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 |
---|---|---|
Piritramide and pethidine. A comparison of their use as supplements in general anaesthesia. | 1974 Nov |
|
[Lack of pre-emptive analgesic effect of low-dose ketamine in postoperative patients. A prospective, randomised double-blind study]. | 2001 Aug |
|
Remifentanil-clonidine-propofol versus sufentanil-propofol anesthesia for coronary artery bypass surgery. | 2002 Dec |
|
Epidural administration of low-dose morphine combined with clonidine for postoperative analgesia after lumbar disc surgery. | 2002 Jan |
|
Effect of celecoxib and dexamethasone on postoperative pain after lumbar disc surgery. | 2003 Aug |
|
Emetic effects of morphine and piritramide. | 2003 Aug |
|
[Anaesthesia for caesarean section. Comparison of two general anaesthetic regimens and spinal anaesthesia]. | 2003 Jan |
|
Comparison between instillation of bupivacaine versus caudal analgesia for postoperative analgesia following inguinal herniotomy in children. | 2003 Jun |
|
Auricular acupuncture for pain relief after total hip arthroplasty - a randomized controlled study. | 2005 Apr |
|
Clonidine premedication in patients with sleep apnea syndrome: a randomized, double-blind, placebo-controlled study. | 2005 Nov |
|
Electronically monitored single-use patient-controlled analgesia pumps in postoperative pain control. | 2005 Nov-Dec |
|
Pharmacokinetics of piritramide in newborns, infants and young children in intensive care units. | 2006 Apr |
|
[Delta(9)-tetrahydrocannabinol and the opioid receptor agonist piritramide do not act synergistically in postoperative pain]. | 2006 Apr |
|
The efficacy of the non-opioid analgesics parecoxib, paracetamol and metamizol for postoperative pain relief after lumbar microdiscectomy. | 2006 Jul |
|
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 May |
|
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 Apr |
|
[Experimental study of the use of piritramide as intrathecal analgesic]. | 2007 Jan-Feb |
|
Randomized clinical trial of the influence of intraperitoneal local anaesthesia on pain after laparoscopic surgery. | 2007 Jul |
|
Influence of pain treatment by epidural fentanyl and bupivacaine on homing of opioid-containing leukocytes to surgical wounds. | 2007 Jul |
|
Postoperative analgosedation with S(+)-ketamine decreases the incidences of postanesthetic shivering and nausea and vomiting after cardiac surgery. | 2008 Dec |
|
Osseointegration of zirconia implants compared with titanium: an in vivo study. | 2008 Dec 11 |
|
Physostigmine and anaesthesia emergence delirium in preschool children: a randomized blinded trial. | 2008 Jan |
|
Millimetre wave therapy for pain relief after total knee arthroplasty: a randomised controlled trial. | 2008 Jul |
|
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 |
|
Acute human self-poisoning with imidacloprid compound: a neonicotinoid insecticide. | 2009 |
|
Water-filtered infrared-A (wIRA) in acute and chronic wounds. | 2009 Dec 16 |
|
Increased duration of mechanical ventilation is associated with decreased diaphragmatic force: a prospective observational study. | 2010 |
|
Prospective assessment of postoperative pain after craniotomy. | 2010 Jul |
|
Transient downbeat nystagmus after intravenous administration of the opioid piritramide. | 2010 Jun |
|
Magnesium and headache after aneurysmal subarachnoid haemorrhage. | 2010 May |
|
Systemic allergic contact dermatitis from intravenous piritramide. | 2010 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
by
admin
on
Edited
Fri Dec 16 15:52:07 UTC 2022
by
admin
on
Fri Dec 16 15:52:07 UTC 2022
|
Record UNII |
4RP92LYZ2F
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Systematic Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
NCI_THESAURUS |
C1506
Created by
admin on Fri Dec 16 15:52:07 UTC 2022 , Edited by admin on Fri Dec 16 15:52:07 UTC 2022
|
||
|
NCI_THESAURUS |
C67413
Created by
admin on Fri Dec 16 15:52:07 UTC 2022 , Edited by admin on Fri Dec 16 15:52:07 UTC 2022
|
||
|
DEA NO. |
9642
Created by
admin on Fri Dec 16 15:52:07 UTC 2022 , Edited by admin on Fri Dec 16 15:52:07 UTC 2022
|
||
|
WHO-ATC |
N02AC03
Created by
admin on Fri Dec 16 15:52:07 UTC 2022 , Edited by admin on Fri Dec 16 15:52:07 UTC 2022
|
||
|
WHO-VATC |
QN02AC03
Created by
admin on Fri Dec 16 15:52:07 UTC 2022 , Edited by admin on Fri Dec 16 15:52:07 UTC 2022
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
SUB09920MIG
Created by
admin on Fri Dec 16 15:52:07 UTC 2022 , Edited by admin on Fri Dec 16 15:52:07 UTC 2022
|
PRIMARY | |||
|
C119750
Created by
admin on Fri Dec 16 15:52:07 UTC 2022 , Edited by admin on Fri Dec 16 15:52:07 UTC 2022
|
PRIMARY | |||
|
Piritramide
Created by
admin on Fri Dec 16 15:52:07 UTC 2022 , Edited by admin on Fri Dec 16 15:52:07 UTC 2022
|
PRIMARY | |||
|
206-124-3
Created by
admin on Fri Dec 16 15:52:07 UTC 2022 , Edited by admin on Fri Dec 16 15:52:07 UTC 2022
|
PRIMARY | |||
|
PIRITRAMIDE
Created by
admin on Fri Dec 16 15:52:07 UTC 2022 , Edited by admin on Fri Dec 16 15:52:07 UTC 2022
|
PRIMARY | |||
|
CHEMBL559288
Created by
admin on Fri Dec 16 15:52:07 UTC 2022 , Edited by admin on Fri Dec 16 15:52:07 UTC 2022
|
PRIMARY | |||
|
DB12492
Created by
admin on Fri Dec 16 15:52:07 UTC 2022 , Edited by admin on Fri Dec 16 15:52:07 UTC 2022
|
PRIMARY | |||
|
8354
Created by
admin on Fri Dec 16 15:52:07 UTC 2022 , Edited by admin on Fri Dec 16 15:52:07 UTC 2022
|
PRIMARY | RxNorm | ||
|
9331
Created by
admin on Fri Dec 16 15:52:07 UTC 2022 , Edited by admin on Fri Dec 16 15:52:07 UTC 2022
|
PRIMARY | |||
|
DTXSID00184293
Created by
admin on Fri Dec 16 15:52:07 UTC 2022 , Edited by admin on Fri Dec 16 15:52:07 UTC 2022
|
PRIMARY | |||
|
D010892
Created by
admin on Fri Dec 16 15:52:07 UTC 2022 , Edited by admin on Fri Dec 16 15:52:07 UTC 2022
|
PRIMARY | |||
|
1343
Created by
admin on Fri Dec 16 15:52:07 UTC 2022 , Edited by admin on Fri Dec 16 15:52:07 UTC 2022
|
PRIMARY | |||
|
302-41-0
Created by
admin on Fri Dec 16 15:52:07 UTC 2022 , Edited by admin on Fri Dec 16 15:52:07 UTC 2022
|
PRIMARY | |||
|
4RP92LYZ2F
Created by
admin on Fri Dec 16 15:52:07 UTC 2022 , Edited by admin on Fri Dec 16 15:52:07 UTC 2022
|
PRIMARY | |||
|
3478
Created by
admin on Fri Dec 16 15:52:07 UTC 2022 , Edited by admin on Fri Dec 16 15:52:07 UTC 2022
|
PRIMARY | |||
|
M8881
Created by
admin on Fri Dec 16 15:52:07 UTC 2022 , Edited by admin on Fri Dec 16 15:52:07 UTC 2022
|
PRIMARY | Merck Index |
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |