Details
Stereochemistry | ACHIRAL |
Molecular Formula | C27H34N4O |
Molecular Weight | 430.5851 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC(=O)C1(CCN(CCC(C#N)(C2=CC=CC=C2)C3=CC=CC=C3)CC1)N4CCCCC4
InChI
InChIKey=IHEHEFLXQFOQJO-UHFFFAOYSA-N
InChI=1S/C27H34N4O/c28-22-26(23-10-4-1-5-11-23,24-12-6-2-7-13-24)14-19-30-20-15-27(16-21-30,25(29)32)31-17-8-3-9-18-31/h1-2,4-7,10-13H,3,8-9,14-21H2,(H2,29,32)
Molecular Formula | C27H34N4O |
Molecular Weight | 430.5851 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Piritramide is a synthetic opioid that has been used formore than 30 years in parts of Europe as the analgesic of choice for the management of postoperative pain. Piritramide was discovered at Janssen Pharmaceutica in 1960 and is currently manufactured and distributed within continental Europe and some other places by Janssen-Cilag. Piritramide is not available in all countries. It is marketed under the brand name Dipidolor in Germany, Lithuania, Slovenia, Austria. Piritramide is most commonly prescribed i.m. or i.v. for postoperative analgesia. It is used successfully for patient-controlled analgesia in adults 14 and more recently in chil-dren. Piritramide has potency 0.65 to 0.75 times that of morphine. Upon administration, piritramide binds to and activates mu-opioid receptors in the central nervous system (CNS), thereby mimicking the effects of endogenous opioids and producing analgesic relief. The most common side effect of piritramide appears tobe a dose-related incidence of sedation. It is reported in many studies, but rarely accurately quantified. Diaphoresis, urinary retention, flushing, focal myopathy and thrombophlebitis have all been reported. Piritramide is a strong opioid and therefore is regulated much the same as morphine in all known jurisdictions. It was never introduced in the United States and is therefore a Schedule I/Narcotic controlled substance. It is listed under international treaties and other laws such as the German Betabungsmittelgesetz, the Austrian Suchtgiftmittelgesetz, the Opium Laws of various other European countries, Canadian controlled substances act, UK Misuse of Drugs Act of 1971, and equivalents elsewhere.
CNS Activity
Sources: https://ncit.nci.nih.gov/ncitbrowser/ConceptReport.jsp?dictionary=NCI_Thesaurus&ns=NCI_Thesaurus&code=C119750
Curator's Comment: Piritramide is a diphenylpropylamine and opioid receptor agonist, with analgesic activity. Upon administration, piritramide binds to and activates mu-opioid receptors in the central nervous system (CNS), thereby mimicking the effects of endogenous opioids and producing analgesic relief.
Approval Year
PubMed
Title | Date | PubMed |
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[Stand-by and conscious sedation--possibilities and limits of anesthesiological management]. | 2001 |
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[Lack of pre-emptive analgesic effect of low-dose ketamine in postoperative patients. A prospective, randomised double-blind study]. | 2001 Aug |
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Efficacy and safety of patient-controlled opioid analgesia for acute postoperative pain. A quantitative systematic review. | 2001 Aug |
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Comparison of continuous epidural infusion of ropivacaine and sufentanil with intravenous patient-controlled analgesia after total hip replacement. | 2001 Dec |
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[Intrathecal morphine for postoperative analgesia in cardiac surgery]. | 2002 |
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Endoscopic treatment of solitary, bilateral, multiple, and recurrent pheochromocytomas and paragangliomas. | 2002 Aug |
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Remifentanil-clonidine-propofol versus sufentanil-propofol anesthesia for coronary artery bypass surgery. | 2002 Dec |
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[Is the combination of remifentanil and propopfol suitable for transsphenoid resection of the hypophysis?]. | 2003 |
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Emetic effects of morphine and piritramide. | 2003 Aug |
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Preoperative oral administration of fast-release morphine sulfate reduces postoperative piritramide consumption. | 2003 Jul 15 |
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Piritramide and alfentanil display similar respiratory depressant potency. | 2003 Nov |
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[New insights in postoperative pain therapy]. | 2004 Mar |
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Postoperative condition after the use of remifentanil with a small dose of piritramide compared with a fentanyl-based protocol in patients undergoing craniotomy. | 2005 Jun |
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Electronically monitored single-use patient-controlled analgesia pumps in postoperative pain control. | 2005 Nov-Dec |
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Quantitative determination of piritramide in human plasma and urine by off- and on-line solid-phase extraction liquid chromatography coupled to tandem mass spectrometry. | 2006 |
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Pharmacokinetics of piritramide in newborns, infants and young children in intensive care units. | 2006 Apr |
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Vasopressin improves survival in a porcine model of abdominal vascular injury. | 2007 |
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Therapy of acute wounds with water-filtered infrared-A (wIRA). | 2007 Dec 28 |
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Determination of opioid analgesics in hair samples using liquid chromatography/tandem mass spectrometry and application to patients under palliative care. | 2007 Oct |
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Effects of inhaled iloprost on right ventricular contractility, right ventriculo-vascular coupling and ventricular interdependence: a randomized placebo-controlled trial in an experimental model of acute pulmonary hypertension. | 2008 |
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[Drugs for postoperative analgesia: routine and new aspects. Part 1: non-opioids]. | 2008 Apr |
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Opioid sparing effect of epidural levobupivacaine on postoperative pain treatment in major spinal surgery. | 2008 Feb |
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Physostigmine and anaesthesia emergence delirium in preschool children: a randomized blinded trial. | 2008 Jan |
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Acute human self-poisoning with imidacloprid compound: a neonicotinoid insecticide. | 2009 |
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mu-opioid receptor-stimulated synthesis of reactive oxygen species is mediated via phospholipase D2. | 2009 Aug |
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Stability of piritramide in patient-controlled analgesia (PCA) solutions. | 2009 Jun |
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Effect of somatostatin analogue octreotide on pain relief after major abdominal surgery. | 2009 Sep |
Patents
Sample Use Guides
Use in adults
A usual single dose is 15-30 mg if this medicine is given into a muscle or under the skin.
Single doses of 7.5-22.5 mg will be slowly given into a vein (10 mg per minute).
Use in children
A usual single dose is 0.05-0.2 mg per kg body weight if this medicine is given into a muscle or under the skin.
A usual single dose should be 0.05-0.1mg per kg body weight if Piritramide [MAH] is given into a vein.
Method of administration
This medicine can be given as an injection into a muscle (intramuscular), under the skin (subcutaneous) or into a vein (intravenous).
Route of Administration:
Parenteral
Substance Class |
Chemical
Created
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admin
on
Edited
Fri Dec 15 14:59:43 UTC 2023
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on
Fri Dec 15 14:59:43 UTC 2023
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Record UNII |
4RP92LYZ2F
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Record Status |
Validated (UNII)
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NCI_THESAURUS |
C1506
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NCI_THESAURUS |
C67413
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DEA NO. |
9642
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WHO-ATC |
N02AC03
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WHO-VATC |
QN02AC03
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SUB09920MIG
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C119750
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Piritramide
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206-124-3
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PIRITRAMIDE
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CHEMBL559288
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DB12492
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8354
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100000086577
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9331
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DTXSID00184293
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D010892
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1343
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302-41-0
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4RP92LYZ2F
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3478
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m8881
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ACTIVE MOIETY |