Identification

Name
Propacetamol
Accession Number
DB09288
Type
Small Molecule
Groups
Approved, Investigational
Description

Propacetamol is a non-opioid analgesic devoid of the major contraindications.[1] It is a derivative of 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]

Structure
Thumb
Synonyms
Not Available
Product Ingredients
IngredientUNIICASInChI Key
Propacetamol hydrochlorideSH41QYH8E566532-86-3WGTYJNGARJPYKG-UHFFFAOYSA-N
International/Other Brands
Pro-dafalgan
Categories
UNII
5CHW4JMR82
CAS number
66532-85-2
Weight
Average: 264.325
Monoisotopic: 264.147392512
Chemical Formula
C14H20N2O3
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

Pharmacology

Indication

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

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
Human
AProstaglandin G/H synthase 2
antagonist
Human
ATransient receptor potential cation channel subfamily V member 1
antagonist
Human
ACannabinoid receptor 1
antagonist
Human
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]

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]

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]

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(4R)-limoneneThe risk or severity of adverse effects can be increased when (4R)-limonene is combined with Propacetamol.
16-BromoepiandrosteroneThe risk or severity of adverse effects can be increased when Propacetamol is combined with 16-Bromoepiandrosterone.
19-norandrostenedioneThe risk or severity of adverse effects can be increased when Propacetamol is combined with 19-norandrostenedione.
5-androstenedioneThe risk or severity of adverse effects can be increased when Propacetamol is combined with 5-androstenedione.
AbciximabThe risk or severity of bleeding and hemorrhage can be increased when Propacetamol is combined with Abciximab.
AcebutololPropacetamol may decrease the antihypertensive activities of Acebutolol.
AceclofenacThe risk or severity of adverse effects can be increased when Propacetamol is combined with Aceclofenac.
AcemetacinThe risk or severity of adverse effects can be increased when Propacetamol is combined with Acemetacin.
AcenocoumarolPropacetamol may increase the anticoagulant activities of Acenocoumarol.
AcetaminophenPropacetamol may decrease the excretion rate of Acetaminophen which could result in a higher serum level.
Food Interactions
Not Available

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. [PubMed:8116325]
  2. Jozwiak-Bebenista M, Nowak JZ: Paracetamol: mechanism of action, applications and safety concern. Acta Pol Pharm. 2014 Jan-Feb;71(1):11-23. [PubMed:24779190]
  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. [PubMed:1633071]
  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. [PubMed:14711849]
  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]
External Links
KEGG Drug
D07294
PubChem Compound
68865
PubChem Substance
310265180
ChemSpider
62097
ChEBI
135089
ChEMBL
CHEMBL1851805
Wikipedia
Propacetamol
ATC Codes
N02BE05 — Propacetamol
MSDS
Download (40.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
Not AvailableCompletedPreventionPonv / Propacetamol1
Not AvailableCompletedTreatmentProphylaxis against postoperative nausea and vomiting1
Not AvailableNot Yet RecruitingTreatmentInguinal Hernias1
Not AvailableNot Yet RecruitingTreatmentPain / Thyroidectomy1
Not AvailableRecruitingSupportive CareArrythmias1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
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/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Alpha-amino acid ester / Acetanilide / Phenol ester / N-acetylarylamine / Anilide / Phenoxy compound / N-arylamide / Monocyclic benzene moiety / Benzenoid / Acetamide
show 16 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
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]
Kind
Protein
Organism
Human
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]
Kind
Protein
Organism
Human
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]
Kind
Protein
Organism
Human
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

Kind
Protein
Organism
Human
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. [PubMed:14711849]
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
Inhibitor
Inducer
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. 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. [PubMed:11811955]
  3. Tegretol FDA label [Link]
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. 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. [PubMed:11095574]
  3. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
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. [PubMed:2729995]
  2. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. 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. [PubMed:11095574]
Kind
Protein
Organism
Human
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. [PubMed:8494539]
Kind
Protein
Organism
Human
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. [PubMed:11714888]
  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. [PubMed:15284531]
Kind
Protein
Organism
Human
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. [PubMed:8494539]
  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. [PubMed:29654492]
Kind
Protein
Organism
Human
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. [PubMed:21666065]
Kind
Protein
Organism
Human
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. [PubMed:15781124]
Kind
Protein
Organism
Human
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. [PubMed:18232020]
Kind
Protein
Organism
Human
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. [PubMed:18232020]
Kind
Protein
Organism
Human
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. [PubMed:18232020]
Kind
Protein
Organism
Human
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. [PubMed:18232020]
Kind
Protein
Organism
Human
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. [PubMed:9918139]
Kind
Protein
Organism
Human
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

Drug created on October 29, 2015 13:38 / Updated on September 13, 2018 15:59