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Identification
NameDapsone
Accession NumberDB00250  (APRD00345)
TypeSmall Molecule
GroupsApproved, Investigational
Description

A sulfone active against a wide range of bacteria but mainly employed for its actions against mycobacterium leprae. Its mechanism of action is probably similar to that of the sulfonamides which involves inhibition of folic acid synthesis in susceptible organisms. It is also used with pyrimethamine in the treatment of malaria. (From Martindale, The Extra Pharmacopoeia, 30th ed, p157-8)

Structure
Thumb
Synonyms
1,1'-Sulfonylbis(4-aminobenzene)
1,1'-Sulfonylbis[4-aminobenzene]
4-(4-amino-Benzenesulfonyl)-phenylamine
4-(4-Aminophenylsulfonyl)aniline
4-(4-Aminophenylsulfonyl)benzenamine
4-Aminophenyl sulfone
4,4'-Dapsone
4,4'-Diaminodiphenyl sulfone
4,4'-Diaminodiphenyl sulphone
4,4'-Diaminodiphenylsulfone
4,4'-Sulfonylbisaniline
4,4'-Sulfonylbisbenzenamine
4,4'-Sulfonylbisbenzeneamine
4,4'-Sulfonyldianilin
4,4'-sulfonyldianiline
Bis(4-aminophenyl)sulfone
Bis(P-aminophenyl) sulfone
DADPS
Dapsona
DAPSONE
Dapsonum
DDS
DIAPHENYLSULFONE
P-Aminophenyl sulfone
P,P-Sulphonylbisbenzamine
P,P-Sulphonylbisbenzenamine
P,P'-diaminodiphenyl sulfone
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Aczonegel50 mg/gtopicalAllergan, Inc.2009-06-24Not applicableUs
Aczonegel5 %topicalValeant Canada Lp Valeant Canada S.E.C.2011-10-21Not applicableCanada
Aczone (dapsone) Gel, 7.5%gel75 mg/gtopicalAllergan, Inc.2016-02-26Not applicableUs
Avlosulfon Tab 100mgtablet100 mgoralAyerst Laboratories1971-12-311996-09-10Canada
Dapsonetablet100 mgoralJacobus Pharmaceutical Company, Inc.1994-12-31Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Dapsonetablet100 mg/1oralREMEDYREPACK INC.2010-11-18Not applicableUs
Dapsonetablet100 mg/1oralSeton Pharmaceuticals2016-03-10Not applicableUs
Dapsonetablet25 mg/1oralSeton Pharmaceuticals2016-03-10Not applicableUs
Dapsonetablet100 mg/1oralPhysicians Total Care, Inc.2005-12-16Not applicableUs
Dapsonetablet25 mg/1oralPhysicians Total Care, Inc.2009-04-22Not applicableUs
Dapsonetablet25 mg/1oralJacobus Pharmaceutical Company, Inc.1979-07-03Not applicableUs
Dapsonetablet100 mg/1oralDepartment Of State Health Services, Pharmacy Branch2008-08-15Not applicableUs
Dapsonetablet100 mg/1oralJacobus Pharmaceutical Company, Inc.1979-07-03Not applicableUs
Dapsonetablet25 mg/1oralDepartment Of State Health Services, Pharmacy Branch2008-08-15Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII8W5C518302
CAS number80-08-0
WeightAverage: 248.301
Monoisotopic: 248.061948328
Chemical FormulaC12H12N2O2S
InChI KeyInChIKey=MQJKPEGWNLWLTK-UHFFFAOYSA-N
InChI
InChI=1S/C12H12N2O2S/c13-9-1-5-11(6-2-9)17(15,16)12-7-3-10(14)4-8-12/h1-8H,13-14H2
IUPAC Name
4-(4-aminobenzenesulfonyl)aniline
SMILES
NC1=CC=C(C=C1)S(=O)(=O)C1=CC=C(N)C=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as sulfonylanilines. These are compounds containing an aniline moiety which bears a sulfonyl group at ring position 4.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAnilines
Direct ParentSulfonylanilines
Alternative Parents
Substituents
  • Sulfonylaniline
  • Substituted aniline
  • Primary aromatic amine
  • Sulfonyl
  • Sulfone
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment and management of leprosy and dermatitis herpetiformis.
PharmacodynamicsDapsone is a sulfone with anti-inflammatory immunosuppressive properties as well as antibacterial and antibiotic properties. Dapsone is the principal drug in a multidrug regimen recommended by the World Health Organization for the treatment of leprosy. As an anti-infective agent, it is also used for treating malaria and, recently, for Pneumocystic carinii pneumonia in AIDS patients. Dapsone is absorbed rapidly and nearly completely from the gastrointestinal tract. Dapsone is distributed throughout total body water and is present in all tissues. However, it tends to be retained in skin and muscle and especially in the liver and kidney: traces of the drug are present in these organs up to 3 weeks after therapy cessation.
Mechanism of actionDapsone acts against bacteria and protozoa in the same way as sulphonamides, that is by inhibiting the synthesis of dihydrofolic acid through competition with para-amino-benzoate for the active site of dihydropteroate synthetase. The anti-inflammatory action of the drug is unrelated to its antibacterial action and is still not fully understood.
Related Articles
AbsorptionBioavailability is 70 to 80% following oral administration.
Volume of distributionNot Available
Protein binding70 to 90%
Metabolism

Hepatic, mostly CYP2E1-mediated.

SubstrateEnzymesProduct
Dapsone
dapsone hydroxylamineDetails
Dapsone
N-AcetyldapsoneDetails
dapsone hydroxylamine
Not Available
Nitroso-dapsoneDetails
Nitroso-dapsone
Not Available
Dapsone mercaptal intermediateDetails
Dapsone mercaptal intermediate
Not Available
Dapsone GSH conjugateDetails
Route of eliminationRenal
Half life28 hours (range 10-50 hours)
ClearanceNot Available
ToxicityOverdosage might be expected to produce nasal congestion, syncope, or hallucinations. Measures to support blood pressure should be taken if necessary.
Affected organisms
  • Mycobacteria
  • Mycobacterium leprae
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8476
Blood Brain Barrier+0.9705
Caco-2 permeable+0.5879
P-glycoprotein substrateNon-substrate0.8699
P-glycoprotein inhibitor INon-inhibitor0.9311
P-glycoprotein inhibitor IINon-inhibitor0.9572
Renal organic cation transporterNon-inhibitor0.8739
CYP450 2C9 substrateNon-substrate0.7416
CYP450 2D6 substrateSubstrate0.86
CYP450 3A4 substrateNon-substrate0.7175
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.8955
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorInhibitor0.6127
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.556
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.5795
BiodegradationNot ready biodegradable0.9778
Rat acute toxicity2.3635 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9859
hERG inhibition (predictor II)Non-inhibitor0.864
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Jacobus pharmaceutical co
Packagers
Dosage forms
FormRouteStrength
Geltopical5 %
Geltopical50 mg/g
Geltopical75 mg/g
Tabletoral100 mg
Tabletoral100 mg/1
Tabletoral25 mg/1
Prices
Unit descriptionCostUnit
Dapsone 30 100 mg tablet Box42.99USD box
Dapsone 30 25 mg tablet Box35.99USD box
Aczone 5% gel5.52USD g
Dapsone powder5.38USD g
Dapsone 100 mg tablet0.86USD tablet
Dapsone 25 mg tablet0.2USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2265461 No2004-11-302017-09-10Canada
US5863560 No1996-09-112016-09-11Us
US6060085 No1996-09-112016-09-11Us
US6620435 No1996-09-112016-09-11Us
US9161926 No2013-11-182033-11-18Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point175.5 °CNot Available
water solubility380 mg/L (at 37 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP0.97HANSCH,C ET AL. (1995)
logS-2.82ADME Research, USCD
pKa2.41PERRIN,DD (1965)
Predicted Properties
PropertyValueSource
Water Solubility0.284 mg/mLALOGPS
logP1.19ALOGPS
logP1.27ChemAxon
logS-2.9ALOGPS
pKa (Strongest Basic)2.39ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area86.18 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity68.99 m3·mol-1ChemAxon
Polarizability25.05 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (9.27 KB)
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-052g-8930000000-c51783649020dadfb20fView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
References
Synthesis Reference

Weijiard, J.and Messerly, J.P.; U.S. Patent 2,385,899; October 2,1945; assigned to Merck
& Co., Inc.

General ReferencesNot Available
External Links
ATC CodesD10AX05J04BA02
AHFS Codes
  • 08:16.92
PDB EntriesNot Available
FDA labelDownload (515 KB)
MSDSDownload (53.5 KB)
Interactions
Drug Interactions
Drug
AcetaminophenThe risk or severity of adverse effects can be increased when Dapsone is combined with Acetaminophen.
Amyl NitriteThe risk or severity of adverse effects can be increased when Dapsone is combined with Amyl Nitrite.
AntipyrineThe risk or severity of adverse effects can be increased when Dapsone is combined with Antipyrine.
ArtemetherThe risk or severity of adverse effects can be increased when Artemether is combined with Dapsone.
ArtesunateThe risk or severity of adverse effects can be increased when Artesunate is combined with Dapsone.
AtovaquoneThe risk or severity of adverse effects can be increased when Atovaquone is combined with Dapsone.
BenzocaineThe risk or severity of adverse effects can be increased when Dapsone is combined with Benzocaine.
Benzoyl peroxideThe risk or severity of adverse effects can be increased when Benzoyl peroxide is combined with Dapsone.
BexaroteneThe serum concentration of Dapsone can be decreased when it is combined with Bexarotene.
BosentanThe serum concentration of Dapsone can be decreased when it is combined with Bosentan.
ButalbitalThe risk or severity of adverse effects can be increased when Dapsone is combined with Butalbital.
CaffeineThe risk or severity of adverse effects can be increased when Dapsone is combined with Caffeine.
CelecoxibThe risk or severity of adverse effects can be increased when Dapsone is combined with Celecoxib.
ChloroquineThe risk or severity of adverse effects can be increased when Chloroquine is combined with Dapsone.
ConivaptanThe serum concentration of Dapsone can be increased when it is combined with Conivaptan.
DabrafenibThe serum concentration of Dapsone can be decreased when it is combined with Dabrafenib.
DasatinibThe serum concentration of Dapsone can be increased when it is combined with Dasatinib.
DeferasiroxThe serum concentration of Dapsone can be decreased when it is combined with Deferasirox.
FloxuridineThe metabolism of Dapsone can be decreased when combined with Floxuridine.
FluconazoleThe metabolism of Dapsone can be decreased when combined with Fluconazole.
FlutamideThe risk or severity of adverse effects can be increased when Dapsone is combined with Flutamide.
FosaprepitantThe serum concentration of Dapsone can be increased when it is combined with Fosaprepitant.
Fusidic AcidThe serum concentration of Dapsone can be increased when it is combined with Fusidic Acid.
HydroxychloroquineThe risk or severity of adverse effects can be increased when Hydroxychloroquine is combined with Dapsone.
IdelalisibThe serum concentration of Dapsone can be increased when it is combined with Idelalisib.
IsomethepteneThe risk or severity of adverse effects can be increased when Dapsone is combined with Isometheptene.
IsosorbideThe risk or severity of adverse effects can be increased when Dapsone is combined with Isosorbide.
Isosorbide DinitrateThe risk or severity of adverse effects can be increased when Dapsone is combined with Isosorbide Dinitrate.
Isosorbide MononitrateThe risk or severity of adverse effects can be increased when Dapsone is combined with Isosorbide Mononitrate.
IvacaftorThe serum concentration of Dapsone can be increased when it is combined with Ivacaftor.
LidocaineThe risk or severity of adverse effects can be increased when Dapsone is combined with Lidocaine.
LuliconazoleThe serum concentration of Dapsone can be increased when it is combined with Luliconazole.
LumefantrineThe risk or severity of adverse effects can be increased when Lumefantrine is combined with Dapsone.
MafenideThe risk or severity of adverse effects can be increased when Dapsone is combined with Mafenide.
MefloquineThe risk or severity of adverse effects can be increased when Mefloquine is combined with Dapsone.
MetoclopramideThe risk or severity of adverse effects can be increased when Dapsone is combined with Metoclopramide.
MifepristoneThe serum concentration of Dapsone can be increased when it is combined with Mifepristone.
MitotaneThe serum concentration of Dapsone can be decreased when it is combined with Mitotane.
NelfinavirThe metabolism of Dapsone can be decreased when combined with Nelfinavir.
NetupitantThe serum concentration of Dapsone can be increased when it is combined with Netupitant.
Nitric OxideThe risk or severity of adverse effects can be increased when Nitric Oxide is combined with Dapsone.
NitrofurantoinThe risk or severity of adverse effects can be increased when Dapsone is combined with Nitrofurantoin.
NitroglycerinThe risk or severity of adverse effects can be increased when Dapsone is combined with Nitroglycerin.
NitroprussideThe risk or severity of adverse effects can be increased when Dapsone is combined with Nitroprusside.
PalbociclibThe serum concentration of Dapsone can be increased when it is combined with Palbociclib.
PhenazopyridineThe risk or severity of adverse effects can be increased when Dapsone is combined with Phenazopyridine.
PhenobarbitalThe risk or severity of adverse effects can be increased when Dapsone is combined with Phenobarbital.
PhenytoinThe risk or severity of adverse effects can be increased when Dapsone is combined with Phenytoin.
Picosulfuric acidThe therapeutic efficacy of Sodium picosulfate can be decreased when used in combination with Dapsone.
PrilocaineThe risk or severity of adverse effects can be increased when Dapsone is combined with Prilocaine.
PrimaquineThe risk or severity of adverse effects can be increased when Primaquine is combined with Dapsone.
ProbenecidThe serum concentration of Dapsone can be increased when it is combined with Probenecid.
ProguanilThe risk or severity of adverse effects can be increased when Proguanil is combined with Dapsone.
PyrimethamineThe risk or severity of adverse effects can be increased when Pyrimethamine is combined with Dapsone.
QuinineThe risk or severity of adverse effects can be increased when Quinine is combined with Dapsone.
RifabutinThe metabolism of Dapsone can be increased when combined with Rifabutin.
RifampicinThe metabolism of Dapsone can be increased when combined with Rifampicin.
RifapentineThe metabolism of Dapsone can be increased when combined with Rifapentine.
SecobarbitalThe metabolism of Dapsone can be increased when combined with Secobarbital.
SiltuximabThe serum concentration of Dapsone can be decreased when it is combined with Siltuximab.
SimeprevirThe serum concentration of Dapsone can be increased when it is combined with Simeprevir.
Sodium NitriteThe risk or severity of adverse effects can be increased when Dapsone is combined with Sodium Nitrite.
St. John's WortThe serum concentration of Dapsone can be decreased when it is combined with St. John's Wort.
StiripentolThe serum concentration of Dapsone can be increased when it is combined with Stiripentol.
SulfadiazineThe risk or severity of adverse effects can be increased when Dapsone is combined with Sulfadiazine.
SulfamethoxazoleThe serum concentration of Dapsone can be increased when it is combined with Sulfamethoxazole.
SulfisoxazoleThe metabolism of Dapsone can be decreased when combined with Sulfisoxazole.
TocilizumabThe serum concentration of Dapsone can be decreased when it is combined with Tocilizumab.
TrimethoprimThe serum concentration of Dapsone can be increased when it is combined with Trimethoprim.
ZopicloneThe risk or severity of adverse effects can be increased when Dapsone is combined with Zopiclone.
Food Interactions
  • Take without regard to meals.

Targets

Kind
Protein
Organism
Mycobacterium leprae (strain TN)
Pharmacological action
yes
Actions
inhibitor
General Function:
Dihydropteroate synthase activity
Specific Function:
Has very low affinity for the DHPS substrate 6-hydroxymethyl-7,8-dihydropterin-pyrophosphate, but can bind the inhibitor dapsone. Seems to lack dihydropteroate synthase activity, and does probably not function in folate metabolism (By similarity).
Gene Name:
folP2
Uniprot ID:
P0C0X2
Molecular Weight:
30850.89 Da
References
  1. Gillis TP, Williams DL: Dapsone resistance does not appear to be associated with a mutation in the dihydropteroate synthase-2 gene of Mycobacterium leprae. Indian J Lepr. 1999 Jan-Mar;71(1):11-8. [PubMed:10439322 ]
  2. Williams DL, Spring L, Harris E, Roche P, Gillis TP: Dihydropteroate synthase of Mycobacterium leprae and dapsone resistance. Antimicrob Agents Chemother. 2000 Jun;44(6):1530-7. [PubMed:10817704 ]
  3. Gengenbacher M, Xu T, Niyomrattanakit P, Spraggon G, Dick T: Biochemical and structural characterization of the putative dihydropteroate synthase ortholog Rv1207 of Mycobacterium tuberculosis. FEMS Microbiol Lett. 2008 Oct;287(1):128-35. doi: 10.1111/j.1574-6968.2008.01302.x. Epub 2008 Aug 1. [PubMed:18680522 ]
Kind
Protein
Organism
Mycobacterium leprae (strain TN)
Pharmacological action
yes
Actions
inhibitor
General Function:
Metal ion binding
Specific Function:
Catalyzes the condensation of para-aminobenzoate (pABA) with 6-hydroxymethyl-7,8-dihydropterin diphosphate (DHPt-PP) to form 7,8-dihydropteroate, the immediate precursor of folate derivatives.
Gene Name:
folP1
Uniprot ID:
P0C0X1
Molecular Weight:
29447.355 Da
References
  1. Cambau E, Carthagena L, Chauffour A, Ji B, Jarlier V: Dihydropteroate synthase mutations in the folP1 gene predict dapsone resistance in relapsed cases of leprosy. Clin Infect Dis. 2006 Jan 15;42(2):238-41. Epub 2005 Dec 12. [PubMed:16355335 ]
  2. Lee SB, Kim SK, Kang TJ, Chae GT, Chun JH, Shin HK, Kim JP, Ko YH, Kim NH: The prevalence of folP1 mutations associated with clinical resistance to dapsone, in Mycobacterium leprae isolates from South Korea. Ann Trop Med Parasitol. 2001 Jun;95(4):429-32. [PubMed:11454253 ]
  3. Williams DL, Spring L, Harris E, Roche P, Gillis TP: Dihydropteroate synthase of Mycobacterium leprae and dapsone resistance. Antimicrob Agents Chemother. 2000 Jun;44(6):1530-7. [PubMed:10817704 ]
  4. Gengenbacher M, Xu T, Niyomrattanakit P, Spraggon G, Dick T: Biochemical and structural characterization of the putative dihydropteroate synthase ortholog Rv1207 of Mycobacterium tuberculosis. FEMS Microbiol Lett. 2008 Oct;287(1):128-35. doi: 10.1111/j.1574-6968.2008.01302.x. Epub 2008 Aug 1. [PubMed:18680522 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinducer
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
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 ]
  3. Winter HR, Wang Y, Unadkat JD: CYP2C8/9 mediate dapsone N-hydroxylation at clinical concentrations of dapsone. Drug Metab Dispos. 2000 Aug;28(8):865-8. [PubMed:10901692 ]
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 or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Molecular Weight:
56848.42 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:
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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
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. 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. Ekins S, Bravi G, Wikel JH, Wrighton SA: Three-dimensional-quantitative structure activity relationship analysis of cytochrome P-450 3A4 substrates. J Pharmacol Exp Ther. 1999 Oct;291(1):424-33. [PubMed:10490933 ]
  4. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Trimethylamine monooxygenase activity
Specific Function:
Involved in the oxidative metabolism of a variety of xenobiotics such as drugs and pesticides. It N-oxygenates primary aliphatic alkylamines as well as secondary and tertiary amines. Plays an important role in the metabolism of trimethylamine (TMA), via the production of TMA N-oxide (TMAO). Is also able to perform S-oxidation when acting on sulfide compounds (PubMed:9224773).
Gene Name:
FMO3
Uniprot ID:
P31513
Molecular Weight:
60032.975 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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
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 gastric epithelial cells, it is a key step in the generation of prostaglandins, such as prostaglandin E2 (PGE2), which plays an important role in cytoprotection. In platelets, it is involved in the gener...
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular Weight:
68685.82 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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
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 brain, and in pathological conditions, such as in cancer. PTGS2 is responsible for production of inflammatory prostaglandins. Up-regulation of PTGS2 is also associated with increased cell adhesion, p...
Gene Name:
PTGS2
Uniprot ID:
P35354
Molecular Weight:
68995.625 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 ]
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme...
Gene Name:
CYP2C8
Uniprot ID:
P10632
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. 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:
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 imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
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 bioactivate several known carcinogens.
Gene Name:
NAT2
Uniprot ID:
P11245
Molecular Weight:
33542.235 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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxygen binding
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 unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular Weight:
57108.065 Da
References
  1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxygen binding
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 unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A7
Uniprot ID:
P24462
Molecular Weight:
57525.03 Da
References
  1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Peroxidase activity
Specific Function:
Part of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production of hypohalous acids, primarily hypochlorous acid in physiologic situations, and other toxic intermediates that greatly enhance PMN microbicidal activity.
Gene Name:
MPO
Uniprot ID:
P05164
Molecular Weight:
83867.71 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 ]
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 unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP2C18
Uniprot ID:
P33260
Molecular Weight:
55710.075 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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 24, 2016 02:00