Piritramide

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Structural formula
Structure of piritamide
General
Non-proprietary name Piritramide
other names

1- (3-cyano-3,3-diphenyl-propyl) -4- (1-piperidyl) piperidine-4-carboxamide

Molecular formula C 27 H 34 N 4 O
External identifiers / databases
CAS number 302-41-0
EC number 206-124-3
ECHA InfoCard 100.005.569
PubChem 9331
Wikidata Q416439
Drug information
ATC code

N02 AC03

Drug class

Opioid - analgesic

Mechanism of action

μ 1 receptor - agonist

properties
Molar mass 430.59 g · mol -1
Physical state

firmly

Melting point

225-227 ° C

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
07 - Warning 09 - Dangerous for the environment

Caution

H and P phrases H: 302-336-411
P: ?
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Piritramide is a synthetic opioid that is used as a medicinal substance ( analgesic ). It is subject to the Narcotics Act . It was synthesized by Paul Janssen in 1960 and was the first potent 4-aminopiperidine derivative used clinically. Piritramid is mainly used in continental Europe and is little known in the Anglo-American language area. It is the most widely used opioid in Germany in the postoperative phase.

pharmacology

Piritramid is a µ-receptor agonist and is used in postoperative and palliative pain therapy for the treatment of moderate to severe pain. The analgesic potency is about 0.7, i.e. H. 15–20 mg piritramide correspond to approx. 10–15 mg morphine . In a study from 1971, piritramide had a greater hypnotic effect and fewer side effects such as nausea, vomiting and hypotension compared to the equivalent amount of morphine . These results could not be proven later in independent studies. The respiratory depressive effect is comparable to the equivalent dose of morphine and completely reversible by naloxone . The plasma half-life is 4–10 hours. Piritramide is almost completely metabolised by the liver and renal excretion is low.

Indications

Piritramide is suitable as an analgesic in the postoperative phase. For this purpose, a patient-controlled analgesia used (PCA). It can also be used to treat breakthrough pain.

Contraindications

Piritramide is contraindicated for the following diseases, symptoms and comedications, among others:

  • severe obstructive pulmonary disease
  • Comedication with MAO inhibitors
  • existing respiratory depression
  • Hypersensitivity
  • comatose states

Side effects

The side effects of piritramide are similar to those of morphine. However, piritramide has a more sedating effect than morphine. The respiratory depressive effect is comparable to the equivalent dose of morphine and can be completely antagonized by naloxone .

application

Piritramide can be administered intravenously (iv), subcutaneously (sc) and intramuscularly (im). The therapeutic single dose has a duration of action of 5–8 hours.

Piritramide is also used for patient-directed analgesia (PCA).

It is more expensive than morphine, but is not superior to it in patient-controlled analgesia. A disadvantage, especially in palliative medicine, is the immiscibility with Metamizol (trade names: Novalgin , Novalminsulfon ) and possibly also with other pharmaceuticals.

Trade names

Piritramid is commercially available in Germany and Austria under the name Dipidolor .

literature

  • Eberhard Klaschik : Pain therapy and symptom control in palliative medicine. In: Stein Husebø , Eberhard Klaschik (ed.): Palliative medicine. 5th edition, Springer, Heidelberg 2009, ISBN 3-642-01548-4 , pp. 207-313, here: pp. 234 and 464.

Web links

Commons : Piritramid  - collection of pictures, videos and audio files

Individual evidence

  1. ^ The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, p. 1293, ISBN 978-0-911910-00-1 .
  2. ↑ Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of piritramide in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), which was accessed on July 10, 2020, is reproduced from a self-classification by distributors .
  3. ^ Rolf Rossaint, Christian Werner, Bernhard Zwißler: Die Anästhesiologie. Springer, 2004, pp. 261-262.
  4. ↑ a b F. J. Kretz, J. Schäffer: Anesthesia, intensive care medicine, emergency medicine, pain therapy . Springer, 2006, p. 44.
  5. ↑ B. Kay: A clinical investigation of Piritramide in the treatment of postoperative pain. In: British Journal of Anesthesia. Vol. 43, No. 12, 1971, pp. 1167-1171.
  6. ↑ Döpfmer UR, Schenk MR, Kuscic S, Beck DH, Döpfmer S, Kox WJ .: A randomized controlled double-blind trial comparing piritramide and morphine for analgesia after hysterectomy . Eur J Anesthesiol 2001; 18: 389-393.
  7. ↑ C. Breitfeld, J. Peters, T. Vockel, C. Lorenz, M. Eikermann: Emetic effects of morphine and piritramide . In: British Journal of Anesthesia. Volume 91, No. 2, 2003, pp. 218-223.
  8. ↑ a b c Enno Freye: Opioids in medicine . 8th, updated edition. Springer Medizin Verlag, Heidelberg 2010, ISBN 978-3-540-88797-3 .
  9. ↑ a b c d DocCheck Medical Services GmbH: Piritramid. Retrieved April 7, 2020 .
  10. ↑ a b c PharmaWiki - Piritramid. Retrieved April 18, 2020 .
  11. ^ Bausewein, Rémi, Twycross, Wilcock: Drug therapy in palliative medicine . Elsevier, 2005, pp. 200-201.
  12. ↑ F. Musshoff, SA Padosch, B. Madea: Death during patient-controlled analgesia: Piritramide overdose and tissue distribution of the drug. In: Forensic Sci. Int. Volume, 154, No. 2-3, pp. 247-251, PMID 16182973 .
  13. ^ Rolf Rossaint, Christian Werner, Bernhard Zwißler: Die Anästhesiologie. Springer, 2004, pp. 261-262.
  14. ↑ Constanze Rémi: Mixed infusions in palliative medicine. Compatibility and stability of drug mixtures relevant to palliative medicine . Dissertation Munich 2017.
  15. ↑ Eberhard Klaschik : Pain therapy and symptom control in palliative medicine. 2009, p. 464.