Misoprostol (free acid)
(Synonyms: 米索前列醇酸) 目录号 : GC41442An EP2, EP3, and EP4 receptor agonist
Cas No.:112137-89-0
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >97.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Misoprostol is a prostaglandin E1 analog with agonist activity mediated by EP2, EP3, and EP4 receptors. It has been shown to inhibit the formation of gastric lesions in rats (ED50 = 0.31 µg/kg), inhibit superoxide generation in human neutrophils (EC50 = 0.35 µM), and relax fetal rabbit ductus arteriosus (EC50 = 0.36 nM) in a concentration dependent manner. Misoprostol is commonly used in clinical medicine for the prevention of peptic ulcer disease. It has also been used in conjunction with mifepristone for the oral induction of first trimester abortion. Misoprostol contains a C-1 methyl ester and is readily absorbed and rapidly hydrolyzed in humans to the active free acid.
| Cas No. | 112137-89-0 | SDF | |
| 别名 | 米索前列醇酸 | ||
| Canonical SMILES | O[C@H]1[C@H](/C=C/CC(C)(O)CCCC)[C@@H](CCCCCCC(O)=O)C(C1)=O | ||
| 分子式 | C21H36O5 | 分子量 | 368.5 |
| 溶解度 | DMF: >100 mg/ml (from PGE1),DMSO: >50 mg/ml (from PGE1),Ethanol: >50 mg/ml (from PGE1),PBS pH 7.2: 1.67 mg/ml (from PGE1) | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.7137 mL | 13.5685 mL | 27.137 mL |
| 5 mM | 0.5427 mL | 2.7137 mL | 5.4274 mL |
| 10 mM | 0.2714 mL | 1.3569 mL | 2.7137 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Expression of gastric antisecretory and prostaglandin E receptor binding activity of Misoprostol by Misoprostol free acid
Dig Dis Sci 1991 May;36(5):588-93.PMID:1850690DOI:10.1007/BF01297024.
In enriched canine parietal cell preparations, Misoprostol, an analog of prostaglandin E1 methyl ester, was rapidly deesterified to Misoprostol free acid. Under this circumstance, Misoprostol and Misoprostol free acid exhibited equal antisecretory potency against histamine-stimulated acid secretion and bound equally well to prostaglandin E receptors. When the deesterification of Misoprostol was inhibited by paraoxon, an esterase inhibitor, the antisecretory and receptor binding activity of Misoprostol was markedly reduced, with potency much less than Misoprostol free acid. These results indicate that Misoprostol free acid is the active biological form of Misoprostol that binds to prostaglandin E receptors and mediates the antisecretory action of Misoprostol.
Effects of Misoprostol and omeprazole on basal gastric pH and free acid content in horses
Res Vet Sci 1989 Nov;47(3):350-4.PMID:2512598doi
The basal gastric pH and free acid contents from five young adult healthy horses were determined at one hour intervals for eight hours. The basal gastric pH and free acid contents varied from 1.63 +/- 0.06 to 1.97 +/- 0.11 and 26.42 +/- 4.14 to 17.92 +/- 5.28 mmol litre-1, respectively. Misoprostol, a methylester analogue of prostaglandin (5 micrograms kg-1, orally) produced a time-dependent increase in the basal gastric pH to above 3.5 (P less than 0.05) at three, four and five hours after administration with a concomitant reduction of 80 to 90 per cent in the basal gastric free acid contents throughout the eight hour period monitored. Omeprazole, a benzimidazole derivative (0.5 mg kg-1, intravenously) increased the basal gastric pH to above 3.5 at two and three hours after administration with a concomitant reduction of 65 to 90 per cent in the basal gastric free acid contents for seven of the eight hour periods monitored. These results confirm that the horse is a basal acid secretor, and both Misoprostol and omeprazole are effective inhibitors of the basal gastric acid secretion, thus establishing that both prostaglandins and H+/K+-ATPase play an important role in controlling parietal cell function of the equine gastric mucosa.
Development and validation of highly sensitive method for determination of Misoprostol free acid in human plasma by liquid chromatography-electrospray ionization tandem mass spectrometry: application to a clinical pharmacokinetic study
J Chromatogr B Analyt Technol Biomed Life Sci 2011 Sep 15;879(26):2827-33.PMID:21872541DOI:10.1016/j.jchromb.2011.08.006.
A highly sensitive, selective and evaporation free SPE extraction, ESI-LC-MS/MS method has been developed for estimation of Misoprostol free acid in human plasma using Misoprostol acid-d(5) as an internal standard (IS). The analyte was separated using isocratic mobile phase on reverse phase column and analyzed by MS/MS in the multiple reaction monitoring mode using the respective [M-H] anions, m/z 367-249 for Misoprostol acid and m/z 372-249 for the IS. The total run time was 5.0 min and the elution of Misoprostol acid and Misoprostol acid-d(5) (IS) occurred at 3.6 min. The developed method was validated in human plasma with a lower limit of quantification of 2.5 pg/mL. A linear response function was established for the range of concentrations 2.5-1200 pg/mL (r>0.998) for Misoprostol acid in human plasma. The intra and inter-day precision values for Misoprostol acid met the acceptance as per FDA guidelines. Misoprostol acid was stable in the battery of stability studies viz., bench-top, auto-sampler and freeze/thaw cycles. The developed assay method was applied to an oral pharmacokinetic study in humans.
Demonstration of specific E-type prostaglandin receptors using enriched preparations of canine parietal cells and [3H]Misoprostol free acid
Am J Med 1987 Jul 27;83(1A):9-14.PMID:2887113DOI:10.1016/0002-9343(87)90572-9.
High-affinity, E-type prostaglandin binding sites in enriched canine parietal cell preparations were identified with [3H] Misoprostol free acid, a prostaglandin E1 analogue. Saturable, reversible, and highly stereospecific binding was identified, with approximately 8,000 binding sites per cell. Prostaglandin I and F bound weakly, and cimetidine and histamine did not bind. The results indicate that [3H] Misoprostol free acid binds to E-type prostaglandin receptors, which suggests that the ulcer-healing inhibition of gastric acid secretion by Misoprostol results from its interaction with a specific E-type prostaglandin receptor.
Determination of Misoprostol free acid in human breast milk and serum by gas chromatography/negative ion chemical ionization tandem mass spectrometry
J Mass Spectrom 2002 Sep;37(9):927-33.PMID:12271435DOI:10.1002/jms.351.
To study an expected transition of Misoprostol from human blood into breast milk, a novel method for the determination of its active metabolite Misoprostol acid (MPA) was developed. MPA was determined in serum and breast milk samples by an isotope dilution assay using gas chromatography/negative ion chemical ionization tandem mass spectrometry (GC/NICI-MS/MS). After addition of (15S)-15-methylprostaglandin E(2) (15-methyl-PGE(2)) as an internal standard, MPA was extracted from both matrices using a reversed-phase cartridge. The prostanoids were derivatized with O-2,3,4,5,6-pentafluorobenzylhydroxylamine hydrochloride (PFBHA) and 2,3,4,5,6-pentafluorobenzyl bromide (PFBB) to the pentafluorobenzyl oxime (PFBO)-pentafluorobenzyl ester (PFB) derivatives. The sample was subjected to thin-layer chromatography with ethyl acetate-hexane (1 : 1 (v/v)) as the developing solvent. The corresponding zone was extracted. After derivatization to the trimethylsilyl ether, MPA was determined by GC/NICI-MS/MS using the [molecule (M) - pentafluorobenzyl (PFB)](-) ([P](-)) ions as precursor in the negative ion chemical ionization mode. The product ions used for quantification were [P - 2TMSOH - C(6)F(5)CH(2)OH](-) (MPA) and [P - 2TMSOH - C(6)F(5)CH(2)OH - CO(2)](-)(15-methyl-PGE(2)), respectively. The limit of quantification for MPA was approximately 1 pg ml(-1) in breast milk and serum samples. The correlation coefficients of the calibration curves for MPA were r > 0.997 in the 0.5-2000 pg ml(-1) range for both tested matrices.