Alprostadil

CAS# 745-65-3

Alprostadil

2D Structure

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Alprostadil

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Chemical Properties of Alprostadil

Cas No. 745-65-3 SDF Download SDF
PubChem ID 5280723 Appearance Powder
Formula C20H34O5 M.Wt 354.48
Type of Compound N/A Storage Desiccate at -20°C
Synonyms PGE1
Solubility Soluble to 71 mg/mL (200.29 mM) in DMSO
Chemical Name 7-[(1R,2R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]heptanoic acid
SMILES CCCCCC(C=CC1C(CC(=O)C1CCCCCCC(=O)O)O)O
Standard InChIKey GMVPRGQOIOIIMI-DWKJAMRDSA-N
Standard InChI InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h12-13,15-17,19,21,23H,2-11,14H2,1H3,(H,24,25)/b13-12+/t15-,16+,17+,19+/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Alprostadil

DescriptionProstaglandin with some selectivity for EP3 and EP4 receptors (Ki values are 1.1, 2.1, 36, 10 and 33 nM for mouse EP3, EP4, EP1, EP2 and IP receptors respectively). Inhibits platelet aggregation and is a vasodilator in vivo.

Alprostadil Dilution Calculator

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Preparing Stock Solutions of Alprostadil

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.821 mL 14.1052 mL 28.2103 mL 56.4207 mL 70.5258 mL
5 mM 0.5642 mL 2.821 mL 5.6421 mL 11.2841 mL 14.1052 mL
10 mM 0.2821 mL 1.4105 mL 2.821 mL 5.6421 mL 7.0526 mL
50 mM 0.0564 mL 0.2821 mL 0.5642 mL 1.1284 mL 1.4105 mL
100 mM 0.0282 mL 0.1411 mL 0.2821 mL 0.5642 mL 0.7053 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Alprostadil

Prostaglandin E1 (Alprostadil) is a prostaglandin, which is used in the treatment of erectile dysfunction and has vasodilatory properties.

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References on Alprostadil

The effect of alprostadil on preventing contrast-induced nephropathy for percutaneous coronary intervention in diabetic patients: A systematic review and meta-analysis.[Pubmed:27861357]

Medicine (Baltimore). 2016 Nov;95(46):e5306.

BACKGROUND: At present, there are a lot of research about the effect of Alprostadil on preventing contrast-induced nephropathy for percutaneous coronary intervention (PCI) in diabetic patients, but the clinical efficacy is not consistent, so we conduct this study and therefore determine the dominant strategy for the treatment of PCI in diabetic patients based on the best evidence currently. METHODS: An electronic database search was conducted in MEDLINE, Embase, Cochrane library, CBM, CNKI, VIP, and WanFang to retrieve randomized controlled trial (RCT) comparing Alprostadil versus hydration on preventing CIN for PCI in diabetic patients. Reference lists of relevant articles were also screened manually to retrieve additional ones. Two investigators independently assessed the eligibility of retrieved articles using predefined inclusion and exclusion criteria. All characteristics as well as outcome variables including incidence of CIN, blood urea nitrogen (BUN), cystatin C (CysC), glomerular filtration rate (GFR), serum creatinine (Scr), serum beta 2-microspheres (beta2-MG) presented in each included study were extracted. Heterogeneity was thought to be significant when I > 50%. All of the meta-analytic procedures were performed by using Review Manager software, version 5.3. RESULTS: Finally, data from 8 articles including 969 patients were included into this meta-analysis, among them, 487 patients in the experience group, and 482 patients in the control group. Meta analysis showed that the incidence of CIN in the experimental group was significantly lower than that in the control group (OR = 0.28,95%CI[0.18,0.42]). The incidence of adverse reactions in the experimental group was significantly lower than that in the control group (OR = 0.46,95%CI[0.24,0.85]). The BUN of 24 hours, 48 hours, and 72 hours in the experimental group were significantly lower than that of control group (MD = -0.77, 95%CI [-1.22, -0.32]; MD = -1.38, 95%CI [-1.83,-0.92]; MD = -2.43, 95%CI [-2.68,-2.19], respectively). The CysC of 24 hours, 48 hours, and 72 hours in the experimental group were significantly lower than that of control group (MD = -0.30, 95%CI [-0.40, -0.21]; MD = -0.54, 95%CI [-0.68,-0.41]; MD = -0.49, 95%CI [-0.63, -0.35], respectively). The GFR of 24 hours, 48 hours, and 72 hours in the experimental group were significantly higher than that of control group (MD = 7.86, 95%CI [4.44, 11.29], MD = 18.23, 95%CI [13.76,22.69], MD = 12.81, 95%CI [8.51,17.11], respectively). The Scr of 24 hours, 48 hours, and 72 hours in the experimental group were significantly lower than that of control group (MD = -9.09, 95%CI [-12.67, -5.51], MD = -19.14, 95%CI [-23.61, -14.66], MD = -6.50, 95%CI [-8.29, -4.71], respectively). The beta2-MG of 24 hours, 48 hours, and 72 hours in the experimental group were significantly lower than that of control group (MD = -0.12, 95%CI [-0.27, 0.03], MD = -0.55, 95%CI [-0.71, -0.39], MD = -0.50, 95%CI [-0.60, -0.39], respectively). CONCLUSION: Our result suggested that comparing with conventional Hydration, Alprostadil can significantly reduce the incidence of CIN, adverse reaction, and protect renal function in PCI in diabetic patients. Due to the limitations of the quality and quantity of the articles, this conclusion still needs further research to confirm.

Stability of Alprostadil in 0.9% Sodium Chloride Stored in Polyvinyl Chloride Containers.[Pubmed:28346210]

Int J Pharm Compd. 2017 Mar-Apr;21(2):150-153.

The stability of Alprostadil diluted in 0.9% sodium chloride stored in polyvinyl chloride (VIAFLEX) containers at refrigerated temperature, protected from light, is reported. Five solutions of Alprostadil 11 mcg/mL were prepared in 250 mL 0.9% sodium chloride polyvinyl chloride (PL146) containers. The final concentration of alcohol was 2%. Samples were stored under refrigeration (2 degrees C to 8 degrees C) with protection from light. Two containers were submitted for potency testing and analyzed in duplicate with the stability-indicating high-performance liquid chromatography assay at specific time points over 14 days. Three containers were submitted for pH and visual testing at specific time points over 14 days. Stability was defined as retention of 90% to 110% of initial Alprostadil concentration, with maintenance of the original clear, colorless, and visually particulate-free solution. Study results reported retention of 90% to 110% initial Alprostadil concentration at all time points through day 10. One sample exceeded 110% potency at day 14. pH values did not change appreciably over the 14 days. There were no color changes or particle formation detected in the solutions over the study period. This study concluded that during refrigerated, light-protected storage in polyvinyl chloride (VIAFLEX) containers, a commercial alcohol-containing Alprostadil formulation diluted to 11 mcg/mL with 0.9% sodium chloride 250 mL was stable for 10 days.

Alprostadil cream in the treatment of erectile dysfunction: clinical evidence and experience.[Pubmed:27928427]

Ther Adv Urol. 2016 Aug;8(4):249-256.

Erectile dysfunction (ED) is a very common disorder with a deep impact on quality of life on both patients and partners. Several options are available for treating ED: oral pharmacotherapy with phosphodiesterase 5 (PDE5) inhibitors currently represents the first-line option for many patients with ED. Alprostadil, a prostaglandin, has been marketed for many years as a urethral stick and an intracavernous injection for the treatment of ED. It is now available in the form of a cream (Vitaros/Virirec), a noninvasive treatment which combines an active drug (Alprostadil, a synthetic prostaglandin E1) with a skin enhancer improving its local absorption directly at the site of action. Alprostadil has a favourable pharmacodynamic profile and is poorly absorbed in systemic circulation, which makes it suitable in a lot of circumstances and results in a reduced risk of adverse effects (AEs). Systemic AEs are reported in only 3% of the treated population. Clinical efficacy has been demonstrated in both phase II and III trials, showing a global efficacy up to 83% with the 300 mug dose in patients with severe ED, significantly better than placebo. Its fast onset of action and lack of interactions with other drugs makes Alprostadil cream a possible first-line therapeutic option for some patients with ED: individuals who are reluctant to take systemic treatments or have AEs, patients who do not respond, cannot tolerate, or do not accept PDE5 inhibitor therapy, and patients treated with nitrates. Therefore, this new treatment for ED can be offered to patients and could help address the needs unmet by other treatments.

Efficacy and Safety of Alprostadil in Patients with Peripheral Arterial Occlusive Disease Fontaine Stage IV: Results of a Placebo Controlled Randomised Multicentre Trial (ESPECIAL).[Pubmed:28189475]

Eur J Vasc Endovasc Surg. 2017 Apr;53(4):559-566.

OBJECTIVES: The aim was to assess the efficacy and safety of Alprostadil in patients with peripheral arterial occlusive disease (PAOD) Fontaine Stage IV. METHODS: This was a multinational, prospective, randomised, double blind, placebo controlled, parallel group trial. Patients with Stage IV PAOD were equally randomised to either 4 weeks of Alprostadil treatment twice daily or to placebo treatment twice daily. The primary efficacy variables were the rate of complete healing of all necrosis and ulceration 12 weeks after the end of treatment and the frequency of major amputations 24 weeks after the end of treatment. RESULTS: A total of 840 patients were randomised between 2004 and 2013. At baseline, no major differences between treatment groups were found. The rate of "complete healing" was 18.4% in patients on Alprostadil and 17.2% in patients on placebo. The rates of "major amputations" were 12.6% in patients on Alprostadil and 14.6% in patients on placebo. The adjusted difference between Alprostadil and placebo including their 95% confidence intervals was 1.1 (-4.0 to 6.3) for "complete healing" and -2.1 (-6.7 to 2.5) for "major amputations." In the subgroup of diabetic patients the rates of major amputations were numerically lower in the Alprostadil than placebo group (10.6% vs. 17.4%). Within the total cohort a non-significant difference in "decrease in ulcer area >/=50%" was reached in 30.2% of patients on Alprostadil and in 24.3% of patients on placebo at end of treatment. CONCLUSIONS: In this study, superiority of Alprostadil over placebo could not be shown. Nevertheless, a slight numerical but not clinically relevant advantage for Alprostadil emerged from the "area decrease of ulcers by >/= 50%," indicating that a healing effect may have started. The results have to be considered in the light of several limitations in study design and conduct.

Description

Alprostadil is used as a drug in the treatment of erectile dysfunction and has vasodilatory properties. It is a Prostaglandin Analog and Prostaglandin E1 Agonist.

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