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MedKoo Cat#: 574417 | Name: Sulprostone
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Sulprostone is a metabolism resistant synthetic analog of PGE2. It is a selective agonist for EP3 receptors and is a potent stimulator of uterine smooth muscle contractions with high abortifacient activity.

Chemical Structure

Sulprostone
Sulprostone
CAS#60325-46-4

Theoretical Analysis

MedKoo Cat#: 574417

Name: Sulprostone

CAS#: 60325-46-4

Chemical Formula: C23H31NO7S

Exact Mass: 465.1821

Molecular Weight: 465.56

Elemental Analysis: C, 59.34; H, 6.71; N, 3.01; O, 24.06; S, 6.89

Price and Availability

Size Price Availability Quantity
1mg USD 350.00 2 Weeks
5mg USD 800.00 2 Weeks
10mg USD 1,300.00 2 Weeks
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Related CAS #
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Synonym
Sulprostone
IUPAC/Chemical Name
N-(methylsulfonyl)-9-oxo-11α,15R-dihydroxy-16-phenoxy-17,18,19,20-tetranor-prosta-5Z,13E-dien-1-amide
InChi Key
UQZVCDCIMBLVNR-TWYODKAFSA-N
InChi Code
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
SMILES Code
O=C1[C@H](C/C=C\CCCC(NS(=O)(C)=O)=O)[C@@H](/C=C/[C@@H](O)COC2=CC=CC=C2)[C@H](O)C1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 465.56 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Lu CC. Effect of PGE2 on TT cells viability and division. Prostaglandins Other Lipid Mediat. 2024 Oct;174:106880. doi: 10.1016/j.prostaglandins.2024.106880. Epub 2024 Aug 8. PMID: 39121944. 2: Xu JH, He TH, Wang NP, Gao WM, Cheng YJ, Ji QF, Wu SH, Wei YL, Tang Y, Yang WZ, Zhang J. Thermoregulatory pathway underlying the pyrogenic effects of prostaglandin E2 in the lateral parabrachial nucleus of male rats. Acta Pharmacol Sin. 2024 Sep;45(9):1832-1847. doi: 10.1038/s41401-024-01289-6. Epub 2024 May 3. PMID: 38702500; PMCID: PMC11336216. 3: Denoyelle J, Dujardin C, Ramdane N, Leleu A, Ghesquière L, Garabedian C. Peut-on prévenir l’échec du ballon de tamponnement intra-utérin selon la voie d’accouchement ? [Can we predict intrauterine balloon tamponade failure according to the mode of delivery?]. Gynecol Obstet Fertil Senol. 2024 Sep;52(9):511-516. French. doi: 10.1016/j.gofs.2024.03.013. Epub 2024 Mar 29. PMID: 38556133. 4: Bryson TD, Zurek M, Moore C, Taube D, Datta I, Levin A, Harding P. Prostaglandin E2 affects mitochondrial function in adult mouse cardiomyocytes and hearts. Prostaglandins Leukot Essent Fatty Acids. 2024 Feb;201:102614. doi: 10.1016/j.plefa.2024.102614. Epub 2024 Mar 6. PMID: 38471265; PMCID: PMC11180573. 5: Deniau B, Ricbourg A, Weiss E, Paugam-Burtz C, Bonnet MP, Goffinet F, Mignon A, Morel O, Le Guen M, Binczak M, Carbonnel M, Michelet D, Dahmani S, Pili- Floury S, Ducloy Bouthors AS, Mebazaa A, Gayat E. Association of severe postpartum hemorrhage and development of psychological disorders: Results from the prospective and multicentre HELP MOM study. Anaesth Crit Care Pain Med. 2024 Apr;43(2):101340. doi: 10.1016/j.accpm.2023.101340. Epub 2023 Dec 19. PMID: 38128731. 6: Nazabal A, Mendiguren A, Pineda J. Inhibition of rat locus coeruleus neurons by prostaglandin E2 EP3 receptors: pharmacological characterization ex vivo. Front Pharmacol. 2023 Nov 15;14:1290605. doi: 10.3389/fphar.2023.1290605. PMID: 38035000; PMCID: PMC10684765. 7: Szpot P, Wachełko O, Zawadzki M. Determination of Prostaglandins (Carboprost, Cloprostenol, Dinoprost, Dinoprostone, Misoprostol, Sulprostone) by UHPLC-MS/MS in Toxicological Investigations. Toxics. 2023 Sep 22;11(10):802. doi: 10.3390/toxics11100802. PMID: 37888653; PMCID: PMC10611191. 8: Madar H, Deneux-Tharaux C, Froeliger A, Bouchghoul H, Sentilhes L. Réponse de H. Madar, C. Deneux-Tharaux, A. Froeliger, H. Bouchghoul, L. Sentilhes à l’article de R. Cahierc et al. « Évolution du Shock Index obstétrical lors d’une hémorragie du post-partum selon le recours à la sulprostone ». Gynecol Obstet Fertil 2023; 51(10): Doi: 10.1016/j.gofs.2023.08.001 [H. Madar, C. Deneux- Tharaux, A. Froeliger, H. Bouchghoul, L. Sentilhes in reply to the article R Cahierc et al. entitled « Evolution of the obstetrical Shock Index in post- partum haemorrhage according to the use of sulprostone». Gynecol Obstet Fertil 2023; 51(10): Doi: 10.1016/j.gofs.2023.08.001]. Gynecol Obstet Fertil Senol. 2023 Nov-Dec;51(11-12):545-546. French. doi: 10.1016/j.gofs.2023.09.001. Epub 2023 Sep 11. PMID: 37703918. 9: Futcher F, Moufawad G, Centini G, Hayek J, Tarchichi J, Bakar J, Habib N. Intrauterine Tamponade Balloon for Management of Severe Postpartum Haemorrhage: Does Early Insertion Change the Outcome? A Retrospective Study on Blood Loss. J Clin Med. 2023 Aug 22;12(17):5439. doi: 10.3390/jcm12175439. PMID: 37685506; PMCID: PMC10487974. 10: Zomer PML, van Teeffelen MPA, Otterspoor LC, Kamps MJA. Postpartum cardiogenic shock due to coronary artery spasm after methylergometrine and sulprostone administration. Neth Heart J. 2023 Oct;31(10):408-409. doi: 10.1007/s12471-023-01805-z. Epub 2023 Sep 8. PMID: 37682458; PMCID: PMC10516809. 11: Cahierc R, Debost-Legrand A, Lane S, Rouzaire M, Bonnin M, Delabaere A, Gallot D. Évolution du Shock Index obstétrical lors d’une hémorragie du post- partum selon le recours à la sulprostone [Evolution of the obstetrical Shock Index in postpartum haemorrhage according to the use of sulprostone]. Gynecol Obstet Fertil Senol. 2023 Oct;51(10):448-454. French. doi: 10.1016/j.gofs.2023.08.001. Epub 2023 Aug 25. PMID: 37634804. 12: Schaid MD, Harrington JM, Kelly GM, Sdao SM, Merrins MJ, Kimple ME. EP3 signaling is decoupled from the regulation of glucose-stimulated insulin secretion in β-cells compensating for obesity and insulin resistance. Islets. 2023 Dec 31;15(1):2223327. doi: 10.1080/19382014.2023.2223327. PMID: 37415404; PMCID: PMC10332234. 13: Rozenberg P, Sentilhes L, Goffinet F, Vayssiere C, Senat MV, Haddad B, Morel O, Garabedian C, Vivanti A, Perrotin F, Kayem G, Azria E, Raynal P, Verspyck E, Sananes N, Gallot D, Bretelle F, Seco A, Winer N, Deneux-Tharaux C; Groupe de Recherche en Obstétrique et Gynécologie. Efficacy of early intrauterine balloon tamponade for immediate postpartum hemorrhage after vaginal delivery: a randomized clinical trial. Am J Obstet Gynecol. 2023 Nov;229(5):542.e1-542.e14. doi: 10.1016/j.ajog.2023.05.014. Epub 2023 May 18. PMID: 37209893. 14: Liu Y, Liu R, Huang L, Zuo G, Dai J, Gao L, Shi H, Fang Y, Lu Q, Okada T, Wang Z, Hu X, Lenahan C, Tang J, Xiao J, Zhang JH. Inhibition of Prostaglandin E2 Receptor EP3 Attenuates Oxidative Stress and Neuronal Apoptosis Partially by Modulating p38MAPK/FOXO3/Mul1/Mfn2 Pathway after Subarachnoid Hemorrhage in Rats. Oxid Med Cell Longev. 2022 Dec 9;2022:7727616. doi: 10.1155/2022/7727616. PMID: 36531208; PMCID: PMC9757947. 15: Normand C, Breton B, Salze M, Barbeau E, Mancini A, Audet M. A systematic analysis of prostaglandin E2 type 3 receptor isoform signaling reveals isoform- and species-dependent L798106 Gαz-biased agonist responses. Eur J Pharmacol. 2022 Jul 15;927:175043. doi: 10.1016/j.ejphar.2022.175043. Epub 2022 May 20. PMID: 35598847. 16: Osaka T. The EP3 and EP4 Receptor Subtypes both Mediate the Fever-producing Effects of Prostaglandin E2 in the Rostral Ventromedial Preoptic Area of the Hypothalamus in Rats. Neuroscience. 2022 Jul 1;494:25-37. doi: 10.1016/j.neuroscience.2022.05.001. Epub 2022 May 10. PMID: 35550162. 17: Franke JF, Oelmeier K, Möllers M, Möllmann U, Braun J, Kerschke L, Köster HA, Klockenbusch W, Schmitz R, Hammer K. Termination of pregnancy in the second trimester - the course of different therapy regimens. J Perinat Med. 2022 May 10;50(8):1053-1060. doi: 10.1515/jpm-2022-0001. PMID: 35532780. 18: Jiang T, Samapati R, Klassen S, Lei D, Erfinanda L, Jankowski V, Simmons S, Yin J, Arenz C, Dietrich A, Gudermann T, Adam D, Schaefer M, Jankowski J, Flockerzi V, Nüsing R, Uhlig S, Kuebler WM. Stimulation of the EP3 receptor causes lung oedema by activation of TRPC6 in pulmonary endothelial cells. Eur Respir J. 2022 Oct 13;60(4):2102635. doi: 10.1183/13993003.02635-2021. PMID: 35450969. 19: Tao X, Zhang R, Du R, Yu T, Yang H, Li J, Wang Y, Liu Q, Zuo S, Wang X, Lazarus M, Zhou L, Wang B, Yu Y, Shen Y. EP3 enhances adhesion and cytotoxicity of NK cells toward hepatic stellate cells in a murine liver fibrosis model. J Exp Med. 2022 May 2;219(5):e20212414. doi: 10.1084/jem.20212414. Epub 2022 Apr 14. PMID: 35420633; PMCID: PMC9014794. 20: Ye Y, Peng L, Chelariu-Raicu A, Kuhn C, Dong X, Jeschke U, von Schönfeldt V. Prostaglandin E2 receptor 3 promotes M1 macrophages polarization in unexplained recurrent pregnancy loss. Biol Reprod. 2022 May 17;106(5):910-918. doi: 10.1093/biolre/ioac030. PMID: 35134851.