Misoprostol

Modify Date: 2024-01-02 08:36:53

Misoprostol Structure
Misoprostol structure
 Common Name Misoprostol
CAS Number 59122-46-2 Molecular Weight 382.534
Density 1.1±0.1 g/cm3 Boiling Point 497.3±45.0 °C at 760 mmHg
Molecular Formula C22H38O5 Melting Point 261-263°C
MSDS USA Flash Point 160.4±22.2 °C
Symbol GHS06 GHS08
GHS06, GHS08		 Signal Word Danger

 Use of Misoprostol


Misoprostol(SC29333) is a synthetic prostaglandin E1 (PGE1) analog that is used to prevent gastric ulcers, to treat missed miscarriage, to induce labor, and to induce abortion.Target: Prostaglandin ReceptorMisoprostol is a synthetic analog of natural prostaglandin E1. It produces a dose-related inhibition of gastric acid and pepsin secretion, and enhances mucosal resistance to injury. It is an effective anti-ulcer agent and also has oxytocic properties. Misoprostol seems to inhibit gastric acid secretion by a direct action on the parietal cells through binding to the prostaglandin receptor. Administration of misoprostol to EP3+/+ and EP3-/- mice showed similar levels of infarct rescue, indicating that misoprostol protection was not mediated through the EP3 receptor. Taken together, these findings suggest a novel function for misoprostol as a protective agent in cerebral ischemia acting via the PGE(2) EP2 and/or EP4 receptors [1, 2].

 Names

Name Misoprostol
Synonym More Synonyms

 Misoprostol Biological Activity

Description Misoprostol(SC29333) is a synthetic prostaglandin E1 (PGE1) analog that is used to prevent gastric ulcers, to treat missed miscarriage, to induce labor, and to induce abortion.Target: Prostaglandin ReceptorMisoprostol is a synthetic analog of natural prostaglandin E1. It produces a dose-related inhibition of gastric acid and pepsin secretion, and enhances mucosal resistance to injury. It is an effective anti-ulcer agent and also has oxytocic properties. Misoprostol seems to inhibit gastric acid secretion by a direct action on the parietal cells through binding to the prostaglandin receptor. Administration of misoprostol to EP3+/+ and EP3-/- mice showed similar levels of infarct rescue, indicating that misoprostol protection was not mediated through the EP3 receptor. Taken together, these findings suggest a novel function for misoprostol as a protective agent in cerebral ischemia acting via the PGE(2) EP2 and/or EP4 receptors [1, 2].
Related Catalog
References

[1]. Li, J., et al., Misoprostol, an anti-ulcer agent and PGE2 receptor agonist, protects against cerebral ischemia. Neurosci Lett, 2008. 438(2): p. 210-5.

[2]. http://www.drugbank.ca/drugs/DB00929

 Chemical & Physical Properties

Density 1.1±0.1 g/cm3
Boiling Point 497.3±45.0 °C at 760 mmHg
Melting Point 261-263°C
Molecular Formula C22H38O5
Molecular Weight 382.534
Flash Point 160.4±22.2 °C
Exact Mass 382.271912
PSA 83.83000
LogP 2.91
Vapour Pressure 0.0±2.9 mmHg at 25°C
Index of Refraction 1.525
Storage condition −20°C

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
UK8390000
CHEMICAL NAME :
Prost-13-en-1-oic acid, 11,16-dihydroxy-16-methyl-9-oxo-, methyl ester, (11-alpha,13E)-(+-)-
CAS REGISTRY NUMBER :
59122-46-2
LAST UPDATED :
199709
DATA ITEMS CITED :
20
MOLECULAR FORMULA :
C22-H38-O5
MOLECULAR WEIGHT :
382.60

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
81 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - cyanosis Gastrointestinal - hypermotility, diarrhea
REFERENCE :
JZKEDZ Jitchuken Zenrinsho Kenkyuho. Central Institute for Experimental Animals, Research Reports. (Jikken Dobutsu Chuo Kenkyusho, 1433 Nogawa, Takatsu-ku, Kawasaki 211, Japan) V.1- 1975- Volume(issue)/page/year: 11,33,1985
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
40 mg/kg
TOXIC EFFECTS :
Behavioral - changes in motor activity (specific assay) Gastrointestinal - hypermotility, diarrhea
REFERENCE :
DDSCDJ Digestive Diseases and Sciences. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) V.24- 1979- Volume(issue)/page/year: 30,142S,1985
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
19 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - cyanosis Gastrointestinal - hypermotility, diarrhea
REFERENCE :
JZKEDZ Jitchuken Zenrinsho Kenkyuho. Central Institute for Experimental Animals, Research Reports. (Jikken Dobutsu Chuo Kenkyusho, 1433 Nogawa, Takatsu-ku, Kawasaki 211, Japan) V.1- 1975- Volume(issue)/page/year: 11,33,1985
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
27 mg/kg
TOXIC EFFECTS :
Behavioral - changes in motor activity (specific assay) Gastrointestinal - hypermotility, diarrhea
REFERENCE :
DDSCDJ Digestive Diseases and Sciences. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) V.24- 1979- Volume(issue)/page/year: 30,142S,1985
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
70 mg/kg
TOXIC EFFECTS :
Behavioral - changes in motor activity (specific assay) Gastrointestinal - hypermotility, diarrhea
REFERENCE :
DDSCDJ Digestive Diseases and Sciences. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) V.24- 1979- Volume(issue)/page/year: 30,142S,1985
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
16 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - cyanosis Gastrointestinal - hypermotility, diarrhea
REFERENCE :
JZKEDZ Jitchuken Zenrinsho Kenkyuho. Central Institute for Experimental Animals, Research Reports. (Jikken Dobutsu Chuo Kenkyusho, 1433 Nogawa, Takatsu-ku, Kawasaki 211, Japan) V.1- 1975- Volume(issue)/page/year: 11,33,1985 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
3285 mg/kg/1Y-I
TOXIC EFFECTS :
Gastrointestinal - hypermotility, diarrhea Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Nutritional and Gross Metabolic - changes in iron
REFERENCE :
DDSCDJ Digestive Diseases and Sciences. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) V.24- 1979- Volume(issue)/page/year: 30,142S,1985
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
56 mg/kg/5W-I
TOXIC EFFECTS :
Endocrine - changes in pituitary weight Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - true cholinesterase
REFERENCE :
JZKEDZ Jitchuken Zenrinsho Kenkyuho. Central Institute for Experimental Animals, Research Reports. (Jikken Dobutsu Chuo Kenkyusho, 1433 Nogawa, Takatsu-ku, Kawasaki 211, Japan) V.1- 1975- Volume(issue)/page/year: 11,39,1985
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
140 mg/kg/28D-I
TOXIC EFFECTS :
Gastrointestinal - nausea or vomiting Blood - changes in erythrocyte (RBC) count Blood - changes in leukocyte (WBC) count
REFERENCE :
JZKEDZ Jitchuken Zenrinsho Kenkyuho. Central Institute for Experimental Animals, Research Reports. (Jikken Dobutsu Chuo Kenkyusho, 1433 Nogawa, Takatsu-ku, Kawasaki 211, Japan) V.1- 1975- Volume(issue)/page/year: 11,157,1985
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
109 ug/kg/1Y-I
TOXIC EFFECTS :
Gastrointestinal - hypermotility, diarrhea Nutritional and Gross Metabolic - body temperature increase Related to Chronic Data - death
REFERENCE :
DDSCDJ Digestive Diseases and Sciences. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) V.24- 1979- Volume(issue)/page/year: 30,142S,1985
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
140 mg/kg/2W-I
TOXIC EFFECTS :
Gastrointestinal - ulceration or bleeding from stomach Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death
REFERENCE :
JZKEDZ Jitchuken Zenrinsho Kenkyuho. Central Institute for Experimental Animals, Research Reports. (Jikken Dobutsu Chuo Kenkyusho, 1433 Nogawa, Takatsu-ku, Kawasaki 211, Japan) V.1- 1975- Volume(issue)/page/year: 11,229,1985 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
12 ug/kg
SEX/DURATION :
female 5-8 week(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - other developmental abnormalities
REFERENCE :
AJMGDA American Journal of Medical Genetics. (John Wiley & Sons Ltd., 605 Third Ave., New York, NY 10158) V.1- 1977- Volume(issue)/page/year: 47,59,1993
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Multiple routes
DOSE :
16 ug/kg
SEX/DURATION :
female 5-8 week(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - body wall
REFERENCE :
AJMGDA American Journal of Medical Genetics. (John Wiley & Sons Ltd., 605 Third Ave., New York, NY 10158) V.1- 1977- Volume(issue)/page/year: 47,59,1993
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
16 gm/kg
SEX/DURATION :
male 10 week(s) pre-mating female 3 week(s) pre-mating - 7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)
REFERENCE :
JZKEDZ Jitchuken Zenrinsho Kenkyuho. Central Institute for Experimental Animals, Research Reports. (Jikken Dobutsu Chuo Kenkyusho, 1433 Nogawa, Takatsu-ku, Kawasaki 211, Japan) V.1- 1975- Volume(issue)/page/year: 11,167,1985
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
320 mg/kg
SEX/DURATION :
female 17-22 day(s) after conception lactating female 26 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
REFERENCE :
JZKEDZ Jitchuken Zenrinsho Kenkyuho. Central Institute for Experimental Animals, Research Reports. (Jikken Dobutsu Chuo Kenkyusho, 1433 Nogawa, Takatsu-ku, Kawasaki 211, Japan) V.1- 1975- Volume(issue)/page/year: 11,213,1985
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
440 mg/kg
SEX/DURATION :
female 7-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
REFERENCE :
JZKEDZ Jitchuken Zenrinsho Kenkyuho. Central Institute for Experimental Animals, Research Reports. (Jikken Dobutsu Chuo Kenkyusho, 1433 Nogawa, Takatsu-ku, Kawasaki 211, Japan) V.1- 1975- Volume(issue)/page/year: 11,189,1985
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
15 mg/kg
SEX/DURATION :
female 7-9 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)
REFERENCE :
SCYYDZ Shengzhi Yu Biyun. Reproduction and Contraception. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) 1980- Volume(issue)/page/year: 15,47,1995
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
3 mg/kg
SEX/DURATION :
female 7-9 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)
REFERENCE :
SCYYDZ Shengzhi Yu Biyun. Reproduction and Contraception. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) 1980- Volume(issue)/page/year: 15,47,1995
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1320 mg/kg
SEX/DURATION :
female 6-18 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
JZKEDZ Jitchuken Zenrinsho Kenkyuho. Central Institute for Experimental Animals, Research Reports. (Jikken Dobutsu Chuo Kenkyusho, 1433 Nogawa, Takatsu-ku, Kawasaki 211, Japan) V.1- 1975- Volume(issue)/page/year: 11,237,1985
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
4 mg/kg
SEX/DURATION :
female 11-12 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - uterus, cervix, vagina
REFERENCE :
SCYYDZ Shengzhi Yu Biyun. Reproduction and Contraception. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) 1980- Volume(issue)/page/year: 15,47,1995

 Safety Information

Symbol GHS06 GHS08
GHS06, GHS08
Signal Word Danger
Hazard Statements H301-H360
Precautionary Statements P201-P301 + P310 + P330-P308 + P313
Hazard Codes T: Toxic;
Risk Phrases R60;R61;R25
Safety Phrases S53-S22-S36/37/39-S45
RIDADR UN 2810 6.1/PG 3
WGK Germany 2
RTECS UK8390000
Hazard Class 6.1

 Synthetic Route

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 Synonyms

Methyl (11α,13E)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oate
MISOPROSTOL ACID
SC 2933
CYTOTEC
Misoprosto
MFCD07772001
Prost-13-en-1-oic acid, 11,16-dihydroxy-16-methyl-9-oxo-, methyl ester, (11α,13E)-
Misoprostil
UNII:0E43V0BB57
(11a,13E)-(±)-11,16-Dihydroxy-16-methyl-9-oxoprost-13-en-1-oic Acid Methyl Ester
Misoprostol
methyl 7-{(1R,2R,3R)-3-hydroxy-2-[(1E)-4-hydroxy-4-methyloct-1-en-1-yl]-5-oxocyclopentyl}heptanoate
Methyl-7-{(1R,2R,3R)-3-hydroxy-2-[(1E)-4-hydroxy-4-methyloct-1-en-1-yl]-5-oxocyclopentyl}heptanoat
Misogon
DL-MISOPROSTOL
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