NAV

Propacetamol

Identification

Generic Name
Propacetamol
DrugBank Accession Number
DB09288
Background

Propacetamol is a non-opioid analgesic devoid of the major contraindications.1 It is a derivative of acetaminophen, or paracetamol, with the molecular formula glycine, N, N-diethyl-,4-(acetylamino)phenyl ester. Propacetamol is a parenteral formulation of paracetamol and thus, it is a prodrug that is completely hydrolyzed to paracetamol.3 It is not available in the United States but this prodrug has been widely used in other countries such as France since 1985.5

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 264.325
Monoisotopic: 264.147392512
Chemical Formula
C14H20N2O3
Synonyms
  • Propacetamol
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Pharmacology

Indication

Propacetamol is a paracetamol prodrug of intravenous administration used to control fever and pain of perioperative period in multimodal analgesia therapy.7

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Propacetamol is hydrolyzed to paracetamol and then it presents a weak inhibition of COX-1 and COX-2 which is translated into a low anti-inflammatory activity. Therefore, in high inflammatory conditions, such as rheumatoid arthritis, these agents show limited in vivo suppression of inflammation and platelet activity. The formation of N-arachidonoylphenolamine, donates paracetamol with analgesic and antipyretic properties.8

Mechanism of action

As propacetamol is a prodrug, its mechanism of action is directly linked to the activity of paracetamol. The mechanism of action of paracetamol is described by the inhibition of prostaglandin synthesis.7 This inhibition is attained by inhibition of COX-1 and COX-2 in an environment where arachidonic acid and peroxides are kept low.8 It is considered that paracetamol presents a very complex mechanism of action involving effects in the peripheral system, described by direct COX inhibition; the central system, characterized by inhibition of COX, serotonergic descending neuronal pathway, L-arginine/NO pathway and cannabinoid system; and a redox mechanism.2 In the brain and spinal cord, paracetamol can combine with arachidonic acid to form N-arachidonoylphenolamine. This metabolite is an activator of capsaicin receptor (TRPV1) and cannabinoid CB1.8

TargetActionsOrganism
AProstaglandin G/H synthase 1
antagonist
Humans
AProstaglandin G/H synthase 2
antagonist
Humans
ATransient receptor potential cation channel subfamily V member 1
antagonist
Humans
ACannabinoid receptor 1
antagonist
Humans
Absorption

The bioavailability of 2g of propacetamol is similar to the bioavailability found in 1 g of intravenous paracetamol. Peak plasma concentration is obtained as and from the end of infusion. Pharmacokinetic analysis with intravenous propacetamol showed a significantly higher and earlier maximum plasma concentration than orally administered paracetamol. The Cmax, Tmax and AUC are 12.72 mcg/ml, 0.25 h and 25.5 mcg.h/ml. After infusion with propacetamol, significant concentrations of paracetamol are observed in cerebrospinal fluid.6

Volume of distribution

The volume of distribution of propacetamol is 1.29 l/kg.6

Protein binding

Propacetamol is very rapidly converted into paracetamol and this later component tends to present a very negligible binding to plasma proteins.3

Metabolism

After administration, propacetamol is completely converted by plasma esterases into N, N-diethylglycine and paracetamol. The latest is the active metabolite. It is reported that the active metabolite of propacetamol can be transformed to N-acetil-p-benzoquinone imine by CYP2E1 which is a hepatotoxic metabolite.7

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Route of elimination

The metabolites of propacetamol are mainly excreted in the urine. From the elimination rate, 90% of the administered dose is excreted in 24 hours mainly as glucuronide and sulfate conjugates. Less than 5% is eliminated as unchanged paracetamol.9

Half-life

The half-life of propacetamol is of 3.6 h.6

Clearance

The clearance rate of propacetamol is 0.28 l.h/kg.6

Adverse Effects
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Toxicity

The intravenous administration of paracetamol in the form of propacetamol has no effect on fertility. There is no evidence of carcinogenic potential in mice but there is a report in female rats at 0.7 times the maximum clinical exposure where there was a report of mononuclear cell leukemia. There is a potential clastogenic effect at doses of 8 times the maximum anticipated clinical exposure.9

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Integrate drug-drug
interactions in your software
AbacavirPropacetamol may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbametapirThe serum concentration of Propacetamol can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Propacetamol can be increased when combined with Abatacept.
AbciximabThe risk or severity of bleeding and hemorrhage can be increased when Propacetamol is combined with Abciximab.
AbirateroneThe serum concentration of Propacetamol can be increased when it is combined with Abiraterone.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Propacetamol hydrochlorideSH41QYH8E566532-86-3WGTYJNGARJPYKG-UHFFFAOYSA-N
International/Other Brands
Pro-dafalgan

Categories

ATC Codes
N02BE05 — Propacetamol
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Alpha amino acid esters
Alternative Parents
Phenol esters / Acetanilides / N-acetylarylamines / Phenoxy compounds / Acetamides / Trialkylamines / Secondary carboxylic acid amides / Carboxylic acid esters / Monocarboxylic acids and derivatives / Organopnictogen compounds
show 3 more
Substituents
Acetamide / Acetanilide / Alpha-amino acid ester / Amine / Anilide / Aromatic homomonocyclic compound / Benzenoid / Carbonyl group / Carboxamide group / Carboxylic acid ester
show 16 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
5CHW4JMR82
CAS number
66532-85-2
InChI Key
QTGAJCQTLIRCFL-UHFFFAOYSA-N
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)
IUPAC Name
4-acetamidophenyl 2-(diethylamino)acetate
SMILES
CCN(CC)CC(=O)OC1=CC=C(NC(C)=O)C=C1

References

General References
  1. Hans P, Brichant JF, Bonhomme V, Triffaux M: Analgesic efficiency of propacetamol hydrochlorid after lumbar disc surgery. Acta Anaesthesiol Belg. 1993;44(4):129-33. [Article]
  2. Jozwiak-Bebenista M, Nowak JZ: Paracetamol: mechanism of action, applications and safety concern. Acta Pol Pharm. 2014 Jan-Feb;71(1):11-23. [Article]
  3. Bannwarth B, Netter P, Lapicque F, Gillet P, Pere P, Boccard E, Royer RJ, Gaucher A: Plasma and cerebrospinal fluid concentrations of paracetamol after a single intravenous dose of propacetamol. Br J Clin Pharmacol. 1992 Jul;34(1):79-81. [Article]
  4. Allegaert K, Van der Marel CD, Debeer A, Pluim MA, Van Lingen RA, Vanhole C, Tibboel D, Devlieger H: Pharmacokinetics of single dose intravenous propacetamol in neonates: effect of gestational age. Arch Dis Child Fetal Neonatal Ed. 2004 Jan;89(1):F25-8. [Article]
  5. Anaesthesia, pain and intensive care [Link]
  6. New zealand perfalgan report [Link]
  7. Sociedade brasileira de quimica [Link]
  8. Update in anaesthesia [Link]
  9. Monograph [Link]
KEGG Drug
D07294
PubChem Compound
68865
PubChem Substance
310265180
ChemSpider
62097
ChEBI
135089
ChEMBL
CHEMBL1851805
ZINC
ZINC000055161176
Wikipedia
Propacetamol
MSDS
Download (40.9 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
Not AvailableCompletedPreventionPost Operative Nausea and Vomiting (PONV) / Propacetamol1
Not AvailableCompletedSupportive CareArrhythmia1
Not AvailableCompletedTreatmentInguinal Hernias1
Not AvailableCompletedTreatmentPain / Thyroidectomy1
Not AvailableCompletedTreatmentPost Operative Nausea and Vomiting (PONV)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Powder, for solution
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
boiling point (°C)434.5ºC at 760 mmHg'MSDS'
water solubilitySolubleOscier, Bosley and Milner. (2007). Update in Anaesthesia.
logP1.65'MSDS'
Predicted Properties
PropertyValueSource
Water Solubility0.513 mg/mLALOGPS
logP1.96ALOGPS
logP1.42Chemaxon
logS-2.7ALOGPS
pKa (Strongest Acidic)14.67Chemaxon
pKa (Strongest Basic)6.83Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area58.64 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity74.98 m3·mol-1Chemaxon
Polarizability29.17 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00xr-0090000000-f50323407bfee66917a3
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-1940000000-7308a4bd5833b69b15f0
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-053r-0910000000-2b51f138895dc9d2e8d8
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0159-1900000000-38303d6aa4e690a829a1
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0pvi-3910000000-872636796a94d2c0e931
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-1900000000-4a14ef7a0083e47e7b6f
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-178.5906662
predicted
DarkChem Lite v0.1.0
[M-H]-163.2792
predicted
DeepCCS 1.0 (2019)
[M+H]+179.2644662
predicted
DarkChem Lite v0.1.0
[M+H]+165.6372
predicted
DeepCCS 1.0 (2019)
[M+Na]+178.6108662
predicted
DarkChem Lite v0.1.0
[M+Na]+171.73036
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Details1. Prostaglandin G/H synthase 1
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
Gene Name
PTGS1
Uniprot ID
P23219
Uniprot Name
Prostaglandin G/H synthase 1
Molecular Weight
68685.82 Da
References
  1. Update in anaesthesia [Link]
Details2. Prostaglandin G/H synthase 2
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...
Gene Name
PTGS2
Uniprot ID
P35354
Uniprot Name
Prostaglandin G/H synthase 2
Molecular Weight
68995.625 Da
References
  1. Update in anaesthesia [Link]
Details3. Transient receptor potential cation channel subfamily V member 1
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Transmembrane signaling receptor activity
Specific Function
Ligand-activated non-selective calcium permeant cation channel involved in detection of noxious chemical and thermal stimuli. Seems to mediate proton influx and may be involved in intracellular aci...
Gene Name
TRPV1
Uniprot ID
Q8NER1
Uniprot Name
Transient receptor potential cation channel subfamily V member 1
Molecular Weight
94955.33 Da
References
  1. Update in anaesthesia [Link]
Details4. Cannabinoid receptor 1
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Drug binding
Specific Function
Involved in cannabinoid-induced CNS effects. Acts by inhibiting adenylate cyclase. Could be a receptor for anandamide. Inhibits L-type Ca(2+) channel current. Isoform 2 and isoform 3 have altered l...
Gene Name
CNR1
Uniprot ID
P21554
Uniprot Name
Cannabinoid receptor 1
Molecular Weight
52857.365 Da
References
  1. Update in anaesthesia [Link]

Enzymes

Details1. Cholinesterase
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Identical protein binding
Specific Function
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name
BCHE
Uniprot ID
P06276
Uniprot Name
Cholinesterase
Molecular Weight
68417.575 Da
References
  1. Allegaert K, Van der Marel CD, Debeer A, Pluim MA, Van Lingen RA, Vanhole C, Tibboel D, Devlieger H: Pharmacokinetics of single dose intravenous propacetamol in neonates: effect of gestational age. Arch Dis Child Fetal Neonatal Ed. 2004 Jan;89(1):F25-8. [Article]
Details2. Cytochrome P450 2E1
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Curator comments
This enzyme is responsible for the metabolism of acetaminophen, the active metabolite of propacetamol.
General Function
Steroid hydroxylase activity
Specific Function
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
Gene Name
CYP2E1
Uniprot ID
P05181
Uniprot Name
Cytochrome P450 2E1
Molecular Weight
56848.42 Da
References
  1. Dong H, Haining RL, Thummel KE, Rettie AE, Nelson SD: Involvement of human cytochrome P450 2D6 in the bioactivation of acetaminophen. Drug Metab Dispos. 2000 Dec;28(12):1397-400. [Article]
  2. Raucy JL, Lasker JM, Lieber CS, Black M: Acetaminophen activation by human liver cytochromes P450IIE1 and P450IA2. Arch Biochem Biophys. 1989 Jun;271(2):270-83. [Article]
  3. Flockhart Table of Drug Interactions [Link]
Details3. Cytochrome P450 1A2
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Raucy JL, Lasker JM, Lieber CS, Black M: Acetaminophen activation by human liver cytochromes P450IIE1 and P450IA2. Arch Biochem Biophys. 1989 Jun;271(2):270-83. [Article]
  2. Flockhart Table of Drug Interactions [Link]
  3. Propacetamol Monograph [File]
Details4. Cytochrome P450 2D6
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Curator comments
This enzyme is responsible for the metabolism of acetaminophen, the active metabolite of propacetamol.
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Dong H, Haining RL, Thummel KE, Rettie AE, Nelson SD: Involvement of human cytochrome P450 2D6 in the bioactivation of acetaminophen. Drug Metab Dispos. 2000 Dec;28(12):1397-400. [Article]
Details5. UDP-glucuronosyltransferase 1-1
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Steroid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
Gene Name
UGT1A1
Uniprot ID
P22309
Uniprot Name
UDP-glucuronosyltransferase 1-1
Molecular Weight
59590.91 Da
References
  1. Bock KW, Forster A, Gschaidmeier H, Bruck M, Munzel P, Schareck W, Fournel-Gigleux S, Burchell B: Paracetamol glucuronidation by recombinant rat and human phenol UDP-glucuronosyltransferases. Biochem Pharmacol. 1993 May 5;45(9):1809-14. [Article]
Details6. UDP-glucuronosyltransferase 1-6
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Protein homodimerization activity
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols. Isoform 3 lacks trans...
Gene Name
UGT1A6
Uniprot ID
P19224
Uniprot Name
UDP-glucuronosyltransferase 1-6
Molecular Weight
60750.215 Da
References
  1. Court MH, Duan SX, von Moltke LL, Greenblatt DJ, Patten CJ, Miners JO, Mackenzie PI: Interindividual variability in acetaminophen glucuronidation by human liver microsomes: identification of relevant acetaminophen UDP-glucuronosyltransferase isoforms. J Pharmacol Exp Ther. 2001 Dec;299(3):998-1006. [Article]
  2. Nagar S, Zalatoris JJ, Blanchard RL: Human UGT1A6 pharmacogenetics: identification of a novel SNP, characterization of allele frequencies and functional analysis of recombinant allozymes in human liver tissue and in cultured cells. Pharmacogenetics. 2004 Aug;14(8):487-99. [Article]
Details7. UDP-glucuronosyltransferase 1-9
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Retinoic acid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols. Isoform 2 lacks trans...
Gene Name
UGT1A9
Uniprot ID
O60656
Uniprot Name
UDP-glucuronosyltransferase 1-9
Molecular Weight
59940.495 Da
References
  1. Bock KW, Forster A, Gschaidmeier H, Bruck M, Munzel P, Schareck W, Fournel-Gigleux S, Burchell B: Paracetamol glucuronidation by recombinant rat and human phenol UDP-glucuronosyltransferases. Biochem Pharmacol. 1993 May 5;45(9):1809-14. [Article]
  2. Linakis MW, Cook SF, Kumar SS, Liu X, Wilkins DG, Gaedigk R, Gaedigk A, Sherwin CMT, van den Anker JN: Polymorphic Expression of UGT1A9 is Associated with Variable Acetaminophen Glucuronidation in Neonates: A Population Pharmacokinetic and Pharmacogenetic Study. Clin Pharmacokinet. 2018 Apr 13. pii: 10.1007/s40262-018-0634-9. doi: 10.1007/s40262-018-0634-9. [Article]
Details8. UDP-glucuronosyltransferase 2B15
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Glucuronosyltransferase activity
Specific Function
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme displays activity toward several classes of xeno...
Gene Name
UGT2B15
Uniprot ID
P54855
Uniprot Name
UDP-glucuronosyltransferase 2B15
Molecular Weight
61035.815 Da
References
  1. Navarro SL, Chen Y, Li L, Li SS, Chang JL, Schwarz Y, King IB, Potter JD, Bigler J, Lampe JW: UGT1A6 and UGT2B15 polymorphisms and acetaminophen conjugation in response to a randomized, controlled diet of select fruits and vegetables. Drug Metab Dispos. 2011 Sep;39(9):1650-7. doi: 10.1124/dmd.111.039149. Epub 2011 Jun 10. [Article]
Details9. UDP-glucuronosyltransferase 1-10
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Protein kinase c binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Isoform 2 lacks transferase activity but acts as a negative reg...
Gene Name
UGT1A10
Uniprot ID
Q9HAW8
Uniprot Name
UDP-glucuronosyltransferase 1-10
Molecular Weight
59809.075 Da
References
  1. Kiang TK, Ensom MH, Chang TK: UDP-glucuronosyltransferases and clinical drug-drug interactions. Pharmacol Ther. 2005 Apr;106(1):97-132. Epub 2005 Jan 12. [Article]
Details10. Sulfotransferase 1A1
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Sulfotransferase activity
Specific Function
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of catecholamines, phenolic drugs and neurotransmitters. Has also estroge...
Gene Name
SULT1A1
Uniprot ID
P50225
Uniprot Name
Sulfotransferase 1A1
Molecular Weight
34165.13 Da
References
  1. Adjei AA, Gaedigk A, Simon SD, Weinshilboum RM, Leeder JS: Interindividual variability in acetaminophen sulfation by human fetal liver: implications for pharmacogenetic investigations of drug-induced birth defects. Birth Defects Res A Clin Mol Teratol. 2008 Mar;82(3):155-65. doi: 10.1002/bdra.20535. [Article]
Details11. Sulfotransferase 1A3/1A4
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Specific Function
Amine sulfotransferase activity
Gene Name
SULT1A3
Uniprot ID
P0DMM9
Uniprot Name
Sulfotransferase 1A3
Molecular Weight
34195.96 Da
References
  1. Adjei AA, Gaedigk A, Simon SD, Weinshilboum RM, Leeder JS: Interindividual variability in acetaminophen sulfation by human fetal liver: implications for pharmacogenetic investigations of drug-induced birth defects. Birth Defects Res A Clin Mol Teratol. 2008 Mar;82(3):155-65. doi: 10.1002/bdra.20535. [Article]
Details12. Estrogen sulfotransferase
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Sulfotransferase activity
Specific Function
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of estradiol and estrone. May play a role in the regulation of estrogen r...
Gene Name
SULT1E1
Uniprot ID
P49888
Uniprot Name
Estrogen sulfotransferase
Molecular Weight
35126.185 Da
References
  1. Adjei AA, Gaedigk A, Simon SD, Weinshilboum RM, Leeder JS: Interindividual variability in acetaminophen sulfation by human fetal liver: implications for pharmacogenetic investigations of drug-induced birth defects. Birth Defects Res A Clin Mol Teratol. 2008 Mar;82(3):155-65. doi: 10.1002/bdra.20535. [Article]
Details13. Bile salt sulfotransferase
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Sulfotransferase activity
Specific Function
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfonation of steroids and bile acids in the liver and adrenal glands.
Gene Name
SULT2A1
Uniprot ID
Q06520
Uniprot Name
Bile salt sulfotransferase
Molecular Weight
33779.57 Da
References
  1. Adjei AA, Gaedigk A, Simon SD, Weinshilboum RM, Leeder JS: Interindividual variability in acetaminophen sulfation by human fetal liver: implications for pharmacogenetic investigations of drug-induced birth defects. Birth Defects Res A Clin Mol Teratol. 2008 Mar;82(3):155-65. doi: 10.1002/bdra.20535. [Article]
Details14. Arylamine N-acetyltransferase 2
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Arylamine n-acetyltransferase activity
Specific Function
Participates in the detoxification of a plethora of hydrazine and arylamine drugs. Catalyzes the N- or O-acetylation of various arylamine and heterocyclic amine substrates and is able to bioactivat...
Gene Name
NAT2
Uniprot ID
P11245
Uniprot Name
Arylamine N-acetyltransferase 2
Molecular Weight
33542.235 Da
References
  1. Rothen JP, Haefeli WE, Meyer UA, Todesco L, Wenk M: Acetaminophen is an inhibitor of hepatic N-acetyltransferase 2 in vitro and in vivo. Pharmacogenetics. 1998 Dec;8(6):553-9. [Article]
Details15. Cytochrome P450 2C9
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
Details16. Cytochrome P450 3A4
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inducer
Curator comments
Acetaminophen, the active metabolite of propacetamol, interacts with this enzyme.
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Feierman DE, Melnikov Z, Zhang J: The paradoxical effect of acetaminophen on CYP3A4 activity and content in transfected HepG2 cells. Arch Biochem Biophys. 2002 Feb 1;398(1):109-17. doi: 10.1006/abbi.2001.2677. [Article]
  2. Cao L, Kwara A, Greenblatt DJ: Metabolic interactions between acetaminophen (paracetamol) and two flavonoids, luteolin and quercetin, through in-vitro inhibition studies. J Pharm Pharmacol. 2017 Dec;69(12):1762-1772. doi: 10.1111/jphp.12812. Epub 2017 Sep 5. [Article]
  3. Laine JE, Auriola S, Pasanen M, Juvonen RO: Acetaminophen bioactivation by human cytochrome P450 enzymes and animal microsomes. Xenobiotica. 2009 Jan;39(1):11-21. doi: 10.1080/00498250802512830 . [Article]

Drug created at October 29, 2015 19:38 / Updated at February 02, 2024 22:52