Misoprostol

Base Information

• Chemical Name: Misoprostol
• CAS No.: 59122-46-2
• Deprecated CAS: 62015-39-8,92999-98-9,138284-96-5,143913-16-0
• Molecular Formula: C22H38O5
• Molecular Weight: 382.541
• Hs Code.: 2937500000
• European Community (EC) Number: 664-288-5
• UNII: 0E43V0BB57
• DSSTox Substance ID: DTXSID7020897
• Nikkaji Number: J345.358H
• Wikipedia: Misoprostol
• Wikidata: Q416025
• NCI Thesaurus Code: C1313
• RXCUI: 42331
• Pharos Ligand ID: FC6K2A14A3DV
• Metabolomics Workbench ID: 43194
• ChEMBL ID: CHEMBL606
• Mol file: 59122-46-2.mol

Synonyms:Cytotec;Isprelor;Misogon;Misoprost;Misoprostil;SC 29333;

Chemical Property of Misoprostol

Chemical Property:

• Appearance/Colour: water-soluble, viscous liquid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 261-263°C
• Refractive Index: 1.51
• Boiling Point: 497.3 °C at 760 mmHg
• PKA: 13.92±0.60(Predicted)
• Flash Point: 160.3 °C
• PSA: 83.83000
• Density: 1.078 g/cm³
• LogP: 3.95360
• Storage Temp.: −20°C
• Solubility.: Practically insoluble in water, soluble in ethanol (96 per cent), sparingly soluble in acetonitrile.
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 14
• Exact Mass: 382.27192431
• Heavy Atom Count: 27
• Complexity: 487

Purity/Quality:

99% ^*data from raw suppliers

Misoprostol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 45-60-61-25-36/37/38
• Safety Statements: 53-22-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCC(C)(CC=CC1C(CC(=O)C1CCCCCCC(=O)OC)O)O
• Isomeric SMILES: CCCCC(C)(C/C=C/[C@H]1[C@@H](CC(=O)[C@@H]1CCCCCCC(=O)OC)O)O
• Recent ClinicalTrials: Balloon to Induce Labor in Generous Women.
• Recent EU Clinical Trials: Labour induction in an outpatient setting - a multicenter randomized controlled trial. OPTION - OutPatienT InductiON
• Recent NIPH Clinical Trials: Oral versus vaginal administration of misoprostol for induction of labor in women with pre labour rupture of membranes. Results of a randomized controlled trial
• Description: Misoprostol is a synthetic prostaglandin E1 analog that is commonly used for medical abortion, management of miscarriage, cervical priming, management of postpartum hemorrhage, and induction of labor. Because of misoprostol’s wide use in reproductive health, the drug is in the World Health Organization (WHO) Model List of Essential Medicines. As a synthetic analog of prostaglandin E1, misoprostol can avoid the major side effects caused by PGE1, including fetal bradycardia, pregnant women’s emesis, somnolence, and headache. Misoprostol is an orally-active PGEl analog useful in the treatment of gastric and duodenal ulcers. As with other agents of this type, misoprostol may prove useful as a gastric cytoprotective when administered concurrently with irritating drugs such as nonsteroidal antiinflammatories.
• Uses: Inducing Labor Misoprostol is an effective and safe way of inducing labor although the Food and Drug Administration (FDA) has not yet approved it for use in pregnancy. However, the European Union (EU) approved its use after a study that was done between 2002 and 2012. It acts by causing uterine ripening and constrictions of the cervix. Abortion Misoprostol is normally used in combination with other drugs, such as methotrexate or mifepristone for medical abortion. It works by softening the cervix, causing it to open. Also, it makes the uterine muscles contract, thus inducing labor to expel the fetus. Misoprostol is a similar to prostaglandin which as a hormone that can cause a stronger reaction from the uterus. Most of the time, the drug is given in a clinic or hospital birthing centers. Misoprostol can be best administered when one has passed 12 or more weeks of pregnancy to avoid possible severe complications. It can also be administered if there is a possibility of ectopic pregnancy or if one has an intrauterine device (IUD). Misoprostol can be used either vaginally or orally if the pregnancy is still in the first trimester. The pregnant woman is advised to use 12 tablets of 200 grams and should put four tablets into the vagina or under the tongue and let it dissolve for 30 minutes. The woman is further advised to wait for 3 hours and repeat with four more pills in the vagina or under the tongue for 30 minutes. The drug is more effective when inserted into the vagina; however, doctors usually administer it orally due to the possibility of infection when used vaginally. When used together with mifepristone, misoprostol is effective in approximately 95% of early pregnancies. Postpartum Hemorrhage Misoprostol is normally used both as treatment and prevention of postpartum hemorrhage secondary to its uterotonic properties. Studies have revealed that orally administered misoprostol is less effective as compared to oxytocin, but it still plays a vital role in treating postpartum hemorrhage when other agents fail or are not available. Prevention of Ulcer Misoprostol is commonly used for the treatment and prevention of NSAID-induced gastric and duodenal ulcers due to its analgesic and anti-inflammatory properties. It acts by inhibiting gastric acid inhibition of adenylate cyclase by G-protein coupled receptor that leads to decreased proton pump activity and decreased intracellular cyclic AMP levels at the apical surface of the parietal cell. Failed Miscarriage Misoprostol is used in treating a mother in case of fetal death that can result in miscarriage. It is also used in the termination of pregnancy for fetal anomalies. Initially, a low dose is administered and doubled for the extra doses until delivery. Misoprostol is a cytoprotective prostaglandin PGE1 analogue that inhibits gastric acid secretion. It has many medical uses, including nine obstetric indications. The drug was originally produced by Pfizer for the treatment of gastric ulcers. Misoprostol is commonly used to prevent NSAID-induced gastric ulcers in patients at high risk of complications from a gastric ulcer, such as elderly patients and patients with a history of ulcer. It has also been used in treating duodenal ulcers unresponsive to histamine H2-antagonists; the drug does not prevent duodenal ulcers,however, in patients taking NSAIDS. Misoprostol can cause miscarriage, often associated with potentially dangerous bleeding.
• Indications: Misoprostol (Cytotec), which is an analogue of prostaglandin E1, has been approved for use in the prevention of nonsteroidal antiinflammatory drug–induced ulceration. It also is approved in other countries for the treatment of peptic ulcer disease.
• Therapeutic Function: Antiulcer
• Clinical Use: Benign gastric and duodenal ulceration and NSAID associated ulceration Prophylaxis of NSAID induced ulceration

Technology Process of Misoprostol

There total 35 articles about Misoprostol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

methyl 7-(5-oxo-3-[(triethylsilyl)-oxy]-1-cyclopenten-1-yl)-heptanoate (112713-92-5) → misoprostol (59122-46-2)

Guidance literature:

With (lithium)2(CN)(methyl)2cuprate; In tetrahydrofuran; water; acetic acid;

DOI:10.1021/ja00216a045

Reference yield: 88.0%

7-[(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-((E)-4-methyl-4-trimethylsilanyloxy-oct-1-enyl)-5-oxo-cyclopentyl]-heptanoic acid methyl ester (104334-05-6,106363-24-0) → misoprostol (59122-46-2)

Guidance literature:

With pyridine hydrogenfluoride; In acetonitrile; for 2h; Ambient temperature;

DOI:10.1016/S0040-4020(01)90018-3

Reference yield:

(±)-(11α,13E)-16-methyl-9-oxo-11,16-bis[(trimethylsilyl)oxy]-13-en-prostanoic acid methyl ester → misoprostol (59122-46-2)

Guidance literature:

With pyridinium p-toluenesulfonate; In methanol; Large scale;

upstream raw materials:

2-(6-methoxycarbonylhexyl)-4-(tetrahydropyran-2-yloxy)cyclopent-2-enone

4-methyl-4-trimethylsilyloxyl-1-octyne

(+/-)-4-Methyl-4-triethylsilyloxy-trans-1-octenyliodid

7-[(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-((E)-4-methyl-4-trimethylsilanyloxy-oct-1-enyl)-5-oxo-cyclopentyl]-heptanoic acid methyl ester

Downstream raw materials:

7-[(1S,2R)-2-((E)-4-Hydroxy-4-methyl-oct-1-enyl)-5-oxo-cyclopent-3-enyl]-heptanoic acid methyl ester

Refernces

• 1、 -. "PROCESS FOR THE PREPARATION AND PURIFICATION OF MISOPROSTOL". . . Retrieved 2019/01/30.
• 2、 -. "Cyclopenteneheptenoic acid derivatives and method of preparation thereof". . . Retrieved 2008/06/13.