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Misoprostol (Synonyms: SC 29333)

Katalog-Nr.GC16074 Copy One-Click Copy Product Info

Misoprostol (SC-29333) ist ein oral aktives synthetisches Prostaglandin E1 (PGE1)-Analogon, das fÜr die Erforschung von MagengeschwÜren verwendet wird.

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Misoprostol Chemische Struktur

Cas No.: 59122-46-2

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10mM (in 1mL DMSO)
43,00 $
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5mg
37,00 $
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Sample solution is provided at 25 µL, 10mM.



Description of Misoprostol

Misoprostol is an orally active prostaglandin E1 (PGE1) analog used to prevent gastric ulcers, treat missed abortion, induce labor and induce miscarriage[1, 2]. Misoprostol is used to prevent gastric ulcers induced by nonsteroidal anti-inflammatory drugs. It can bind to prostaglandin receptors and directly act on parietal cells to inhibit gastric acid secretion[3].

In vitro, Misoprostol (10μM) pretreatment of human peripheral blood mononuclear cells (PBMC) and RAW264.7 cells for 90min significantly increased the phosphorylation of cAMP response element binding protein (CREB) in cells[4]. Misoprostol (10μM) treatment of HCT-116 cells for 2h significantly activated intracellular protein kinase A (PKA)[5]. Misoprostol (8ng/mL) treatment of 3D cultured annular cells significantly increased the epidermal growth factor (EGF) level of cells[6].

In vivo, oral administration of Misoprostol (0.2mg/kg/day) to rats with doxorubicin-induced cardiac injury for 6 days alleviated cardiac injury in rats, significantly reduced serum cardiac troponin-I (cTn-I) and brain natriuretic peptide (BNP) levels, and reduced lactate dehydrogenase (LDH), aspartate aminotransferase (AST), alanine aminotransferase (ALT), and creatine kinase isoenzyme-MB (CK-MB) activities[7].

References:
[1] Ahmed T A, Mohammed A H. Brief Overview About Prostaglandins & Misoprostol For Cervical Ripening[J]. Journal of Pharmaceutical Negative Results, 2023, 14(2).
[2] Chong Y S, Su L L, Arulkumaran S. Misoprostol: a quarter century of use, abuse, and creative misuse[J]. Obstetrical & gynecological survey, 2004, 59(2): 128-140.
[3] Sostres C, Lanas A. Prostaglandins and other mucosal protecting agents[J]. Pocket Guide to Gastrointestinal Drugs, 2014: 44-56.
[4] Gobejishvili L, Ghare S, Khan R, et al. Misoprostol modulates cytokine expression through a cAMP pathway: Potential therapeutic implication for liver disease[J]. Clinical Immunology, 2015, 161(2): 291-299.
[5] Field J T, Martens M D, Mughal W, et al. Misoprostol regulates Bnip3 repression and alternative splicing to control cellular calcium homeostasis during hypoxic stress[J]. Cell Death Discovery, 2018, 4(1): 98.
[6] Gruber H E, Hoelscher G, Loeffler B, et al. Prostaglandin E1 and misoprostol increase epidermal growth factor production in 3D-cultured human annulus cells[J]. The Spine Journal, 2009, 9(9): 760-766.
[7] Bilgic S, Ozgocmen M, Ozer M K, et al. Misoprostol ameliorates doxorubicin induced cardiac damage by decreasing oxidative stress and apoptosis in rats[J]. Biotechnic & Histochemistry, 2020, 95(7): 514-521.

Protocol of Misoprostol

Cell experiment [1]:

Cell lines

Human peripheral blood mononuclear cells (PBMCs)、RAW264.7 cells

Preparation Method

Cells were plated at 0.5 million/mL density, treated with 10μM Misoprostol for 90min and further stimulated with LPS, 100ng/mL. PKA inhibitor, H89 was used at 10μM concentration 30min before Misoprostol treatment. Nuclear extracts were subjected to Western blot analysis.

Reaction Conditions

10μM; 90min

Applications

Misoprostol exposure resulted in increased phosphorylation of cAMP response element-binding protein (CREB) in both PBMCs and RAW cells; pretreatment with PKA inhibitor, H89 prevented Misoprostol effect on CREB phosphorylation.

Animal experiment [2]:

Animal models

Sprague-Dawley rats

Preparation Method

Divided the rats randomly into three groups of seven: group 1, control; group 2, Doxorubicin; group 3, Doxorubicin+ MP. The control group was injected intraperitoneally (i.p.) with 0.5mL 0.9% NaCl and given 1mL 0.9% NaCl orally for 6 days. The Doxorubicin group was injected i.p. with a single dose of 20mg/kg Doxorubicin on the third day of the study. The Doxorubicin+Misoprostol group was injected i.p. with a single 20mg/kg dose of Doxorubicin on day 3 of the study and given 0.2mg/kg/day Misoprostol orally for 6 days. The treatment course lasted 6 days for all groups.

Dosage form

0.2mg/kg/day for 6 days; p.o.

Applications

Cardiac damage caused by Doxorubicin was attenuated by Misoprostol treatment. Treatment with Misoprostol decreased significantly serum cardiac troponin-I, brain natriuretic peptide levels, and lactate dehydrogenase, aspartate aminotransferase, alanine transaminase and creatine kinase isoenzyme-MB activities. Misoprostol also decreased NADPH oxidase-4 and caspase-3 levels.

References:
[1]Gobejishvili L, Ghare S, Khan R, et al. Misoprostol modulates cytokine expression through a cAMP pathway: Potential therapeutic implication for liver disease[J]. Clinical Immunology, 2015, 161(2): 291-299.
[2]Bilgic S, Ozgocmen M, Ozer M K, et al. Misoprostol ameliorates doxorubicin induced cardiac damage by decreasing oxidative stress and apoptosis in rats[J]. Biotechnic & Histochemistry, 2020, 95(7): 514-521.

Chemical Properties of Misoprostol

Cas No. 59122-46-2 SDF
Überlieferungen SC 29333
Chemical Name methyl 7-((1R,2R,3R)-3-hydroxy-2-((E)-4-hydroxy-4-methyloct-1-en-1-yl)-5-oxocyclopentyl)heptanoate
Canonical SMILES CCCCC(C/C([H])=C([H])/[C@]1([H])[C@@](C(C[C@@]1([H])O)=O)([H])CCCCCCC(OC)=O)(O)C
Formula C22H38O5 M.Wt 382.53
Löslichkeit ≥ 11.05mg/mL in DMSO Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table of Misoprostol

Prepare stock solution
1 mg 5 mg 10 mg
1 mM 2.6142 mL 13.0709 mL 26.1417 mL
5 mM 522.8 μL 2.6142 mL 5.2283 mL
10 mM 261.4 μL 1.3071 mL 2.6142 mL
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Average Rating: 5 ★★★★★ (Based on Reviews and 20 reference(s) in Google Scholar.)

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