Page last updated: 2024-11-05

pirinitramide

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth

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

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"The results of this study show that postoperative patient-controlled pain therapy in children with piritramide is - in a similar way as with adults - a safe method involving a low incidence of side effects."( On-demand analgesia with piritramide in children. A study on dosage specification and safety.
Klein, U; Meissner, W; Petrat, G, 1997
)
0.3
" This investigation evaluated clinical practice and monitoring as well as PCIA-associated adverse events and critical incidents in German hospitals."( [Safety and monitoring of patient-controlled intravenous analgesia : Clinical practice in German hospitals].
Emons, MI; Erlenwein, J; Maring, M; Petzke, F; Pogatzki-Zahn, E; Stamer, UM, 2021
)
0.62
" Of the department, 158 (82%) reported adverse events in connection with the use of PCIA within the six-month period preceding the survey (most frequently due to patients' noncompliance [52%], dislocated intravenous lines [41%], communication errors [16%], administration of additional analgesics [16%] and/ or sedatives [14%], problems with the pump [16%], programming errors [9%], incorrect opioid concentration in the reservoir [8%], non-observance of contraindications [7%], incorrect dosing [6%] and self-dosing by the patient [4%] or by third parties [3%], filling the reservoir with thewrong medication [2%]; and other problems [5%])."( [Safety and monitoring of patient-controlled intravenous analgesia : Clinical practice in German hospitals].
Emons, MI; Erlenwein, J; Maring, M; Petzke, F; Pogatzki-Zahn, E; Stamer, UM, 2021
)
0.62
" Adverse events occurred to a significant extent, with a considerable part of them, which might be preventable."( [Safety and monitoring of patient-controlled intravenous analgesia : Clinical practice in German hospitals].
Emons, MI; Erlenwein, J; Maring, M; Petzke, F; Pogatzki-Zahn, E; Stamer, UM, 2021
)
0.62

Pharmacokinetics

ExcerptReferenceRelevance
" Pharmacokinetic data of the drug have not been reported so far."( Pharmacokinetics of piritramide after an intravenous bolus in surgical patients.
Bouillon, T; Briede, I; Gundert-Remy, U; Kettler, D; Kietzmann, D, 1996
)
0.29
" time data were evaluated by nonlinear regression analysis, and the mean values and SD of the individual pharmacokinetic parameters were calculated."( Pharmacokinetics of piritramide after an intravenous bolus in surgical patients.
Bouillon, T; Briede, I; Gundert-Remy, U; Kettler, D; Kietzmann, D, 1996
)
0.29
"Since the elimination half-life of piritramide appears to exceed the duration of clinically effective analgesia observed during the treatment of acute pain, the dose of piritramide should be titrated carefully during long-term treatment to avoid accumulation that may lead to adverse effects."( Pharmacokinetics of piritramide after an intravenous bolus in surgical patients.
Bouillon, T; Briede, I; Gundert-Remy, U; Kettler, D; Kietzmann, D, 1996
)
0.29
" Target-controlled infusions and intermittent bolus regimens were simulated to identify a regimen suitable for patient-controlled analgesia based on population pharmacokinetics and published pharmacodynamic data."( Population pharmacokinetics of piritramide in surgical patients.
Bouillon, T; Hoeft, A; Kietzmann, D; Meineke, I; Port, R, 1999
)
0.3
" The values of the pharmacokinetic parameters are: V1 = 50."( Population pharmacokinetics of piritramide in surgical patients.
Bouillon, T; Hoeft, A; Kietzmann, D; Meineke, I; Port, R, 1999
)
0.3
" Both the steady-state volume of distribution (782 L) and the terminal elimination half-life (17."( The pharmacokinetics of piritramide after prolonged administration to intensive care patients.
Bouillon, T; Groeger, P; Kietzmann, D, 2004
)
0.32
"Despite increasing terminal elimination half-life and volume of distribution at steady state (increasing drug load for a given plasma concentration), the context-sensitive half-time of piritramide after 3 days of administration is lower than predicted from bolus kinetics, making the drug a suitable candidate for intensive care unit analgesia."( The pharmacokinetics of piritramide after prolonged administration to intensive care patients.
Bouillon, T; Groeger, P; Kietzmann, D, 2004
)
0.32
" The following pharmacokinetic parameters: maximum plasma concentration (C(max)), distribution half-life (t 1/2 alpha), elimination half-life (t 1/2 beta), total clearance (Cl(t)) and median volume of distribution at equilibrium (Vd(ss)) were calculated using a non-compartment and a two-compartment model for the disposition of piritramide (TOPFIT and NONMEM-pharmacokinetic analysis)."( Pharmacokinetics of piritramide in newborns, infants and young children in intensive care units.
Doroshyenko, O; Harlfinger, S; Hering, F; Hünseler, C; Jetter, A; Kremer, W; Müller, C; Roth, B; Theisohn, M, 2006
)
0.33
" Little pharmacokinetic and pharmacodynamic data for the pediatric population is available."( Prospective evaluation of the pharmacodynamics of piritramide in neonates and infants.
Borucki, D; Hering, F; Huenseler, C; Kremer, W; Mueller, C; Roth, B; Theisohn, M, 2008
)
0.35
" pharmacokinetic data on 670 drugs representing, to our knowledge, the largest publicly available set of human clinical pharmacokinetic data."( Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
Lombardo, F; Obach, RS; Waters, NJ, 2008
)
0.35

Compound-Compound Interactions

ExcerptReferenceRelevance
"15 mg/kg) combined with Piritramid (0."( [Midazolam in combination with piritramid versus Thalamonal in premedication in ambulatory ENT interventions in childhood].
Bein, T; Heyde, G; Tremel, H, 1988
)
0.27
"This study evaluates the efficacy and side effects of a low dose of epidural morphine combined with clonidine for postoperative pain relief after lumbar disc surgery."( Epidural administration of low-dose morphine combined with clonidine for postoperative analgesia after lumbar disc surgery.
Bonhomme, V; Brichant, JF; Dewandre, PY; Doll, A; Ghassempour, K; Hans, P, 2002
)
0.31
" In this study we examined midazolam and clonidine for premedication in combination with target controlled infusion anaesthesia (TCI) in patients undergoing orthopaedic shoulder surgery and analysed the effects on the peri- and postoperative course."( [Comparison of premedication with clonidine and midazolam combined with TCI for orthopaedic shoulder surgery].
Dietrich, PJ; Grottke, O; Krause, TH; Müller, J; Wappler, F, 2003
)
0.32
"Premedication with the alpha(2)-adrenoceptor agonist clonidine is as good as with benzodiazepines in combination with TCI."( [Comparison of premedication with clonidine and midazolam combined with TCI for orthopaedic shoulder surgery].
Dietrich, PJ; Grottke, O; Krause, TH; Müller, J; Wappler, F, 2003
)
0.32

Dosage Studied

ExcerptRelevanceReference
" The aim in postoperative pain therapy is a time-contingent dosing after careful intravenous titration of the compound in the lower dose range during continuous supervision."( [Postoperative pain treatment].
Freye, E, 1991
)
0.28
" The two patients with coma of unknown origin demonstrated no clinical response to flumazenil at a dosage of 2 mg."( [The efficacy of the benzodiazepine antagonist flumazenil (Ro 15-1788) based on the EEG of mechanically ventilated intensive care patients].
Kulka, PJ; Lauven, PM; Rommelsheim, K; Schwilden, H, 1989
)
0.28
" The main advantages were not only continuous pain relief despite the fact that the nonepidural control group required more than twice the dosage of morphine derivatives; also, the respiratory and pain-related recovery time was reduced."( [Catheter epidural analgesia in serial rib fractures].
Glatzl, A; Poigenfürst, J; Sandtner, W; Thonke, N, 1989
)
0.28
" We tested the dosage of drugs needed in relation to the length of treatment, the size of the stone and the overall energy output of the lithotriptor."( [Extracorporeal shockwave lithotripsy in sedation-analgesia].
Berger, M; Brandstetter, A; Chowanetz, E; Gasser, G; Mossig, H; Schmidt, P, 1988
)
0.27
"On the basis of investigations of three groups of dogs (7 in each) the effects of high dosage piritramide anesthesia were analyzed."( [High-dose piritramide basal anesthesia in experimental anesthesia and surgery].
Bergermann, M; Hauss, J; Schönleben, K; Spiegel, HU; Wendt, M, 1986
)
0.27
" Under this treatment the patients' ability to cooperate and communicate was maintained and allowed a patient-controlled readjustment of pyridostigmine dosage and weaning from the respirator."( [A new method of pain sedation following thymectomy in myasthenia gravis. 2 cases].
Engler, J; Hiotakis, K, 1994
)
0.29
" Although the dosage of piritramide was not different in the three groups, we recommend the protocol of group 3 because of the lower refusal of bolus application."( [Patient-controlled analgesia (PCA) after urologic interventions].
Gust, VR; Henn-Beilharz, A; Krier, C; Weber, R, 1995
)
0.29
" The authors consider that preventive ganglionic blocking without hypotonus attained by a combination of a dosed injection of a ganglion blocker and injection of a highly selective adrenomimetic dopamine in the microcirculation dose ensure the hemodynamic and metabolic stability of balanced anesthesia based on epidural blocking in elderly and senile patients subjected to extensive abdominal interventions."( [Balanced regional anesthesia based on epidural blockade in extensive abdominal interventions in aged patients].
Kozlov, SP; Ragozin, AV; Semenichenko, GG; Svetlov, VA,
)
0.13
" Therefore, a change in protein binding, which might be one factor to be considered in determining piritramide dosage in the postoperative period, does not have to be taken into account."( Protein binding of piritramide: influence of various protein concentrations and the postoperative acute phase response.
Gruber, M; Hoerauf, K; Taeger, K; Wiesner, G; Wild, K, 1999
)
0.3
" Four patients had to be excluded from the study (2 postoperative confusion, 1 elevated piritramid dosage caused by chronic pain therapy, 1 stressed by PCA pump handling)."( Pain therapy following joint replacement.A randomized study of patient-controlled analgesia versus conventional pain therapy.
Forst, J; Forst, R; Thamm, P; Wolff, S, 1999
)
0.3
" Here we examined whether enhanced inflammation and END expression within the synovial tissue of patients undergoing arthroscopic knee surgery might shift the analgesic dose-response curve of intra-articular (i."( Increased numbers of opioid expressing inflammatory cells do not affect intra-articular morphine analgesia.
Koppert, W; Likar, R; Mousa, SA; Philippitsch, G; Schäfer, M; Stein, C; Steinkellner, H, 2004
)
0.32
" These dose-response relationships were not different between patients with low versus high numbers of inflammatory and END-containing synovial cells (P>0."( Increased numbers of opioid expressing inflammatory cells do not affect intra-articular morphine analgesia.
Koppert, W; Likar, R; Mousa, SA; Philippitsch, G; Schäfer, M; Stein, C; Steinkellner, H, 2004
)
0.32
" The mean piritramide dosage was 64 +/- 24 microg/kg."( Prospective evaluation of the pharmacodynamics of piritramide in neonates and infants.
Borucki, D; Hering, F; Huenseler, C; Kremer, W; Mueller, C; Roth, B; Theisohn, M, 2008
)
0.35
" Many exhibit methodologic problems with dosing regimes or study design."( Therapeutic effect of intrathecal morphine after posterior lumbar interbody fusion surgery: a prospective, double-blind, randomized study.
Bauer, C; Fritsch, E; Mencke, T; Müller, BI; Silomon, M; Soltesz, S; Ziegeler, S, 2008
)
0.35
" Piritramide dosage and incidence of side effects were not reduced."( Efficacy of intravenous paracetamol compared to dipyrone and parecoxib for postoperative pain management after minor-to-intermediate surgery: a randomised, double-blind trial.
Brodner, G; Cosanne, I; Ellger, B; Freise, H; Gogarten, W; Hahnenkamp, K; Huppertz-Thyssen, M; Van Aken, H; Wempe, C, 2011
)
0.37
" To reduce the risk for potential psychodysleptic side effects, however, ketamine dosing tends to be limited to low-dose regimens."( 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.
Bornemann-Cimenti, H; Edler, A; Michaeli, K; Sandner-Kiesling, A; Wejbora, M, 2016
)
0.43
" Especially lacking are in-depth studies about its mechanisms of action, receptor pharmacology, dose-response relationships and clinical dosing regimens."( [Piritramide : A critical review].
Bantel, C; Hinrichs, M; Weyland, A, 2017
)
0.46
" Variant OPRM1 118G allele carriers required higher opioid dosing and suffered from more adverse effects, however, the differences between genotypes have been less pronounced in the PCA patients likely due to improved pain management via PCA."( Analgesic effects of piritramide in acute postoperative pain - comparison of intramuscular administration with patient-controlled intravenous analgesia and impact of OPRM1 and ABCB1 polymorphisms.
Adamek, S; Bartosova, O; Lischke, R; Perlik, F; Polanecky, O; Sima, M; Slanar, O, 2022
)
0.72
" Of the department, 158 (82%) reported adverse events in connection with the use of PCIA within the six-month period preceding the survey (most frequently due to patients' noncompliance [52%], dislocated intravenous lines [41%], communication errors [16%], administration of additional analgesics [16%] and/ or sedatives [14%], problems with the pump [16%], programming errors [9%], incorrect opioid concentration in the reservoir [8%], non-observance of contraindications [7%], incorrect dosing [6%] and self-dosing by the patient [4%] or by third parties [3%], filling the reservoir with thewrong medication [2%]; and other problems [5%])."( [Safety and monitoring of patient-controlled intravenous analgesia : Clinical practice in German hospitals].
Emons, MI; Erlenwein, J; Maring, M; Petzke, F; Pogatzki-Zahn, E; Stamer, UM, 2021
)
0.62
"The aim of this study is to assess the current situation in out of hospital pain management in Germany regarding the substances, indications, dosage and the delegation of the use of analgesics to emergency medical service (EMS) staff."( Application of analgesics in emergency services in Germany: a survey of the medical directors.
Scharonow, M; Scharonow, O; Vilcane, S; Weilbach, C, 2023
)
0.91
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

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

TrialOutcome
NCT01115101 (1) [back to overview]Difference of Pain Scores on the Visual Analog Scale

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

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