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Basic Information

Molecular Structure:
CAS No.:	59122-46-2
Name:	Misoprostol
Article Data:	10

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

Synthetic route

: 112713-92-5
methyl 7-(5-oxo-3-[(triethylsilyl)-oxy]-1-cyclopenten-1-yl)-heptanoate

(n-Bu)3CH=CHCH2C(Me)(OSiMe3)C4H9 (3): (n-Bu)3CH=CHCH2C(Me)(OSiMe3)C4H9 (3)

: 59122-46-2
misoprostol

Conditions

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

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

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

Conditions	Yield
Multistep reaction;

: 14273-90-6
methyl 6-bromohexanoate

: 59122-46-2
misoprostol

Conditions

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

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

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

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

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

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

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

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) iBu2AlH, (ii) I2, THF View Scheme

Raw Materials

Total:192 Page 1 of 6 1 2 3 4 5 6 Next>>

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Chemistry

Molecular Structure:

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): Toxic 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.