Page last updated: 2024-09-21

pirinitramide

Description

Pirinitramide: A diphenylpropylamine with intense narcotic analgesic activity of long duration. It is a derivative of MEPERIDINE with similar activity and usage. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID9331
CHEMBL ID559288
CHEBI ID135699
SCHEMBL ID26151
MeSH IDM0016897

Synonyms (43)

Synonym
1'-(3-cyano-3,3-diphenylpropyl)-(1,4'-bipiperidine)-4'-carboxamide
r 3365
piritramide [inn:ban:dcf]
2,2-diphenyl-4-(4-piperidino-4-carbamoylpiperidino)butyronitrile
brn 0501362
dipiritramide
dea no. 9642
piritramide
einecs 206-124-3
piridolan
piritramid
1'-(3-cyano-3,3-diphenylpropyl)(1,4'-bipiperidine)-4'-carboxamide
piritramida [inn-spanish]
dipidolor
(1,4'-bipiperidine)-4'-carboxamide, 1'-(3-cyano-3,3-diphenylpropyl)-
piritramidum [inn-latin]
pirinitramide
piritramide (inn)
302-41-0
D07288
dipidolor (tn)
CHEBI:135699
1-(3-cyano-3,3-diphenylpropyl)-4-piperidin-1-ylpiperidine-4-carboxamide
CHEMBL559288
ids-np-013
r-3365
1'-(3-cyano-3,3-diphenylpropyl)-[1,4'-bipiperidine]-4'-carboxamide
piritramida
4rp92lyz2f ,
unii-4rp92lyz2f
piritramidum
piritramide [mart.]
piritramide [who-dd]
piritramide [inn]
piritramide [mi]
SCHEMBL26151
isonipecotamide, 1-(3-cyano-3,3-diphenylpropyl)-4-piperidino-
[1,4'-bipiperidine]-4'-carboxamide, 1'-(3-cyano-3,3-diphenylpropyl)-
IHEHEFLXQFOQJO-UHFFFAOYSA-N
1-(3-cyano-3,3-diphenylpropyl)-4-(piperidin-1-yl)piperidine-4-carboximidic acid
DTXSID00184293
DB12492
Q416439

Drug Classes (1)

ClassDescription
nitrileA compound having the structure RC#N; thus a C-substituted derivative of hydrocyanic acid, HC#N. In systematic nomenclature, the suffix nitrile denotes the triply bound #N atom, not the carbon atom attached to it.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (7)

Assay IDTitleYearJournalArticle
AID540210Clearance in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID540212Mean residence time in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID425653Renal clearance in human2009Journal of medicinal chemistry, Aug-13, Volume: 52, Issue:15
Physicochemical determinants of human renal clearance.
AID540209Volume of distribution at steady state in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID540211Fraction unbound in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID425652Total body clearance in human2009Journal of medicinal chemistry, Aug-13, Volume: 52, Issue:15
Physicochemical determinants of human renal clearance.
AID540213Half life in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (244)

TimeframeStudies, This Drug (%)All Drugs %
pre-199057 (23.36)18.7374
1990's59 (24.18)18.2507
2000's65 (26.64)29.6817
2010's54 (22.13)24.3611
2020's9 (3.69)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials115 (41.52%)5.53%
Reviews6 (2.17%)6.00%
Case Studies15 (5.42%)4.05%
Observational3 (1.08%)0.25%
Other138 (49.82%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (9)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
Influence of Peri-operative Opioid Analgesia on Circulating Tumor Cells in Patients Undergoing Laparoscopic Colorectal Cancer Surgery - Multi-center, Randomized Clinical Trial[NCT03700541]Phase 471 participants (Actual)Interventional2019-01-07Completed
Influence of Peri-operative Opioid Analgesia on Circulating Tumor Cells in Patients Undergoing Open Colorectal Cancer Surgery - Multi-center, Randomized Clinical Trial[NCT03700411]Phase 4125 participants (Actual)Interventional2019-01-07Completed
Pain Management After Elective Shoulder Surgery: A Randomized Quantitative Study Comparing Hydromorphone With Piritramide[NCT03541759]Phase 448 participants (Actual)Interventional2018-01-02Completed
Serratus Anterior Plane Block Versus Standard of Care After Totally Endoscopic Aortic Valve Replacement: a Double-blinded Randomized Controlled Trial.[NCT04699422]80 participants (Actual)Interventional2020-12-03Completed
Efficacy of Ropivacaine Wound Infiltration for Postoperative Pain Management After Minimally Invasive Aortic Valve Surgery[NCT03079830]76 participants (Actual)Interventional2016-10-31Completed
Large-scale Prospective Double-blind Randomized Controlled Trial of Pecs II Block for Breast Surgery: Effect on Postoperative Pain and Opioid Consumption[NCT02544282]Phase 4140 participants (Actual)Interventional2014-04-30Completed
Comparison of Three Different Pain and Anxiety Reducing Methods in Adult Patients Undergoing Bone Marrow Puncture[NCT00188227]Phase 4748 participants Interventional2001-09-30Completed
A Randomized Controlled Trial: Pain Management After Cesarean Section: Oxycodon vs. Intravenous Piritramide[NCT01115101]Phase 4239 participants (Actual)Interventional2009-07-31Completed
Effects of Different Types of Perioperative Analgesia on Minimal Residual Disease Development After Colon Cancer Surgery[NCT02314871]Phase 460 participants (Anticipated)Interventional2015-01-31Completed
[information is prepared from clinicaltrials.gov, extracted Sep-2024]

Trial Outcomes

Difference of Pain Scores on the Visual Analog Scale

"The primary outcome measure was the change in patients assessment of pain after cesarean (CS) from baseline.~For pain assessment a visual analog scale (VAS) was used. Women were asked to quantify pain using an eleven point numerical rating score from 0 to 10, with 0 indicating no pain, and 10 the worst pain.~Single value were calculated (averaged)." (NCT01115101)
Timeframe: Pain level was evaluated before therapy (2h after CS), 12h, 24h, 32h, 40h, 48 and 72h after CS.

InterventionVAS score at 24 hours (Mean)
Oxycodon5.88
Patient Controlled Device With Pritramid4.85

Research Highlights

Safety/Toxicity (3)

ArticleYear
[Safety and monitoring of patient-controlled intravenous analgesia : Clinical practice in German hospitals].
Der Anaesthesist, Volume: 70, Issue: 6
2021
[Piritramide versus oxycodone for patient-controlled intravenous analgesia. Opioid-induced side effects].
Schmerz (Berlin, Germany), Volume: 28, Issue: 6
2014
On-demand analgesia with piritramide in children. A study on dosage specification and safety.
European journal of pediatric surgery : official journal of Austrian Association of Pediatric Surgery ... [et al] = Zeitschrift fur Kinderchirurgie, Volume: 7, Issue: 1
1997
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Long-term Use (1)

ArticleYear
[Patient-controlled analgesia. PCA in a three year old child after traumatic amputation].
Der Anaesthesist, Volume: 47, Issue: 3
1998
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Pharmacokinetics (8)

ArticleYear
Physicochemical determinants of human renal clearance.
Journal of medicinal chemistry, Aug-13, Volume: 52, Issue: 15
2009
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
Drug metabolism and disposition: the biological fate of chemicals, Volume: 36, Issue: 7
2008
Prospective evaluation of the pharmacodynamics of piritramide in neonates and infants.
European journal of pediatrics, Volume: 167, Issue: 8
2008
Pharmacokinetics of piritramide in newborns, infants and young children in intensive care units.
European journal of pediatrics, Volume: 165, Issue: 4
2006
The pharmacokinetics of piritramide after prolonged administration to intensive care patients.
European journal of anaesthesiology, Volume: 21, Issue: 9
2004
Opioid-induced respiratory depression is associated with increased tidal volume variability.
European journal of anaesthesiology, Volume: 20, Issue: 2
2003
Population pharmacokinetics of piritramide in surgical patients.
Anesthesiology, Volume: 90, Issue: 1
1999
Pharmacokinetics of piritramide after an intravenous bolus in surgical patients.
Acta anaesthesiologica Scandinavica, Volume: 40, Issue: 8 Pt 1
1996
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Dosage (29)

ArticleYear
Application of analgesics in emergency services in Germany: a survey of the medical directors.
BMC emergency medicine, 09-14, Volume: 23, Issue: 1
2023
[Safety and monitoring of patient-controlled intravenous analgesia : Clinical practice in German hospitals].
Der Anaesthesist, Volume: 70, Issue: 6
2021
Analgesic effects of piritramide in acute postoperative pain - comparison of intramuscular administration with patient-controlled intravenous analgesia and impact of OPRM1 and ABCB1 polymorphisms.
Biomedical papers of the Medical Faculty of the University Palacky, Olomouc, Czechoslovakia, Volume: 166, Issue: 1
2022
[Piritramide : A critical review].
Schmerz (Berlin, Germany), Volume: 31, Issue: 4
2017
The effects of minimal-dose versus low-dose S-ketamine on opioid consumption, hyperalgesia, and postoperative delirium: a triple-blinded, randomized, active- and placebo-controlled clinical trial.
Minerva anestesiologica, Volume: 82, Issue: 10
2016
Efficacy of intravenous paracetamol compared to dipyrone and parecoxib for postoperative pain management after minor-to-intermediate surgery: a randomised, double-blind trial.
European journal of anaesthesiology, Volume: 28, Issue: 2
2011
Therapeutic effect of intrathecal morphine after posterior lumbar interbody fusion surgery: a prospective, double-blind, randomized study.
Spine, Oct-15, Volume: 33, Issue: 22
2008
Prospective evaluation of the pharmacodynamics of piritramide in neonates and infants.
European journal of pediatrics, Volume: 167, Issue: 8
2008
Pharmacokinetics of piritramide in newborns, infants and young children in intensive care units.
European journal of pediatrics, Volume: 165, Issue: 4
2006
Increased numbers of opioid expressing inflammatory cells do not affect intra-articular morphine analgesia.
British journal of anaesthesia, Volume: 93, Issue: 3
2004
[Comparison of premedication with clonidine and midazolam combined with TCI for orthopaedic shoulder surgery].
Anasthesiologie, Intensivmedizin, Notfallmedizin, Schmerztherapie : AINS, Volume: 38, Issue: 12
2003
Pain therapy following joint replacement.A randomized study of patient-controlled analgesia versus conventional pain therapy.
Archives of orthopaedic and trauma surgery, Volume: 119, Issue: 5-6
1999
Protein binding of piritramide: influence of various protein concentrations and the postoperative acute phase response.
European journal of clinical pharmacology, Volume: 54, Issue: 11
1999
On-demand analgesia with piritramide in children. A study on dosage specification and safety.
European journal of pediatric surgery : official journal of Austrian Association of Pediatric Surgery ... [et al] = Zeitschrift fur Kinderchirurgie, Volume: 7, Issue: 1
1997
Posterior retroperitoneoscopy as a new minimally invasive approach for adrenalectomy: results of 30 adrenalectomies in 27 patients.
World journal of surgery, Volume: 20, Issue: 7
1996
[Patient-controlled analgesia with clonidine and piritramide].
Der Anaesthesist, Volume: 45, Issue: 1
1996
[Patient-controlled analgesia (PCA) after urologic interventions].
Anaesthesiologie und Reanimation, Volume: 20, Issue: 5
1995
[A new method of pain sedation following thymectomy in myasthenia gravis. 2 cases].
Anasthesiologie, Intensivmedizin, Notfallmedizin, Schmerztherapie : AINS, Volume: 29, Issue: 1
1994
Etomidate-analgesic combinations for the induction of anaesthesia in cardiac patients. Part I: Studies in patients with coronary artery disease.
Der Anaesthesist, Volume: 31, Issue: 2
1982
Clinical experimental studies of postoperative infusion analgesia.
Clinical therapeutics, Volume: 5, Issue: 6
1983
[Clinical experimental studies of postoperative infusion analgesia].
Der Anaesthesist, Volume: 32, Issue: 6
1983
[High-dose piritramide basal anesthesia in experimental anesthesia and surgery].
Der Anaesthesist, Volume: 35, Issue: 1
1986
[Extracorporeal shockwave lithotripsy in sedation-analgesia].
Der Urologe. Ausg. A, Volume: 27, Issue: 2
1988
[Catheter epidural analgesia in serial rib fractures].
Der Unfallchirurg, Volume: 92, Issue: 4
1989
[The efficacy of the benzodiazepine antagonist flumazenil (Ro 15-1788) based on the EEG of mechanically ventilated intensive care patients].
Der Anaesthesist, Volume: 38, Issue: 8
1989
[Clonidine supplemented analgesia and sedation in prevention of postoperative delirium].
Anasthesie, Intensivtherapie, Notfallmedizin, Volume: 25, Issue: 4
1990
[Postoperative pain treatment].
Anaesthesiologie und Reanimation, Volume: 16, Issue: 6
1991
[Effect of high dosages of morphine and meperidine on haemodynamics, coronary blood flow and myocardial oxygen consumption in comparison to fentanyl and piritramide (author's transl)].
Der Anaesthesist, Volume: 26, Issue: 5
1977
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Interactions (3)

ArticleYear
[Comparison of premedication with clonidine and midazolam combined with TCI for orthopaedic shoulder surgery].
Anasthesiologie, Intensivmedizin, Notfallmedizin, Schmerztherapie : AINS, Volume: 38, Issue: 12
2003
Epidural administration of low-dose morphine combined with clonidine for postoperative analgesia after lumbar disc surgery.
Journal of neurosurgical anesthesiology, Volume: 14, Issue: 1
2002
[Midazolam in combination with piritramid versus Thalamonal in premedication in ambulatory ENT interventions in childhood].
Anasthesie, Intensivtherapie, Notfallmedizin, Volume: 23, Issue: 4
1988
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]