Methylergometrine

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Structural formula
Structural formula of methylergometrine
General
Non-proprietary name Methylergometrine
other names
  • N - (1-Hydroxy-2-butyl) -6-methyl-9,10-didehydroergoline-8 β -carbamide ( IUPAC )
  • Methylergometrinum ( Latin )
  • Methylergonovine
  • Methylergobasin
Molecular formula C 20 H 25 N 3 O 2
External identifiers / databases
CAS number
  • 113-42-8
  • 57432-61-8 (hydrogen maleate 1: 1)
  • 6209-37-6 (tartrate 2: 1)
EC number 204-027-0
ECHA InfoCard 100.003.661
PubChem 8226
ChemSpider 7933
DrugBank DB00353
Wikidata Q424477
Drug information
ATC code

G02 AB01

Drug class

Ergot alkaloids

properties
Molar mass 339.43 g · mol -1
Physical state

firmly

Melting point

172 ° C (decomposition); 185–195 ° C (hydrogen maleate)

pK s value

6.7 (24 ° C)

solubility

slightly soluble in water; Easily soluble in ethanol , acetone

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
06 - Toxic or very toxic 08 - Dangerous to health

danger

H and P phrases H: 301-311-331-361
P: 261-280-301 + 310-311
Toxicological data

93 mg kg −1 ( LD 50ratoral , methylergometrine maleate)

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Methylergonovine ( INN ), and methylergonovine or methylergobasine called, is a semi-synthetically from the ergot ergonovine manufactured drug . It is used in obstetrics to reduce bleeding and to contract the uterus (uterus) during the postpartum period and in the puerperium . In addition, this substance is the main metabolite of the migraine prophylactic drug methysergide . It is used as a tartrate and as a hydrogen maleate.

Methylergometrine was patented in 1941 by Sandoz , today a subgroup of the pharmaceutical company Novartis , and launched as a drug under the trade name Methergin .

Clinical information

application areas

Methylergometrine is mainly used in obstetrics to contract the uterus. The drug may only be given after the child's head has penetrated; it then reduces uterine bleeding and promotes uterine involution in the puerperium in women who are not breastfeeding. Another indication is bleeding after a miscarriage .

Methylergometrine is also orally effective, but since poisoning incidents following medication errors became known in Germany, it has only been used parenterally (as an intramuscular injection).

Contraindications

Medicines containing methylergometrine must not be used:

Special patient groups

Impaired kidney function

Since the Qo value of methylergometrine is high (Qo = 0.95), no dose adjustment is necessary in the case of impaired renal function. Many drugs with a high Qo value produce renally eliminated metabolites, the activity of which is not always known. Accordingly, caution should be exercised in the case of severe kidney function impairments.

Pregnant women

There is clear evidence of risks to the human fetus . Methylergometrine is absolutely contraindicated in pregnancy because of its pronounced uterotonic effect with an increased risk of miscarriage or premature labor . However, accidental use during the first trimester does not justify a risk-based termination of pregnancy .

Breastfeeding

Methylergometrine passes into breast milk . There have been isolated reports of intoxication in breastfed infants whose mothers have been treated with the drug for several days. One or more of the following symptoms (and their resolution after discontinuation of the drug) have been observed in the infant:

  • increased blood pressure, bradycardia, or tachycardia
  • Vomiting, diarrhea , restlessness, clonic convulsions

In view of possible adverse effects in the child, use is not recommended during breastfeeding. Methylergometrine is the second choice when other uterine-contracting substances such as oxytocin , prostaglandins or their derivatives are ineffective or contraindicated.

unwanted effects

Possible, dose-dependent adverse drug effects are:

Pharmacological properties

Methylergometrine acts as a highly active and specific uterotonic agent via serotonin receptors of the subtype 5-HT 2A on the smooth muscles of the uterus. It increases the basic tone, frequency and amplitude of rhythmic muscle contractions . At higher doses there is a risk of permanent contractions. Therefore, methylergometrine is contraindicated during labor.

Trade names

Methergine

literature

Web links

See also

Individual evidence

  1. ^ A b The Merck Index : An Encyclopedia of Chemicals, Drugs, and Biologicals, 14th Edition (Merck & Co., Inc.), Whitehouse Station, NJ, USA, 2006; ISBN 978-0-911910-00-1 .
  2. a b c Entry on methylergometrine. In: Römpp Online . Georg Thieme Verlag, accessed on July 15, 2019.
  3. Sean Sweetman (Editor): Martindale: The Complete Drug Reference, 35th Edition: Book and CD-ROM Package . Pharmaceutical Press, ISBN 978-0-85369-704-6 .
  4. a b Data sheet Methylergonovine maleate salt from Sigma-Aldrich , accessed on April 10, 2011 ( PDF ).
  5. Datasheet METHYLERGOMETRINE MALEATE CRS (PDF) at EDQM , accessed on October 12, 2009.
  6. Information letter for healthcare professionals on methergine. (PDF; 45 kB) BfArM , October 11, 2011, accessed on September 27, 2017 .
  7. a b c Technical information for: Methylergometrine hydrogen maleate ( Memento from May 13, 2014 in the Internet Archive ). (Sample text from the BfArM ; RTF ; 71 kB), as of January 16, 2009.
  8. Dose adjustment in case of renal insufficiency with Dosing ( Memento of June 19, 2009 in the Internet Archive ).
  9. Christof Schaefer, et al .: Medication prescription during pregnancy and breastfeeding. Elsevier, Urban & Fischer, Munich 2007, ISBN 978-3-437-21332-8 .
  10. Heinz Pertz, Eckart Eich: Ergot alkaloids and their derivatives as ligands for serotoninergic, dopaminergic and adrenergic receptors . In: Vladimír Křen, Ladislav Cvak (eds.): Ergot: the genus Claviceps . CRC Press, 1999, ISBN 978-90-5702-375-0 , pp. 411-440.