CAS 745‑65‑3 Alprostadil Powder Synthetic Prostaglandin‑E1 for Vascular‑Biology and Smooth‑Muscle Pharmacology Research

High‑purity off‑white Alprostadil (Prostaglandin‑E1, PGE1) powder CAS 745‑65‑3, a well‑studied synthetic endogenous prostaglandin‑E1 prostanoid‑receptor ligand. It binds with high‑affinity to EP1‑EP4 and IP prostaglandin receptors, raises intracellular c‑AMP concentration, triggers blood‑vessel vasodilation, relaxes smooth‑muscle tissue and restrains platelet aggregation. This bio‑active compound improves micro‑circulation perfusion, regulates vascular‑endothelial activity and mediates multiple inflammatory‑response pathways. Widely utilised for laboratory‑scale research on peripheral‑arterial disease, ductus‑arteriosus patency study, cavernous smooth‑muscle assay, ischaemic‑tissue injury, platelet‑function testing and prostaglandin‑targeted drug‑screening projects. Every batch passes HPLC purity inspection, customized‑packaging and bulk‑powder supply are available for global vascular‑biology and pre‑clinical pharmacology researchers. This compound is sold exclusively for laboratory scientific‑research use.

Alprostadil (Prostaglandin E1, PGE1) CAS 745-65-3 | EP Receptor Agonist, Vasodilator Research Powder

Alprostadil CAS 745-65-3
Prostaglandin E1 (PGE1) — EP Receptor Agonist

A naturally occurring 20-carbon eicosanoid derived from dihomo-γ-linolenic acid, alprostadil is a broad-spectrum agonist at the EP1, EP2, EP3 and EP4 prostanoid receptors. Gs-coupled EP2/EP4 activation raises intracellular cAMP, producing potent vasodilation, vascular and cavernosal smooth muscle relaxation and inhibition of platelet aggregation. The reference prostaglandin for erectile dysfunction, patent ductus arteriosus (PDA), peripheral arterial disease and critical limb ischemia research.

Prostaglandin E1 / PGE1 EP1–EP4 Agonist Potent Vasodilator Antiplatelet Smooth Muscle Relaxant cAMP / PKA Signaling Neonatal Cardiology
354.48
MW (C20H34O5)
≥98%
Purity (HPLC)
EP1–EP4
Prostanoid Receptors

Molecular Information

Name: Alprostadil (PGE1)
CAS: 745-65-3
Formula: C20H34O5
MW: 354.48 g/mol
Purity: ≥98% (HPLC)
SMILES: CCCCC[C@H](O)/C=C/
  [C@H]1[C@@H](O)CC(=O)
  [C@@H]1CCCCCCC(=O)O
InChIKey: GMVPRGQOIOIIMI
  -DWKJAMRDSA-N
MP: ~115-116°C
Appearance: White to off-white powder
Solubility: Ethanol, DMSO, methanol
Synonyms: Prostaglandin E1 / PGE1
Storage: -20°C, protect from light & heat
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CAS Number
745-65-3
⚖️
Molecular Weight
354.48
🎯
Primary Targets
EP1–EP4
Purity
≥98%

Alprostadil (PGE1) Technical Specifications & QC Data

Complete physicochemical properties and quality control parameters for research-grade Alprostadil / Prostaglandin E1 powder (CAS 745-65-3)

📋 Physicochemical Properties

  • Product NameAlprostadil (Prostaglandin E1)
  • IUPAC Name7-[(1R,2R,3R)-3-Hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]heptanoic acid
  • CAS Number745-65-3
  • SynonymsPGE1 / Prostaglandin E1 / Alprostadilum
  • Molecular FormulaC20H34O5
  • Molecular Weight354.48 g/mol
  • Exact Mass354.241 Da
  • Stereochemistry9-oxo, 11α-OH, 15S-OH, 13E
  • SMILESCCCCC[C@H](O)/C=C/[C@H]1[C@@H](O)CC(=O)[C@@H]1CCCCCCC(=O)O
  • InChIKeyGMVPRGQOIOIIMI-DWKJAMRDSA-N
  • AppearanceWhite to off-white crystalline powder
  • Melting Point~115-116°C
  • Biosynthetic PrecursorDihomo-γ-linolenic acid (DGLA)
  • MDL NumberMFCD00078661
  • PubChem CID5280723

🔬 Quality Control & Handling

  • Purity (HPLC)≥98%
  • Related SubstancesPGA1 / PGB1 / 15-keto-PGE1 controlled
  • FormCrystalline powder / lyophilized solid
  • ColorWhite to off-white
  • Storage Condition-20°C, sealed, dry, protect from light
  • Stability NoteHeat/acid/base labile — dehydrates to PGA1 then isomerizes to PGB1
  • ShippingCold chain with gel/dry ice recommended
  • SolubilityEthanol, methanol, DMSO, DMF; sparingly soluble in water
  • QC DocumentationCOA / HPLC / NMR / MS / optical rotation / MSDS
  • Pack Sizes1g / 5g / 10g / 100g / 1KG
  • Stock StatusIn Stock
  • Use StatementResearch use only; not for human/clinical use

Prostanoid Receptor Targets & Signaling Partners

Alprostadil is a broad-spectrum E-prostanoid agonist — its tissue-specific effects are dictated by which EP subtype and G-protein predominate in a given cell type

🎯 EP1 (PTGER1) — Gq / Ca²⁺ 💠 EP2 (PTGER2) — Gs / cAMP↑ 🔻 EP3 (PTGER3) — Gi / cAMP↓ 💠 EP4 (PTGER4) — Gs / cAMP↑ 🩸 IP Receptor (Cross-activity) 🌡️ DP1 Receptor (Cross-activity) ⚡ Adenylyl Cyclase 🔑 Protein Kinase A (PKA) 🧬 CREB Phosphorylation 🔓 K_ATP Channel Opening 📉 Myosin Light Chain Kinase 🛡️ 15-PGDH (Metabolism)

How Alprostadil Works: From EP Receptor Binding to Vasodilation

A stepwise view of the cAMP-dependent signaling cascade that underpins PGE1's vasodilator, antiplatelet and smooth muscle relaxant activity

1

Biosynthesis from DGLA

Endogenous PGE1 is generated from dihomo-γ-linolenic acid via cyclooxygenase (COX-1/COX-2) and PGE synthase, forming the 1-series prostaglandin with a single omega-chain double bond.

2

EP Receptor Engagement

Alprostadil binds the four E-prostanoid GPCR subtypes. Vasodilator effects are driven mainly by Gs-coupled EP2 and EP4; EP1 (Gq) raises Ca²⁺ and EP3 (Gi) lowers cAMP, giving tissue-dependent pharmacology.

3

Adenylyl Cyclase → cAMP Rise

Gs activation stimulates adenylyl cyclase, sharply increasing intracellular cyclic AMP in vascular smooth muscle, corpus cavernosum smooth muscle, ductal myocytes and platelets.

4

PKA Activation & Ca²⁺ Fall

cAMP activates protein kinase A, which phosphorylates myosin light chain kinase, promotes sarcoplasmic Ca²⁺ sequestration and opens K channels — lowering cytosolic calcium and relaxing the contractile apparatus.

5

Vasodilation & Platelet Inhibition

Arterial and arteriolar smooth muscle relaxes, increasing regional blood flow; in platelets the same cAMP/PKA rise suppresses GPIIb/IIIa activation, granule release and aggregation, and improves microcirculatory rheology.

6

Rapid Enzymatic Inactivation

PGE1 undergoes extensive first-pass metabolism in the lung (up to ~70-80% in a single circulation) via 15-hydroxyprostaglandin dehydrogenase, giving a plasma half-life of minutes — the basis for local/regional delivery strategies.

Research Applications of Alprostadil (Prostaglandin E1)

From urology and neonatal cardiology to vascular biology and prostanoid receptor pharmacology

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Prostaglandin & Prostanoid Receptor Signaling

A cornerstone reference agonist for EP1-EP4 pharmacology. Used in cAMP accumulation assays, radioligand binding, β-arrestin recruitment, GloSensor reporter systems and receptor-deconvolution studies alongside selective tools such as butaprost (EP2), sulprostone (EP1/EP3) and L-902688 (EP4).

GPCR Pharmacology
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Erectile Dysfunction & Cavernosal Smooth Muscle

Raises cAMP in corpus cavernosum smooth muscle through a pathway independent of the NO/cGMP/PDE5 axis, making it a key probe when PDE5-dependent signaling is impaired. Used in organ bath studies of human and rabbit cavernosal strips and intracavernosal pressure models. Clinically formulated for intracavernosal injection and intraurethral (MUSE) delivery.

Urology / MUSE
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Patent Ductus Arteriosus (PDA) & Neonatal Cardiology

PGE1 reactivates EP4 signaling in ductal smooth muscle to maintain ductus arteriosus patency in ductal-dependent congenital heart disease — a landmark application established by Freed et al. (Circulation 1981). Central to studies of oxygen-mediated ductal constriction and prostaglandin-dependent ductal tone.

Ductal Patency
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Peripheral Arterial Disease & Critical Limb Ischemia

Studied for arteriolar vasodilation, enhanced microcirculatory perfusion, reduced leukocyte-endothelial adhesion and improved erythrocyte deformability. Typical endpoints include transcutaneous oxygen tension (TcPO₂), laser Doppler flux, ischemic ulcer healing and rest pain resolution.

Vascular Medicine
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Platelet Biology & Antithrombotic Research

A classic cAMP-elevating platelet inhibitor used as a positive control in aggregometry, VASP phosphorylation assays, flow-chamber thrombus formation studies and platelet-rich plasma preparation protocols where reversible aggregation blockade is required.

Hemostasis
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Pulmonary Hypertension & Cardiac Research

Investigated as an inhaled and intravenous pulmonary vasodilator, for right ventricular afterload reduction, in ischemia-reperfusion injury protection and in vasoreactivity testing protocols in preclinical pulmonary hypertension models.

Cardiopulmonary
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Endothelial Function & Microcirculation

Used to probe endothelium-independent vasodilation, capillary recruitment, nitric oxide crosstalk, VEGF-associated angiogenic signaling and cAMP-dependent barrier stabilization in cultured endothelial monolayers and intravital microscopy models.

Microvascular Biology
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Inflammation & Immune Modulation

EP2/EP4-mediated cAMP elevation suppresses TNF-α production, modulates macrophage polarization, dampens T-cell proliferation and shapes dendritic cell maturation — making PGE1 a useful tool in immunopharmacology and cytokine regulation studies.

Immunopharmacology
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Analytical Reference & Formulation Science

Supplied as a reference standard for LC-MS/MS eicosanoid profiling, prostaglandin impurity and degradation studies (PGA1/PGB1), lipid emulsion and cyclodextrin inclusion complex development, and stability-indicating method validation.

Reference Standard

Key Publications on Alprostadil & Prostaglandin E1

From the Nobel Prize-winning isolation of prostaglandins to landmark clinical applications in urology and neonatal cardiology

Bergström S, Sjövall J. The isolation of prostaglandin E from sheep prostate glands. Acta Chemica Scandinavica. 1960;14:1701-1705. (Foundational work recognised by the 1982 Nobel Prize in Physiology or Medicine awarded to Bergström, Samuelsson and Vane.)
doi: 10.3891/acta.chem.scand.14-1701
Freed MD, Heymann MA, Lewis AB, Roehl SL, Kensey RC. Prostaglandin E1 in infants with ductus arteriosus-dependent congenital heart disease. Circulation. 1981;64(5):899-905.
doi: 10.1161/01.CIR.64.5.899
Linet OI, Ogrinc FG. Efficacy and safety of intracavernosal alprostadil in men with erectile dysfunction. New England Journal of Medicine. 1996;334(14):873-877.
doi: 10.1056/NEJM199604043341401
Padma-Nathan H, Hellstrom WJG, Kaiser FE, et al. Treatment of men with erectile dysfunction with transurethral alprostadil (MUSE). New England Journal of Medicine. 1997;336(1):1-7.
doi: 10.1056/NEJM199701023360101
Narumiya S, Sugimoto Y, Ushikubi F. Prostanoid receptors: structures, properties, and functions. Physiological Reviews. 1999;79(4):1193-1226.
doi: 10.1152/physrev.1999.79.4.1193
The ICAI Study Group. Prostanoids for chronic critical leg ischemia: a randomized, controlled, open-label trial with prostaglandin E1. Annals of Internal Medicine. 1999;130(5):412-421.
doi: 10.7326/0003-4819-130-5-199903020-00005

Alprostadil Pack Sizes & Ordering Information

Research-grade Alprostadil / Prostaglandin E1 powder (CAS 745-65-3) available in 1g / 5g / 10g / 100g / 1KG with full QC documentation and cold-chain logistics

TierPack SizeStock StatusSuitable ForLead Time & Shipping
Standard1 gIn StockEP receptor cAMP assays, organ bath and platelet aggregation studiesSame/next-day ship; cold pack, amber vial
Medium5 gIn StockIn vivo vascular pharmacology, ischemia and ductal patency modelsSame/next-day ship; insulated cold chain
Large10 gIn StockMulti-arm preclinical programs, extended dosing studiesSame/next-day ship; DHL/FedEx cold chain
Bulk100 gIn StockLipid emulsion and cyclodextrin formulation development, scale-upQuote to confirm; light-protected drum, dry ice
Industrial1 KGMade to orderPilot/production scale, CMO supply, long-term supply agreementsScheduled batch delivery; validated cold-chain freight

💡 Reference sizes shown above; alprostadil is light- and heat-sensitive and ships under temperature-controlled conditions. For exact bulk pricing please contact us for a quote. Bulk orders qualify for tiered discounts.

Alprostadil (PGE1) FAQ — Frequently Asked Questions

What is Alprostadil (CAS 745-65-3) and how does it relate to prostaglandin E1?
Alprostadil is prostaglandin E1 — "alprostadil" is simply the international nonproprietary (pharmaceutical) name for naturally occurring PGE1. It is a 20-carbon eicosanoid with molecular formula C20H34O5 and molecular weight 354.48 g/mol, biosynthesized from dihomo-γ-linolenic acid (DGLA) via the cyclooxygenase pathway. It acts as a broad agonist across the EP1-EP4 prostanoid receptor family.
What is the difference between PGE1 and PGE2?
Both act on the same EP1-EP4 receptor family but differ in precursor and unsaturation. PGE1 (C20H34O5) comes from dihomo-γ-linolenic acid and has one omega-chain double bond (13,14-trans). PGE2 / dinoprostone (C20H32O5) comes from arachidonic acid and carries an extra cis double bond at 5,6. Functionally, PGE1 is the classic vasodilator and antiplatelet prostaglandin used clinically, while PGE2 is more strongly linked to fever, inflammatory hyperalgesia, uterine contraction and cervical ripening. The difference of a single double bond meaningfully shifts receptor bias and metabolic handling.
Which EP receptors mediate alprostadil's vasodilator effect?
The vasodilator and antiplatelet actions are driven predominantly by the Gs-coupled EP2 and EP4 receptors, which stimulate adenylyl cyclase → cAMP ↑ → PKA activation → reduced intracellular Ca²⁺ → smooth muscle relaxation. EP1 is Gq-coupled and raises Ca²⁺ (often contractile), while EP3 is mainly Gi-coupled and lowers cAMP. Alprostadil also shows measurable cross-activity at the prostacyclin IP receptor and DP1. Because it is not subtype-selective, pair it with selective agonists/antagonists to attribute effects to a specific EP subtype.
How is alprostadil used in erectile dysfunction (ED) research and what is MUSE?
Erection requires cavernosal smooth muscle relaxation. Alprostadil raises cAMP in corpus cavernosum smooth muscle via EP2/EP4 — a route that runs parallel to and independent of the NO/cGMP/PDE5 pathway, so it remains effective in models where NO signaling is impaired. Clinically it is delivered by intracavernosal injection (Caverject, Edex) or as an intraurethral pellet known as MUSE — the Medicated Urethral System for Erection — which was evaluated in the landmark NEJM 1997 study by Padma-Nathan et al. In the laboratory it is a standard agonist in cavernosal organ bath and intracavernosal pressure experiments.
How does alprostadil keep the ductus arteriosus open in neonates?
During fetal life, high circulating prostaglandins maintain ductal patency. After birth prostaglandin levels fall and oxygen tension rises, triggering ductal constriction and closure. In infants with ductal-dependent congenital heart disease, exogenous PGE1 re-engages EP4 receptors on ductal smooth muscle, elevating cAMP and holding the patent ductus arteriosus (PDA) open until corrective surgery can be performed. This application, established by Freed et al. (Circulation 1981), transformed neonatal cardiology and remains a core research topic in ductal biology.
Why is alprostadil so unstable, and how should it be stored?
The β-hydroxy ketone in the cyclopentanone ring is the weak point: under acidic, basic or elevated-temperature conditions PGE1 dehydrates to PGA1 and then isomerizes to PGB1, both of which are far less active. It is also light sensitive. Store the solid at -20°C or lower, sealed, dry and protected from light. Prepare stocks in ethanol or DMSO, aliquot into single-use amber vials, store at -80°C and avoid freeze-thaw cycling. Prepare aqueous working dilutions fresh and keep them cold. Our COA reports PGA1/PGB1 related-substance levels for each lot.
What solvents should be used to dissolve alprostadil?
Alprostadil dissolves readily in ethanol, methanol, DMSO and DMF and is only sparingly soluble in water. Ethanol is often preferred for eicosanoid work because it is compatible with LC-MS workflows and evaporates cleanly. For cell assays, prepare a concentrated organic stock and dilute at least 1000-fold into buffer or medium, keeping the final solvent concentration ≤0.1% v/v. Because of its lipophilicity, avoid prolonged contact with plastics that can adsorb prostaglandins — glass or low-binding vials are recommended.
Why does alprostadil have such a short half-life in vivo?
PGE1 undergoes extremely efficient pulmonary first-pass metabolism — a large fraction (commonly cited as roughly 70-80%) is inactivated in a single passage through the lungs, primarily by 15-hydroxyprostaglandin dehydrogenase (15-PGDH) followed by Δ13-reduction and β-oxidation. The resulting plasma half-life is on the order of minutes. This is precisely why clinical and preclinical use relies on local or regional delivery (intracavernosal, intraurethral, intra-arterial) or continuous infusion rather than oral dosing.
Can alprostadil be used as a platelet aggregation inhibitor control?
Yes — it is a classic one. By raising platelet cAMP through Gs-coupled EP2/EP4 (and IP cross-activity), alprostadil suppresses GPIIb/IIIa activation, dense granule release and aggregation, with VASP phosphorylation as a convenient readout. It is widely used as a positive control in light-transmission aggregometry and flow-chamber thrombosis assays, and to keep platelets quiescent during platelet-rich plasma isolation and washing protocols.
What documentation and pack sizes do you supply for alprostadil?
Each lot ships with a Certificate of Analysis (COA) covering HPLC purity (≥98%), related prostaglandin substances (PGA1, PGB1, 15-keto-PGE1), 1H NMR confirmation, LC-MS identity, optical rotation, water content and residual solvents. MSDS/SDS, stability data and Certificate of Origin are available on request. Catalog pack sizes are 1 g, 5 g, 10 g, 100 g and 1 KG, with the first four in stock and the 1 KG industrial tier made to order — contact us for cold-chain bulk quotations.

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The reference EP receptor agonist for vasodilation, erectile dysfunction, PDA and prostanoid signaling research — request a quote today

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Weight 10 g