Page last updated: 2024-09-23

propacetamol

Description

propacetamol: prodrug for acetaminophen; structure given in UD; RN given refers to HCl; RN for parent cpd not available 5/90 [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID68865
CHEMBL ID1851805
CHEBI ID135089
SCHEMBL ID26155
MeSH IDM0175922

Synonyms (33)

Synonym
propacetamolum [latin]
n,n-diethylglycine, ester with 4'-hydroxyacetanilide
propacetamol [inn]
einecs 266-390-1
propacetamol
propacetamol (inn)
D07294
66532-85-2
CHEBI:135089
(4-acetamidophenyl) 2-(diethylamino)acetate
propacetamol [inn:ban]
propacetamolum
5chw4jmr82 ,
unii-5chw4jmr82
CHEMBL1851805
FT-0630766
AKOS015890722
propacetamol [mi]
propacetamol [who-dd]
SCHEMBL26155
cas-66532-85-2
tox21_113811
NCGC00253689-01
dtxsid3057800 ,
dtxcid7031589
glycine, n,n-diethyl-, 4-(acetylamino)phenyl ester
DB09288
4-acetamidophenyl 2-(diethylamino)acetate
BCP13498
Q907888
MS-23737
CS-0374746
HY-145453

Research Excerpts

Overview

ExcerptReference
"Propacetamol is a prodrug form of paracetamol (APAP) licensed for human use as a pain reliever in postoperative care. "( Gajda, A; Gbylik-Sikorska, M; Giorgi, M; Kim, TW; Lisowski, A; Pietruk, K; Poapolathep, A; Sartini, I; Ɓebkowska-Wieruszewska, B, 2022)
"Propacetamol is an APAP prodrug, which is clinically bioequivalent to APAP."( Ko, JL; Lai, YY; Liou, GG; Tsai, MS; Tsou, HK; Wang, SH; Wang, YH, 2018)
"Propacetamol (PPCM) is a prodrug of paracetamol (PCM), which was generated to increase water solubility of PCM for intravenous delivery. "( Eberhardt, E; Eberhardt, M; Leffler, A; Schillers, F, 2016)
"Propacetamol was found to be a major suspected drug of pharmacologically associated hypotension in Korea. "( Ban, GY; Jeong, CG; Kim, SH; Lee, HY; Lee, JH; Lee, YH; Park, SH; Ye, YM, 2017)
"Propacetamol is an injectable pro-drug of paracetamol (acetaminophen) with analgesic and antipyretic activities, especially used in the post-operative period. "( Hiesse-Provost, O; Hynes, D; McCarroll, M, 2006)
"Propacetamol is an acetaminophen prodrug that was available in Europe as an IV formu lation for the treatment of pain and fever for some time. "( Chesney, R; Jones, J; Rodarte, A; Walson, PD, 2006)

Actions

ExcerptReference
"Propacetamol did not enhance analgesia, nor did it decrease cumulative opioid consumption or reduce adverse effects in a dose of 2 g given every sixth hour for 3 days after surgery."( Hakala, T; Hendolin, H; Hynynen, M; Kokki, H; Lahtinen, P, 2002)

Drug Classes (1)

ClassDescription
alpha-amino acid esterThe amino acid ester derivative obtained the formal condensation of an alpha-amino acid with an alcohol.
[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]

Protein Targets (2)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
RAR-related orphan receptor gammaMus musculus (house mouse)Potency37.57800.006038.004119,952.5996AID1159521
nuclear receptor subfamily 1, group I, member 3Homo sapiens (human)Potency2.98490.001022.650876.6163AID1224838
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (50)

Assay IDTitleYearJournalArticle
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID1079936Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source]
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID1079935Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source]
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID1079931Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source]
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID1079933Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is
AID1079945Animal toxicity known. [column 'TOXIC' in source]
AID1079941Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source]
AID1079938Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source]
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID1347154Primary screen GU AMC qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347094qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for BT-37 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347093qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SK-N-MC cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347091qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SJ-GBM2 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347102qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh18 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347099qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for NB1643 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347107qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh30 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347108qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Rh41 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1347100qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for LAN-5 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347101qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for BT-12 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347089qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for TC32 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347095qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for NB-EBc1 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347103qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for OHS-50 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347106qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for control Hh wild type fibroblast cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID1347096qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for U-2 OS cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347090qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for DAOY cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347407qHTS to identify inhibitors of the type 1 interferon - major histocompatibility complex class I in skeletal muscle: primary screen against the NCATS Pharmaceutical Collection2020ACS chemical biology, 07-17, Volume: 15, Issue:7
High-Throughput Screening to Identify Inhibitors of the Type I Interferon-Major Histocompatibility Complex Class I Pathway in Skeletal Muscle.
AID1347105qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for MG 63 (6-TG R) cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347098qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for SK-N-SH cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347424RapidFire Mass Spectrometry qHTS Assay for Modulators of WT P53-Induced Phosphatase 1 (WIP1)2019The Journal of biological chemistry, 11-15, Volume: 294, Issue:46
Physiologically relevant orthogonal assays for the discovery of small-molecule modulators of WIP1 phosphatase in high-throughput screens.
AID1347425Rhodamine-PBP qHTS Assay for Modulators of WT P53-Induced Phosphatase 1 (WIP1)2019The Journal of biological chemistry, 11-15, Volume: 294, Issue:46
Physiologically relevant orthogonal assays for the discovery of small-molecule modulators of WIP1 phosphatase in high-throughput screens.
AID1347097qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for Saos-2 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347104qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for RD cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1347092qHTS of pediatric cancer cell lines to identify multiple opportunities for drug repurposing: Primary screen for A673 cells2018Oncotarget, Jan-12, Volume: 9, Issue:4
Quantitative high-throughput phenotypic screening of pediatric cancer cell lines identifies multiple opportunities for drug repurposing.
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (120)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (1.67)18.7374
1990's36 (30.00)18.2507
2000's50 (41.67)29.6817
2010's20 (16.67)24.3611
2020's12 (10.00)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 (%)
Trials64 (51.61%)5.53%
Reviews5 (4.03%)6.00%
Case Studies5 (4.03%)4.05%
Observational1 (0.81%)0.25%
Other49 (39.52%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (7)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
[NCT02116257]108 participants (Actual)Interventional2013-11-30Completed
[NCT02577068]84 participants (Actual)Interventional2015-11-15Completed
Perioperative Regular Usage of Propacetamol to Reduce Post Cesarean Section Uterine Contraction Pain and Opioid Consumption[NCT03878082]100 participants (Actual)Interventional2019-08-12Completed
The Effect of Dexamethasone Versus Local Infiltration Technique on Postoperative Nausea and Vomiting After Tonsillectomy in Children: A Randomized Double-blind Clinical Trial[NCT02355678]129 participants (Actual)Interventional2015-01-31Completed
[NCT01833728]16 participants (Actual)Interventional2013-04-30Completed
Comparison of the Effect of Propacetamol, Ibuprofen or Their Combination on Postoperative Pain and Quality of Recovery After Laparoscopic Hernia Repair in Children[NCT03352362]159 participants (Actual)Interventional2017-12-15Completed
[NCT02515188]98 participants (Actual)Interventional2015-08-07Completed
[information is prepared from clinicaltrials.gov, extracted Sep-2024]

Research Highlights

Safety/Toxicity (7)

ArticleYear
The antipyretic efficacy and safety of propacetamol compared with dexibuprofen in febrile children: a multicenter, randomized, double-blind, comparative, phase 3 clinical trial.
BMC pediatrics, 06-23, Volume: 18, Issue: 1
2018
Galangin Prevents Acute Hepatorenal Toxicity in Novel Propacetamol-Induced Acetaminophen-Overdosed Mice.
Journal of medicinal food, Volume: 18, Issue: 11
2015
Comparison of the efficacy and safety of different doses of propacetamol for postoperative pain control after breast surgery.
Pain management nursing : official journal of the American Society of Pain Management Nurses, Volume: 16, Issue: 3
2015
Clinical analgesic efficacy and side effects of dexmedetomidine in the early postoperative period after arthroscopic knee surgery.
Journal of clinical anesthesia, Volume: 19, Issue: 8
2007
Antipyretic efficacy and safety of a single intravenous administration of 15 mg/kg paracetamol versus 30 mg/kg propacetamol in children with acute fever due to infection.
International journal of clinical pharmacology and therapeutics, Volume: 45, Issue: 4
2007
Adjunctive analgesia with intravenous propacetamol does not reduce morphine-related adverse effects.
British journal of anaesthesia, Volume: 90, Issue: 3
2003
Analgesic efficacy and safety of nefopam vs. propacetamol following hepatic resection.
Anaesthesia, Volume: 56, Issue: 6
2001
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Pharmacokinetics (7)

ArticleYear
Propacetamol in dogs: First description of its pharmacokinetics after intravenous and oral administration.
Research in veterinary science, Volume: 144
2022
Pharmacokinetics and analgesic effects of intravenous propacetamol vs rectal paracetamol in children after major craniofacial surgery.
Paediatric anaesthesia, Volume: 18, Issue: 7
2008
Intravenous paracetamol (propacetamol) pharmacokinetics in term and preterm neonates.
European journal of clinical pharmacology, Volume: 60, Issue: 3
2004
Pharmacokinetics of single dose intravenous propacetamol in neonates: effect of gestational age.
Archives of disease in childhood. Fetal and neonatal edition, Volume: 89, Issue: 1
2004
Rapid liquid chromatographic assay for the determination of acetaminophen in plasma after propacetamol administration: application to pharmacokinetic studies.
Journal of pharmaceutical and biomedical analysis, Volume: 20, Issue: 1-2
1999
Pharmacokinetics of paracetamol in the neonate and infant after administration of propacetamol chlorhydrate.
Developmental pharmacology and therapeutics, Volume: 20, Issue: 3-4
1993
Tolerance and pharmacokinetics of propacetamol, a paracetamol formulation for intravenous use.
Fundamental & clinical pharmacology, Volume: 6, Issue: 6
1992
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioavailability (2)

ArticleYear
Physiologically relevant orthogonal assays for the discovery of small-molecule modulators of WIP1 phosphatase in high-throughput screens.
The Journal of biological chemistry, 11-15, Volume: 294, Issue: 46
2019
Tolerance and pharmacokinetics of propacetamol, a paracetamol formulation for intravenous use.
Fundamental & clinical pharmacology, Volume: 6, Issue: 6
1992
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Dosage (13)

ArticleYear
Galangin Prevents Acute Hepatorenal Toxicity in Novel Propacetamol-Induced Acetaminophen-Overdosed Mice.
Journal of medicinal food, Volume: 18, Issue: 11
2015
Effect of intravenous propacetamol on blood pressure in febrile critically ill patients.
Pharmacotherapy, Volume: 28, Issue: 10
2008
Clinical analgesic efficacy and side effects of dexmedetomidine in the early postoperative period after arthroscopic knee surgery.
Journal of clinical anesthesia, Volume: 19, Issue: 8
2007
Analgesic efficacy of parenteral paracetamol (propacetamol) and diclofenac in post-operative orthopaedic pain.
Acta anaesthesiologica Scandinavica, Volume: 50, Issue: 3
2006
Propacetamol and diclofenac alone and in combination for analgesia after elective tonsillectomy.
Acta anaesthesiologica Scandinavica, Volume: 48, Issue: 9
2004
Intravenous paracetamol (propacetamol) pharmacokinetics in term and preterm neonates.
European journal of clinical pharmacology, Volume: 60, Issue: 3
2004
Bioequivalence study comparing a new paracetamol solution for injection and propacetamol after single intravenous infusion in healthy subjects.
International journal of clinical pharmacology and therapeutics, Volume: 42, Issue: 1
2004
Assessing analgesia in single and repeated administrations of propacetamol for postoperative pain: comparison with morphine after dental surgery.
Anesthesia and analgesia, Volume: 98, Issue: 1
2004
Symptomatic intravenous antipyretic therapy: efficacy of metamizol, diclofenac, and propacetamol.
Journal of pain and symptom management, Volume: 24, Issue: 6
2002
[Metamizol versus propacetamol: comparative study of the hemodynamic and antipyretic effects in critically ill patients].
Revista espanola de anestesiologia y reanimacion, Volume: 49, Issue: 8
2002
Propacetamol versus ketorolac for treatment of acute postoperative pain after total hip or knee replacement.
Anesthesia and analgesia, Volume: 92, Issue: 6
2001
Isobolographic analysis of interactions between intravenous morphine, propacetamol, and diclofenac in carrageenin-injected rats.
Anesthesiology, Volume: 87, Issue: 2
1997
Pharmacokinetics of paracetamol in the neonate and infant after administration of propacetamol chlorhydrate.
Developmental pharmacology and therapeutics, Volume: 20, Issue: 3-4
1993
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Interactions (2)

ArticleYear
A double-blinded evaluation of propacetamol versus ketorolac in combination with patient-controlled analgesia morphine: analgesic efficacy and tolerability after gynecologic surgery.
Anesthesia and analgesia, Volume: 88, Issue: 3
1999
[Comparison of the analgesic efficacy of nalbuphine and its combination with propacetamol during the immediate postoperative period in gynecologic-obstetric surgery].
Annales francaises d'anesthesie et de reanimation, Volume: 13, Issue: 2
1994
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]