Antipyrine

Identification

Summary

Antipyrine is an antipyretic agent used for the symptomatic treatment of acute otitis media, most commonly in combination with benzocaine.

Generic Name
Antipyrine
DrugBank Accession Number
DB01435
Background

An analgesic and antipyretic that has been given by mouth and as ear drops. Antipyrine is often used in testing the effects of other drugs or diseases on drug-metabolizing enzymes in the liver. (From Martindale, The Extra Pharmacopoeia, 30th ed, p29)

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 188.2258
Monoisotopic: 188.094963016
Chemical Formula
C11H12N2O
Synonyms
  • 1,2-Dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one
  • 2,3-Dimethyl-1-phenyl-5-pyrazolone
  • Analgesine
  • Antipyrine
  • Fenazon
  • Fenazona
  • Phenazon
  • Phenazone

Pharmacology

Indication

Antipyrine is an analgesic often used to test effects of other drugs on liver enzymes.

In combination with benzocaine in otic solutions, antipyrine is indicated for the symptomatic relief of acute otitis media arising from various etiologies.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofCoughing••••••••••••••••••
Treatment ofCoughing••••••••••••••••••
Used in combination for symptomatic treatment ofOtitis media (om)Combination Product in combination with: Lidocaine (DB00281)••••••••••••••••••••
Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

Antipyrine is an analgesic and antipyretic that has been given by mouth and as ear drops. Antipyrine is often used in testing the effects of other drugs or diseases on drug-metabolizing enzymes in the liver. (From Martindale, The Extra Pharmacopoeia, 30th ed, p29)

Mechanism of action

Antipyrine is thought to act primarily in the CNS, increasing the pain threshold by inhibiting both isoforms of cyclooxygenase, COX-1, COX-2, and COX-3 enzymes involved in prostaglandin (PG) synthesis.

TargetActionsOrganism
UProstaglandin G/H synthase 2
inhibitor
Humans
UProstaglandin G/H synthase 1
inhibitor
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Hover over products below to view reaction partners

Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
PathwayCategory
Antipyrine Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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
AbacavirAntipyrine may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbametapirThe serum concentration of Antipyrine can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Antipyrine can be increased when combined with Abatacept.
AbciximabThe risk or severity of bleeding and hemorrhage can be increased when Antipyrine is combined with Abciximab.
AbirateroneThe serum concentration of Antipyrine can be increased when it is combined with Abiraterone.
Food Interactions
  • Take with or without food. When taken after meals, the Cmax and Tmax of oral antipyrine are reduced, but the overall bioavailability is not significantly impacted.

Products

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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
TROPEX EAR DROPS 5% w/vSolution5 % w/vAuricular (otic)DCH AURIGA SINGAPORE1990-06-26Not applicableSingapore flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Antidouleurs RezallAntipyrine (180 mg / 30 mL) + Sodium salicylate (600 mg / 30 mL)LiquidOralProduits Francais Labs Inc.1930-12-311997-05-30Canada flag
AuralganAntipyrine (54 mg / mL) + Benzocaine (14 mg / mL)SolutionAuricular (otic)Paladin Labs Inc.2011-02-282021-11-01Canada flag
Auralgan EardropsAntipyrine (54 mg / mL) + Benzocaine (14 mg / mL)Solution / dropsAuricular (otic)Wyeth Ltd.1994-12-312006-08-04Canada flag
Auralgan SolutionAntipyrine (54 mg / mL) + Benzocaine (14 mg / mL)SolutionAuricular (otic)Wyeth Ltd.1993-12-312011-08-05Canada flag
DOLPACK SOLUCIÓN BUCALAntipyrine (3 g) + Benzocaine (2.5 g)SolutionBuccal; OralSEVERIANO FERNANDEZ M S.A.S.2013-04-052020-11-13Colombia flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Acella Antipyrine and Benzocaine OticAntipyrine (54 mg/1mL) + Benzocaine (14 mg/1mL)SolutionAuricular (otic)Proficient Rx LP2010-11-092015-12-31US flag
Acella Antipyrine and Benzocaine OticAntipyrine (54 mg/1mL) + Benzocaine (14 mg/1mL)SolutionAuricular (otic)Acella Pharmaceuticals, LLC2010-03-122017-04-30US flag
Antipyrine and BenzocaineAntipyrine (54 mg/1mL) + Benzocaine (14 mg/1mL)LiquidTopicalVirtus Pharmaceuticals2012-09-122015-07-01US flag
Antipyrine and BenzocaineAntipyrine (54 mg/1mL) + Benzocaine (14 mg/1mL)SolutionAuricular (otic)Directrx2014-01-012017-07-26US flag
Antipyrine and BenzocaineAntipyrine (54 mg/1mL) + Benzocaine (14 mg/1mL)SolutionAuricular (otic)Remedy Repack2015-06-082015-06-09US flag

Categories

ATC Codes
N02BB51 — Phenazone, combinations excl. psycholepticsN02BB71 — Phenazone, combinations with psycholepticsN02BB01 — PhenazoneS02DA03 — Phenazone
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenylpyrazoles. These are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Azoles
Sub Class
Pyrazoles
Direct Parent
Phenylpyrazoles
Alternative Parents
Pyrazolones / Benzene and substituted derivatives / Vinylogous amides / Heteroaromatic compounds / Lactams / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Organic oxides
show 1 more
Substituents
Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Heteroaromatic compound / Hydrocarbon derivative / Lactam / Monocyclic benzene moiety / Organic nitrogen compound / Organic oxide / Organic oxygen compound
show 6 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
pyrazolone (CHEBI:31225)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
T3CHA1B51H
CAS number
60-80-0
InChI Key
VEQOALNAAJBPNY-UHFFFAOYSA-N
InChI
InChI=1S/C11H12N2O/c1-9-8-11(14)13(12(9)2)10-6-4-3-5-7-10/h3-8H,1-2H3
IUPAC Name
1,5-dimethyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one
SMILES
CN1N(C(=O)C=C1C)C1=CC=CC=C1

References

Synthesis Reference

Andreas Burgard, "Xanthine-and phenazone-acesulfame-H complexes having improved taste, process for their preparation and their use." U.S. Patent US20030008865, issued January 09, 2003.

US20030008865
General References
  1. INVIMA Product Authorization: Calzas (antipyrine/benzocaine) oral solution [Link]
Human Metabolome Database
HMDB0015503
KEGG Drug
D01776
KEGG Compound
C13244
PubChem Compound
2206
PubChem Substance
46505216
ChemSpider
2121
BindingDB
50103600
RxNav
1001
ChEBI
31225
ChEMBL
CHEMBL277474
ZINC
ZINC000000061044
Therapeutic Targets Database
DNC001118
PharmGKB
PA448453
PDRhealth
PDRhealth Drug Page
Wikipedia
Phenazone
MSDS
Download (73 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3RecruitingTreatmentAcute Otitis Media (AOM) / Pain1
2CompletedTreatmentAcute Otitis Media (AOM)1
2Not Yet RecruitingTreatmentAsthma1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Deston Therapeutics
Dosage Forms
FormRouteStrength
LiquidTopical
Solution / dropsAuricular (otic)
SolutionOral
LiquidAuricular (otic)
SolutionBuccal; Oral
LiquidOral
SolutionAuricular (otic)
SuspensionOphthalmic
SolutionTopical
SolutionAuricular (otic)5 % w/v
Prices
Unit descriptionCostUnit
Auralgan ear drops13.11USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)114 °CPhysProp
boiling point (°C)319 °CPhysProp
water solubility5.19E+004 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP0.38HANSCH,C ET AL. (1995)
Caco2 permeability-4.55ADME Research, USCD
pKa1.4SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility47.4 mg/mLALOGPS
logP1.18ALOGPS
logP1.22Chemaxon
logS-0.6ALOGPS
pKa (Strongest Basic)0.49Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area23.55 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity56.42 m3·mol-1Chemaxon
Polarizability20.4 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9931
Caco-2 permeable+0.8273
P-glycoprotein substrateNon-substrate0.8995
P-glycoprotein inhibitor INon-inhibitor0.8782
P-glycoprotein inhibitor IINon-inhibitor0.8737
Renal organic cation transporterNon-inhibitor0.8837
CYP450 2C9 substrateNon-substrate0.6871
CYP450 2D6 substrateNon-substrate0.9115
CYP450 3A4 substrateSubstrate0.6459
CYP450 1A2 substrateNon-inhibitor0.8617
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9444
CYP450 2C19 inhibitorNon-inhibitor0.9533
CYP450 3A4 inhibitorNon-inhibitor0.9615
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7357
Ames testNon AMES toxic0.9261
CarcinogenicityNon-carcinogens0.9202
BiodegradationNot ready biodegradable0.9761
Rat acute toxicity2.0746 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9816
hERG inhibition (predictor II)Non-inhibitor0.8733
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (8.41 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-00ri-4900000000-83deafb6ee63b89d8830
GC-MS Spectrum - CI-BGC-MSsplash10-000i-0900000000-1ac29db9e7ca9b1271ed
GC-MS Spectrum - EI-BGC-MSsplash10-0550-9600000000-0c90aa2dd40a0fac3c48
GC-MS Spectrum - EI-BGC-MSsplash10-000i-9600000000-297680e0a5f2e22c7de5
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001a-0900000000-94d2c7fe629bedc897b3
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-ebc5f64904e52ff3d68e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-602baaec0430c9c48fc7
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-a3fafbc8e8baf10dba96
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-ad19708445bbe9cd2bff
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-052s-2900000000-efb8c895ae384b102f76
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-4900000000-80fc3f4f0ffbc6d8c8bb
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-3a2d3f4534b07f6de875
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-dbaaf801a6650b53331b
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-0258999e6a4bf7041dea
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-4b511d8866a35ece5abd
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4s-2900000000-eea7fbb638b6e5146e90
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-4900000000-80478740d36be900a6e7
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-01q1-0900000000-e6dcb2d1a0ca860186fb
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-ae7f87ba95e0fc52493e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-1011-1900000000-a520cee151b2f2b6fcd1
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-4fe0a2e33ea5e0c5c876
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-01wb-0900000000-1eaec6590298997b716e
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0900000000-65a45a9258dc65cd80a4
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0900000000-478b62fc9b49f02d00a5
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0pea-4900000000-56c25ac15fc6499fff0a
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-056r-9700000000-189e518b80900e1831f5
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004i-9300000000-3975b66276ed6889196d
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-000i-0900000000-5e1eb3bf34fe1cf98763
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-0900000000-f8b01a9e69af21118a26
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-052f-0900000000-0dae43de166d1a48d6e7
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0900000000-c0601c81c92074ba3828
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0900000000-4049f2aebad14ec7f8d3
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-2900000000-f460306b23f80a527f46
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kf-9200000000-58b005be2abfad7110bb
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01bc-9300000000-c3a05bdac45f2c4b1ac0
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9200000000-653bfce8bc4ab6dda343
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]-147.049516
predicted
DarkChem Lite v0.1.0
[M-H]-146.812216
predicted
DarkChem Lite v0.1.0
[M-H]-136.22133
predicted
DeepCCS 1.0 (2019)
[M+H]+148.092216
predicted
DarkChem Lite v0.1.0
[M+H]+147.8811847
predicted
DarkChem Lite v0.1.0
[M+H]+138.61688
predicted
DeepCCS 1.0 (2019)
[M+Na]+147.632716
predicted
DarkChem Lite v0.1.0
[M+Na]+154.0670831
predicted
DarkChem Lite v0.1.0
[M+Na]+145.66899
predicted
DeepCCS 1.0 (2019)

Targets

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Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
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Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
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. Brune K, Neubert A: Pharmacokinetic and pharmacodynamic aspects of the ideal COX-2 inhibitor: a pharmacologist's perspective. Clin Exp Rheumatol. 2001 Nov-Dec;19(6 Suppl 25):S51-7. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
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. Brune K, Neubert A: Pharmacokinetic and pharmacodynamic aspects of the ideal COX-2 inhibitor: a pharmacologist's perspective. Clin Exp Rheumatol. 2001 Nov-Dec;19(6 Suppl 25):S51-7. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Const...
Gene Name
CYP2A6
Uniprot ID
P11509
Uniprot Name
Cytochrome P450 2A6
Molecular Weight
56501.005 Da
References
  1. Sharer JE, Wrighton SA: Identification of the human hepatic cytochromes P450 involved in the in vitro oxidation of antipyrine. Drug Metab Dispos. 1996 Apr;24(4):487-94. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. Engel G, Hofmann U, Heidemann H, Cosme J, Eichelbaum M: Antipyrine as a probe for human oxidative drug metabolism: identification of the cytochrome P450 enzymes catalyzing 4-hydroxyantipyrine, 3-hydroxymethylantipyrine, and norantipyrine formation. Clin Pharmacol Ther. 1996 Jun;59(6):613-23. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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
CYP2C18
Uniprot ID
P33260
Uniprot Name
Cytochrome P450 2C18
Molecular Weight
55710.075 Da
References
  1. Engel G, Hofmann U, Heidemann H, Cosme J, Eichelbaum M: Antipyrine as a probe for human oxidative drug metabolism: identification of the cytochrome P450 enzymes catalyzing 4-hydroxyantipyrine, 3-hydroxymethylantipyrine, and norantipyrine formation. Clin Pharmacol Ther. 1996 Jun;59(6):613-23. [Article]
  2. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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. Engel G, Hofmann U, Heidemann H, Cosme J, Eichelbaum M: Antipyrine as a probe for human oxidative drug metabolism: identification of the cytochrome P450 enzymes catalyzing 4-hydroxyantipyrine, 3-hydroxymethylantipyrine, and norantipyrine formation. Clin Pharmacol Ther. 1996 Jun;59(6):613-23. [Article]
  2. Sharer JE, Wrighton SA: Identification of the human hepatic cytochromes P450 involved in the in vitro oxidation of antipyrine. Drug Metab Dispos. 1996 Apr;24(4):487-94. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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. Sharer JE, Wrighton SA: Identification of the human hepatic cytochromes P450 involved in the in vitro oxidation of antipyrine. Drug Metab Dispos. 1996 Apr;24(4):487-94. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
  2. Engel G, Hofmann U, Heidemann H, Cosme J, Eichelbaum M: Antipyrine as a probe for human oxidative drug metabolism: identification of the cytochrome P450 enzymes catalyzing 4-hydroxyantipyrine, 3-hydroxymethylantipyrine, and norantipyrine formation. Clin Pharmacol Ther. 1996 Jun;59(6):613-23. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
  2. Engel G, Hofmann U, Heidemann H, Cosme J, Eichelbaum M: Antipyrine as a probe for human oxidative drug metabolism: identification of the cytochrome P450 enzymes catalyzing 4-hydroxyantipyrine, 3-hydroxymethylantipyrine, and norantipyrine formation. Clin Pharmacol Ther. 1996 Jun;59(6):613-23. [Article]
  3. Sharer JE, Wrighton SA: Identification of the human hepatic cytochromes P450 involved in the in vitro oxidation of antipyrine. Drug Metab Dispos. 1996 Apr;24(4):487-94. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
  2. Engel G, Hofmann U, Heidemann H, Cosme J, Eichelbaum M: Antipyrine as a probe for human oxidative drug metabolism: identification of the cytochrome P450 enzymes catalyzing 4-hydroxyantipyrine, 3-hydroxymethylantipyrine, and norantipyrine formation. Clin Pharmacol Ther. 1996 Jun;59(6):613-23. [Article]
  3. Sotaniemi EA, Pelkonen O, Arranto AJ, Tapanainen P, Rautio A, Pasanen M: Diabetes and elimination of antipyrine in man: an analysis of 298 patients classified by type of diabetes, age, sex, duration of disease and liver involvement. Pharmacol Toxicol. 2002 Mar;90(3):155-60. [Article]
  4. Lu P, Schrag ML, Slaughter DE, Raab CE, Shou M, Rodrigues AD: Mechanism-based inhibition of human liver microsomal cytochrome P450 1A2 by zileuton, a 5-lipoxygenase inhibitor. Drug Metab Dispos. 2003 Nov;31(11):1352-60. doi: 10.1124/dmd.31.11.1352. [Article]
  5. Sharer JE, Wrighton SA: Identification of the human hepatic cytochromes P450 involved in the in vitro oxidation of antipyrine. Drug Metab Dispos. 1996 Apr;24(4):487-94. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Sharer JE, Wrighton SA: Identification of the human hepatic cytochromes P450 involved in the in vitro oxidation of antipyrine. Drug Metab Dispos. 1996 Apr;24(4):487-94. [Article]
  2. Engel G, Hofmann U, Heidemann H, Cosme J, Eichelbaum M: Antipyrine as a probe for human oxidative drug metabolism: identification of the cytochrome P450 enzymes catalyzing 4-hydroxyantipyrine, 3-hydroxymethylantipyrine, and norantipyrine formation. Clin Pharmacol Ther. 1996 Jun;59(6):613-23. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
  2. Engel G, Hofmann U, Heidemann H, Cosme J, Eichelbaum M: Antipyrine as a probe for human oxidative drug metabolism: identification of the cytochrome P450 enzymes catalyzing 4-hydroxyantipyrine, 3-hydroxymethylantipyrine, and norantipyrine formation. Clin Pharmacol Ther. 1996 Jun;59(6):613-23. [Article]
  3. Sharer JE, Wrighton SA: Identification of the human hepatic cytochromes P450 involved in the in vitro oxidation of antipyrine. Drug Metab Dispos. 1996 Apr;24(4):487-94. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
Molecular Weight
61815.78 Da
References
  1. Apiwattanakul N, Sekine T, Chairoungdua A, Kanai Y, Nakajima N, Sophasan S, Endou H: Transport properties of nonsteroidal anti-inflammatory drugs by organic anion transporter 1 expressed in Xenopus laevis oocytes. Mol Pharmacol. 1999 May;55(5):847-54. [Article]

Drug created at July 26, 2007 10:19 / Updated at September 28, 2021 21:54