Meptazinol
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| 1: 1 mixture of ( R ) -form (top) and ( S ) -form (bottom) |
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| Non-proprietary name | Meptazinol | |||||||||
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Opioid analgesic |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | ||||||||||
Meptazinol (trade name Meptid ® , manufactured by Riemser drug ) is an opioid - analgesic for moderate to severe pain of various causes. Along with tramadol and nalbuphine, meptazinol is one of the three injectable opioid analgesics that are not covered by the BtMG . The analgesic potency is 0.1 times that of morphine . There is no dependency development.
Clinical information
Application areas (indications)
Meptazinol is mainly for the treatment of birth pain (for Kupierung of labor pains used). Due to the better side effect profile, Meptazinol is increasingly displacing pethidine from the delivery rooms. The decisive advantage of meptazinol is that it leads to less frequent and less pronounced respiratory depression in newborns.
Meptazinol has its primary areas of application in the following areas:
- Treatment of labor pain
- as a postoperative analgesic for mild to moderate pain
- as a basic analgesic in the context of opioid-assisted anesthesia
- because of the minimal to no respiratory depression as an analgesic for acute, traumatic pain in the context of emergency medicine
- because of the lack of impairment of vigilance and only 27% protein binding as an analgesic in pain therapy for old patients
- because of the low circulatory stimulating, adrenergic effect in all painful situations with simultaneous heavy blood loss
- Because of the antiarrhythmic effect with a simultaneous low impairment of vigilance and minimal protein binding as the analgesic of choice for moderate pain of old and very old patients
Type and duration of application
The duration of the application depends on the cause of the pain or the type of illness. The injection is given intramuscularly or slowly intravenously.
Contraindications (contraindications)
If you are hypersensitive to meptazinol, this drug should not be used.
Drug interactions
Liver enzyme-inducing drugs can weaken the effect of meptazinol.
Use during pregnancy and breastfeeding
Not to be used during pregnancy, except to relieve pain in labor. In the newborn, respiratory depression is possible in rare cases.
Adverse effects (side effects)
The possible side effects essentially include nausea and vomiting, tiredness through to drowsiness and dizziness, cephalgia and gastrointestinal alterations .
Pharmacological properties
Mechanism of action (pharmacodynamics)
For the analgesic effect meptazinol binds as a partial agonist of the μ 1 - opioid receptor . There is only a very low affinity for the μ 2 receptor, which causes respiratory depression. In contrast to other analgesics, the analgesic effect is additionally supported by central cholinergic effects.
Stereoisomerism
Meptazinol contains a stereocenter , so there are two stereoisomers , the ( R ) enantiomer and the mirror image ( S ) enantiomer. It is known that stereoisomers have different pharmacological effects. Nevertheless, Meptazinol is marketed as a racemate (1: 1 mixture of the two enantiomers).
synthesis
A multi-stage synthesis of meptazinol starting from 2- (3-methoxyphenyl) butyronitrile and ethyl 4-iodobutyrate is described in the literature. In the second step, the nitrile is reduced to the primary amine, which then cyclizes to the substituted caprolactam. The carbonyl function of the lactam is then reduced with lithium aluminum hydride, resulting in a secondary heterocyclic amine which is methylated on nitrogen. In the last stage, the methyl ether is split, producing the phenolic meptazinol as a racemate.
Synthesis of racemic meptazinol (* = stereocenter )
Individual evidence
- ^ The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals. 14th edition. 2006, ISBN 0-911910-00-X , pp. 1013-1014.
- ↑ a b c Entry on Meptazinol. In: Römpp Online . Georg Thieme Verlag, accessed on May 29, 2014.
- ↑ a b data sheet Meptazinol hydrochloride from Sigma-Aldrich , accessed on April 9, 2011 ( PDF ).
- ↑ a b Enno Freye: Opioids in medicine. 7th edition. Springer Medizin Verlag, Heidelberg 2008, pp. 314-316.
- ↑ PG Goode, KF Rhodes, JF Waterfall: The analgesic and respiratory effects of meptazinol, morphine and pentazocine in the rat. In: J Pharm Pharmacol . 31, 1979, pp. 793-795.
- ^ RE Johnson, DR Jasinski: Human pharmacology and abuse potential of meptazinol. In: Clin Pharmacol Ther . 41, 1987, pp. 426-433.
- ↑ a b U. Friebe-Hoffmann, L. Beck: Medicinal analgesia in obstetrics. In: Gynecologist. 40, 2007, pp. 190-193.
- ^ A b G. W. Pasternak, AR Gintzler, RA Houghten, GS Ling, RR Goodman, K. Spiegel, S. Nishimura, N. Johnson, LD law: Biochemical and pharmacological evidence for opioid receptor multiplicity in the central nervous system. In: Life Sci. 33 Suppl 1, 1983, pp. 167-173.
- ^ DJ Bill, JE Hartley, RJ Stephens, AM Thompson: The antinociceptive activity of meptazinol depends on both opiate and cholinergic mechanisms. In: Br J Pharmacol . 79 (1), 1983, pp. 191-199.
- ^ EJ Ariëns: Stereochemistry, a basis for sophisticated nonsense in pharmacokinetics and clinical pharmacology. In: European Journal of Clinical Pharmacology . 26, 1984, pp. 663-668, doi: 10.1007 / BF00541922 .
- ^ Axel Kleemann , Jürgen Engel, Bernd Kutscher, Dietmar Reichert: Pharmaceutical Substances. 4th edition. 2 volumes. Thieme-Verlag, Stuttgart 2000, ISBN 1-58890-031-2 . (online since 2003 with biannual additions and updates)
