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Key Documents

P6188

Sigma-Aldrich

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:
Molecular Weight:
374.45
Beilstein:
6472195
EC Number:
UNSPSC Code:
12352401
eCl@ss:
42020658
PubChem Substance ID:
NACRES:
NA.77

biological source

synthetic

Quality Level

Assay

≥96% (HPLC)

form

powder

color

white to off-white

solubility

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

functional group

carboxylic acid
hydroxyl

shipped in

ambient

storage temp.

−20°C

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]

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

InChI key

OURCVRVJQMLUNA-QFDVFERUSA-M

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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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Anna-Karin Larsson-Callerfelt et al.
Respiratory research, 14, 21-21 (2013-02-15)
Prostacyclin analogs are potent vasodilators and possess anti-inflammatory properties. However, the effect of prostacyclin on extracellular matrix (ECM) in COPD is not well known. Collagen fibrils and proteoglycans are essential ECM components in the lung and fibroblasts are key players
G J Dusting et al.
Clinical and experimental pharmacology & physiology. Supplement, 25, S34-S41 (1998-11-11)
1. Nitric oxide (NO) has important roles in physiological vasodilatation, cytotoxicity and vascular disease. Nitric oxide and prostacyclin (PGI2), both released from the endothelium, act synergistically to inhibit platelet aggregation and adhesion. These autacoids also inhibit the adhesion and migration

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