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S8692

Sulprostone

Name: Sulprostone
Brand: SIGMA

≥95% (HPLC), prostanoid receptor agonist, 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

NACRES:

NA.77

PubChem Substance ID:

24724621

UNSPSC Code:

12352200

EC Number:

262-173-0

MDL number:

MFCD00216056

Assay:

≥95% (HPLC)

Form:

oil

Quality level:

100

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Product Name

Sulprostone, ≥95% (HPLC), oil

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

Related Categories

Bioactive Small Molecules

Application

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

Biochem/physiol Actions

Selective EP₃ prostanoid receptor agonist.

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

pictograms

GHS08,GHS07

signalword

Danger

hcodes

H315,H319,H335,H360

pcodes

P201 - P302 + P352 - P305 + P351 + P338 - P308 + P313

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

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

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Regulatory Information

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Possible involvement of brain prostaglandin E2 and prostanoid EP3 receptors in prostaglandin E2 glycerol ester-induced activation of central sympathetic outflow in the rat.

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

Prostaglandin E2 analogue sulprostone for treatment of atonic postpartum hemorrhage.

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

Signalling transduction events involved in agonist-induced PGE2/EP4 receptor externalization in cultured rat dorsal root ganglion neurons.

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

Uterotonic agents for preventing postpartum haemorrhage: a network meta-analysis.

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

Capsaicin-induced vasodilatation in human nasal vasculature is mediated by modulation of cyclooxygenase-2 activity and abrogated by sulprostone.

Koen Van Crombruggen et al.

Naunyn-Schmiedeberg's archives of pharmacology, 383(6), 613-626 (2011-04-28)

Extensively based on evidence gained from experimental animal models, the transient receptor potential vanilloid receptor type 1 (TRPV1)-activator capsaicin is regarded as a valuable tool in the research on neurogenic inflammation. Although capsaicin-related drugs gained renewed interest as a therapeutic

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Global Trade Item Number

SKU	GTIN
S8692-1MG	04061826677001
S8692-5MG	04061832786346

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