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S8692

Sigma-Aldrich

Sulprostone

≥95% (HPLC), oil

Synonym(s):

(5Z,11α,13E,15R)--11,15-Dihydroxy-9-oxo-16-phenoxy-17,18,19,20-tetranorprosta-5,13-dienoic acid methane sulfonamide, CP-34089, SHB-286, ZK-57671

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About This Item

Empirical Formula (Hill Notation):
C23H31NO7S
CAS Number:
60325-46-4
Molecular Weight:
465.56
EC Number:
262-173-0
MDL number:
MFCD00216056
UNSPSC Code:
12352200
PubChem Substance ID:
24724621
NACRES:
NA.77

Quality Level

100

Assay

≥95% (HPLC)

form

oil

color

colorless to yellow-brown

solubility

DMSO: >10 mg/mL

shipped in

wet ice

storage temp.

−20°C

SMILES string

CS(=O)(=O)NC(=O)CCC\C=C/C[C@@H]1[C@@H](\C=C\[C@@H](O)COc2ccccc2)[C@H](O)CC1=O

InChI

1S/C23H31NO7S/c1-32(29,30)24-23(28)12-8-3-2-7-11-19-20(22(27)15-21(19)26)14-13-17(25)16-31-18-9-5-4-6-10-18/h2,4-7,9-10,13-14,17,19-20,22,25,27H,3,8,11-12,15-16H2,1H3,(H,24,28)/b7-2-,14-13+/t17-,19-,20-,22-/m1/s1

InChI key

UQZVCDCIMBLVNR-TWYODKAFSA-N

Application

Human chondrocytes3 and mouse adrenal chromaffin cells4 were treated with sulprostone to study the biological effects of PGE2.

Biochem/physiol Actions

Sulprostone is an analog of prostaglandin E2 (PGE2)1 and antagonizes vasopressin-induced antidiuretic responses in cells from rat renal inner medullae by a mechanism that involves activation of Rho.2
Selective EP3 prostanoid receptor agonist.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

Hazard Statements

H315,H319,H335,H360

Hazard Classifications

Eye Irrit. 2 - Repr. 1B - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

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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N Foudi et al.
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The body is exposed to foreign pathogens every day, but remarkably, most pathogens are effectively cleared by the innate immune system without the need to invoke the adaptive immune response. Key cellular components of the innate immune system include macrophages
Pierre Pasquier et al.
Anesthesia and analgesia, 116(1), 155-161 (2012-12-12)
Postpartum hemorrhage is the leading cause of maternal death worldwide. Recent data from trauma patients and patients with hemorrhagic shock have suggested that an increased fresh frozen plasma:red blood cell (FFP:RBC) ratio may be of benefit in massive bleeding. We
Xin Li et al.
Arthritis and rheumatism, 60(2), 513-523 (2009-01-31)
To elucidate the pathophysiologic links between prostaglandin E(2) (PGE(2)) and osteoarthritis (OA) by characterizing the catabolic effects of PGE(2) and its unique receptors in human adult articular chondrocytes. Human adult articular chondrocytes were cultured in monolayer or alginate beads with
Keith Morrison et al.
The Journal of pharmacology and experimental therapeutics, 365(3), 727-733 (2018-03-29)
Selexipag [2-{4-[(5,6-diphenylpyrazin-2-yl)(isopropyl)amino]butoxy}-N-(methylsulfonyl)acetamide] is a selective nonprostanoid prostacyclin (PGI2) receptor (IP receptor) agonist that is approved for the treatment of pulmonary arterial hypertension (PAH). In contrast to selexipag, PGI2 analogs used in the clinic are nonselective agonists at prostanoid receptors and
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