger's disease and arteriosclerosis obliterans. Comparative data from a large randomised trial indicated that the drug appears as effective as ticlopidine in patients with these conditions. In patients with intermittent claudication, significant benefits of beraprost compared with placebo were reported in a randomised clinical trial; however, the use of beraprost in these patients is not supported by recent preliminary unpublished data from a large, phase III, placebo-controlled study. Limited data suggest some efficacy with long-term beraprost treatment of patients with PAH, where options are few and where oral administration of the drug could be a considerable advantage over intravenous prostacyclin (PGI2) therapy.
- Mechanism of action
Beraprost acts by binding to prostacyclin membrane receptors ultimately inhibiting the release of Ca2+ from intracellular storage sites. This reduction in the influx of Ca2+ has been postulated to cause relaxation of the smooth muscle cells and vasodilation.
Target Actions Organism UProstacyclin receptor Not Available Humans - Absorption
Oral bioavailability is 50–70%.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
35–40 minutes
- Clearance
Not Available
- Adverse Effects
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Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbatacept The metabolism of Beraprost can be increased when combined with Abatacept. Abciximab The risk or severity of bleeding can be increased when Abciximab is combined with Beraprost. Abiraterone The metabolism of Beraprost can be decreased when combined with Abiraterone. Abrocitinib The risk or severity of bleeding and thrombocytopenia can be increased when Beraprost is combined with Abrocitinib. Aceclofenac The risk or severity of bleeding and hemorrhage can be increased when Aceclofenac is combined with Beraprost. - Food Interactions
- Avoid herbs and supplements with anticoagulant/antiplatelet activity. Examples include garlic, ginger, bilberry, danshen, piracetam, and ginkgo biloba.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Beraprost sodium 15K99VDU5F 88475-69-8 YTCZZXIRLARSET-VJRSQJMHSA-M
Categories
- ATC Codes
- B01AC19 — Beraprost
- Drug Categories
- Anticoagulants
- Antiplatelet agents
- Autacoids
- Biological Factors
- Blood and Blood Forming Organs
- Cardiovascular Agents
- Cryoprotective Agents
- Cytochrome P-450 CYP2C8 Substrates
- Cytochrome P-450 Substrates
- Eicosanoids
- Fatty Acids
- Fatty Acids, Unsaturated
- Hematologic Agents
- Inflammation Mediators
- Lipids
- Platelet Aggregation Inhibitors Excl. Heparin
- Prostacyclin Analogues
- Prostaglandins
- Prostaglandins I
- Vasodilating Agents
- Classification
- Not classified
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 35E3NJJ4O6
- CAS number
- 88430-50-6
- InChI Key
- CTPOHARTNNSRSR-APJZLKAGSA-N
- InChI
- InChI=1S/C24H30O5/c1-3-4-7-15(2)19(25)13-12-17-20(26)14-21-23(17)18-10-5-8-16(24(18)29-21)9-6-11-22(27)28/h5,8,10,12-13,15,17,19-21,23,25-26H,6-7,9,11,14H2,1-2H3,(H,27,28)/b13-12+/t15?,17-,19+,20+,21-,23-/m0/s1
- IUPAC Name
- 4-[(2S,3R,4R,6S)-4-hydroxy-3-[(1E,3S)-3-hydroxy-4-methyloct-1-en-6-yn-1-yl]-7-oxatricyclo[6.4.0.0^{2,6}]dodeca-1(8),9,11-trien-9-yl]butanoic acid
- SMILES
- [H][C@]12C[C@@H](O)[C@H](\C=C\[C@@H](O)C(C)CC#CC)[C@@]1([H])C1=C(O2)C(CCCC(O)=O)=CC=C1
References
- General References
- Lin H, Lee JL, Hou HH, Chung CP, Hsu SP, Juan SH: Molecular mechanisms of the antiproliferative effect of beraprost, a prostacyclin agonist, in murine vascular smooth muscle cells. J Cell Physiol. 2008 Feb;214(2):434-41. [Article]
- Melian EB, Goa KL: Beraprost: a review of its pharmacology and therapeutic efficacy in the treatment of peripheral arterial disease and pulmonary arterial hypertension. Drugs. 2002;62(1):107-33. [Article]
- External Links
- MSDS
- Download (15.1 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Treatment Pediatric Pulmonary Hypertension 1 4 Completed Treatment Peripheral Microvascular Symptoms / Type 2 Diabetes Mellitus 1 4 Terminated Prevention Type 2 Diabetes Mellitus 1 4 Unknown Status Treatment Chronic Renal Diseases 1 2 Completed Treatment Pulmonary Arterial Hypertension (PAH) 5
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Tablet, coated Oral 20 mcg Tablet, film coated Oral 20 mcg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0099 mg/mL ALOGPS logP 3.45 ALOGPS logP 3.6 Chemaxon logS -4.6 ALOGPS pKa (Strongest Acidic) 4.2 Chemaxon pKa (Strongest Basic) -1.4 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 86.99 Å2 Chemaxon Rotatable Bond Count 9 Chemaxon Refractivity 112.72 m3·mol-1 Chemaxon Polarizability 44.74 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.8736 Blood Brain Barrier + 0.7754 Caco-2 permeable + 0.5868 P-glycoprotein substrate Substrate 0.6165 P-glycoprotein inhibitor I Non-inhibitor 0.9641 P-glycoprotein inhibitor II Non-inhibitor 0.9395 Renal organic cation transporter Non-inhibitor 0.9342 CYP450 2C9 substrate Non-substrate 0.7409 CYP450 2D6 substrate Non-substrate 0.8255 CYP450 3A4 substrate Non-substrate 0.5132 CYP450 1A2 substrate Inhibitor 0.5177 CYP450 2C9 inhibitor Non-inhibitor 0.8578 CYP450 2D6 inhibitor Non-inhibitor 0.8834 CYP450 2C19 inhibitor Non-inhibitor 0.7827 CYP450 3A4 inhibitor Inhibitor 0.6633 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7365 Ames test AMES toxic 0.5331 Carcinogenicity Non-carcinogens 0.9445 Biodegradation Not ready biodegradable 0.5301 Rat acute toxicity 3.6575 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8871 hERG inhibition (predictor II) Non-inhibitor 0.9611
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-03e9-0009000000-f1c77f29922dc611c092 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0002-0009000000-fb50ea99279483698d3e Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-03g1-0039000000-04cbb8745b1354495693 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-03dl-0159000000-ce10af2d11e904b006ad Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0wmj-2189000000-e3276410b856d15c69a2 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0fbi-9874000000-0d405d8c2be279e52b6c Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Not Available
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Guanyl-nucleotide exchange factor activity
- Specific Function
- Receptor for prostacyclin (prostaglandin I2 or PGI2). The activity of this receptor is mediated by G(s) proteins which activate adenylate cyclase.
- Gene Name
- PTGIR
- Uniprot ID
- P43119
- Uniprot Name
- Prostacyclin receptor
- Molecular Weight
- 40955.485 Da
References
- Melian EB, Goa KL: Beraprost: a review of its pharmacology and therapeutic efficacy in the treatment of peripheral arterial disease and pulmonary arterial hypertension. Drugs. 2002;62(1):107-33. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C8
- Uniprot ID
- P10632
- Uniprot Name
- Cytochrome P450 2C8
- Molecular Weight
- 55824.275 Da
References
- Fukazawa T, Yajima K, Miyamoto Y: Evaluation of drug-drug interaction potential of beraprost sodium mediated by P450 in vitro. Yakugaku Zasshi. 2008 Oct;128(10):1459-65. [Article]
Drug created at October 21, 2007 22:24 / Updated at August 28, 2021 08:41