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Structure of Prostaglandin E1
CAS No.: 745-65-3
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Alprostadil is an analog of prostaglandin which is prostaglandin E1 agonist with vasodilatory properties and can be used to treat erectile dysfunction.
Synonyms: PGE1; Alprostadil; Liprostin
4.5
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CAS No. : | 745-65-3 |
Formula : | C20H34O5 |
M.W : | 354.48 |
SMILES Code : | O=C(CCCCCC[C@@H]1[C@H]([C@@H](CC1=O)O)/C=C/[C@H](CCCCC)O)O |
Synonyms : |
PGE1; Alprostadil; Liprostin
|
MDL No. : | MFCD00077860 |
InChI Key : | GMVPRGQOIOIIMI-DWKJAMRDSA-N |
Pubchem ID : | 5280723 |
GHS Pictogram: |
![]() |
Signal Word: | Danger |
Hazard Statements: | H301 |
Precautionary Statements: | P264-P270-P301+P310+P330-P405-P501 |
Class: | 6.1 |
UN#: | 2811 |
Packing Group: | Ⅲ |
Description |
Prostaglandin E1 (Alprostadil) is a ligand for prostanoid receptors, exhibiting Kis of 1.1 nM, 2.1 nM, 10 nM, 33 nM, and 36 nM for mouse EP3, EP4, EP2, IP, and EP1 receptors respectively. It induces vasodilation and inhibits platelet aggregation, being researched as a vasodilator for peripheral vascular diseases[1].[2].[3].
|
In Vitro:
Cell Line
|
Concentration | Treated Time | Description | References |
H9c2 cells | 0.5 µM | 12 hours hypoxia followed by 12 hours reoxygenation | To investigate the effects of PGE1 on the H/R model, results showed that PGE1 treatment significantly reduced apoptosis in H9c2 cells, inhibited mPTP opening, and decreased cytochrome c and cleaved caspase-3 expression. | PMC7723157 |
Mesenchymal stem cells | 10 ng/mL | 24 hours | PGE1 reduces MSC apoptosis and increases CXCR4 expression, MSC migration, and VEGF secretion by activating the HIF-1α pathway | PMC9288720 |
Human umbilical vein endothelial cells (HUVECs) | 0.25, 0.50, 1.00 µM | 24 hours | To investigate the protective effects of PGE1 against H2O2-induced oxidative damage. PGE1 markedly restored the viability of HUVECs under oxidative stress, scavenged intracellular reactive oxygen species induced by H2O2, suppressed the production of lipid peroxides such as MDA, restored the activities of endogenous antioxidants including SOD and GSH-Px, and inhibited cell apoptosis. Additionally, PGE1 significantly increased NO content, eNOS protein, and mRNA expression. | PMC4007667 |
Mouse trigeminal ganglion neurons | 100 nM | 3 minutes | To investigate the effect of PGE1 on Ih current, results showed that PGE1 significantly enhanced the amplitude of Ih current | PMC8706703 |
PTEN-knockdown PASMCs | 100 nM | 30 minutes to 24 hours | PGE1 induced pCREB expression at 30 min, increased PTEN expression at 6 h, and decreased pAKT levels from 6 to 24 h. | PMC5577102 |
HK-2 cells | 0.1 –100 µM | 48 hours | To evaluate the effect of PGE1 on HK-2 cell viability under high glucose conditions, results showed PGE1 significantly enhanced cell viability | PMC7471471 |
K562 cells | 10 μM | 6 hours | Repressed AP-1 factors expression, simulating the effect of Tcf1/Lef1 deficiency | PMC5678929 |
Primary cardiomyocytes | 2.0 μM | 6 hours hypoxia followed by 6 hours reoxygenation | PGE1 protected primary cardiomyocytes against H/R-induced injuries, increased the viability of H/R-induced primary cardiomyocytes, and decreased LDH levels in a dose-dependent manner. | PMC6923339 |
Rat H9C2 cells | 0.5, 1.0, and 2.0 μM | 6 hours hypoxia followed by 6 hours reoxygenation | PGE1 significantly diminished the cell cytotoxicity and apoptosis induced by the 6H/6R regimen, and also decreased expression of IL-2, IL-6, P-p65, TNF-α, and cleaved-caspase-3. In addition, PGE1 up-regulated miR-21-5p expression and reduced the apoptosis ability of H/R-injured rat cardiomyocytes by affecting the miR-21-5p/FASLG axis. | PMC6923339 |
In Vivo:
Species
|
Animal Model
|
Administration | Dosage | Frequency | Description | References |
Mice | CML model | Intraperitoneal injection | 2.5-5 mg/kg | Once daily for the duration of treatment | Significantly reduced the number of leukemic stem cells, prolonged survival, and showed synergistic effects when combined with imatinib | PMC5678929 |
Wistar rats | Pulmonary arterial hypertension model | Tail vein injection | 10 ng/mL | Single injection | After transplantation of PGE1-preconditioned MSCs, the pulmonary artery systolic pressure, mean pulmonary artery pressure, right ventricular hypertrophy index, %WT, and %WA decreased in rats with PAH, showing better therapeutic effects than non-preconditioned MSCs | PMC9288720 |
Wistar rats | Hypoperfused rat liver model | Perfusion | 100 μg/liter | 20 min pretreatment followed by 25% low flow perfusion | Prostaglandin E1 significantly attenuated hypoperfusion-induced early reductive stress and mitochondrial dysfunction, and diminished subsequent oxidative injury and cell death | PMC293748 |
Wistar rats | Diabetic kidney disease model | Intravenous injection | 10 µg/kg | Once daily for 10 consecutive days | To evaluate the effect of PGE1 on kidney injury in diabetic kidney disease rats, results showed PGE1 significantly reduced proteinuria and renal tubular apoptosis | PMC7471471 |
Sprague-Dawley rats | Permanent middle cerebral artery occlusion model | Intravenous injection | 22.6 nmol/kg or 45.2 nmol/kg | Single administration | To examine the effects of a mixed formulation composed of prostaglandin E1 and lithium (PGE1+Li mixture) on brain damage after cerebral ischemia. The results showed that the mixture significantly reduced infarct volume and neurological deficits, and upregulated cytoprotective HSP70, GRP78, HSP60, and Bcl-2 protein levels, while decreasing p53 expression. | PMC4002767 |
Wistar P7 rats | Neonatal ischemia-reperfusion model | Intraperitoneal injection | 20 µg/kg | Every 5 minutes for 4 times, lasting 50 minutes | To evaluate whether prostaglandin E1 improves collateral recruitment and brain damage after ischemia in neonatal rats. Results showed that prostaglandin E1 delayed and improved ipsilateral reperfusion by decreasing thromboxane A synthase-1 gene expression, reducing the density of reactive astrocytes and lesion volume. | PMC6213314 |
Sprague-Dawley rats | Monocrotaline-induced pulmonary arterial hypertension (PAH) model | Intraperitoneal injection | 5 mg/kg | Once daily for 3 weeks | PGE1 prevented pulmonary arterial remodeling and improved hemodynamics via the induced expression of PTEN. | PMC5577102 |
C57BL/6 mice | Orofacial pain model | Subcutaneous injection | 10 ng/10 μL and 20 ng/10 μL | Single injection, observed for 90 minutes | To investigate PGE1-induced orofacial pain behavior, results showed that PGE1 induced mechanical allodynia in a dose-dependent manner | PMC8706703 |
Wistar rats | Asphyxia-induced cardiac arrest model | Intravenous injection | 1 µg/kg | Single dose | To evaluate the protective effects of PGE1 on post-cardiac arrest myocardial dysfunction, results showed that PGE1 significantly increased ejection fraction and cardiac output, improved survival rate, and reduced cardiomyocyte apoptosis. | PMC7723157 |
Clinical Trial:
NCT Number | Conditions | Phases | Recruitment | Completion Date | Locations |
NCT04312555 | Critical Limb Ischemia | PHASE4 | UNKNOWN | 2021-10-01 | - |
NCT00610051 | Heart Failure | PHASE3 | NOT_YET_RECRUITING | 2025-12-26 | Medical university Vienna, Vie... More >>nna, Austria Less << |
NCT01776320 | Erectile Dysfunction | PHASE4 | WITHDRAWN | 2025-12-15 | St. Joseph's Health Care Londo... More >>n, London, Ontario, N6A 4V2, Canada Less << |
NCT04496050 | Pyloric Stenosis;Acquired|Cong... More >>enital Heart Disease Less << | UNKNOWN | 2020-11-30 | Hacettepe University, Ankara, ... More >>Turkey Less << | |
NCT03027219 | Diabetes | COMPLETED | 2018-11-29 | Asan Medical Center, Seoul, 05... More >>505, Korea, Republic of Less << |
Tags: Prostaglandin E1 | Alprostadil | PGE1 | Prostaglandin E 1 | Prostaglandin E-1 | PGE1 | PGE 1 | PGE-1 | Prostaglandin Receptor | Endogenous Metabolite | prostanoid | prostanoid receptor ligand | vasodilation | platelet aggregation | G protein-coupled receptor | GPCRs | prostaglandin E receptor 3 | 745-65-3
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