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| CAS No.: | 59122-46-2 |
|---|---|
| Name: | Misoprostol |
| Molecular Structure: | |
|
|
|
| Formula: | C22H38O5 |
| Molecular Weight: | 382.541 |
| Synonyms: | Cytotec;Isprelor;Misogon;Misoprost;Misoprostil;SC 29333; |
| EINECS: | 664-288-5 |
| Density: | 1.078 g/cm3 |
| Melting Point: | 261-263°C |
| Boiling Point: | 497.3 °C at 760 mmHg |
| Flash Point: | 160.3 °C |
| Appearance: | water-soluble, viscous liquid |
| Hazard Symbols: |
 T
|
| Risk Codes: | 45-60-61-25-36/37/38 |
| Safety: | 53-22-36/37/39-45 |
| Transport Information: | UN 2810 6.1/PG 3 |
| PSA: | 83.83000 |
| LogP: | 3.95360 |
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- 112713-92-5
methyl 7-(5-oxo-3-[(triethylsilyl)-oxy]-1-cyclopenten-1-yl)-heptanoate
- 59122-46-2
misoprostol
| Conditions | Yield |
|---|---|
| With (lithium)2(CN)(methyl)2cuprate In tetrahydrofuran; water; acetic acid | 91% |
- 104334-05-6, 106363-24-0
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
- 59122-46-2
misoprostol
| Conditions | Yield |
|---|---|
| With pyridine hydrogenfluoride In acetonitrile for 2h; Ambient temperature; | 88% |
- 40098-24-6
2-(6-methoxycarbonylhexyl)-4-(tetrahydropyran-2-yloxy)cyclopent-2-enone
- 66792-28-7
4-methyl-4-trimethylsilyloxyl-1-octyne
- 59122-46-2
misoprostol
| Conditions | Yield |
|---|---|
| Multistep reaction; |
- 40098-24-6
2-(6-methoxycarbonylhexyl)-4-(tetrahydropyran-2-yloxy)cyclopent-2-enone
- 58682-78-3
(+/-)-4-Methyl-4-triethylsilyloxy-trans-1-octenyliodid
- 59122-46-2
misoprostol
| Conditions | Yield |
|---|---|
| Multistep reaction; |
- 14273-90-6
methyl 6-bromohexanoate
- 59122-46-2
misoprostol
| Conditions | Yield |
|---|---|
| Multi-step reaction with 6 steps 1: 51 percent / sodium nitrite, phloroglucinol / dimethylsulfoxide / 20 h / Ambient temperature 2: 1) 3N sodium hydroxide; 3) acetic acid / 1) H2O, 0 deg C, 3 h; 2) H2O, 0 deg C, 5 h; 3) H2O, room temp., 20 h 3: 79 percent / mesyl chloride, triethylamine / CH2Cl2 / 1 h / 0 °C 4: 1) t-butyllithium; 2) copper(I)iodide, tributylphosphine 5: 42 percent / tributyltin hydride, azobisisobutyronitrile / toluene / 0.17 h / 110 °C 6: 88 percent / hydrogen fluoride-pyridine / acetonitrile / 2 h / Ambient temperature View Scheme |
- 88462-11-7
Methyl 6-nitro-6-heptenoate
- 59122-46-2
misoprostol
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1: 1) t-butyllithium; 2) copper(I)iodide, tributylphosphine 2: 42 percent / tributyltin hydride, azobisisobutyronitrile / toluene / 0.17 h / 110 °C 3: 88 percent / hydrogen fluoride-pyridine / acetonitrile / 2 h / Ambient temperature View Scheme |
- 13154-40-0
6-nitrohexanoic acid methyl ester
- 59122-46-2
misoprostol
| Conditions | Yield |
|---|---|
| Multi-step reaction with 5 steps 1: 1) 3N sodium hydroxide; 3) acetic acid / 1) H2O, 0 deg C, 3 h; 2) H2O, 0 deg C, 5 h; 3) H2O, room temp., 20 h 2: 79 percent / mesyl chloride, triethylamine / CH2Cl2 / 1 h / 0 °C 3: 1) t-butyllithium; 2) copper(I)iodide, tributylphosphine 4: 42 percent / tributyltin hydride, azobisisobutyronitrile / toluene / 0.17 h / 110 °C 5: 88 percent / hydrogen fluoride-pyridine / acetonitrile / 2 h / Ambient temperature View Scheme |
- 112329-43-8
7-Hydroxy-6-nitro-heptanoic acid methyl ester
- 59122-46-2
misoprostol
| Conditions | Yield |
|---|---|
| Multi-step reaction with 4 steps 1: 79 percent / mesyl chloride, triethylamine / CH2Cl2 / 1 h / 0 °C 2: 1) t-butyllithium; 2) copper(I)iodide, tributylphosphine 3: 42 percent / tributyltin hydride, azobisisobutyronitrile / toluene / 0.17 h / 110 °C 4: 88 percent / hydrogen fluoride-pyridine / acetonitrile / 2 h / Ambient temperature View Scheme |
- 101642-17-5, 112354-59-3
7-[(1S,2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-((E)-4-methyl-4-trimethylsilanyloxy-oct-1-enyl)-5-oxo-cyclopentyl]-6-nitro-heptanoic acid methyl ester
- 59122-46-2
misoprostol
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: 42 percent / tributyltin hydride, azobisisobutyronitrile / toluene / 0.17 h / 110 °C 2: 88 percent / hydrogen fluoride-pyridine / acetonitrile / 2 h / Ambient temperature View Scheme |
- 58682-77-2
(4-methyloct-1-yn-4-yloxy)triethylsilane
- 59122-46-2
misoprostol
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: (i) iBu2AlH, (ii) I2, THF View Scheme |
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Chemistry
Molecular Structure:
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Molecular Formula: C22H38O5
Molecular Weight: 382.5341
IUPAC Name: methyl 7-[(1R,2R,3R)-3-Hydroxy-2-[(E)-4-hydroxy-4-methyloct-1-enyl]-5-oxocyclopentyl]heptanoate
Synonyms of Misoprostol (CAS NO.59122-46-2): (+-)-Methyl (1R,2R,3R)-3-hydroxy-2-((E)-(4RS)-4-hydroxy-4-methyl-1-octenyl)-5-oxocyclopentaneheptanoate ; (11-alpha,13E)-(+-)-11,16-Dihydroxy-16-methyl-9-oxoprost-13-en-1-oic acid methyl ester ; BRN 4155643 ; CCRIS 6859 ; Cytotec ; HSDB 3573 ; Methyl (+-)-11-alpha,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate ; Misoprostol ; Misoprostolum ; Misoprostolum [INN-Latin] ; Misotol ; SC 29333 ; SC-29333 ; UNII-0E43V0BB57 ;
CAS NO: 59122-46-2
Classification Code: Abortifacient Agents ; Abortifacient agents, nonsteroidal ; Anti-ulcer agents ; Anti-ulcerative ; Drug / Therapeutic Agent ; Gastrointestinal Agents ; Human Data ; Oxytocics ; Reproductive Control Agents ; Reproductive Effect
Index of Refraction: 1.524
Molar Refractivity: 108.72 cm3
Molar Volume: 354.7 cm3
Surface Tension: 46 dyne/cm
Density: 1.078 g/cm3
Flash Point: 160.3 °C
Enthalpy of Vaporization: 88.14 kJ/mol
Boiling Point: 497.3 °C at 760 mmHg
Vapour Pressure: 5.64E-12 mmHg at 25°C
Uses
Misoprostol (CAS NO.59122-46-2) is a drug that is used for the prevention of non-steroidal anti-inflammatory drug (NSAID)-induced gastric ulcers, for early abortion, to treat missed miscarriage, and to induce labor. The last use is controversial in the United States. It was invented and marketed by G.D. Searle & Company (now Pfizer) under the trade name Cytotec (often misspelled Cyotec), but other brand-name and generic formulations are now available as well.Chemically, it is a synthetic prostaglandin E1 (PGE1) analogue.
Toxicity Data With Reference
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| dog | LDLo | oral | 10mg/kg (10mg/kg) | Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 35, Pg. 1055, 1993. | |
| mouse | LD50 | intramuscular | 16mg/kg (16mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: CYANOSIS GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | Jitchuken Zenrinsho Kenkyuho. Central Institute for Experimental Animals, Research Reports. Vol. 11, Pg. 33, 1985. |
| mouse | LD50 | intraperitoneal | 70mg/kg (70mg/kg) | BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | Digestive Diseases and Sciences. Vol. 30, Pg. 142S, 1985. |
| mouse | LD50 | oral | 27mg/kg (27mg/kg) | BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | Digestive Diseases and Sciences. Vol. 30, Pg. 142S, 1985. |
| rat | LD50 | intramuscular | 19mg/kg (19mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: CYANOSIS GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | Jitchuken Zenrinsho Kenkyuho. Central Institute for Experimental Animals, Research Reports. Vol. 11, Pg. 33, 1985. |
| rat | LD50 | intraperitoneal | 40mg/kg (40mg/kg) | BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | Digestive Diseases and Sciences. Vol. 30, Pg. 142S, 1985. |
| rat | LD50 | oral | 81mg/kg (81mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: CYANOSIS GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | Jitchuken Zenrinsho Kenkyuho. Central Institute for Experimental Animals, Research Reports. Vol. 11, Pg. 33, 1985. |
Safety Profile
Hazard Codes of Misoprostol (CAS NO.59122-46-2): 
T
Risk Statements: 45-60-61-25-36/37/38
R45: May cause cancer.
R60: May impair fertility.
R61: May cause harm to the unborn child.
R25: Toxic if swallowed.
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 53-22-36/37/39-45
S53: Avoid exposure - obtain special instructions before use.
S22: Do not breathe dust.
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: UN 2810 6.1/PG 3
WGK Germany: 2
RTECS: UK8390000
Specification
The most commonly reported adverse effect of taking a Misoprostol (CAS NO.59122-46-2) 200 μg tablet by mouth four times a day to reduce the risk of NSAID-induced gastric ulcers is diarrhea. In clinical trials, an average 13% of patients reported diarrhea, which was dose-related and usually developed early in the course of therapy (after 13 days) and was usually self-limiting (often resolving within 8 days), but sometimes (in 2% of patients) required discontinuation of misoprostol.
The next most commonly reported adverse effects of taking a misoprostol 200 μg tablet by mouth four times a day to reduce the risk of NSAID-induced gastric ulcers are: abdominal pain, nausea, flatulence, headache, dyspepsia, vomiting, and constipation, but none of these adverse effects occurred significantly more often than when taking placebos.
Misoprostol should not be taken by pregnant women to reduce the risk of NSAID-induced gastric ulcers because it increases uterine tone and contractions in pregnancy which may cause partial or complete abortions, and because its use in pregnancy has been associated with birth defects.
A study published in the Journal of Immunology (June 15, 2008 online) suggests that the immunosuppressive effect of misoprostol, if given vaginally rather than orally along with RU-486 to terminate a pregnancy, is likely the reason a small number of women taking the two-drug combination have contracted a fatal bacterial infection.In animal and cell culture studies, the researchers found that misoprostol, when given directly in the reproductive tract (vaginally), suppresses key immune responses and can allow a normally non-threatening bacterium, Clostridium sordellii, to gain the upper hand and cause deadly infection. When absorbed through the stomach (orally), however, the drug did not compromise immune defenses or cause illness.