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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

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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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
Preparation of washed platelet suspensions from human and rodent blood
Platelets and megakaryocytes, 13-28 (2004)
Sophie Blaise et al.
Journal of clinical pharmacology, 53(1), 58-66 (2013-02-13)
Prostacyclin analogues are the most effective drugs to treat sclerodermic digital ulcers, but their systemic use is limited by their frequent side effects. The authors tested whether the prostacyclin analogues treprostinil and iloprost, delivered by cutaneous iontophoresis, induce sustained vasodilatation.
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
Effects of ethanol on aggregation, serotonin release, and amyloid precursor protein processing in rat and human platelets
Ehrlich D and Humpel C
Platelets, 25(1), 16-22 (2014)

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