Sulfinpyrazone

Identification

Summary

Sulfinpyrazone is a platelet inhibitory and uricosuric agent used to inhibit thrombotic and embolic processes and to manage the chronic phases of gout .

Generic Name
Sulfinpyrazone
DrugBank Accession Number
DB01138
Background

A uricosuric drug that is used to reduce the serum urate levels in gout therapy. It lacks anti-inflammatory, analgesic, and diuretic properties.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 404.482
Monoisotopic: 404.119463206
Chemical Formula
C23H20N2O3S
Synonyms
  • 1,2-Diphenyl-3,5-dioxo-4-(2-phenylsulfinylethyl)pyrazolidine
  • 1,2-Diphenyl-4-(2'-phenylsulfinethyl)-3,5-pyrazolidinedione
  • 4-(2-Benzenesulfinylethyl)-1,2-diphenylpyrazolidine-3,5-dione
  • Sulfinpyrazone
  • Sulfoxyphenylpyrazolidine
  • Sulphinpyrazone
External IDs
  • NSC-75925
  • USAF GE-13

Pharmacology

Indication

For the treatment of gout and gouty arthritis.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofHyperuricemia••••••••••••
Treatment ofPlatelet aggregation••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Sulfinpyrazone's pharmacologic activity is the potentiation of the urinary excretion of uric acid. It is useful for reducing the blood urate levels in patients with chronic tophaceous gout and acute intermittent gout, and for promoting the resorption of tophi.

Mechanism of action

Sulfinpyrazone is an oral uricosuric agent (pyrazolone derivative) used to treat chronic or intermittent gouty arthritis. Sulfinpyrazone competitively inhibits the reabsorption of uric acid at the proximal convoluted tubule, thereby facilitating urinary excretion of uric acid and decreasing plasma urate concentrations. This is likely done through inhibition of the urate anion transporter (hURAT1) as well as the human organic anion transporter 4 (hOAT4). Sulfinpyrazone is not intended for the treatment of acute attacks because it lacks therapeutically useful analgesic and anti-inflammatory effects. Sulfinpyrazone and its sulfide metabolite possess COX inhibitory effects. Sulfinpyrazone has also been shown to be a UDP-glucuronsyltransferase inhibitor and a very potent CYP2C9 inhibitor. Sulfinpyrazone is also known to be a cystic fibrosis transmembrane conductance regulator (CFTR) inhibitor as well as an inhibitor of several multridrug resistance proteins (MRPs).

TargetActionsOrganism
ASolute carrier family 22 member 12
inhibitor
Humans
AMultidrug resistance-associated protein 1
inhibitor
Humans
ACanalicular multispecific organic anion transporter 1
inhibitor
Humans
UNuclear receptor subfamily 1 group I member 2
activator
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

98-99%

Metabolism

Hover over products below to view reaction partners

Route of elimination

Not Available

Half-life

Approximately 4-6 hours

Clearance

Not Available

Adverse Effects
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Toxicity

Symptoms of overdose include nausea, vomiting, diarrhea, epigastric pain, ataxia, labored respiration, convulsions, coma. Possible symptoms, seen after overdosage with other pyrazolone derivatives: anemia, jaundice, and ulceration.

Pathways
Not Available
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
AbametapirThe serum concentration of Sulfinpyrazone can be increased when it is combined with Abametapir.
AbciximabThe risk or severity of bleeding can be increased when Sulfinpyrazone is combined with Abciximab.
AbemaciclibThe metabolism of Abemaciclib can be increased when combined with Sulfinpyrazone.
AbrocitinibThe risk or severity of bleeding and thrombocytopenia can be increased when Sulfinpyrazone is combined with Abrocitinib.
AcalabrutinibThe metabolism of Acalabrutinib can be increased when combined with Sulfinpyrazone.
Food Interactions
  • Take with food.

Products

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dosage, form, labeller, route of administration, and marketing period.
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Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Antazone Tab 100mgTablet100 mgOralIcn Pharmaceuticals1980-12-312005-04-26Canada flag
Antazone Tab 200mgTablet200 mgOralIcn Pharmaceuticals1980-12-312005-04-26Canada flag
Anturan 100mgTablet100 mg / tabOralNovartis1959-12-311999-08-04Canada flag
Anturan 200mgTablet200 mg / tabOralNovartis1961-12-311999-08-04Canada flag
AnturaneTablet100 mg/1OralNovartis1959-05-132001-03-01US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo Sulfinpyrazone Tab 100mgTablet100 mgOralApotex Corporation1978-12-312008-02-19Canada flag
Novo-pyrazone Tab 100mgTablet100 mgOralNovopharm Limited1979-12-312005-08-10Canada flag
Novo-pyrazone Tab 200mgTablet200 mgOralNovopharm Limited1979-12-312005-08-10Canada flag
Nu-sulfinpyrazone Tab 100mgTablet100 mgOralNu Pharm Inc1993-12-312008-02-20Canada flag
Nu-sulfinpyrazone Tab 200mgTablet200 mgOralNu Pharm Inc1993-12-312012-09-04Canada flag

Categories

ATC Codes
M04AB02 — Sulfinpyrazone
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenyl sulfoxides. These are organosulfur compounds containing a sulfoxide group substituted with a phenyl group.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenyl sulfoxides
Direct Parent
Phenyl sulfoxides
Alternative Parents
Pyrazolidinones / 1,3-dicarbonyl compounds / Sulfoxides / Carboxylic acid hydrazides / Sulfinyl compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
1,3-dicarbonyl compound / Aromatic heteromonocyclic compound / Azacycle / Carbonyl group / Carboxylic acid derivative / Carboxylic acid hydrazide / Hydrocarbon derivative / Organic nitrogen compound / Organic oxide / Organic oxygen compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
sulfoxide, pyrazolidines (CHEBI:9342)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
V6OFU47K3W
CAS number
57-96-5
InChI Key
MBGGBVCUIVRRBF-UHFFFAOYSA-N
InChI
InChI=1S/C23H20N2O3S/c26-22-21(16-17-29(28)20-14-8-3-9-15-20)23(27)25(19-12-6-2-7-13-19)24(22)18-10-4-1-5-11-18/h1-15,21H,16-17H2
IUPAC Name
4-[2-(benzenesulfinyl)ethyl]-1,2-diphenylpyrazolidine-3,5-dione
SMILES
O=C1C(CCS(=O)C2=CC=CC=C2)C(=O)N(N1C1=CC=CC=C1)C1=CC=CC=C1

References

General References
  1. Didisheim P, Kazmier FJ, Fuster V: Platelet inhibition in the management of thrombosis. Thromb Diath Haemorrh. 1974 Sep 30;32(1):21-34. [Article]
  2. Margulies EH, White AM, Sherry S: Sulfinpyrazone: a review of its pharmacological properties and therapeutic use. Drugs. 1980 Sep;20(3):179-97. [Article]
  3. Schrader BJ, Berk SI: Antiplatelet agents in coronary artery disease. Clin Pharm. 1990 Feb;9(2):118-24. [Article]
  4. van Gijn J, Algra A: Aspirin and stroke prevention. Thromb Res. 2003 Jun 15;110(5-6):349-53. [Article]
Human Metabolome Database
HMDB0015269
KEGG Drug
D00449
KEGG Compound
C07317
PubChem Compound
5342
PubChem Substance
46504918
ChemSpider
5149
BindingDB
50237626
RxNav
10205
ChEBI
9342
ChEMBL
CHEMBL832
Therapeutic Targets Database
DAP000794
PharmGKB
PA451550
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Sulfinpyrazone

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Barr Pharmaceuticals
  • Ivax Pharmaceuticals
  • Major Pharmaceuticals
  • Novartis AG
  • Spectrum Chemicals and Laboratory Products
Dosage Forms
FormRouteStrength
TabletOral100 mg / tab
TabletOral200 mg / tab
CapsuleOral200 mg/1
TabletOral100 mg/1
TabletOral400 MG
TabletOral200 mg
TabletOral100 mg
Prices
Unit descriptionCostUnit
Apo-Sulfinpyrazone 200 mg Tablet0.31USD tablet
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)136-137 °CPhysProp
water solubility31.2 mg/LNot Available
logP2.30HANSCH,C ET AL. (1995)
pKa3.25SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.323 mg/mLALOGPS
logP2.92ALOGPS
logP3.19Chemaxon
logS-3.1ALOGPS
pKa (Strongest Acidic)3.86Chemaxon
pKa (Strongest Basic)-8.2Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area57.69 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity113.62 m3·mol-1Chemaxon
Polarizability42.1 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9961
Blood Brain Barrier+0.9776
Caco-2 permeable-0.5583
P-glycoprotein substrateNon-substrate0.9163
P-glycoprotein inhibitor INon-inhibitor0.858
P-glycoprotein inhibitor IINon-inhibitor0.6257
Renal organic cation transporterNon-inhibitor0.8111
CYP450 2C9 substrateNon-substrate0.5504
CYP450 2D6 substrateNon-substrate0.8878
CYP450 3A4 substrateSubstrate0.5146
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorInhibitor0.8949
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorInhibitor0.796
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6332
Ames testNon AMES toxic0.6195
CarcinogenicityNon-carcinogens0.6932
BiodegradationNot ready biodegradable0.9577
Rat acute toxicity3.0218 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9712
hERG inhibition (predictor II)Non-inhibitor0.8418
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-004i-2962000000-94e8774039d3f0fcca8f
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-004i-0002900000-472e293a011d716bb5a8
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-0550-2930000000-70abc4e49a7459cc1980
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a6r-0591500000-4b27d64be1dee69f96e6
MS/MS Spectrum - , positiveLC-MS/MSsplash10-004i-0002900000-472e293a011d716bb5a8
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0550-2930000000-70abc4e49a7459cc1980
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0040900000-035106d1e55617ff7571
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a70-0094500000-10591193e1f8a2704301
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0790000000-0dc27aedb60038bcf14d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01ri-3492000000-f6c2ed06a0177b3d89c1
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0945100000-6a27cee8fcf75efda2f0
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00o0-3791000000-ddaa98261118f38d0635
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]-213.926417
predicted
DarkChem Lite v0.1.0
[M-H]-196.87657
predicted
DeepCCS 1.0 (2019)
[M+H]+215.467817
predicted
DarkChem Lite v0.1.0
[M+H]+199.26091
predicted
DeepCCS 1.0 (2019)
[M+Na]+213.738817
predicted
DarkChem Lite v0.1.0
[M+Na]+206.42207
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Urate transmembrane transporter activity
Specific Function
Required for efficient urate re-absorption in the kidney. Regulates blood urate levels. Mediates saturable urate uptake by facilitating the exchange of urate against organic anions.
Gene Name
SLC22A12
Uniprot ID
Q96S37
Uniprot Name
Solute carrier family 22 member 12
Molecular Weight
59629.57 Da
References
  1. Shin HJ, Takeda M, Enomoto A, Fujimura M, Miyazaki H, Anzai N, Endou H: Interactions of urate transporter URAT1 in human kidney with uricosuric drugs. Nephrology (Carlton). 2011 Feb;16(2):156-62. doi: 10.1111/j.1440-1797.2010.01368.x. [Article]
  2. Tan PK, Ostertag TM, Miner JN: Mechanism of high affinity inhibition of the human urate transporter URAT1. Sci Rep. 2016 Oct 7;6:34995. doi: 10.1038/srep34995. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Transporter activity
Specific Function
Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotre...
Gene Name
ABCC1
Uniprot ID
P33527
Uniprot Name
Multidrug resistance-associated protein 1
Molecular Weight
171589.5 Da
References
  1. Evers R, de Haas M, Sparidans R, Beijnen J, Wielinga PR, Lankelma J, Borst P: Vinblastine and sulfinpyrazone export by the multidrug resistance protein MRP2 is associated with glutathione export. Br J Cancer. 2000 Aug;83(3):375-83. [Article]
  2. Morrow CS, Smitherman PK, Diah SK, Schneider E, Townsend AJ: Coordinated action of glutathione S-transferases (GSTs) and multidrug resistance protein 1 (MRP1) in antineoplastic drug detoxification. Mechanism of GST A1-1- and MRP1-associated resistance to chlorambucil in MCF7 breast carcinoma cells. J Biol Chem. 1998 Aug 7;273(32):20114-20. [Article]
  3. Bakos E, Evers R, Sinko E, Varadi A, Borst P, Sarkadi B: Interactions of the human multidrug resistance proteins MRP1 and MRP2 with organic anions. Mol Pharmacol. 2000 Apr;57(4):760-8. [Article]
  4. Depeille P, Cuq P, Mary S, Passagne I, Evrard A, Cupissol D, Vian L: Glutathione S-transferase M1 and multidrug resistance protein 1 act in synergy to protect melanoma cells from vincristine effects. Mol Pharmacol. 2004 Apr;65(4):897-905. [Article]
  5. Raggers RJ, van Helvoort A, Evers R, van Meer G: The human multidrug resistance protein MRP1 translocates sphingolipid analogs across the plasma membrane. J Cell Sci. 1999 Feb;112 ( Pt 3):415-22. [Article]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Organic anion transmembrane transporter activity
Specific Function
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name
ABCC2
Uniprot ID
Q92887
Uniprot Name
Canalicular multispecific organic anion transporter 1
Molecular Weight
174205.64 Da
References
  1. Bakos E, Evers R, Sinko E, Varadi A, Borst P, Sarkadi B: Interactions of the human multidrug resistance proteins MRP1 and MRP2 with organic anions. Mol Pharmacol. 2000 Apr;57(4):760-8. [Article]
  2. Evers R, de Haas M, Sparidans R, Beijnen J, Wielinga PR, Lankelma J, Borst P: Vinblastine and sulfinpyrazone export by the multidrug resistance protein MRP2 is associated with glutathione export. Br J Cancer. 2000 Aug;83(3):375-83. [Article]
  3. Morrow CS, Smitherman PK, Townsend AJ: Role of multidrug-resistance protein 2 in glutathione S-transferase P1-1-mediated resistance to 4-nitroquinoline 1-oxide toxicities in HepG2 cells. Mol Carcinog. 2000 Nov;29(3):170-8. [Article]
  4. Ito K, Oleschuk CJ, Westlake C, Vasa MZ, Deeley RG, Cole SP: Mutation of Trp1254 in the multispecific organic anion transporter, multidrug resistance protein 2 (MRP2) (ABCC2), alters substrate specificity and results in loss of methotrexate transport activity. J Biol Chem. 2001 Oct 12;276(41):38108-14. Epub 2001 Aug 10. [Article]
  5. Flanagan SD, Cummins CL, Susanto M, Liu X, Takahashi LH, Benet LZ: Comparison of furosemide and vinblastine secretion from cell lines overexpressing multidrug resistance protein (P-glycoprotein) and multidrug resistance-associated proteins (MRP1 and MRP2). Pharmacology. 2002;64(3):126-34. [Article]
  6. Hagos Y, Stein D, Ugele B, Burckhardt G, Bahn A: Human renal organic anion transporter 4 operates as an asymmetric urate transporter. J Am Soc Nephrol. 2007 Feb;18(2):430-9. Epub 2007 Jan 17. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Activator
General Function
Zinc ion binding
Specific Function
Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism an...
Gene Name
NR1I2
Uniprot ID
O75469
Uniprot Name
Nuclear receptor subfamily 1 group I member 2
Molecular Weight
49761.245 Da
References
  1. Faucette SR, Wang H, Hamilton GA, Jolley SL, Gilbert D, Lindley C, Yan B, Negishi M, LeCluyse EL: Regulation of CYP2B6 in primary human hepatocytes by prototypical inducers. Drug Metab Dispos. 2004 Mar;32(3):348-58. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
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
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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. Luo G, Cunningham M, Kim S, Burn T, Lin J, Sinz M, Hamilton G, Rizzo C, Jolley S, Gilbert D, Downey A, Mudra D, Graham R, Carroll K, Xie J, Madan A, Parkinson A, Christ D, Selling B, LeCluyse E, Gan LS: CYP3A4 induction by drugs: correlation between a pregnane X receptor reporter gene assay and CYP3A4 expression in human hepatocytes. Drug Metab Dispos. 2002 Jul;30(7):795-804. [Article]
  2. He M, Rettie AE, Neal J, Trager WF: Metabolism of sulfinpyrazone sulfide and sulfinpyrazone by human liver microsomes and cDNA-expressed cytochrome P450s. Drug Metab Dispos. 2001 May;29(5):701-11. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
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. Faucette SR, Wang H, Hamilton GA, Jolley SL, Gilbert D, Lindley C, Yan B, Negishi M, LeCluyse EL: Regulation of CYP2B6 in primary human hepatocytes by prototypical inducers. Drug Metab Dispos. 2004 Mar;32(3):348-58. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
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. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
No
General Function
Transporter activity
Specific Function
FABP are thought to play a role in the intracellular transport of long-chain fatty acids and their acyl-CoA esters. FABP2 is probably involved in triglyceride-rich lipoprotein synthesis. Binds satu...
Gene Name
FABP2
Uniprot ID
P12104
Uniprot Name
Fatty acid-binding protein, intestinal
Molecular Weight
15207.165 Da
References
  1. Rowland A, Knights KM, Mackenzie PI, Miners JO: Characterization of the binding of drugs to human intestinal fatty acid binding protein (IFABP): potential role of IFABP as an alternative to albumin for in vitro-in vivo extrapolation of drug kinetic parameters. Drug Metab Dispos. 2009 Jul;37(7):1395-403. doi: 10.1124/dmd.109.027656. Epub 2009 Apr 27. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Organic anion transmembrane transporter activity
Specific Function
May act as an inducible transporter in the biliary and intestinal excretion of organic anions. Acts as an alternative route for the export of bile acids and glucuronides from cholestatic hepatocyte...
Gene Name
ABCC3
Uniprot ID
O15438
Uniprot Name
Canalicular multispecific organic anion transporter 2
Molecular Weight
169341.14 Da
References
  1. Zelcer N, Saeki T, Reid G, Beijnen JH, Borst P: Characterization of drug transport by the human multidrug resistance protein 3 (ABCC3). J Biol Chem. 2001 Dec 7;276(49):46400-7. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Atpase activity, coupled to transmembrane movement of substances
Specific Function
May be an organic anion pump relevant to cellular detoxification.
Gene Name
ABCC4
Uniprot ID
O15439
Uniprot Name
Multidrug resistance-associated protein 4
Molecular Weight
149525.33 Da
References
  1. Chen ZS, Lee K, Walther S, Raftogianis RB, Kuwano M, Zeng H, Kruh GD: Analysis of methotrexate and folate transport by multidrug resistance protein 4 (ABCC4): MRP4 is a component of the methotrexate efflux system. Cancer Res. 2002 Jun 1;62(11):3144-50. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Organic anion transmembrane transporter activity
Specific Function
Acts as a multispecific organic anion pump which can transport nucleotide analogs.
Gene Name
ABCC5
Uniprot ID
O15440
Uniprot Name
Multidrug resistance-associated protein 5
Molecular Weight
160658.8 Da
References
  1. Wijnholds J, Mol CA, van Deemter L, de Haas M, Scheffer GL, Baas F, Beijnen JH, Scheper RJ, Hatse S, De Clercq E, Balzarini J, Borst P: Multidrug-resistance protein 5 is a multispecific organic anion transporter able to transport nucleotide analogs. Proc Natl Acad Sci U S A. 2000 Jun 20;97(13):7476-81. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Transporter activity
Specific Function
Isoform 1: May participate directly in the active transport of drugs into subcellular organelles or influence drug distribution indirectly. Transports glutathione conjugates as leukotriene-c4 (LTC4...
Gene Name
ABCC6
Uniprot ID
O95255
Uniprot Name
Multidrug resistance-associated protein 6
Molecular Weight
164904.81 Da
References
  1. Chen ZS, Hopper-Borge E, Belinsky MG, Shchaveleva I, Kotova E, Kruh GD: Characterization of the transport properties of human multidrug resistance protein 7 (MRP7, ABCC10). Mol Pharmacol. 2003 Feb;63(2):351-8. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Transporter activity
Specific Function
Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotre...
Gene Name
ABCC1
Uniprot ID
P33527
Uniprot Name
Multidrug resistance-associated protein 1
Molecular Weight
171589.5 Da
References
  1. Evers R, de Haas M, Sparidans R, Beijnen J, Wielinga PR, Lankelma J, Borst P: Vinblastine and sulfinpyrazone export by the multidrug resistance protein MRP2 is associated with glutathione export. Br J Cancer. 2000 Aug;83(3):375-83. [Article]
  2. Parasrampuria DA, Lantz MV, Benet LZ: A human lymphocyte based ex vivo assay to study the effect of drugs on P-glycoprotein (P-gp) function. Pharm Res. 2001 Jan;18(1):39-44. [Article]
  3. Decleves X, Regina A, Laplanche JL, Roux F, Boval B, Launay JM, Scherrmann JM: Functional expression of P-glycoprotein and multidrug resistance-associated protein (Mrp1) in primary cultures of rat astrocytes. J Neurosci Res. 2000 Jun 1;60(5):594-601. doi: 10.1002/(SICI)1097-4547(20000601)60:5<594::AID-JNR4>3.0.CO;2-6. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Organic anion transmembrane transporter activity
Specific Function
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name
ABCC2
Uniprot ID
Q92887
Uniprot Name
Canalicular multispecific organic anion transporter 1
Molecular Weight
174205.64 Da
References
  1. Flanagan SD, Cummins CL, Susanto M, Liu X, Takahashi LH, Benet LZ: Comparison of furosemide and vinblastine secretion from cell lines overexpressing multidrug resistance protein (P-glycoprotein) and multidrug resistance-associated proteins (MRP1 and MRP2). Pharmacology. 2002;64(3):126-34. [Article]
  2. Evers R, de Haas M, Sparidans R, Beijnen J, Wielinga PR, Lankelma J, Borst P: Vinblastine and sulfinpyrazone export by the multidrug resistance protein MRP2 is associated with glutathione export. Br J Cancer. 2000 Aug;83(3):375-83. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Transporter activity
Specific Function
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
Gene Name
ABCB11
Uniprot ID
O95342
Uniprot Name
Bile salt export pump
Molecular Weight
146405.83 Da
References
  1. Pedersen JM, Matsson P, Bergstrom CA, Hoogstraate J, Noren A, LeCluyse EL, Artursson P: Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). Toxicol Sci. 2013 Dec;136(2):328-43. doi: 10.1093/toxsci/kft197. Epub 2013 Sep 6. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48