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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
Structure of PIRITRAMIDE

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)

HIDE SMILES / InChI

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

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

PubMed

TitleDatePubMed
Systemic allergic contact dermatitis from intravenous piritramide.
2010-09
Prospective assessment of postoperative pain after craniotomy.
2010-07
Postoperative analgesia with parecoxib, acetaminophen, and the combination of both: a randomized, double-blind, placebo-controlled trial in patients undergoing thyroid surgery.
2010-06
Transient downbeat nystagmus after intravenous administration of the opioid piritramide.
2010-06
Recovery index, attentiveness and state of memory after xenon or isoflurane anaesthesia: a randomized controlled trial.
2010-05-07
Magnesium and headache after aneurysmal subarachnoid haemorrhage.
2010-05
The role of diclofenac and piritramide in the management of acute postoperative pain in hernioplasty.
2010
Increased duration of mechanical ventilation is associated with decreased diaphragmatic force: a prospective observational study.
2010
Water-filtered infrared-A (wIRA) in acute and chronic wounds.
2009-12-16
Effect of somatostatin analogue octreotide on pain relief after major abdominal surgery.
2009-09
mu-opioid receptor-stimulated synthesis of reactive oxygen species is mediated via phospholipase D2.
2009-08
[Influence of acupuncture on postoperative pain, nausea and vomiting after visceral surgery : a prospective, randomized comparative study of metamizole and standard treatment].
2009-08
Tolerability of inhaled N-chlorotaurine in the pig model.
2009-07-14
Stability of piritramide in patient-controlled analgesia (PCA) solutions.
2009-06
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
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
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
Physostigmine and anaesthesia emergence delirium in preschool children: a randomized blinded trial.
2008-01
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
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

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 Mon Mar 31 17:34:26 GMT 2025
Edited
by admin
on Mon Mar 31 17:34:26 GMT 2025
Record UNII
4RP92LYZ2F
Record Status Validated (UNII)
Record Version
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Name Type Language
PIRITRAMIDE
INN   MART.   MI   WHO-DD  
INN  
Official Name English
IDS-NP-013
Preferred Name English
piritramide [INN]
Common Name English
R-3365
Code English
PIRITRAMIDE [MART.]
Common Name English
R 3365
Code English
Piritramide [WHO-DD]
Common Name English
PIRITRAMIDE [MI]
Common Name English
DIPIDOLOR
Common Name English
PIRINITRAMIDE
Common Name English
2,2-DIPHENYL-4-(4-PIPERIDINO-4-CARBAMOYLPIPERIDINO)BUTYRONITRILE
Systematic Name English
1'-(3-CYANO-3,3-DIPHENYLPROPYL)-(1,4'-BIPIPERIDINE)-4'-CARBOXAMIDE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C1506
Created by admin on Mon Mar 31 17:34:26 GMT 2025 , Edited by admin on Mon Mar 31 17:34:26 GMT 2025
NCI_THESAURUS C67413
Created by admin on Mon Mar 31 17:34:26 GMT 2025 , Edited by admin on Mon Mar 31 17:34:26 GMT 2025
DEA NO. 9642
Created by admin on Mon Mar 31 17:34:26 GMT 2025 , Edited by admin on Mon Mar 31 17:34:26 GMT 2025
WHO-ATC N02AC03
Created by admin on Mon Mar 31 17:34:26 GMT 2025 , Edited by admin on Mon Mar 31 17:34:26 GMT 2025
WHO-VATC QN02AC03
Created by admin on Mon Mar 31 17:34:26 GMT 2025 , Edited by admin on Mon Mar 31 17:34:26 GMT 2025
Code System Code Type Description
EVMPD
SUB09920MIG
Created by admin on Mon Mar 31 17:34:26 GMT 2025 , Edited by admin on Mon Mar 31 17:34:26 GMT 2025
PRIMARY
NCI_THESAURUS
C119750
Created by admin on Mon Mar 31 17:34:26 GMT 2025 , Edited by admin on Mon Mar 31 17:34:26 GMT 2025
PRIMARY
LACTMED
Piritramide
Created by admin on Mon Mar 31 17:34:26 GMT 2025 , Edited by admin on Mon Mar 31 17:34:26 GMT 2025
PRIMARY
ECHA (EC/EINECS)
206-124-3
Created by admin on Mon Mar 31 17:34:26 GMT 2025 , Edited by admin on Mon Mar 31 17:34:26 GMT 2025
PRIMARY
WIKIPEDIA
PIRITRAMIDE
Created by admin on Mon Mar 31 17:34:26 GMT 2025 , Edited by admin on Mon Mar 31 17:34:26 GMT 2025
PRIMARY
ChEMBL
CHEMBL559288
Created by admin on Mon Mar 31 17:34:26 GMT 2025 , Edited by admin on Mon Mar 31 17:34:26 GMT 2025
PRIMARY
DRUG BANK
DB12492
Created by admin on Mon Mar 31 17:34:26 GMT 2025 , Edited by admin on Mon Mar 31 17:34:26 GMT 2025
PRIMARY
RXCUI
8354
Created by admin on Mon Mar 31 17:34:26 GMT 2025 , Edited by admin on Mon Mar 31 17:34:26 GMT 2025
PRIMARY RxNorm
SMS_ID
100000086577
Created by admin on Mon Mar 31 17:34:26 GMT 2025 , Edited by admin on Mon Mar 31 17:34:26 GMT 2025
PRIMARY
PUBCHEM
9331
Created by admin on Mon Mar 31 17:34:26 GMT 2025 , Edited by admin on Mon Mar 31 17:34:26 GMT 2025
PRIMARY
EPA CompTox
DTXSID00184293
Created by admin on Mon Mar 31 17:34:26 GMT 2025 , Edited by admin on Mon Mar 31 17:34:26 GMT 2025
PRIMARY
MESH
D010892
Created by admin on Mon Mar 31 17:34:26 GMT 2025 , Edited by admin on Mon Mar 31 17:34:26 GMT 2025
PRIMARY
INN
1343
Created by admin on Mon Mar 31 17:34:26 GMT 2025 , Edited by admin on Mon Mar 31 17:34:26 GMT 2025
PRIMARY
CAS
302-41-0
Created by admin on Mon Mar 31 17:34:26 GMT 2025 , Edited by admin on Mon Mar 31 17:34:26 GMT 2025
PRIMARY
FDA UNII
4RP92LYZ2F
Created by admin on Mon Mar 31 17:34:26 GMT 2025 , Edited by admin on Mon Mar 31 17:34:26 GMT 2025
PRIMARY
DRUG CENTRAL
3478
Created by admin on Mon Mar 31 17:34:26 GMT 2025 , Edited by admin on Mon Mar 31 17:34:26 GMT 2025
PRIMARY
MERCK INDEX
m8881
Created by admin on Mon Mar 31 17:34:26 GMT 2025 , Edited by admin on Mon Mar 31 17:34:26 GMT 2025
PRIMARY Merck Index
Related Record Type Details
ACTIVE MOIETY