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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:01:06 UTC
Update Date2020-02-26 21:39:23 UTC
HMDB IDHMDB0014096
Secondary Accession Numbers
  • HMDB14096
Metabolite Identification
Common Name5'-Hydroxypiroxicam
Description5'-Hydroxypiroxicam belongs to the class of organic compounds known as benzothiazines. These are organic compounds containing a benzene fused to a thiazine ring (a six-membered ring with four carbon atoms, one nitrogen atom and one sulfur atom). 5'-Hydroxypiroxicam is a strong basic compound (based on its pKa). These are organic compounds containing a benzene fused to a thiazine ring (a six-member ring with four carbon atoms, one nitrogen atom and one sulfur atom). 5'-Hydroxypiroxicam is a metabolite of Piroxicam. 5'-Hydroxypiroxicam is only found in individuals that have used or taken Piroxicam.
Structure
Data?1582753163
Synonyms
ValueSource
5-HydroxypiroxicamHMDB
4-Hydroxy-N-(5-hydroxypyridin-2-yl)-2-methyl-1,1-dioxo-2H-1λ⁶,2-benzothiazine-3-carboximidateGenerator
5'-HydroxypiroxicamMeSH
Chemical FormulaC15H13N3O5S
Average Molecular Weight347.346
Monoisotopic Molecular Weight347.057591231
IUPAC Name4-hydroxy-N-(5-hydroxypyridin-2-yl)-2-methyl-1,1-dioxo-2H-1λ⁶,2-benzothiazine-3-carboxamide
Traditional Name4-hydroxy-N-(5-hydroxypyridin-2-yl)-2-methyl-1,1-dioxo-1λ⁶,2-benzothiazine-3-carboxamide
CAS Registry Number77459-78-0
SMILES
CN1C(C(=O)NC2=NC=C(O)C=C2)=C(O)C2=C(C=CC=C2)S1(=O)=O
InChI Identifier
InChI=1S/C15H13N3O5S/c1-18-13(15(21)17-12-7-6-9(19)8-16-12)14(20)10-4-2-3-5-11(10)24(18,22)23/h2-8,19-20H,1H3,(H,16,17,21)
InChI KeyCCKOORANQAQKKV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzothiazines. These are organic compounds containing a benzene fused to a thiazine ring (a six-membered ring with four carbon atoms, one nitrogen atom and one sulfur atom).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiazines
Sub ClassNot Available
Direct ParentBenzothiazines
Alternative Parents
Substituents
  • Alpha-amino acid or derivatives
  • Benzothiazine
  • N-arylamide
  • Hydroxypyridine
  • Ortho-thiazine
  • Pyridine
  • Organosulfonic acid amide
  • Benzenoid
  • Imidolactam
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Heteroaromatic compound
  • Vinylogous acid
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Azacycle
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.21 g/LALOGPS
logP2.07ALOGPS
logP0.3ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)4.66ChemAxon
pKa (Strongest Basic)3.72ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area119.83 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity89.02 m³·mol⁻¹ChemAxon
Polarizability33.29 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+177.81731661259
DarkChem[M-H]-179.24831661259
DeepCCS[M+H]+175.12630932474
DeepCCS[M-H]-172.76830932474
DeepCCS[M-2H]-206.64530932474
DeepCCS[M+Na]+181.87230932474
AllCCS[M+H]+179.132859911
AllCCS[M+H-H2O]+176.032859911
AllCCS[M+NH4]+182.132859911
AllCCS[M+Na]+182.932859911
AllCCS[M-H]-175.232859911
AllCCS[M+Na-2H]-174.932859911
AllCCS[M+HCOO]-174.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5'-HydroxypiroxicamCN1C(C(=O)NC2=NC=C(O)C=C2)=C(O)C2=C(C=CC=C2)S1(=O)=O4933.5Standard polar33892256
5'-HydroxypiroxicamCN1C(C(=O)NC2=NC=C(O)C=C2)=C(O)C2=C(C=CC=C2)S1(=O)=O2554.9Standard non polar33892256
5'-HydroxypiroxicamCN1C(C(=O)NC2=NC=C(O)C=C2)=C(O)C2=C(C=CC=C2)S1(=O)=O3085.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5'-Hydroxypiroxicam,1TMS,isomer #1CN1C(C(=O)NC2=CC=C(O[Si](C)(C)C)C=N2)=C(O)C2=CC=CC=C2S1(=O)=O3151.6Semi standard non polar33892256
5'-Hydroxypiroxicam,1TMS,isomer #2CN1C(C(=O)NC2=CC=C(O)C=N2)=C(O[Si](C)(C)C)C2=CC=CC=C2S1(=O)=O3033.5Semi standard non polar33892256
5'-Hydroxypiroxicam,1TMS,isomer #3CN1C(C(=O)N(C2=CC=C(O)C=N2)[Si](C)(C)C)=C(O)C2=CC=CC=C2S1(=O)=O3049.3Semi standard non polar33892256
5'-Hydroxypiroxicam,2TMS,isomer #1CN1C(C(=O)NC2=CC=C(O[Si](C)(C)C)C=N2)=C(O[Si](C)(C)C)C2=CC=CC=C2S1(=O)=O3112.3Semi standard non polar33892256
5'-Hydroxypiroxicam,2TMS,isomer #2CN1C(C(=O)N(C2=CC=C(O[Si](C)(C)C)C=N2)[Si](C)(C)C)=C(O)C2=CC=CC=C2S1(=O)=O3002.2Semi standard non polar33892256
5'-Hydroxypiroxicam,2TMS,isomer #3CN1C(C(=O)N(C2=CC=C(O)C=N2)[Si](C)(C)C)=C(O[Si](C)(C)C)C2=CC=CC=C2S1(=O)=O2955.1Semi standard non polar33892256
5'-Hydroxypiroxicam,3TMS,isomer #1CN1C(C(=O)N(C2=CC=C(O[Si](C)(C)C)C=N2)[Si](C)(C)C)=C(O[Si](C)(C)C)C2=CC=CC=C2S1(=O)=O3031.4Semi standard non polar33892256
5'-Hydroxypiroxicam,3TMS,isomer #1CN1C(C(=O)N(C2=CC=C(O[Si](C)(C)C)C=N2)[Si](C)(C)C)=C(O[Si](C)(C)C)C2=CC=CC=C2S1(=O)=O3205.9Standard non polar33892256
5'-Hydroxypiroxicam,3TMS,isomer #1CN1C(C(=O)N(C2=CC=C(O[Si](C)(C)C)C=N2)[Si](C)(C)C)=C(O[Si](C)(C)C)C2=CC=CC=C2S1(=O)=O3858.2Standard polar33892256
5'-Hydroxypiroxicam,1TBDMS,isomer #1CN1C(C(=O)NC2=CC=C(O[Si](C)(C)C(C)(C)C)C=N2)=C(O)C2=CC=CC=C2S1(=O)=O3380.5Semi standard non polar33892256
5'-Hydroxypiroxicam,1TBDMS,isomer #2CN1C(C(=O)NC2=CC=C(O)C=N2)=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2S1(=O)=O3358.7Semi standard non polar33892256
5'-Hydroxypiroxicam,1TBDMS,isomer #3CN1C(C(=O)N(C2=CC=C(O)C=N2)[Si](C)(C)C(C)(C)C)=C(O)C2=CC=CC=C2S1(=O)=O3319.9Semi standard non polar33892256
5'-Hydroxypiroxicam,2TBDMS,isomer #1CN1C(C(=O)NC2=CC=C(O[Si](C)(C)C(C)(C)C)C=N2)=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2S1(=O)=O3552.2Semi standard non polar33892256
5'-Hydroxypiroxicam,2TBDMS,isomer #2CN1C(C(=O)N(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=N2)[Si](C)(C)C(C)(C)C)=C(O)C2=CC=CC=C2S1(=O)=O3488.4Semi standard non polar33892256
5'-Hydroxypiroxicam,2TBDMS,isomer #3CN1C(C(=O)N(C2=CC=C(O)C=N2)[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2S1(=O)=O3449.6Semi standard non polar33892256
5'-Hydroxypiroxicam,3TBDMS,isomer #1CN1C(C(=O)N(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=N2)[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2S1(=O)=O3662.1Semi standard non polar33892256
5'-Hydroxypiroxicam,3TBDMS,isomer #1CN1C(C(=O)N(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=N2)[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2S1(=O)=O3870.1Standard non polar33892256
5'-Hydroxypiroxicam,3TBDMS,isomer #1CN1C(C(=O)N(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=N2)[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2S1(=O)=O3994.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5'-Hydroxypiroxicam GC-MS (Non-derivatized) - 70eV, Positivesplash10-066r-1901000000-bca0ad1100e7a763c2c52017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5'-Hydroxypiroxicam GC-MS (2 TMS) - 70eV, Positivesplash10-0096-4191300000-4017f7f23d19f4a7fbdb2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5'-Hydroxypiroxicam GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5'-Hydroxypiroxicam 10V, Positive-QTOFsplash10-0a4j-0904000000-95690a397314ea77af1a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5'-Hydroxypiroxicam 20V, Positive-QTOFsplash10-0a4i-0900000000-d1dba4d53826b8e36d402016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5'-Hydroxypiroxicam 40V, Positive-QTOFsplash10-0a4i-6900000000-eb238be5bf46c09fb6492016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5'-Hydroxypiroxicam 10V, Negative-QTOFsplash10-0002-0319000000-6cc58783b95d25f3be4b2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5'-Hydroxypiroxicam 20V, Negative-QTOFsplash10-0a4j-0869000000-3741c3a0d125983f0fcb2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5'-Hydroxypiroxicam 40V, Negative-QTOFsplash10-0a4l-4900000000-ebc70de8e15626839d142016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5'-Hydroxypiroxicam 10V, Negative-QTOFsplash10-000t-0597000000-d2c3d3f5469942a8cc052021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5'-Hydroxypiroxicam 20V, Negative-QTOFsplash10-01wk-0930000000-f2b3b1a88c48458f8ced2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5'-Hydroxypiroxicam 40V, Negative-QTOFsplash10-114i-3960000000-4792415f0204acfbb3272021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5'-Hydroxypiroxicam 10V, Positive-QTOFsplash10-0002-0009000000-c86c5a1acb4218514ecf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5'-Hydroxypiroxicam 20V, Positive-QTOFsplash10-06r2-0926000000-e264276586b75fd8887f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5'-Hydroxypiroxicam 40V, Positive-QTOFsplash10-0bti-3910000000-fa6a3854baf7225a37e22021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID20129664
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound54676301
PDB IDNot Available
ChEBI ID320793
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in peroxidase activity
Specific function:
Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:
PTGS2
Uniprot ID:
P35354
Molecular weight:
68995.625
References
  1. Blanco FJ, Guitian R, Moreno J, de Toro FJ, Galdo F: Effect of antiinflammatory drugs on COX-1 and COX-2 activity in human articular chondrocytes. J Rheumatol. 1999 Jun;26(6):1366-73. [PubMed:10381057 ]
  2. Bugajski J, Glod R, Gadek-Michalska A, Bugajski AJ: Involvement of constitutive (COX-1) and inducible cyclooxygenase (COX-2) in the adrenergic-induced ACTH and corticosterone secretion. J Physiol Pharmacol. 2001 Dec;52(4 Pt 2):795-809. [PubMed:11785774 ]
  3. Fackovcova D, Kristova V, Kriska M: Renal damage induced by the treatment with non-opioid analgesics--theoretical assumption or clinical significance. Bratisl Lek Listy. 2000;101(8):417-22. [PubMed:11153163 ]
  4. Raju J, Bird RP: Differential modulation of transforming growth factor-betas and cyclooxygenases in the platelet lysates of male F344 rats by dietary lipids and piroxicam. Mol Cell Biochem. 2002 Feb;231(1-2):139-46. [PubMed:11952155 ]
  5. Veiga AP, Duarte ID, Avila MN, da Motta PG, Tatsuo MA, Francischi JN: Prevention by celecoxib of secondary hyperalgesia induced by formalin in rats. Life Sci. 2004 Oct 22;75(23):2807-17. [PubMed:15464832 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in peroxidase activity
Specific function:
May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular weight:
68685.82
References
  1. Blanco FJ, Guitian R, Moreno J, de Toro FJ, Galdo F: Effect of antiinflammatory drugs on COX-1 and COX-2 activity in human articular chondrocytes. J Rheumatol. 1999 Jun;26(6):1366-73. [PubMed:10381057 ]
  2. Bugajski J, Glod R, Gadek-Michalska A, Bugajski AJ: Involvement of constitutive (COX-1) and inducible cyclooxygenase (COX-2) in the adrenergic-induced ACTH and corticosterone secretion. J Physiol Pharmacol. 2001 Dec;52(4 Pt 2):795-809. [PubMed:11785774 ]
  3. Fackovcova D, Kristova V, Kriska M: Renal damage induced by the treatment with non-opioid analgesics--theoretical assumption or clinical significance. Bratisl Lek Listy. 2000;101(8):417-22. [PubMed:11153163 ]
  4. Raju J, Bird RP: Differential modulation of transforming growth factor-betas and cyclooxygenases in the platelet lysates of male F344 rats by dietary lipids and piroxicam. Mol Cell Biochem. 2002 Feb;231(1-2):139-46. [PubMed:11952155 ]
  5. Veiga AP, Duarte ID, Avila MN, da Motta PG, Tatsuo MA, Francischi JN: Prevention by celecoxib of secondary hyperalgesia induced by formalin in rats. Life Sci. 2004 Oct 22;75(23):2807-17. [PubMed:15464832 ]
General function:
Involved in monooxygenase 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, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
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. Pelkonen O, Maenpaa J, Taavitsainen P, Rautio A, Raunio H: Inhibition and induction of human cytochrome P450 (CYP) enzymes. Xenobiotica. 1998 Dec;28(12):1203-53. [PubMed:9890159 ]
  3. 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 ]
General function:
Involved in monooxygenase 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 responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular weight:
55824.275
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 ]

Transporters

General function:
Involved in transporter activity
Specific function:
Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds
Gene Name:
SLC22A11
Uniprot ID:
Q9NSA0
Molecular weight:
59970.9
References
  1. Babu E, Takeda M, Narikawa S, Kobayashi Y, Enomoto A, Tojo A, Cha SH, Sekine T, Sakthisekaran D, Endou H: Role of human organic anion transporter 4 in the transport of ochratoxin A. Biochim Biophys Acta. 2002 Jun 12;1590(1-3):64-75. [PubMed:12063169 ]
  2. Takeda M, Khamdang S, Narikawa S, Kimura H, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of methotrexate transport and its drug interactions with human organic anion transporters. J Pharmacol Exp Ther. 2002 Aug;302(2):666-71. [PubMed:12130730 ]
General function:
Involved in ion 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 molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Molecular weight:
61815.8
References
  1. Mulato AS, Ho ES, Cihlar T: Nonsteroidal anti-inflammatory drugs efficiently reduce the transport and cytotoxicity of adefovir mediated by the human renal organic anion transporter 1. J Pharmacol Exp Ther. 2000 Oct;295(1):10-5. [PubMed:10991954 ]
  2. Jung KY, Takeda M, Kim DK, Tojo A, Narikawa S, Yoo BS, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of ochratoxin A transport by human organic anion transporters. Life Sci. 2001 Sep 21;69(18):2123-35. [PubMed:11669456 ]
  3. Takeda M, Khamdang S, Narikawa S, Kimura H, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of methotrexate transport and its drug interactions with human organic anion transporters. J Pharmacol Exp Ther. 2002 Aug;302(2):666-71. [PubMed:12130730 ]
  4. 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 ]
  5. Tsuda M, Sekine T, Takeda M, Cha SH, Kanai Y, Kimura M, Endou H: Transport of ochratoxin A by renal multispecific organic anion transporter 1. J Pharmacol Exp Ther. 1999 Jun;289(3):1301-5. [PubMed:10336520 ]