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Methylergometrine

HCID 8226
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
113-42-8
Standard SMILES
CC[C@@H](CO)NC(=O)[C@@H]1C=C2c3cccc4[nH]cc(c34)C[C@H]2N(C)C1
InChIKey
UNBRKDKAWYKMIV-QWQRMKEZSA-N
Molecular formula
C20H25N3O2
Average molar mass
339.4 g/mol
Monoisotopic mass
339.19467705

Overview

(6aR,9R)-N-[(2S)-1-hydroxybutan-2-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide is an ergoline alkaloid.

Names & identifiers

Preferred name
Methylergometrine
IUPAC
(6aR,9R)-N-[(2S)-1-hydroxybutan-2-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
English name
METHYLERGONOVINE
Molecular formula
C20H25N3O2
Molecular weight
339.43

Names & synonyms

methylergonovineMethylergometrineMethylergobasinMethylergobasineMethylergobrevinMethylergometrinMethylergonovin113-42-8ParterginBasofortinaErgotylMetilergometrina
Show more names
Prestwick_727MethylergosineMethylergonovine-D3METHYLERGONOVINE USP/EP/BP
MetherginMethylergometrinumErgometrine, methyl-D-Lysergic acid-(+)-butanolamide-(2)(6aR,9R)-N-[(2S)-1-hydroxybutan-2-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamideN-(alpha-(Hydroxymethyl)propyl)-D-lysergamideW53L6FE61VD-lysergic acid 1-butanolamide

Database identifiers

CAS
113-42-8
PubChem CID
8226
DTXSID
DTXSID00904978
ChEMBL
CHEMBL1201356
ChEBI
CHEBI:92607
UNII
W53L6FE61V
EC Number
204-027-0
Nikkaji
J5.132B

Properties

Computed structural properties

XLogP
2.3
Topological polar surface area
68.4 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
3
Rotatable bonds
4
Heavy atoms
25
Formal charge
0
Complexity
549

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
LogP1.2
Color/Form · 2 items

Prisms from methanol, acetone

Shiny crystals from benzene

Solubility · 5 items

Soluble in ethanol, acetone

Freely soluble in alcohol, acetone

Sparingly soluble in water

Insoluble in water

2.04e-01 g/L

Human Drugs · 3 items

Breast Feeding; Lactation; Milk, Human; Ergot Alkaloids; Oxytocics

Pharmaceuticals

Uterotonics

DecompositionWhen heated to decomposition it emits toxic fumes of /nitrogen oxides/.
Melting Point · 2 items

172 °C with some decomposition

172 °C

Optical RotationSpecific optical rotation: -45 deg at 20 °C/D
Physical Description

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Hazard information

Other Safety InformationIMAP assessments - Ergoline-8-carboxamide, 9,10-didehydro-N-[1-(hydroxymethyl)propyl]-6-methyl-, [8.beta.(S)]-: Environment tier I assessment
FDA Requirements · 1 item

The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including methylergonovine maleate, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Methylergonovine maleate/

Hazardous Reactivities and IncompatibilitiesErgonovine maleate and methylergonovine maleate injections are reportedly incompatible with various drugs, but the compatibility depends on several factors (e.g., concentration of the drugs, resulting pH, temperature).

Safety & protection

Fire Fighting Procedures · 2 items

Water spray, dry chemical, carbon dioxide or foam as appropriate for surrounding fire and materials.

As with all fires, evacuate personnel to a safe area. Firefighters should use self-contained breathing equipment and protective clothing.

Storage Conditions · 2 items

Tablets: Store below 25 °C (77 °F); in tight, light-resistant container.

Store in tight, light-resistant container as defined in the USP-NF. This material should be handled and stored per label instructions to ensure product integrity. Store in a refrigerator.

Cleanup Methods · 1 item

Wear approved respiratory protection, chemically compatible gloves and protective clothing. Wipe up spillage or collect spillage using a high efficiency vacuum cleaner. Avoid breathing dust. Place spillage in appropriately labeled container for disposal. Wash spill site.

Chemistry & industry

Pharmacology

ATC Code · 3 items

G02AB01

G - Genito urinary system and sex hormones

QG - Genito urinary system and sex hormones

Pharmacodynamics · 1 item

Methylergometrine is a semisynthetic ergot alkaloid and a derivative of ergonovine and is used for the prevention and control of postpartum and post-abortion hemorrhage. In general, the effects of all the ergot alkaloids appear to results from their actions as partial agonists or antagonists at adrenergic, dopaminergic, and tryptaminergic receptors. The spectrum of effects depends on the agent, dosage, species, tissue, and experimental or physiological conditions. All of the alkaloids of ergot significantly increase the motor activity of the uterus. After small doses contractions are increased in force or frequency, or both, but are followed by a normal degree of relaxation. As the dose is increased, contractions become more forceful and prolonged, resting tonus is markedly increased, and sustained contracture can result.

Mechanism of Action · 5 items

Methylergometrine acts directly on the smooth muscle of the uterus and increases the tone, rate, and amplitude of rhythmic contractions through binding and the resultant antagonism of the dopamine D1 receptor. Thus, it induces a rapid and sustained tetanic uterotonic effect which shortens the third stage of labor and reduces blood loss.

Methylergonovine acts directly on the smooth muscle of the uterus and increases the tone, rate, and amplitude of rhythmic contractions. Thus, it induces a rapid and sustained tetanic uterotonic effect which shortens the third stage of labor and reduces blood loss.

Ergonovine maleate and methylergonovine maleate are pharmacologically similar. Both drugs directly stimulate contractions of uterine and vascular smooth muscle. Following administration of usual therapeutic doses of ergonovine or methylergonovine, intense contractions of the uterus are produced and are usually followed by periods of relaxation. Larger doses of the drugs, however, produce sustained, forceful contractions followed by only short or no periods of relaxation. The drugs increase the amplitude and frequency of uterine contractions and uterine tone which in turn impede uterine blood flow. Ergonovine and methylergonovine also increase contractions of the cervix.

Ergonovine and methylergonovine produce vasoconstriction, mainly of capacitance vessels; increased central venous pressure, elevated blood pressure, and, rarely, peripheral ischemia and gangrene may result. Methylergonovine reportedly may interfere with prolactin secretion, but this effect has not been definitely established.

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Solid
Stability/Shelf LifeIt must be protected from light and heat /Maleate/
Collision Cross Section183.03 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Other Experimental Properties · 2 items

SPECIFIC ROTATION: +44 TO +55; PH (1 IN 5000 SOLN) BETWEEN 4.4 & 5.2 /MALEATE/

Odorless; bitter taste; white to pinkish-tan microcrystalline powder; slightly soluble in water, alcohol; very slightly soluble in ether, chloroform /Methylergonovine maleate/

Physicochemical properties

Melting point
172 · 172-173℃ (decomposition)
alpha
20 · D20 -45° (c = 0.4 in pyridine)
Boiling point
475.4 °C · 475.4°C (rough estimate)
Density
1.1492 · 1.1492 (rough estimate)
refractive index
1.665 · 1.6650 (estimate)
storage temp.
Desiccate at RT
pka
6.65 · pKa 6.65± 0.03(H2O,t =24,I<0.01)(Approximate)
color
2 CO · Prisms from MeOH/Me2CO
FDA UNII
53 L6FE61V · W53L6FE61V
ATC code
2 AB01 · G02AB01
Hazardous Substances Data
113 · 113-42-8(Hazardous Substances Data)
Toxicity
50 orl-rat: · LD50 orl-rat: 93 mg/kg 27ZIAQ -,163,73
Disposal Methods · 2 items

SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.

SRP: At the time of review, regulatory criteria for small quantity disposal are subject to significant revision, however, household quantities of waste pharmaceuticals may be managed as follows: Mix with wet cat litter or coffee grounds, double bag in plastic, discard in trash.

Preventive Measures · 3 items

This material is assumed to be combustible. As with all dry powders it is advisable to ground mechanical equipment in contact with dry material to dissipate the potential buildup of static electricity.

As a general rule, when handling USP Reference Standards avoid all contact and inhalation of dust, mists, and/or vapors associated with the material. Wash thoroughly after handling.

/Wear/ chemically compatible /gloves/ and safety goggles and glasses /for eye protection/. Protect exposed skin.

Personal Protective Equipment (PPE) · 2 items

Engineering controls such as exhaust ventilation are recommended.

Use a NIOSH-approved respirator, if it is determined to be necessary by an industrial hygiene survey involving air monitoring. In the event that a respirator is not required, an approved dust mask should be used.

Toxicology

Treatment · 1 item

Treatment for ergotism consists of vasodilators, anticoagulants and low molecular weight dextrans. If necessary, a sympathetic nerve blockade may be carried out, such as brachial plexus blockade. Temporary sedation (e.g. haloperidol) will be necessary in hallucination and diazepam is used for convulsions. There is no specific antidote. (L1921)

Interactions · 4 items

Caffeine enhances action of ergot alkaloids in treatment of migraine... /Ergot alkaloids/

Peripheral and coronary vasoconstriction may be antagonized by nitrites or papaverine. /Ergot alkaloids/

Concomitant use of methylergonovine and inhibitors of cytochrome (CYP) 3A4 may result in vasospasm, cerebral ischemia, and/or ischemia of the extremities. Concomitant use of ergot alkaloids and human immunodeficiency virus (HIV) protease inhibitors, delavirdine, or nevirapine is contraindicated.

Intravenous atropine sulphate following methylergonovine maleate administration may lead to severe hypertension and tachycardia.

Health EffectsIngestion of ergoline alkaloids is known to cause the disease ergotism. Ergotism occurs in two forms, gangrenous and convulsive, likely depending on the different kinds and amounts of ergoline alkaloids present. (A2913)
Exposure RoutesIngestion (L1920). Absorption is rapid after oral (60% bioavailability) and intramuscular (78% bioavailability) administration.
Milk Concentrations · 3 items

/EXPERIMENTAL:/ Methylergometrine concentrations in the maternal plasma and breast milk were determined by a radioimmunoassay during continuous treatment with 0.125 mg of methylergometrine 3 times daily. On the fifth postpartum day at 8:00 a.m. the patients (n=8) took 2 tablets of Myomergin (0.250 mg of methylergometrine) orally, and the levels in the plasma and milk were determined at 1 and 8 hr after the drug administration. Measurable amounts of the drug were found only in 5 out of 16 milk samples. It was concluded that this oxytocic drug does not appear in the breast milk in quantities sufficient to affect the infant. No accumulation in the plasma or in the breast milk was found.

Reports on the effect of methylergometrine hydrogenmaleate (MEM) on prolactin (PRL) secretion and lactation are still controversial. Therefore a prospective study was designed to follow the influence of MEM on post-partum PRL levels and milk production. MEM was given orally to 30 post-partum women from day 1 to day 7 in a daily dose of 0.6 mg. Thirty untreated women served as control. PRL plasma levels and milk yield were compared at day 1, 3 and 7. PRL levels were significantly lower in the treated group at day 7 (P less than 0.01), while the difference at day 3 was statistically not significant. Milk yield was significantly reduced at day 3 (P less than 0.05) and day 7 (P less than 0.01). These results indicate PRL inhibiting properties of MEM resulting consequently in reduced lactation.

Methylergonovine has been detected in the milk of lactating women, but apparently not in quantities sufficient to affect nursing infants.

Toxicity Summary · 1 item

Ergoline alkaloids have been shown to have the significant affinity towards the 5-HT1 and 5-HT2 serotonin receptors, D1 and D2 dopamine receptors, and alpha-adrenergic receptors. This can result in a number of different effects, including vasoconstriction, convulsions, and hallucinations. (A2914, A2915, A2916)

Signs and Symptoms · 1 item

Convulsive ergotism can cause painful seizures and spasms, diarrhea, paresthesias, itching, headaches, nausea and vomiting. Usually the gastrointestinal effects precede the central nervous system effects. As well as seizures there can be hallucinations and mental effects including mania or psychosis. Gangrenous ergotism causes dry gangrene as a result of vasoconstriction induced in the more poorly vascularized distal structures, such as the fingers and toes. Symptoms include desquamation, weak periphery pulse, loss of peripheral sensation, edema and ultimately the death and loss of affected tissues. (L1920)

Human Toxicity Excerpts · 5 items

/HUMAN EXPOSURE STUDIES/ Reports on the effect of methylergometrine hydrogenmaleate (MEM) on prolactin (PRL) secretion and lactation are still controversial. Therefore a prospective study was designed to follow the influence of MEM on post-partum PRL levels and milk production. MEM was given orally to 30 post-partum women from day 1 to day 7 in a daily dose of 0.6 mg. Thirty untreated women served as control. PRL plasma levels and milk yield were compared at day 1, 3 and 7. PRL levels were significantly lower in the treated group at day 7 (P less than 0.01), while the difference at day 3 was statistically not significant. Milk yield was significantly reduced at day 3 (P less than 0.05) and day 7 (P less than 0.01). These results indicate PRL inhibiting properties of MEM resulting consequently in reduced lactation.

/SIGNS AND SYMPTOMS/ Symptoms of acute overdose may include: nausea, vomiting, abdominal pain, numbness, tingling of the extremities, rise in blood pressure, in severe cases followed by hypotension, respiratory depression, hypothermia, convulsions, and coma.

/SIGNS AND SYMPTOMS/ Several cases of accidental Methergine injection in newborn infants have been reported, and in such cases 0.2 mg represents an overdose of great magnitude. However, recovery occurred in all but one case following a period of respiratory depression, hypothermia, hypertonicity with jerking movements, and, in one case, a single convulsion.

/SIGNS AND SYMPTOMS/ Most common...symptoms are headache, nausea, vomiting, diarrhea, and dizziness. Also there may be noticeable weakness, formication, itching, and coldness of skin. Symptom ... referable to CNS are confusion, depression, drowsiness, and rarely, convulsions, hemiplegia, tabetic manifestations, and fixed miosis. /Ergot alkaloids/

For more Human Toxicity Excerpts (Complete) data for METHYLERGONOVINE (13 total), please visit the HSDB record page.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury · 5 items

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

methylergonovine

DILI Negative

Oral

DOI:10.1016/j.drudis.2019.09.022

Non-Human Toxicity Excerpts · 2 items

/LABORATORY ANIMALS: Acute Exposure/ Overdosage ... may ... /cause/ vomiting, diarrhea, dyspnea ... incoordination, epileptiform convulsions, and agalactia. /Ergonovine maleate/

/OTHER TOXICITY INFORMATION/ Ergot alkaloids specifically injure capillary endothelium, resulting in blocking of capillary flow and vascular stasis. This effect is followed by thrombosis in small arterioles and by dry gangrene. /Ergot alkaloids/

Probable Routes of Human ExposureNIOSH (NOES Survey 1981-1983) has statistically estimated that 295 workers (243 of these were female) were potentially exposed to methylergonovine in the US(1).

Regulatory information

FDA Requirements · 1 item

The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including methylergonovine maleate, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Methylergonovine maleate/

Safety data

Toxicity
LD50 orl-rat: 93 mg/kg 27ZIAQ -,163,73
Hazardous Substances Data
113-42-8(Hazardous Substances Data)

Ergot alkaloids are antagonists of actions of 5-hydroxytryptamine and of certain metabolic actions of catecholamines. /Ergot alkaloids/

Biological Half-Life · 3 items

3.39 hours

The plasma level decline was biphasic with a mean elimination half-life of 3.39 hours (range 1.5 to 12.7 hours).

Plasma concentrations of methylergonovine appear to decline in a biphasic manner. Following IV administration of methylergonovine to adults with normal renal function, the half-life of the drug in the initial phase (t1/2 alpha?) reportedly ranges from about 1-5 minutes and the half-life in the terminal phase (t1/2 beta) ranges from about 0.5-2 hours.

Metabolism/Metabolites · 3 items

Hepatic, with extensive first-pass metabolism.

Ergot alkaloids are mostly eliminated by hepatic metabolism and excretion, and the decrease in bioavailability following oral administration is probably a result of first-pass metabolism in the liver.

Hepatic, with extensive first-pass metabolism. Route of Elimination: Ergot alkaloids are mostly eliminated by hepatic metabolism and excretion, and the decrease in bioavailability following oral administration is probably a result of first-pass metabolism in the liver. Half Life: 3.39 hours

FDA Pharmacological Classification · 6 items

W53L6FE61V

METHYLERGONOVINE

Chemical Structure [CS] - Ergolines

Established Pharmacologic Class [EPC] - Ergot Derivative

Methylergonovine is an Ergot Derivative.

METHYLERGONOVINE

MeSH Pharmacological Classification · 1 item

Drugs that stimulate contraction of the myometrium. They are used to induce LABOR, OBSTETRIC at term, to prevent or control postpartum or postabortion hemorrhage, and to assess fetal status in high risk pregnancies. They may also be used alone or with other drugs to induce abortions (ABORTIFACIENTS). Oxytocics used clinically include the neurohypophyseal hormone OXYTOCIN and certain prostaglandins and ergot alkaloids. (From AMA Drug Evaluations, 1994, p1157)

Absorption, Distribution and Excretion · 6 items

Absorption is rapid after oral (60% bioavailability) and intramuscular (78% bioavailability) administration.

Ergot alkaloids are mostly eliminated by hepatic metabolism and excretion, and the decrease in bioavailability following oral administration is probably a result of first-pass metabolism in the liver.

56.1 ± 0 L

A delayed gastrointestinal absorption (Tmax about 3 hours) of methylergonovine tablets might be observed in postpartum women during continuous treatment with this oxytocic agent.

Pharmacokinetic studies following an iv injection have shown that methylergonovine is rapidly distributed from plasma to peripheral tissues within 2-3 minutes or less. The bioavailability after oral administration was reported to be about 60% with no accumulation after repeated doses. During delivery, with intramuscular injection, bioavailability increased to 78%. Ergot alkaloids are mostly eliminated by hepatic metabolism and excretion, and the decrease in bioavailability following oral administration is probably a result of first-pass metabolism in the liver.

Bioavailability studies conducted in fasting healthy female volunteers have shown that oral absorption of a 0.2 mg methylergonovine tablet was fairly rapid with a mean peak plasma concentration of 3243 +/- 1308 pg/mL observed at 1.12 +/- 0.82 hours.

Cellular LocationsMembrane

Uses & manufacturing

Uses · 2 items

MEDICATION

Methylergometrine is a synthetic analogue of ergonovine, an alkaloid of the ergoline family that occurs in various species of vines of the Convolvulaceae (morning glory) family and in some species of lower fungi like other ergoline alkaloids. Methylergometrine is a blood vessel constrictor and smooth muscle agonist most commonly used to prevent or control excessive bleeding following childbirth and spontaneous or elective abortion. It also causes uterine contractions to aid in expulsion of retained products of conception after a missed abortion (miscarriage in which all or part of the fetus remains in the uterus) and to help deliver the placenta after childbirth. The drug is currently prepared via reaction of (+)-lysergic acid with L-(+)-aminobutanol, using different coupling reagents, and is available under the name Methergine as tablets or injection (IM or IV) or in liquid form to be taken orally. (L1918, L1923)

Methods of Manufacturing · 3 items

METHYLERGONOVINE IS NOT /A/ NATURAL ERGOT ALKALOID. IT IS SYNTHESIZED FROM LYSERGIC ACID BY /THE/ SAME PROCEDURE AS THAT EMPLOYED FOR ERGONOVINE...EXCEPT THAT (+)-2-AMINO-1-BUTANOL IS USED TO FURNISH PEPTIDE MOIETY.

THE BASE, DISSOLVED IN SUITABLE SOLVENT, READILY YIELDS OFFICIAL MALEATE BY REACTION WITH EQUIMOLAR QUANTITY OF MALEIC ACID. /MALEATE/

Preparation: A. Stoll, A. Hofmann, US 2265207 (1941 to Sandoz).

Formulations/Preparations · 2 items

Methylergonovine Maleate preparations: (AHFS, 2011)

Basofortina; Methylergobrevin; Methergin; Ryegonovin; Spametrin-M. /Methylergonovine maleate/

Use ClassificationPharmaceuticals
General Manufacturing InformationMetabolite of methysergide
Applications · 3 items

UsesMethylergonovine is a drug currently used as a smooth muscle constrictor during postpartum hemorrhage, as an inhibitor of the inflammasome complex in ASC-mediated procaspase-1 activation screening.

UsesThis compound is a homologue of ergonovine.It is used in the treatment of postpartumhemorrhage.

UsesOxytocic.

Upstream & downstream products

Downstream products

6-methyl-9,10-didehydro-ergoline-8α-carboxylic acid-((S)-1-hydroxymethyl-propylamide)

Suppliers20 total

Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
湖北瑞玛标物科技有限公司15787879035 15787875101 · [email protected]
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南京望知星医药科技有限公司18569809817 · [email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
山东沃德森生物科技有限公司0531-88723173 18596073690 · [email protected]
Moxin Chemicals+86-17320513646 +86-17320513646 · [email protected]
湖北扬信医药科技有限公司15347293736 · [email protected]
青岛海智微元生物科技有限公司18317699790 18317699790 · [email protected]
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上海知邦生物医药有限公司021-54285032 18116461626 · [email protected]
中梦研(湖北)科技有限公司18062399888; 18062399888 · [email protected]
郑州艾克姆化工有限公司037163312495 13303845143 · [email protected]
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广州奥司汀生物技术有限公司15918640830 13268843209 · [email protected]

Additional notes

DefinitionChEBI: (6aR,9R)-N-[(2S)-1-hydroxybutan-2-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide is an ergoline alkaloid.