Misoprostol

HCID 5282381CAS 59122-46-2

기본 정보

표준 SMILES
CCCCC(C)(O)C/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)OC
InChIKey
OJLOPKGSLYJEMD-URPKTTJQSA-N
분자식
C22H38O5
평균 분자량
382.5 g/mol
단동위원소 질량
382.27192432

개요

Misoprostol can cause developmental toxicity according to state or federal government labeling requirements.

이름 및 식별자

우선 이름
Misoprostol
IUPAC
methyl 7-[(1R,2R,3R)-3-hydroxy-2-[(E)-4-hydroxy-4-methyloct-1-enyl]-5-oxocyclopentyl]heptanoate
영어명
Misoprostol
분자식
C22H38O5
분자량
382.54

이름 및 동의어

misoprostol59122-46-2CytotecMisoprostolumSC-29333SC 29333misoprostoloMysodelleTopogyneDTXSID7020897Apo MisoprostolNovo Misoprostol
이름 더 보기
MisoprostoMisoprostol Powder(11α,13E)-(-)-11,16-Dihydroxy-16-methyl-9-oxo-prost-13-en-1-oicacidmethylesterSC 2933MisogonMisoprostilMesoprostal
0E43V0BB57ARTHROTEC COMPONENT MISOPROSTOLDTXCID70897methyl (11alpha,13E)-11,16-dihydroxy-16-methyl-9-oxoprost-13-en-1-oatemethyl 7-[(1R,2R,3R)-3-hydroxy-2-[(1E)-4-hydroxy-4-methyloct-1-en-1-yl]-5-oxocyclopentyl]heptanoateProst-13-en-1-oic acid, 11,16-dihydroxy-16-methyl-9-oxo-, methyl ester, (11alpha,13E)-Misoprostol 1%methyl 7-((1R,2R,3R)-3-hydroxy-2-((1E)-4-hydroxy-4-methyloct-1-en-1-yl)-5-oxocyclopentyl)heptanoate

데이터베이스 식별자

CAS
59122-46-2
PubChem CID
5282381
DTXSID
DTXSID7020897
ChEMBL
CHEMBL606
ChEBI
CHEBI:94387
UNII
0E43V0BB57
EC Number
664-288-5
Nikkaji
J345.358H

물성

구조 계산 물성

XLogP
3.7
극성 표면적
83.8 Ų
수소 결합 공여자 수
2
수소 결합 수용자 수
5
회전 가능 결합 수
14
무거운 원자 수
27

실험 및 물리화학적 성질

LogP3.6
Color/Form · 2건

Light yellow oil

Viscous liquid

Solubility · 3건

1.6mg/mL

Water-soluble

1.64e-02 g/L

Human Drugs · 4건

Breast Feeding; Lactation; Milk, Human; Abortifacient Agents, Nonsteroidal; Anti-Ulcer Agents; Prostaglandins; Oxytocics; Gastrointestinal Agents

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Medicines for medical abortion

Melting Point261-263
Physical DescriptionLiquid

물리화학적 성질

녹는점
261 · 261-263°C
끓는 점
429.67 °C · 429.67°C (rough estimate)
밀도
1.0323 · 1.0323 (rough estimate)
굴절률
1.612 · 1.6120 (estimate)
저장 조건
-20 °C · Sealed in dry,Store in freezer, under -20°C
용해도
물에는 거의 녹지 않으며, 에탄올(96%)에는 녹고, 아세토니트릴에는 거의 녹지 않습니다.
화학적 성질 · 1건

Misoprostol is a yellow, viscous liquid with a musty odour. Miscible with ethanol, ether or chloroform, extremely insoluble in water or n-hexane. Very unstable at room temperature and undergoes thermal epimerization to the 8-isomer. It is also extremely sensitive to the Ph value. It removes the hydroxyl group at the 11α position in acidity and alkalinity, converts it into A-type prostaglandins, and isomerizes into B-type prostaglandins. However, it is relatively stable in the dispersion system of hydroxypropyl methylcellulose and can be stored at room temperature.

안전 및 규제

GHS 분류

GHS Classification · 4건

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P203, P264, P270, P280, P301+P316, P318, P321, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Regulatory InformationHazard Traits - Developmental Toxicity
FDA Requirements · 1건

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

Hazard Classes and CategoriesAcute Tox. 3 (100%)

안전 및 보호

Storage ConditionsCommercially available misoprostol tablets should be stored in a dry place in well-closed containers at a temperature less than 30 °C.
Disposal Methods · 1건

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

독성 정보

Interactions · 5건

Concurrent use /of magnesium-containing antacids/ with misoprostol may aggravate misoprostol induced diarrhea.

This study aimed to investigate the effect of acetaminophen on the hepatic microvasculature using a vascular casting technique. Acetaminophen was admin at a dose of 650 mg/kg body weight (ip) to fasted male Long Evans rats. Microvascular casting was performed at various points after drug admin. Liver casts from control rats showed good patency with normal hepatic microvasculature. Thirty-six hr after overdose with acetaminophen, liver casts showed rounded centrilobular cavities of various sizes, representing regions in which cast-filled sinusoids were absent with relatively normal microvasculature within periportal regions. Evidence of microvascular injury occurred as early as 5 hr after acetaminophen overdose. This injury consisted of changes to centrilobular sinusoids inc areas of incomplete filling and dilated centrilobular sinusoids. Misoprostol ... treatment (6 x 25 ug/kg) given before and after acetaminophen admin markedly reduced the extent of microvascular injury with only small focal unfilled areas in the casts and a generally intact microvasculature. In conclusion, this study shows that overdosage with acetaminophen resulted in an extensive, characteristic pattern of hepatic microvascular injury in the centrilobular region. The results also suggest that microvascular injury is an early event in the pathogenesis of acetaminophen hepatotoxicity. Misoprostol was found to protect against injury occurring at the microvascular level.

Cyclosporin A has markedly improved graft survival in transplant patients but its side effects, such as renal toxicity and hypertension, pose management problems in transplant recipients. This toxicity has been attributed to prostaglandin inhibition. Concurrent admin of misoprostol ... prevents chronic cyclosporin A-induced nephrotoxicity but not hypertension in rats.

The effects of misoprostol on indomethacin-induced decline in renal function were studied in 6 normotensive and 6 hypertensive female patients (mean age 60.5 yr) who were given 25 mg of indomethacin every 6 hr for 3 days, 200 ug of misoprostol every 6 hr for 3 days, and both together for 3 days, with a 4 day washout period between treatments. All patients received a salt-restricted diet, and the hypertensive patients were treated with hydrochlorothiazide. Three of the hypertensive patients and 3 of the normotensive patients had a decr in glomerular filtration rate (GFR) assoc with indomethacin therapy. when misoprostol was given with the indomethacin, 4 of these 6 patients did not experience a decline in GFR. It in concluded that misoprostol ameliorates indomethacin-induced renal dysfunction in salt-restricted and diuretic-treated middle aged women with normal serum creatinine.

Misoprostol ... was given simultaneously with acetylsalicylic acid in a double-blind, placebo-controlled randomized prospective study of 32 healthy human male subjects. Fecal blood loss was measured for 8 days ... Aspirin (650 mg qid) and misoprostol (25 ug qid) or placebo were given during days 3, 4, and 5. there was a significant (P < 0.05) incr in median blood loss ... from 0.81 to 6.05 ml/day in the aspirin with placebo group (n=16). Median blood loss was incr (from 0.75 to 3.75 ml/day)in the aspirin with misoprostol group (n=16), but this was significantly less ... than the placebo group. Mean serum salicylate concn in the placebo and misoprostol groups were similar (7.8 and 6.8 ug/ml, respectively). There were no significant changes in laboratory values in any of the subjects studied, nor were any major side-effects encountered. This study demonstrates that oral misoprostol reduced aspirin-induced GI bleeding even when admin simultaneously and at a dose level below its threshold for significant acid inhibition. This indicates a potential role for misoprostol in the prevention of gastric mucosal damage in selected patients.

Adverse Effects · 1건

The most commonly reported adverse effects of misoprostol are generally mild and include shivering, chills, diarrhea, abdominal pain, hyperthermia, nausea, vomiting, flatulence, constipation, dyspepsia, headache, breakthrough bleeding, and menstrual irregularities. Less frequently reported mild adverse effects include syncope, lethargy, weakness, and vertigo.

Toxicity Summary · 1건

Misoprostol is generally safe and well-tolerated at standard doses of 400 to 800 mcg.However, a rare case of maternal death has been reported following a misoprostol overdose. A self-administered overdose of 12 mg for a medical abortion resulted in upper gastrointestinal bleeding, hemodynamic instability, and multiorgan failure. Emergency laparotomy revealed gastric and esophageal necrosis, and the patient ultimately succumbed to cardiac arrest despite adequate resuscitation efforts.

Human Toxicity Excerpts · 5건

Misoprostol should not be used in pregnant women or women of childbearing age. In one clinical trial, bleeding occurred in about 50% of pregnant women in the first trimester, and complete or incomplete abortion was induced in 7%. Misoprostol is classified in FDA Pregnancy Category X.

Minor adverse effects include mild nausea, abdominal discomfort, dizziness, and headache; diarrhea has occurred in 14% to 40% of patients.

Following acute misoprostol overdose, sedation, tremor, seizures, dyspnea, abdominal pain, diarrhea, fever, palpitation, hypotension, or bradycardia may occur.

The efficacy and tolerability of mifepristone in combo with misoprostol for termination of early pregnancy (up to 49 days of amenorrhea) are established. We studied the efficacy and tolerability of this combo therapy for termination of pregnancy in women up to 63 days of amenorrhea. We also examined the effect of an additional dose of misoprostol in cases of nonexpulsion within 3 hr after the first dose. The multicenter trial included 1,108 women, mean age 27.9 + or - 6.2 yr. The mean duration of pregnancy was 51.7 + or - 9.2 days. On day 1, the women received an po dose of mifepristone, 600 mg. On day 3, they received an oral dose of misoprostol, 400 ug, and were monitored for up to 3 hr. If they did not expel the conceptus within 3 hr, an additional dose of 200 ug of misoprostol was given and they were monitored for 2 more hours. From days 10-18, the women were followed up with clinical exam, human chorionic gonadotropin measurement, or ultrasound exam. overall, the procedure was successful in 92.9% of women. Efficacy decr with the duration of pregnancy, esp after 56 days of amenorrhea. Up to 42 days of amenorrhea, the success rate was 97.6%; between days 42 and 49, 94.8%; between days 50 and 56, 93.4%; between days 57 and 63, 86.8%; and after day 63, 83.3%. The most common side effects were moderate uterine cramps (80.5) and GI symptoms (34.9), esp vomiting (18.3) and diarrhea (10.5). GI symptoms were generally mild. A second dose of misoprostol was given to 61.6% of the women. In a subgroup analysis, we assessed the efficacy of 600 mg of mifepristone plus 400 or 600 ug of misoprostol (one or two doses) in women with up to 49 days of amenorrhea and compared it with the efficacy in women who received mifepristone plus only 400 ug (one dose) of misoprostol in a previous study. The overall rate of success (termination of pregnancy) was 95.5% in the current study compared with 95.$ in the previous study. The additional dose of misoprostol did not significantly incr the overall rate of success, but did incr the rate of termination within the monitoring period (69.7% versus 64.9% (and within 72 hours after admin of mifepristone (92.7% versus 90.4%). We have confirmed that the combo of mifepristone and misoprostol was effective, safe, and well tolerated for termination of pregnancies at 49 or fewer days of amenorrhea. The efficacy decr slightly between 49 and 56 days, and then decr significantly between 56 and 62 days.

For more Human Toxicity Excerpts (Complete) data for MISOPROSTOL (8 total), please visit the HSDB record page.

Drug Induced Liver Injury · 6건

Drug Induced Liver Injury Rank (DILIrank 2.0)

Misoprostol

Ambiguous-DILI-concern

3

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

Non-Human Toxicity Excerpts · 5건

In animals, overdosage of misoprostol produces diarrhea, GI lesions, emesis, tremors, mydriasis, focal cardiac necrosis, hepatic necrosis, renal tubular necrosis, testicular atrophy, hypertrophy of mucous cells, deepening of gastric pits, respiratory difficulties, reduced motor activity, and CNS depression.

No evidence of misoprostol-induced mutagenicity was seen with several in vitro test systems, including the microbial (Ames test), mammalian (mouse lymphoma), sister chromatid exchange, Saccharomyces cerevisiae point mutation, and cell transformation assays, all performed with and without metabolic activation.

No evidence of carcinogenic potential was seen in rats and mice receiving oral misoprostol dosages up to 2.4 and 16 mg/kg (about 150 and 1000 times the usual human dosage) for 24 and 21 months, respectively. Hyperplasia of gastric mucosa was observed in dogs receiving oral misoprostol dosages of 300 ug/kg daily for 13 weeks.

Prostaglandins appeared protective against acute experimental liver injury of different origin. Misoprostol, stable, orally active, synthetic derivative of PGE1 attenuates several functional alterations in liver mitochondria during ethanol admin. To study its possible hepatoprotective effects on ethanol-induced liver injury in rats we measured: serum activities of alanine aminotransferase (ALT), gamma-glutamyltranspeptidase (GGT) and concn of ammonia in blood and liver tissue. Histopathological evaluation of liver slices was also performed. Activities of both enzymes and ammonia values were elevated after intragastric ethanol admin for 60 days. Treatment for 30 days with misoprostol resulted in their decr. This effect was not observed in the control group. Beneficial results were also obtained in histopathological evaluation of the liver tissue. These results indicate potential therapeutic effects of misoprostol on ethanol-induced liver injury in rats.

The radioprotective nature of misoprostol was extended to examine its ability to influence clonogenic cell survival and induction of oncogenic transformation in Syrian hamster embryo cells exposed to X rays in utero and assayed in vitro. Hamsters in their 12th day of pregnancy were injected sc with misoprostol, and 2 hr later the pregnant hamsters were exposed to graded doses of X rays. Immediately after irradiation, hamsters were euthanized and embryonic tissue was explanted into culture dishes containing complete growth medium. After a 2-wk incubation period, clonogenic cell survival and morphologically transformed foci were determined. Survival of misoprostol-treated SHE cells were incr and yielded a dose reduction factor of 1.5 compared to SHE cells treated with X rays alone. In contrast, radiation-induced oncogenic transformation of misoprostol-treated cells was reduced by a factor of 20 compared to cells treated with X rays alone. These studies suggest that misoprostol not only protects normal tissues in vivo from acute radiation injury, but also protects cells, to a large extent, from injury leading to transforming events.

규제 정보

FDA Requirements · 1건

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

안전 데이터

wgk
2
rtecs
UK8390000
ridadr
UN 2810 6.1/PG 3
독성
LD50 in rats, mice (mg/kg): 40-62, 70-160 i.p.; 81-100, 27-138 orally (Kotsonis)
HS 번호
2937500000
risk_code
45-60-61-25-36/37/38

화학 및 산업

약리 정보

ATC Code · 6건

A02BB01

G - Genito urinary system and sex hormones

A - Alimentary tract and metabolism

QA - Alimentary tract and metabolism

QG - Genito urinary system and sex hormones

G02AD06

Protein BindingMisoprostol is <90% protein bound in serum. Its active metabolite, misoprostol acid, is 81-89% protein bound in serum.
Pharmacodynamics · 1건

Misoprostol is a prostaglandin E1 analog used to reduce the risk of NSAID induced gastric ulcers by reducing secretion of gastric acid from parietal cells. Misoprostol is also used to manage miscarriages and used alone or in combination with mifepristone for first trimester abortions. An oral dose of misoprostol has an 8 minute onset of action and a duration of action of approximately 2 hours, a sublingual dose has an 11 minute onset of action and a duration of action of approximately 3 hours, a vaginal dose has a 20 minute onset of action and a duration of action of approximately 4 hours, and a rectal dose has a 100 minute onset of action and a duration of action of approximately 4 hours.

Mechanism of Action · 3건

Misoprostol is a synthetic prostaglandin E1 analog that stimulates prostaglandin E1 receptors on parietal cells in the stomach to reduce gastric acid secretion. Mucus and bicarbonate secretion are also increased along with thickening of the mucosal bilayer so the mucosa can generate new cells. Misoprostol binds to smooth muscle cells in the uterine lining to increase the strength and frequency of contractions as well as degrade collagen and reduce cervical tone.

Misoprostol enhances natural gastromucosal defense mechanisms and healing in acid-related disorders, probably by increasing production of gastric mucus and mucosal secretion of bicarbonate.

Misoprostol inhibits basal and nocturnal gastric acid secretion by direct action on the parietal cells; also inhibits gastric acid secretion stimulated by food, histamine, and pentagastrin. It decreases pepsin secretion under basal, but not histamine stimulation. Misoprostol has no significant effect on fasting or postprandial gastrin or intrinsic factor output.

Biological Half-Life · 2건

The half life of an 800µg oral dose is 1.0401±0.5090h, for a sublingual dose is 0.8542±0.1170h, and for a buccal dose is 0.8365±0.1346h.

Terminal - 20-40 minutes

Metabolism/Metabolites · 2건

Misoprostol is de-esterified to its active metabolite, misoprostol acid, also known as SC-30695. This metabolite is further reduced to dinor and tetranor metabolites (SC-41411), a prostaglandin F<sub>1</sub> (PGF<sub>1</sub>) analog of SC-41411, and a ω-16-carboxylic acid derivative. However, the majority of these metabolites are not well described in the literature.

Rapidly de-esterified to misoprostol acid (primary biologically active metabolite). The de-esterified metabolite undergoes further metabolism by beta and omega oxidation, which can take place in various tissues in the body.

용도 및 제조

Uses · 2건

Anti-ulcerative

Use (kg) in USA (2002): 14

Methods of ManufacturingPrepn: P.W. Collins, R. Pappo, Belg. pat. 827,127; eidem, U.S. pat. 3,965,143 (1975, 1976 both to Searle); P. W. Collins et al., Tetrahedron Letters 48, 4217 (1975); H.C. Kluender et al., U.S. pat. 4,132,738 (1979 to Miles)
Formulations/Preparations · 2건

Misoprostol contains approximately equal amounts of the two diastereomers

Cytotec oral tablets contain either 100 mcg or 200 mcg of misoprostol

응용 분야 · 3건

개요Misoprostol 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.

역사Misoprostol was discovered by Searle in 1973, it has undergone extensive clinical evaluation for peptic ulcer dis-ease and related conditions. It is a synthetic prostaglandin E1 analog approved by the US Food and Drug Administration (FDA) for preventing and treating gastric ulcers induced by nonsteroidal anti-inflammatory drugs (NSAIDs). Misoprostol has 4 primary effects, which include cytoprotection of the gastrointestinal mucosa, uterotonic properties, and the adverse effects of diarrhea, abdominal pain, and nausea. Although not FDA-approved, misoprostol is indicated for the short-term treatment of active duodenal or gastric ulcers caused by factors other than NSAIDs.

용도Misoprostol 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.

제조 방법 · 1건

synthesis of MisoprostolTo a 1000 ml dried flask under a nitrogen atmosphere was added 74.6 g of(E)-trimethyl-[[1-methyl-1-[3-(tributylstannyl)-2-propenyl]pentyl]oxy]silane,125 ml anhydrous THF and 24.2 g of copper (I) iodide. The mixture wasstirred at room temperature for 30 minutes and then it was cooled to -25 to -30°C. 98.8 ml of methyllithium (2.86 M) in DEM was added dropwise and theresultant solution was stirred at -15°C for 2 hours. Then the reaction mixturewas cooled to -78°C and 25 g of methyl-5-oxo-3-[(triethylsilyl)oxy]-1-cyclopentene-1-heptanoate in 100 ml of THF was added rapidly. After stirringthe mixture for 5 min at -78°C, it was quenched into a mixture of 750 ml ofaqueous ammonium chloride solution and 200 ml of ammonium hydroxide.The resulting mixture was warmed to room temperature and stirred until adeep blue aqueous layer was obtained. Ethyl acetate (250 ml) was used forextraction. Then the combined organic layers were washed with brine andsubsequently dried over magnesium sulfate. After a filtration andconcentration under reduced pressure, an oil (105 g) was obtained. This oilcontaining the protected prostaglandin was subjected to acidic deprotection(cat. PPTS, acetone and water) and purification (chromatography on silica gel)to provide 15.8 g (60%) of misoprostol was identical.

공급사50 곳

北京华美互利生物化工010-56205725 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Shanghai Biolang Biotechnology Co., Ltd.+86-15970428662 +86-13397199602 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
广州隽沐生物科技股份有限公司020-36607679; 13502246435 · [email protected]

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