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P5515

Prostaglandin E₁

Name: Prostaglandin E<SUB>1</SUB>
Brand: SIGMA

≥98% (HPLC), synthetic

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Synonym(s):

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

Empirical Formula (Hill Notation):

C₂₀H₃₄O₅

CAS Number:

745-65-3

Molecular Weight:

354.48

Beilstein:

5294062

EC Number:

212-017-2

MDL number:

MFCD00077860

eCl@ss:

42020658

PubChem Substance ID:

57654538

NACRES:

NA.77

biological source

synthetic

Quality Level

200

Assay

≥98% (HPLC)

form

(powder to crystals)

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

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

GHS06

Signal Word

Danger

Hazard Statements

H301

Precautionary Statements

P301 + P310 + P330

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

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The crystal and molecular structure of prostaglandin E1

Spek, AL

Acta Crystallographica Section B, Structural Science, 33(3), 816-824 (1977)

Responses of the thyroid gland to TSH and other thyroid stimulators in the growth-retarded (grt) mouse

Kobayashi K, et al.

Zoological Science, 18(7), 955-962 (2001)

Dissection of autophagy in human platelets

Feng W, et al.

Autophagy, 10(4), 642-651 (2014)

In vitro evaluation of pathogen-inactivated buffy coat-derived platelet concentrates during storage: psoralen-based photochemical treatment step-by-step.

Mélanie Abonnenc et al.

Blood transfusion = Trasfusione del sangue, 13(2), 255-264 (2014-11-05)

The Intercept Blood SystemTM (Cerus) is used to inactivate pathogens in platelet concentrates (PC). The aim of this study was to elucidate the extent to which the Intercept treatment modifies the functional properties of platelets. A two-arm study was conducted

Prostaglandins and thromboxanes.

B Samuelsson et al.

Annual review of biochemistry, 47, 997-1029 (1978-01-01)

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