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
[Stand-by and conscious sedation--possibilities and limits of anesthesiological management].
2001
[Lack of pre-emptive analgesic effect of low-dose ketamine in postoperative patients. A prospective, randomised double-blind study].
2001 Aug
Efficacy and safety of patient-controlled opioid analgesia for acute postoperative pain. A quantitative systematic review.
2001 Aug
Comparison of continuous epidural infusion of ropivacaine and sufentanil with intravenous patient-controlled analgesia after total hip replacement.
2001 Dec
[Intrathecal morphine for postoperative analgesia in cardiac surgery].
2002
Endoscopic treatment of solitary, bilateral, multiple, and recurrent pheochromocytomas and paragangliomas.
2002 Aug
Remifentanil-clonidine-propofol versus sufentanil-propofol anesthesia for coronary artery bypass surgery.
2002 Dec
[Is the combination of remifentanil and propopfol suitable for transsphenoid resection of the hypophysis?].
2003
Emetic effects of morphine and piritramide.
2003 Aug
Preoperative oral administration of fast-release morphine sulfate reduces postoperative piritramide consumption.
2003 Jul 15
Piritramide and alfentanil display similar respiratory depressant potency.
2003 Nov
[New insights in postoperative pain therapy].
2004 Mar
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
Electronically monitored single-use patient-controlled analgesia pumps in postoperative pain control.
2005 Nov-Dec
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
Pharmacokinetics of piritramide in newborns, infants and young children in intensive care units.
2006 Apr
Vasopressin improves survival in a porcine model of abdominal vascular injury.
2007
Therapy of acute wounds with water-filtered infrared-A (wIRA).
2007 Dec 28
Determination of opioid analgesics in hair samples using liquid chromatography/tandem mass spectrometry and application to patients under palliative care.
2007 Oct
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
[Drugs for postoperative analgesia: routine and new aspects. Part 1: non-opioids].
2008 Apr
Opioid sparing effect of epidural levobupivacaine on postoperative pain treatment in major spinal surgery.
2008 Feb
Physostigmine and anaesthesia emergence delirium in preschool children: a randomized blinded trial.
2008 Jan
Acute human self-poisoning with imidacloprid compound: a neonicotinoid insecticide.
2009
mu-opioid receptor-stimulated synthesis of reactive oxygen species is mediated via phospholipase D2.
2009 Aug
Stability of piritramide in patient-controlled analgesia (PCA) solutions.
2009 Jun
Effect of somatostatin analogue octreotide on pain relief after major abdominal surgery.
2009 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 15 14:59:43 UTC 2023
Edited
by admin
on Fri Dec 15 14:59:43 UTC 2023
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 15 14:59:43 UTC 2023 , Edited by admin on Fri Dec 15 14:59:43 UTC 2023
NCI_THESAURUS C67413
Created by admin on Fri Dec 15 14:59:43 UTC 2023 , Edited by admin on Fri Dec 15 14:59:43 UTC 2023
DEA NO. 9642
Created by admin on Fri Dec 15 14:59:43 UTC 2023 , Edited by admin on Fri Dec 15 14:59:43 UTC 2023
WHO-ATC N02AC03
Created by admin on Fri Dec 15 14:59:43 UTC 2023 , Edited by admin on Fri Dec 15 14:59:43 UTC 2023
WHO-VATC QN02AC03
Created by admin on Fri Dec 15 14:59:43 UTC 2023 , Edited by admin on Fri Dec 15 14:59:43 UTC 2023
Code System Code Type Description
EVMPD
SUB09920MIG
Created by admin on Fri Dec 15 14:59:43 UTC 2023 , Edited by admin on Fri Dec 15 14:59:43 UTC 2023
PRIMARY
NCI_THESAURUS
C119750
Created by admin on Fri Dec 15 14:59:43 UTC 2023 , Edited by admin on Fri Dec 15 14:59:43 UTC 2023
PRIMARY
LACTMED
Piritramide
Created by admin on Fri Dec 15 14:59:43 UTC 2023 , Edited by admin on Fri Dec 15 14:59:43 UTC 2023
PRIMARY
ECHA (EC/EINECS)
206-124-3
Created by admin on Fri Dec 15 14:59:43 UTC 2023 , Edited by admin on Fri Dec 15 14:59:43 UTC 2023
PRIMARY
WIKIPEDIA
PIRITRAMIDE
Created by admin on Fri Dec 15 14:59:43 UTC 2023 , Edited by admin on Fri Dec 15 14:59:43 UTC 2023
PRIMARY
ChEMBL
CHEMBL559288
Created by admin on Fri Dec 15 14:59:43 UTC 2023 , Edited by admin on Fri Dec 15 14:59:43 UTC 2023
PRIMARY
DRUG BANK
DB12492
Created by admin on Fri Dec 15 14:59:43 UTC 2023 , Edited by admin on Fri Dec 15 14:59:43 UTC 2023
PRIMARY
RXCUI
8354
Created by admin on Fri Dec 15 14:59:43 UTC 2023 , Edited by admin on Fri Dec 15 14:59:43 UTC 2023
PRIMARY RxNorm
SMS_ID
100000086577
Created by admin on Fri Dec 15 14:59:43 UTC 2023 , Edited by admin on Fri Dec 15 14:59:43 UTC 2023
PRIMARY
PUBCHEM
9331
Created by admin on Fri Dec 15 14:59:43 UTC 2023 , Edited by admin on Fri Dec 15 14:59:43 UTC 2023
PRIMARY
EPA CompTox
DTXSID00184293
Created by admin on Fri Dec 15 14:59:43 UTC 2023 , Edited by admin on Fri Dec 15 14:59:43 UTC 2023
PRIMARY
MESH
D010892
Created by admin on Fri Dec 15 14:59:43 UTC 2023 , Edited by admin on Fri Dec 15 14:59:43 UTC 2023
PRIMARY
INN
1343
Created by admin on Fri Dec 15 14:59:43 UTC 2023 , Edited by admin on Fri Dec 15 14:59:43 UTC 2023
PRIMARY
CAS
302-41-0
Created by admin on Fri Dec 15 14:59:43 UTC 2023 , Edited by admin on Fri Dec 15 14:59:43 UTC 2023
PRIMARY
FDA UNII
4RP92LYZ2F
Created by admin on Fri Dec 15 14:59:43 UTC 2023 , Edited by admin on Fri Dec 15 14:59:43 UTC 2023
PRIMARY
DRUG CENTRAL
3478
Created by admin on Fri Dec 15 14:59:43 UTC 2023 , Edited by admin on Fri Dec 15 14:59:43 UTC 2023
PRIMARY
MERCK INDEX
m8881
Created by admin on Fri Dec 15 14:59:43 UTC 2023 , Edited by admin on Fri Dec 15 14:59:43 UTC 2023
PRIMARY Merck Index
Related Record Type Details
ACTIVE MOIETY