Propacetamol

Propacetamol
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	IV
ATC code	N02BE05 (WHO) ;
Pharmacokinetic data
Elimination half-life	2.4 hours
Excretion	Renal
Identifiers
	IUPAC name 4-(acetamido)phenyl N,N-diethylglycinate;
CAS Number	66532-85-2;
PubChem CID	68865;
ChemSpider	62097;
UNII	5CHW4JMR82;
CompTox Dashboard (EPA)	DTXSID3057800 ;
ECHA InfoCard	100.060.336
Chemical and physical data
Formula	C14H20N2O3
Molar mass	264.325 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCN(CC)CC(=O)OC1=CC=C(C=C1)NC(=O)C;
	InChI 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); Key:QTGAJCQTLIRCFL-UHFFFAOYSA-N;
	(verify)

Propacetamol is a prodrug form of paracetamol which is formed from esterification of paracetamol, and the carboxylic acid diethylglycine. This has the advantage of making it more water-soluble. It is used in post-operative care and is delivered by I.V.^[2] It is given if the patient is unable to take oral or rectally delivered paracetamol and nonsteroidal anti-inflammatory drugs (NSAIDs) are contraindicated. The onset of analgesia from propacetamol is more rapid than paracetamol given orally.^[3] 2 grams of propacetamol are equivalent to 1g of paracetamol.^[4]

References

^ ^a ^b Bannwarth B, Netter P, Lapicque F, Gillet P, Péré P, Boccard E, Royer RJ, Gaucher A (1992). "Plasma and cerebrospinal fluid concentrations of paracetamol after a single intravenous dose of propacetamol". British Journal of Clinical Pharmacology. 34 (1): 79–81. doi:10.1111/j.1365-2125.1992.tb04112.x. PMC 1381380. PMID 1633071.
^ ^a ^b Binhas M, Decailliot F, Rezaiguia-Delclaux S, Suen P, Dumerat M, François V, Combes X, Duvaldestin P (2004). "Comparative effect of intraoperative propacetamol versus placebo on morphine consumption after elective reduction mammoplasty under remifentanil-based anesthesia: a randomized control trial [ISRCTN71723173]". BMC Anesthesiology. 4 (1): 6. doi:10.1186/1471-2253-4-6. PMC 520811. PMID 15367329.
^ Moller PL, Sindet-Pedersen S, Petersen CT, Juhl GI, Dillenschneider A, Skoglund LA (2005). "Onset of acetaminophen analgesia: comparison of oral and intravenous routes after third molar surgery". British Journal of Anaesthesiology. 94 (5): 642–648. doi:10.1093/bja/aei109. PMID 15790675.
^ Flouvat B, Leneveu A, Fitoussi S, Delhotal-Landes B, Gendron A (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. 42 (1): 50–57. doi:10.5414/cpp42050. PMID 14756388.

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[pmid1633071-1] Bannwarth B, Netter P, Lapicque F, Gillet P, Péré P, Boccard E, Royer RJ, Gaucher A (1992). "Plasma and cerebrospinal fluid concentrations of paracetamol after a single intravenous dose of propacetamol". British Journal of Clinical Pharmacology. 34 (1): 79–81. doi:10.1111/j.1365-2125.1992.tb04112.x. PMC 1381380. PMID 1633071.

[pmid15367329-2] Binhas M, Decailliot F, Rezaiguia-Delclaux S, Suen P, Dumerat M, François V, Combes X, Duvaldestin P (2004). "Comparative effect of intraoperative propacetamol versus placebo on morphine consumption after elective reduction mammoplasty under remifentanil-based anesthesia: a randomized control trial [ISRCTN71723173]". BMC Anesthesiology. 4 (1): 6. doi:10.1186/1471-2253-4-6. PMC 520811. PMID 15367329.

[pmid15790675-3] Moller PL, Sindet-Pedersen S, Petersen CT, Juhl GI, Dillenschneider A, Skoglund LA (2005). "Onset of acetaminophen analgesia: comparison of oral and intravenous routes after third molar surgery". British Journal of Anaesthesiology. 94 (5): 642–648. doi:10.1093/bja/aei109. PMID 15790675.

[pmid14756388-4] Flouvat B, Leneveu A, Fitoussi S, Delhotal-Landes B, Gendron A (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. 42 (1): 50–57. doi:10.5414/cpp42050. PMID 14756388.

[2]

[3]

[4]

[1]

Clinical data

AHFS/Drugs.com	International Drug Names
Routes of administration	IV^[1]^[2]
ATC code	N02BE05 (WHO)
Pharmacokinetic data
Elimination half-life	2.4 hours ^[1]
Excretion	Renal
Identifiers
IUPAC name 4-(acetamido)phenyl N,N-diethylglycinate
CAS Number	66532-85-2
PubChem CID	68865
ChemSpider	62097
UNII	5CHW4JMR82
CompTox Dashboard (EPA)	DTXSID3057800
ECHA InfoCard	100.060.336
Chemical and physical data
Formula	C₁₄H₂₀N₂O₃
Molar mass	264.325 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCN(CC)CC(=O)OC1=CC=C(C=C1)NC(=O)C
InChI 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) Key:QTGAJCQTLIRCFL-UHFFFAOYSA-N
(verify)

Propacetamol

See also

References