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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

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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Ioannis D Gallos et al.
The Cochrane database of systematic reviews, 4, CD011689-CD011689 (2018-04-26)
Postpartum haemorrhage (PPH) is the leading cause of maternal mortality worldwide. Prophylactic uterotonic drugs can prevent PPH, and are routinely recommended. There are several uterotonic drugs for preventing PPH but it is still debatable which drug is best. To identify
W Ma et al.
European journal of pain (London, England), 22(5), 845-861 (2018-01-18)
Prostaglandin E2 (PGE2) enriched in inflamed tissues contributes to chronic pain by sensitizing nociceptive dorsal root ganglion (DRG) neurons (nociceptors). Of four PGE2 receptors (EP1-4), EP4 plays a major role in PGE2-induced nociceptor sensitization. We have previously reported that PGE2
Takahiro Shimizu et al.
Neuropharmacology, 82, 19-27 (2014-03-25)
We recently reported that intracerebroventricularly administered 2-arachidonoylglycerol elevated plasma noradrenaline and adrenaline by brain monoacylglycerol lipase- (MGL) and cyclooxygenase-mediated mechanisms in the rat. These results suggest that 2-arachidonoylglycerol is hydrolyzed by MGL to free arachidonic acid, which is further metabolized
Thomas Schmitz et al.
Obstetrics and gynecology, 118(2 Pt 1), 257-265 (2011-07-22)
Use of prostaglandins, including sulprostone (an E2 analog), is recommended for second-line uterotonic treatment of atonic postpartum hemorrhage and might be considered as an indicator of quality of care in severe atonic postpartum hemorrhage management. Our objective was to estimate
N Foudi et al.
British journal of pharmacology, 163(4), 826-834 (2011-02-18)
Human internal mammary arteries (IMA) and saphenous veins (SV) are frequently used for coronary artery bypass graft surgery. Intra- and postoperatively, the bypass grafts are exposed to inflammatory conditions, under which there is a striking increase in the synthesis of
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