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Details

Stereochemistry ACHIRAL
Molecular Formula C14H20N2O3
Molecular Weight 264.3202
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PROPACETAMOL

SMILES

CCN(CC)CC(=O)OC1=CC=C(NC(C)=O)C=C1

InChI

InChIKey=QTGAJCQTLIRCFL-UHFFFAOYSA-N
InChI=1S/C14H20N2O3/c1-4-16(5-2)10-14(18)19-13-8-6-12(7-9-13)15-11(3)17/h6-9H,4-5,10H2,1-3H3,(H,15,17)

HIDE SMILES / InChI

Molecular Formula C14H20N2O3
Molecular Weight 264.3202
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Propacetamol is a bioprecursor of paracetamol. It is rapidly hydrolyzed by plasma esterases and releases its constituent paracetamol by the end of its intravenous or intramuscular administration. Its metabolism is identical to that of paracetamol. It is used in post-operative care and is delivered by I.V. It is given if the patient is unable to take oral or rectally delivered paracetamol and non-steroidal anti-inflammatory drugs are contraindicated. The onset of analgaesia from propacetamol is more rapid than paracetamol given orally. 2 g of propacetamol are equivalent to 1g of paracetamol.

CNS Activity

Curator's Comment: Propacetamol can cross the blood-brain barrier, producing a central analgesic effect.

Originator

Curator's Comment: Intravenous propacetamol (Propacetamol) was produced by Bristol-Myers Squibb, France, in 1985 under the trade name Pro-dafalgan. # Bristol-Myers Squibb

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PRO-DAFALGAN

Approved Use

Symptomatic treatment of pain: in surgery, particularly postoperative treatment, in oncology. Symptomatic treatment of fever: in infectious diseases, in malignant diseases.

Launch Date

4.73385599E11
Primary
PRO-DAFALGAN

Approved Use

Symptomatic treatment of pain: in surgery, particularly postoperative treatment, in oncology. Symptomatic treatment of fever: in infectious diseases, in malignant diseases.

Launch Date

4.73385599E11
PubMed

PubMed

TitleDatePubMed
Plasma and cerebrospinal fluid concentrations of paracetamol after a single intravenous dose of propacetamol.
1992 Jul
Bioequivalence study comparing a new paracetamol solution for injection and propacetamol after single intravenous infusion in healthy subjects.
2004 Jan
Comparative effect of intraoperative propacetamol versus placebo on morphine consumption after elective reduction mammoplasty under remifentanil-based anesthesia: a randomized control trial [ISRCTN71723173].
2004 Sep 14
Intravenous acetaminophen (paracetamol): comparable analgesic efficacy, but better local safety than its prodrug, propacetamol, for postoperative pain after third molar surgery.
2005 Jul
Onset of acetaminophen analgesia: comparison of oral and intravenous routes after third molar surgery.
2005 May
Clinical analgesic efficacy and side effects of dexmedetomidine in the early postoperative period after arthroscopic knee surgery.
2007 Dec
Patents

Sample Use Guides

Method of administration Intravenous route: Restricted to children weighing 33 kg or more and to adults. It is recommended to use the product immediately following reconstitution. Do not mix with other drugs because of the risk of incompatibility. Children weighing 33 kg or more Propacetamol is used in infusion over 15 minutes after dilution of the product, using a transfer device, in 5% glucose solution or 0.9% sodium chloride solution. In order to comply with blood volume, the maximum volume which may be infused in children is 1 to 2 ml/kg/injection. The 1 g powder should be dissolved in a 50 ml flexible bag. The 2 g powder should be dissolved in a 100 ml flexible bag. Adults After the product is reconstituted using the transfer device, administration takes place using 5% glucose solution or 0.9% sodium chloride solution (about 100 ml) over 15 minutes. Posology In children the posology is 30 mg/kg per injection, i.e. 1.5 ml/kg per injection of the 1 g solution reconstituted in 50 ml or the 2 g solution reconstituted in 100 ml, to be repeated if necessary after an interval of at least 6 hours, without exceeding the maximum daily posology of 120 mg/kg of propacetamol, i.e. 60 mg/kg of paracetamol. In adults the posology is 1 to 2 g, to be repeated if necessary after an interval of 4 hours, without exceeding 6 g per day, or in exeptional cases, 8 g per day. Frequency of administration Systematic administrations will avoid fluctuations of pain or fever. In children, they must be given at least 6 hours apart. In adults, they must be given at least 4 hours apart.
Route of Administration: Intravenous
In Vitro Use Guide
Curator's Comment: To investigate whether PPCM (Propacetamol) exhibits hTRPV1-activating properties, HEK 293 cells expressing wild type hTRPV1 were examined by standard whole-cell voltage clamp. Measuring ramp currents by 500 ms long depolarizations from -100 to +100 mV, we applied PPCM at increasing concentrations (1 uM to 10 mM).
In hTRPV1-expressing cells 100 uM and higher concentrations activated membrane currents with a strong outward rectification in all cells which also generated capsaicin (1 uM)-induced currents
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:14:45 UTC 2023
Edited
by admin
on Fri Dec 15 16:14:45 UTC 2023
Record UNII
5CHW4JMR82
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PROPACETAMOL
INN   MI   WHO-DD  
INN  
Official Name English
propacetamol [INN]
Common Name English
Propacetamol [WHO-DD]
Common Name English
PROPACETAMOL [MI]
Common Name English
Classification Tree Code System Code
WHO-VATC QN02BE05
Created by admin on Fri Dec 15 16:14:45 UTC 2023 , Edited by admin on Fri Dec 15 16:14:45 UTC 2023
NCI_THESAURUS C2356
Created by admin on Fri Dec 15 16:14:45 UTC 2023 , Edited by admin on Fri Dec 15 16:14:45 UTC 2023
WHO-ATC N02BE05
Created by admin on Fri Dec 15 16:14:45 UTC 2023 , Edited by admin on Fri Dec 15 16:14:45 UTC 2023
Code System Code Type Description
MESH
C063776
Created by admin on Fri Dec 15 16:14:45 UTC 2023 , Edited by admin on Fri Dec 15 16:14:45 UTC 2023
PRIMARY
NCI_THESAURUS
C75081
Created by admin on Fri Dec 15 16:14:45 UTC 2023 , Edited by admin on Fri Dec 15 16:14:45 UTC 2023
PRIMARY
WIKIPEDIA
PROPACETAMOL
Created by admin on Fri Dec 15 16:14:45 UTC 2023 , Edited by admin on Fri Dec 15 16:14:45 UTC 2023
PRIMARY
SMS_ID
100000081129
Created by admin on Fri Dec 15 16:14:45 UTC 2023 , Edited by admin on Fri Dec 15 16:14:45 UTC 2023
PRIMARY
EPA CompTox
DTXSID3057800
Created by admin on Fri Dec 15 16:14:45 UTC 2023 , Edited by admin on Fri Dec 15 16:14:45 UTC 2023
PRIMARY
ECHA (EC/EINECS)
266-390-1
Created by admin on Fri Dec 15 16:14:45 UTC 2023 , Edited by admin on Fri Dec 15 16:14:45 UTC 2023
PRIMARY
FDA UNII
5CHW4JMR82
Created by admin on Fri Dec 15 16:14:45 UTC 2023 , Edited by admin on Fri Dec 15 16:14:45 UTC 2023
PRIMARY
INN
5400
Created by admin on Fri Dec 15 16:14:45 UTC 2023 , Edited by admin on Fri Dec 15 16:14:45 UTC 2023
PRIMARY
DRUG CENTRAL
2290
Created by admin on Fri Dec 15 16:14:45 UTC 2023 , Edited by admin on Fri Dec 15 16:14:45 UTC 2023
PRIMARY
ChEMBL
CHEMBL1851805
Created by admin on Fri Dec 15 16:14:45 UTC 2023 , Edited by admin on Fri Dec 15 16:14:45 UTC 2023
PRIMARY
DRUG BANK
DB09288
Created by admin on Fri Dec 15 16:14:45 UTC 2023 , Edited by admin on Fri Dec 15 16:14:45 UTC 2023
PRIMARY
PUBCHEM
68865
Created by admin on Fri Dec 15 16:14:45 UTC 2023 , Edited by admin on Fri Dec 15 16:14:45 UTC 2023
PRIMARY
EVMPD
SUB10093MIG
Created by admin on Fri Dec 15 16:14:45 UTC 2023 , Edited by admin on Fri Dec 15 16:14:45 UTC 2023
PRIMARY
MERCK INDEX
m9176
Created by admin on Fri Dec 15 16:14:45 UTC 2023 , Edited by admin on Fri Dec 15 16:14:45 UTC 2023
PRIMARY Merck Index
CAS
66532-85-2
Created by admin on Fri Dec 15 16:14:45 UTC 2023 , Edited by admin on Fri Dec 15 16:14:45 UTC 2023
PRIMARY
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