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Merck
CN

P5515

Prostaglandin E1

≥98% (HPLC), powder, vasodilator 

Synonym(s):

(11α,13E,15S)-11,15-Dihydroxy-9-oxoprost-13-enoic acid, Alprostadil, PGE1

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About This Item

Empirical Formula (Hill Notation):
C20H34O5
CAS Number:
745-65-3
Molecular Weight:
354.48
NACRES:
NA.77
PubChem Substance ID:
57654538
eCl@ss:
42020658
UNSPSC Code:
12352211
EC Number:
212-017-2
MDL number:
MFCD00077860
Beilstein/REAXYS Number:
5294062
Assay:
≥98% (HPLC)
Form:
(powder to crystals)
Quality level:
200

Key Documents

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Product Name

Prostaglandin E1, ≥98% (HPLC), synthetic

InChI key

GMVPRGQOIOIIMI-DWKJAMRDSA-N

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

SMILES string

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

biological source

synthetic

assay

≥98% (HPLC)

form

(powder to crystals)

solubility

ethanol: 5 mg/mL

storage temp.

−20°C

Quality Level

200

Gene Information

human ... PTGER1(5731), PTGER2(5732), PTGIR(5739)
mouse ... Ptger1(19216), Ptger2(19217), Ptger3(19218), Ptger4(19219)

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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
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

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

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN6230
BCCM0951
BCCL8308
BCCK7636
BCCH1647

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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
Prostaglandins and thromboxanes.
B Samuelsson et al.
Annual review of biochemistry, 47, 997-1029 (1978-01-01)
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)
Synthesis of prostaglandin E 1 phosphate derivatives and their encapsulation in biodegradable nanoparticles
Takeda M, et al.
Pharmaceutical Research, 26(7), 1792-1800 (2009)
Intravenous infusion of prostaglandin E1 therapy in extremity ischemia
Ramakrishna P
Indian Journal of Vascular and Endovascular Surgery, 4(2), 38-38 (2017)
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