CAS 59122-46-2|Misoprostol

Introduction：Basic information about CAS 59122-46-2|Misoprostol, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Misoprostol BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Articles94
7. Synonyms

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	Signal Word	Danger

Names

Name	Misoprostol
Synonym	More Synonyms

Misoprostol BiologicalActivity

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	Signaling Pathways >>GPCR/G Protein >>Prostaglandin ReceptorResearch Areas >>Endocrinology
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

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

Signaling Pathways >>GPCR/G Protein >>Prostaglandin ReceptorResearch Areas >>Endocrinology

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
InChIKey	OJLOPKGSLYJEMD-URPKTTJQSA-N
SMILES	CCCCC(C)(O)CC=CC1C(O)CC(=O)C1CCCCCCC(=O)OC
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
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

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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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