Identification

Name
Antipyrine
Accession Number
DB01435
Type
Small Molecule
Groups
Approved, Investigational
Description

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)

Structure
Thumb
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
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Antidouleurs RezallAntipyrine (180 mg) + Sodium salicylate (600 mg)LiquidOralProduits Francais Labs Inc.1930-12-311997-05-30Canada
AuralganAntipyrine (54 mg) + Benzocaine (14 mg)SolutionAuricular (otic)Paladin Labs Inc2011-02-28Not applicableCanada
Auralgan EardropsAntipyrine (54 mg) + Benzocaine (14 mg)Solution / dropsAuricular (otic)Wyeth Ltd.1994-12-312006-08-04Canada
Auralgan SolutionAntipyrine (54 mg) + Benzocaine (14 mg)SolutionAuricular (otic)Wyeth Ltd.1993-12-312011-08-05Canada
Formule L2Antipyrine (10 mg) + Sodium salicylate (56 mg)LiquidOralHerbages Naturbec LtÉe.1979-12-31Not applicableCanada
Oti CalAntipyrine (58 mg) + Benzocaine (15.3 mg)Solution / dropsAuricular (otic)Produits Francais Labs Inc.1981-12-311997-05-30Canada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Acella Antipyrine and Benzocaine OticAntipyrine (54 mg/1mL) + Benzocaine (14 mg/1mL)SolutionAuricular (otic)Acella Pharmaceuticals, LLC2010-11-092016-11-23Us
Acella Antipyrine and Benzocaine OticAntipyrine (54 mg/1mL) + Benzocaine (14 mg/1mL)SolutionAuricular (otic)Proficient Rx LP2010-11-092015-12-31Us
Antipyrine and BenzocaineAntipyrine (54 mg/1mL) + Benzocaine (14 mg/1mL)SolutionAuricular (otic)Preferreed Pharmaceuticals Inc.2009-04-302016-04-07Us
Antipyrine and BenzocaineAntipyrine (54 mg/1mL) + Benzocaine (14 mg/1mL)SolutionAuricular (otic)Rebel Distributors2009-04-30Not applicableUs
Antipyrine and BenzocaineAntipyrine (54 mg/1mL) + Benzocaine (14 mg/1mL)SolutionAuricular (otic)Boca Pharmacal, Inc.2009-04-302016-01-31Us
Antipyrine and BenzocaineAntipyrine (54 mg/1mL) + Benzocaine (14 mg/1mL)LiquidTopicalDirectrx2014-01-012014-12-31Us
Antipyrine and BenzocaineAntipyrine (54 mg/1mL) + Benzocaine (14 mg/1mL)SolutionAuricular (otic)Bauch & Lomb Incorporated1990-09-302017-05-31Us
Antipyrine and BenzocaineAntipyrine (54 mg/1mL) + Benzocaine (14 mg/1mL)SolutionAuricular (otic)Physicians Total Care, Inc.1995-04-242013-01-15Us
Antipyrine and BenzocaineAntipyrine (54 mg/1mL) + Benzocaine (14 mg/1mL)LiquidTopicalPreferreed Pharmaceuticals Inc.2015-02-232016-04-07Us
Antipyrine and BenzocaineAntipyrine (54 mg/1mL) + Benzocaine (14 mg/1mL)SolutionAuricular (otic)Aidarex Pharmaceuticals LLC1990-09-302016-04-08Us
Categories
UNII
T3CHA1B51H
CAS number
60-80-0
Weight
Average: 188.2258
Monoisotopic: 188.094963016
Chemical Formula
C11H12N2O
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

Pharmacology

Indication

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

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
Human
UProstaglandin G/H synthase 1
inhibitor
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Antipyrine Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of gastrointestinal bleeding can be increased when Antipyrine is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of gastrointestinal bleeding can be increased when Antipyrine is combined with (S)-Warfarin.
3-isobutyl-1-methyl-7H-xanthineThe serum concentration of 3-isobutyl-1-methyl-7H-xanthine can be increased when it is combined with Antipyrine.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Antipyrine.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Antipyrine.
4-MethoxyamphetamineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Antipyrine.
5-androstenedioneThe metabolism of 5-androstenedione can be decreased when combined with Antipyrine.
6-Deoxyerythronolide BThe metabolism of Antipyrine can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe serum concentration of 6-O-benzylguanine can be increased when it is combined with Antipyrine.
7-DeazaguanineThe serum concentration of 7-Deazaguanine can be increased when it is combined with Antipyrine.
Food Interactions
Not Available

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
Not Available
External Links
Human Metabolome Database
HMDB0015503
KEGG Drug
D01776
KEGG Compound
C13244
PubChem Compound
2206
PubChem Substance
46505216
ChemSpider
2121
BindingDB
50103600
ChEBI
31225
ChEMBL
CHEMBL277474
Therapeutic Targets Database
DNC001118
PharmGKB
PA448453
PDRhealth
PDRhealth Drug Page
Wikipedia
Phenazone
ATC Codes
N02BB51 — Phenazone, combinations excl. psycholepticsN02BB01 — PhenazoneN02BB71 — Phenazone, combinations with psycholepticsS02DA03 — Phenazone
MSDS
Download (73 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentAcute Otitis Media1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Deston Therapeutics
Dosage forms
FormRouteStrength
LiquidTopical
Solution / dropsAuricular (otic)
SolutionAuricular (otic)
LiquidAuricular (otic)
LiquidOral
SolutionTopical
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)0.37ChemAxon
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-MSNot Available
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
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
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

Taxonomy

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
Phenylpyrazole / Monocyclic benzene moiety / Pyrazolinone / Benzenoid / Heteroaromatic compound / Vinylogous amide / Lactam / Azacycle / Organic nitrogen compound / Hydrocarbon derivative
show 6 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
pyrazolone (CHEBI:31225)

Targets

Kind
Protein
Organism
Human
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. [PubMed:11695253]
Kind
Protein
Organism
Human
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. [PubMed:11695253]

Enzymes

Kind
Protein
Organism
Human
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. [PubMed:19515014]
  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. [PubMed:8681486]
Kind
Protein
Organism
Human
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. [PubMed:19515014]
  2. 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]
Kind
Protein
Organism
Human
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. [PubMed:19515014]
  2. 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]
  3. 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. [PubMed:8681486]
  4. 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. [PubMed:12071338]
  5. 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. [PubMed:14570767]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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. 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. [PubMed:19515014]
  2. 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]
  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. [PubMed:8801065]
Kind
Protein
Organism
Human
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. [PubMed:19515014]
  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. [PubMed:8681486]
Kind
Protein
Organism
Human
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. [PubMed:8801065]
Kind
Protein
Organism
Human
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. [PubMed:8681486]
Kind
Protein
Organism
Human
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. [PubMed:8681486]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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. [PubMed:8681486]
Kind
Protein
Organism
Human
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. [PubMed:8801065]

Transporters

Kind
Protein
Organism
Human
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. [PubMed:10220563]

Drug created on July 26, 2007 04:19 / Updated on November 02, 2018 05:01