U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
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

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 Fri Dec 16 15:52:07 UTC 2022
Edited
by admin
on Fri Dec 16 15:52:07 UTC 2022
Record UNII
4RP92LYZ2F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PIRITRAMIDE
INN   MART.   MI   WHO-DD  
INN  
Official 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
IDS-NP-013
Code 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 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
EVMPD
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
NCI_THESAURUS
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
LACTMED
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
ECHA (EC/EINECS)
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
WIKIPEDIA
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
ChEMBL
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
DRUG BANK
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
RXCUI
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
PUBCHEM
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
EPA CompTox
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
MESH
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
INN
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
CAS
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
FDA UNII
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
DRUG CENTRAL
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
MERCK INDEX
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