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Merck
CN

P6188

Prostaglandin I2 sodium salt

≥96% (HPLC), synthetic, powder

Synonym(s):

(5Z,9α,11α,13E,15S)-6,9-Epoxy-11,15-dihydroxyprosta-5,13-dien-1-oic acid sodium salt, Epoprostenol sodium salt, PGI2-Na, Prostacyclin sodium salt

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About This Item

Empirical Formula (Hill Notation):
C20H31NaO5
CAS Number:
61849-14-7
Molecular Weight:
374.45
PubChem Substance ID:
24898653
eCl@ss:
42020658
UNSPSC Code:
12352401
NACRES:
NA.77
EC Number:
263-273-7
Beilstein/REAXYS Number:
6472195

Key Documents

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Product Name

Prostaglandin I2 sodium salt, ≥96% (HPLC), synthetic, powder

InChI key

OURCVRVJQMLUNA-QFDVFERUSA-M

InChI

1S/C20H32O5.Na/c1-2-3-4-8-15(21)10-11-16-17(22)12-18-20(16)14(13-25-18)7-5-6-9-19(23)24;/h7,10-11,15-18,20-22H,2-6,8-9,12-13H2,1H3,(H,23,24);/q;+1/p-1/b11-10+,14-7-;/t15-,16-,17+,18-,20+;/m0./s1

SMILES string

CCCCC[C@H](O)/C=C/[C@H]1[C@H](O)C[C@@](O/2)([H])[C@]1([H])CC2=C\CCCC(O)=O.[Na]

biological source

synthetic

assay

≥96% (HPLC)

form

powder

color

white to off-white

solubility

H2O: 1 mg/mL (Hydrolyzes to 6-ketoprostaglandin F1α in aqueous solution.)
ethanol: 50 mg/mL

functional group

carboxylic acid
hydroxyl

shipped in

ambient

storage temp.

−20°C

Quality Level

200

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Application

Prostaglandin I2 sodium salt has been used:
  • in the preparation of stock solution for platelet washing procedure
  • as supplement in platelet-rich-plasma, for platelet preparation
  • to prevent platelet activation

Biochem/physiol Actions

Prostacyclin is a short-lived product of the cyclooxygenase pathway in vascular endothelial cells. It is a potent inhibitor of platelet aggregation by antagonizing thromboxane A2 and stimulating platelet adenylyl cyclase. Nitric oxide is also produced in vascular endothelium where it inhibits platelet aggregation, regulates inducible cyclooxygenase production, and may work synergistically with prostacyclin to attenuate the thrombotic process. Prostacyclin is vasoprotective, protecting arterial walls from injury-induced lesions and cytoprotective in the liver and gastrointestinal tract.
Prostacyclin therapy improves hemodynamics in pulmonary arterial hypertension.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000445997
0000445997
0000433918
0000433918
0000357901

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Vijayakumar Chinnathambi et al.
Hypertension (Dallas, Tex. : 1979), 61(3), 647-654 (2013-01-23)
Sex steroid hormones estradiol and progesterone play an important role in vascular adaptations during pregnancy. However, little is known about the role of androgens. Plasma testosterone (T) levels are elevated in preeclampsia, mothers with polycystic ovary, and pregnant African American
D Salvemini
Cellular and molecular life sciences : CMLS, 53(7), 576-582 (1997-07-01)
Nitric oxide (NO), derived from L-arginine (L-Arg) by the enzyme nitric oxide synthase (NOS) is involved in the regulation of several important physiological and pathophysiological functions. The mechanisms by which NO exerts some of its beneficial or detrimental effects include
Ryszard J Gryglewski
Pharmacological reports : PR, 60(1), 3-11 (2008-02-16)
Prostanoids are cyclic lipid mediators which arise from enzymic cyclooxygenation of linear polyunsaturated fatty acids, e.g. arachidonic acid (20:4 n 6, AA). Biologically active prostanoids deriving from AA include stable prostaglandins (PGs), e.g. PGE(2), PGF(2alpha), PGD(2), PGJ(2) as well as
Y Numaguchi et al.
Arteriosclerosis, thrombosis, and vascular biology, 19(3), 727-733 (1999-03-12)
Prostacyclin (PGI2), a metabolite of arachidonic acid, has the vasoprotective effects of vasodilation, anti-platelet aggregation, and inhibition of smooth muscle cell proliferation. We hypothesized that an overexpression of endogenous PGI2 may accelerate the recovery from endothelial damage and inhibit neointimal
Paola Vitale et al.
Journal of medicinal chemistry, 56(11), 4277-4299 (2013-05-09)
3-(5-Chlorofuran-2-yl)-5-methyl-4-phenylisoxazole (P6), a known selective cyclooxygenase-1 (COX-1) inhibitor, was used to design a new series of 3,4-diarylisoxazoles in order to improve its biochemical COX-1 selectivity and antiplatelet efficacy. Structure-activity relationships were studied using human whole blood assays for COX-1 and
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