Merck
All Photos(4)

P5515

Sigma-Aldrich

Prostaglandin E1

≥98% (HPLC), synthetic

Synonym(s):
(11α,13E,15S)-11,15-Dihydroxy-9-oxoprost-13-enoic acid, Alprostadil, PGE1
Empirical Formula (Hill Notation):
C20H34O5
CAS Number:
Molecular Weight:
354.48
Beilstein:
5294062
EC Number:
MDL number:
eCl@ss:
42020658
PubChem Substance ID:
NACRES:
NA.77

biological source

synthetic

assay

≥98% (HPLC)

form

powder

solubility

ethanol: 5 mg/mL

storage temp.

−20°C

SMILES string

O=C1[C@H](CCCCCCC(O)=O)[C@@H](/C=C/[C@H](CCCCC)O)[C@H](O)C1

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

InChI key

GMVPRGQOIOIIMI-DWKJAMRDSA-N

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Application

Prostaglandin E1 has been used:
  • as a platelet inhibitor to analyse its effect on autophagy
  • in platelet adhesion assay
  • to investigate its effect on cAMP production in thyroid glands of normal and growth-retarded mouse in vitro.

Biochem/physiol Actions

Prostaglandin E1 (PGE1) is a hormone synthesized from dihomo-γ-linolenic acid (DGLA) by the action of enzyme prostaglandin synthase. It is a vasodilator and activates adenylate cyclase. It is majorly present in human semen and is a potent platelet aggregation inhibitor. PGE1 infusions is effective in treating limb ischemia and peripheral vascular disease. It is unstable and is hydrolyzed to PGA1 in the lungs. Nanoparticle encapsulation of PGE1 is essential for its delivery at the vascular injury site. It elicits vasodilator effects on the retinal artery and vein in central retinal artery occlusion (CRAO). PGE1 and its synthetic analog misoprostol interact with E-prostanoid receptor 4 (EP4) and elicits protection in chronic myelogenous leukemia (CML).

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

Prostaglandins and thromboxanes.
B Samuelsson et al.
Annual review of biochemistry, 47, 997-1029 (1978-01-01)
Intravenous infusion of prostaglandin E1 therapy in extremity ischemia
Ramakrishna P
Indian Journal of Vascular and Endovascular Surgery, 4(2), 38-38 (2017)
Prostaglandin E1 and its analog misoprostol inhibit human CML stem cell self-renewal via EP4 receptor activation and repression of AP-1
Li F, et al.
Cell Stem Cell, 21(3), 359-373 (2017)
Yosuke Okamura et al.
Biophysical journal, 100(8), 1855-1863 (2011-04-21)
Eukaryotic cells respond to signaling molecules with picomolar to nanomolar sensitivities. However, molar concentrations give no suggestion of the sufficient number of molecules per cell and are confusing when referring to physiological situations in which signaling molecules act in an
Synthesis of prostaglandin E 1 phosphate derivatives and their encapsulation in biodegradable nanoparticles
Takeda M, et al.
Pharmaceutical Research, 26(7), 1792-1800 (2009)

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