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)
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 |
|---|---|---|
| Systemic allergic contact dermatitis from intravenous piritramide. | 2010-09 |
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| Prospective assessment of postoperative pain after craniotomy. | 2010-07 |
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| Postoperative analgesia with parecoxib, acetaminophen, and the combination of both: a randomized, double-blind, placebo-controlled trial in patients undergoing thyroid surgery. | 2010-06 |
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| Transient downbeat nystagmus after intravenous administration of the opioid piritramide. | 2010-06 |
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| Recovery index, attentiveness and state of memory after xenon or isoflurane anaesthesia: a randomized controlled trial. | 2010-05-07 |
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| Magnesium and headache after aneurysmal subarachnoid haemorrhage. | 2010-05 |
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| The role of diclofenac and piritramide in the management of acute postoperative pain in hernioplasty. | 2010 |
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| Increased duration of mechanical ventilation is associated with decreased diaphragmatic force: a prospective observational study. | 2010 |
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| Water-filtered infrared-A (wIRA) in acute and chronic wounds. | 2009-12-16 |
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| Effect of somatostatin analogue octreotide on pain relief after major abdominal surgery. | 2009-09 |
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| mu-opioid receptor-stimulated synthesis of reactive oxygen species is mediated via phospholipase D2. | 2009-08 |
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| [Influence of acupuncture on postoperative pain, nausea and vomiting after visceral surgery : a prospective, randomized comparative study of metamizole and standard treatment]. | 2009-08 |
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| Tolerability of inhaled N-chlorotaurine in the pig model. | 2009-07-14 |
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| Stability of piritramide in patient-controlled analgesia (PCA) solutions. | 2009-06 |
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| Midline versus transverse incision in major abdominal surgery: a randomized, double-blind equivalence trial (POVATI: ISRCTN60734227). | 2009-06 |
|
| Assessment of recovery, dreaming, hemodynamics, and satisfaction in postcardiac surgery patients receiving supplementary propofol sedation with S(+)-ketamine. | 2009-06 |
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| Tetrahydrocannabinol (Delta 9-THC) Treatment in Chronic Central Neuropathic Pain and Fibromyalgia Patients: Results of a Multicenter Survey. | 2009 |
|
| Patient-controlled intravenous analgesia as an alternative to epidural analgesia during labor: questioning the use of the short-acting opioid remifentanil. Survey in the French part of Belgium (Wallonia and Brussels). | 2009 |
|
| Inflammatory profile of awake function-controlled craniotomy and craniotomy under general anesthesia. | 2009 |
|
| Acute human self-poisoning with imidacloprid compound: a neonicotinoid insecticide. | 2009 |
|
| Osseointegration of zirconia implants compared with titanium: an in vivo study. | 2008-12-11 |
|
| Postoperative analgosedation with S(+)-ketamine decreases the incidences of postanesthetic shivering and nausea and vomiting after cardiac surgery. | 2008-12 |
|
| Osseointegration of zirconia implants: an SEM observation of the bone-implant interface. | 2008-11-06 |
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| Therapeutic effect of intrathecal morphine after posterior lumbar interbody fusion surgery: a prospective, double-blind, randomized study. | 2008-10-15 |
|
| Electroencephalographic Narcotrend Index monitoring during procedural sedation and analgesia in children. | 2008-09 |
|
| Prospective evaluation of the pharmacodynamics of piritramide in neonates and infants. | 2008-08 |
|
| Millimetre wave therapy for pain relief after total knee arthroplasty: a randomised controlled trial. | 2008-07 |
|
| [Drugs for postoperative analgesia: routine and new aspects: Part 2: opioids, ketamine and gabapentinoids]. | 2008-05 |
|
| [Drugs for postoperative analgesia: routine and new aspects. Part 1: non-opioids]. | 2008-04 |
|
| Opioid sparing effect of epidural levobupivacaine on postoperative pain treatment in major spinal surgery. | 2008-02 |
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| Physostigmine and anaesthesia emergence delirium in preschool children: a randomized blinded trial. | 2008-01 |
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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 |
|
| Parecoxib versus dipyrone (metamizole) for postoperative pain relief after hysterectomy : a prospective, single-centre, randomized, double-blind trial. | 2008 |
|
| The place for short-acting opioids: special emphasis on remifentanil. | 2008 |
|
| Therapy of acute wounds with water-filtered infrared-A (wIRA). | 2007-12-28 |
|
| [Intra-articular bupivacaine following hip joint arthroscopy. Effect on postoperative pain]. | 2007-11 |
|
| [Intra-articular ketamine after arthroscopic knee surgery. Optimisation of postoperative analgesia]. | 2007-11 |
|
| Role of early minimal-invasive spine fixation in acute thoracic and lumbar spine trauma. | 2007-10 |
|
| Determination of opioid analgesics in hair samples using liquid chromatography/tandem mass spectrometry and application to patients under palliative care. | 2007-10 |
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| Randomized clinical trial of the influence of intraperitoneal local anaesthesia on pain after laparoscopic surgery. | 2007-07 |
|
| Influence of pain treatment by epidural fentanyl and bupivacaine on homing of opioid-containing leukocytes to surgical wounds. | 2007-07 |
|
| [Experimental study of the use of piritramide as intrathecal analgesic]. | 2007-04-07 |
|
| Continuous psoas and sciatic block after knee arthroplasty: good effects compared to epidural analgesia or i.v. opioid analgesia: a prospective study of 63 patients. | 2007-04 |
|
| Electronically monitored single-use patient-controlled analgesia pumps in postoperative pain control. | 2007-02-27 |
|
| Changes in sedation management in German intensive care units between 2002 and 2006: a national follow-up survey. | 2007 |
|
| Vasopressin improves survival in a porcine model of abdominal vascular injury. | 2007 |
|
| Clinical equivalence of IV paracetamol compared to IV dipyrone for postoperative analgesia after surgery for breast cancer. | 2006-10 |
|
| The efficacy of the non-opioid analgesics parecoxib, paracetamol and metamizol for postoperative pain relief after lumbar microdiscectomy. | 2006-07 |
|
| An automated and fully validated LC-MS/MS procedure for the simultaneous determination of 11 opioids used in palliative care, with 5 of their metabolites. | 2006-05 |
|
| Piritramide and pethidine. A comparison of their use as supplements in general anaesthesia. | 1974-11 |
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
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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