Piroxicam

Identification

Summary

Piroxicam is an NSAID used to treat the symptoms of osteoarthritis and rheumatoid arthritis.

Brand Names
Feldene
Generic Name
Piroxicam
DrugBank Accession Number
DB00554
Background

A cyclooxygenase inhibiting, non-steroidal anti-inflammatory agent (NSAID) that is well established in treating rheumatoid arthritis and osteoarthritis and used for musculoskeletal disorders, dysmenorrhea, and postoperative pain. Its long half-life enables it to be administered once daily.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 331.346
Monoisotopic: 331.062676609
Chemical Formula
C15H13N3O4S
Synonyms
  • 4-Hydroxy-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazin-3-caboxyamid-1,1-dioxid
  • Piroxicam
  • Piroxicam betadex
  • Piroxicamum
  • Pyroxycam
External IDs
  • CP-16,171

Pharmacology

Indication

For treatment of osteoarthritis and rheumatoid arthritis.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Symptomatic treatment ofAnkylosing spondylitis••••••••••••
Symptomatic treatment ofOsteoarthritis••••••••••••
Symptomatic treatment ofRheumatoid arthritis••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Piroxicam is in a class of drugs called nonsteroidal anti-inflammatory drugs (NSAIDs). Piroxicam works by reducing hormones that cause inflammation and pain in the body. Piroxicam is used to reduce the pain, inflammation, and stiffness caused by rheumatoid arthritis and osteoarthritis.

Mechanism of action

The antiinflammatory effect of Piroxicam may result from the reversible inhibition of cyclooxygenase, causing the peripheral inhibition of prostaglandin synthesis. The prostaglandins are produced by an enzyme called Cox-1. Piroxicam blocks the Cox-1 enzyme, resulting into the disruption of production of prostaglandins. Piroxicam also inhibits the migration of leukocytes into sites of inflammation and prevents the formation of thromboxane A2, an aggregating agent, by the platelets.

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

Well absorbed following oral administration.

Volume of distribution
  • 0.14 L/kg
Protein binding

Not Available

Metabolism

Renal

Hover over products below to view reaction partners

Route of elimination

Piroxicam and its biotransformation products are excreted in urine and feces, with about twice as much appearing in the urine as in the feces. Approximately 5% of a piroxicam dose is excreted unchanged. However, a substantial portion of piroxicam elimination occurs by hepatic metabolism. Piroxicam is excreted into human milk.

Half-life

30 to 86 hours

Clearance

Not Available

Adverse Effects
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Toxicity

Symptoms of overdose include drowsiness, nausea, stomach pain, and/or vomiting.

Pathways
PathwayCategory
Piroxicam Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Cytochrome P450 2C9CYP2C9*2Not Available430C>TEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2C9CYP2C9*3Not Available1075A>CEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2C9CYP2C9*4Not Available1076T>CEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2C9CYP2C9*5Not Available1080C>GEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2C9CYP2C9*8Not Available449G>AEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2C9CYP2C9*11Not Available1003C>TEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2C9CYP2C9*12Not Available1465C>TEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2C9CYP2C9*13Not Available269T>CEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2C9CYP2C9*14Not Available374G>AEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2C9CYP2C9*16Not Available895A>GEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2C9CYP2C9*18Not Available1075A>C / 1190A>C  … show all Effect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2C9CYP2C9*26Not Available389C>GEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2C9CYP2C9*28Not Available641A>TEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2C9CYP2C9*30Not Available1429G>AEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2C9CYP2C9*33Not Available395G>AEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2C9CYP2C9*6Not Available818delAEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2C9CYP2C9*15Not Available485C>AEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2C9CYP2C9*25Not Available353_362delAGAAATGGAAEffect InferredPoor drug metabolizer, lower dose requirement.Details
Cytochrome P450 2C9CYP2C9*35Not Available374G>T / 430C>TEffect InferredPoor drug metabolizer, lower dose requirement.Details

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
AbacavirPiroxicam may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbataceptThe metabolism of Piroxicam can be increased when combined with Abatacept.
AbciximabThe risk or severity of bleeding and hemorrhage can be increased when Piroxicam is combined with Abciximab.
AbirateroneThe metabolism of Piroxicam can be decreased when combined with Abiraterone.
AbrocitinibThe metabolism of Abrocitinib can be decreased when combined with Piroxicam.
Food Interactions
  • Avoid alcohol.
  • Take with food.

Products

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dosage, form, labeller, route of administration, and marketing period.
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Product Images
International/Other Brands
Bruxicam / Dolonex / Erazon / Geldène / Improntal / Roxam (Bosnalijek) / Roxiden / Sasulen / Solocalm / Trast
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
FeldeneCapsule20 mg/1OralRemedy Repack2012-07-192013-08-20US flag
FeldeneCapsule20 mg/1OralPfizer Laboratories Div Pfizer Inc1994-05-25Not applicableUS flag
FeldeneCapsule20 mg/1OralPhysicians Total Care, Inc.1994-05-252012-06-30US flag
FeldeneCapsule10 mg/1OralPfizer Laboratories Div Pfizer Inc1994-05-25Not applicableUS flag
Feldene Cap 10mgCapsule10 mgOralPfizer Canada Ulc1981-12-312002-09-06Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Alti-piroxicam-cap 10mgCapsule10 mg / capOralAltimed Pharma Inc.1997-09-242004-08-03Canada flag
Alti-piroxicam-cap 20mgCapsule20 mg / capOralAltimed Pharma Inc.1995-12-312004-08-03Canada flag
Apo Piroxicam Cap 10mgCapsule10 mgOralApotex Corporation1986-12-31Not applicableCanada flag
Apo Piroxicam Cap 20mgCapsule20 mgOralApotex Corporation1986-12-31Not applicableCanada flag
Dom-piroxicamCapsule10 mgOralDominion PharmacalNot applicable2016-10-25Canada flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
FELDENE (0.5% GEL)Gel0.5 %w/wTopicalบริษัท ไฟเซอร์ (ประเทศไทย) จำกัด2006-12-04Not applicableThailand flag
PREDENE GELGel0.5 %w/wTopicalบริษัท โรงงานเภสัชกรรมแอตแลนติค จำกัด2009-07-31Not applicableThailand flag
ROSIDEN GELGel5 mg/gTopicalZYFAS PHARMA PTE LTD1990-03-10Not applicableSingapore flag
ROXIFEN GEL 500 mg/100 gGel500 mg/100gTopicalJOYSON PTE. LTD.1999-05-06Not applicableSingapore flag
ค็อกซ์ซิแคม เจลGel0.5 %w/wTopicalบริษัท โรงงานเภสัชอุตสาหกรรม เจเอสพี (ประเทศไทย) จำกัด (มหาชน)2017-08-182020-09-29Thailand flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
TherafeldaminePiroxicam (20 mg/1) + gamma-Aminobutyric acid (100 mg/1)KitOralPhysician Therapeutics Llc2011-03-03Not applicableUS flag

Categories

ATC Codes
M01AC01 — PiroxicamM02AA07 — PiroxicamS01BC06 — Piroxicam
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound 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).
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzothiazines
Sub Class
Not Available
Direct Parent
Benzothiazines
Alternative Parents
Alpha amino acids and derivatives / Pyridines and derivatives / Organosulfonamides / 1,2-thiazines / Benzenoids / Imidolactams / Heteroaromatic compounds / Secondary carboxylic acid amides / Azacyclic compounds / Carboximidic acids
show 6 more
Substituents
Alpha-amino acid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Benzothiazine / Carbonyl group / Carboximidic acid / Carboxylic acid derivative / Heteroaromatic compound / Hydrocarbon derivative
show 14 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
monocarboxylic acid amide, pyridines, benzothiazine (CHEBI:8249)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
13T4O6VMAM
CAS number
36322-90-4
InChI Key
QYSPLQLAKJAUJT-UHFFFAOYSA-N
InChI
InChI=1S/C15H13N3O4S/c1-18-13(15(20)17-12-8-4-5-9-16-12)14(19)10-6-2-3-7-11(10)23(18,21)22/h2-9,19H,1H3,(H,16,17,20)
IUPAC Name
4-hydroxy-2-methyl-1,1-dioxo-N-(pyridin-2-yl)-2H-1lambda6,2-benzothiazine-3-carboxamide
SMILES
CN1C(C(=O)NC2=NC=CC=C2)=C(O)C2=C(C=CC=C2)S1(=O)=O

References

Synthesis Reference

Paul D. Weeks, "3-Hydroxy 2-methyl benzisothiazolines as intermediates in production of piroxicam." U.S. Patent US4376204, issued April, 1982.

US4376204
General References
Not Available
Human Metabolome Database
HMDB0014694
KEGG Drug
D00127
KEGG Compound
C01608
PubChem Compound
54676228
PubChem Substance
46505225
ChemSpider
10442653
BindingDB
85245
RxNav
8356
ChEBI
8249
ChEMBL
CHEMBL527
ZINC
ZINC000051133897
Therapeutic Targets Database
DAP000181
PharmGKB
PA450985
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Piroxicam
FDA label
Download (74.3 KB)
MSDS
Download (73.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedSupportive CareCytochrome P450 CYP2C9 Enzyme Deficiency / Impacted Third Molar Tooth / Other Surgical Procedures / Pain1
4CompletedSupportive CareSymptomatic Irreversible Pulpitis (SIP)1
4CompletedTreatmentHypertension1
4CompletedTreatmentMenstrual Distress (Dysmenorrhea)1
4CompletedTreatmentPrimary Dysmenorrhoea1

Pharmacoeconomics

Manufacturers
  • Akorn inc
  • Pfizer laboratories div pfizer inc
  • Egis pharmaceuticals
  • Genpharm pharmaceuticals inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Mutual pharmaceutical co inc
  • Mylan pharmaceuticals inc
  • Nostrum laboratories inc
  • Roxane laboratories inc
  • Scs pharmaceuticals
  • Teva pharmaceuticals usa inc
  • Teva pharmaceuticals usa
  • Watson laboratories inc
Packagers
  • Advanced Pharmaceutical Services Inc.
  • Aidarex Pharmacuticals LLC
  • Akorn Inc.
  • Amerisource Health Services Corp.
  • AQ Pharmaceuticals Inc.
  • A-S Medication Solutions LLC
  • Bryant Ranch Prepack
  • Corepharma LLC
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Egis Pharmaceuticals Public Ltd. Co.
  • Goldline Laboratories Inc.
  • Group Health Cooperative
  • H.J. Harkins Co. Inc.
  • Innoviant Pharmacy Inc.
  • Keltman Pharmaceuticals Inc.
  • Lake Erie Medical and Surgical Supply
  • Liberty Pharmaceuticals
  • Major Pharmaceuticals
  • Medisca Inc.
  • Mepha Ltd.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Nostrum Laboratories Inc.
  • Novopharm Ltd.
  • Nucare Pharmaceuticals Inc.
  • Pack Pharmaceuticals
  • Palmetto Pharmaceuticals Inc.
  • PD-Rx Pharmaceuticals Inc.
  • Pfizer Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Pharmedix
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Prescription Dispensing Service Inc.
  • Qualitest
  • Ranbaxy Laboratories
  • Rebel Distributors Corp.
  • Redpharm Drug
  • Remedy Repack
  • Sandhills Packaging Inc.
  • Southwood Pharmaceuticals
  • St Mary's Medical Park Pharmacy
  • Teva Pharmaceutical Industries Ltd.
  • UDL Laboratories
  • United Research Laboratories Inc.
  • Va Cmop Dallas
Dosage Forms
FormRouteStrength
Tablet, coatedOral10 mg
Granule, for solutionOral
Tablet, effervescent
GelTopical0.500 g
SolutionParenteral20 mg
TabletOral2 g
Aerosol, foamTopical10 MG/G
CreamTopical10 mg/g
OintmentTopical0.5 %
OintmentTopical10 mg/g
Granule, for solutionOral20 MG
Tablet, effervescent20 MG
Tablet, effervescentOral20 MG
Injection, powder, for solutionIntramuscular
Injection, powder, for solutionIntramuscular20 MG/2ML
Capsule, coatedOral10 mg
Tablet, coatedOral500 mg
GelTopical1 %
TabletOral20.000 mg
PatchTopical
SolutionParenteral21 mg
CapsuleOral10.000 mg
GelCutaneous0.500 g
SolutionIntramuscular20.000 mg
GelTopical0.5 %
GelTopical
CapsuleOral
Injection, solutionIntramuscular
Tablet, for suspensionOral20 mg
Tablet, orally disintegratingOral20 mg
CapsuleOral20.000 mg
Injection, solutionIntramuscular20 MG/1ML
TabletOral20 mg
SuppositoryRectal10 mg / sup
SuppositoryRectal20 mg / sup
Tablet, solubleOral20 MG
CreamTopical
Aerosol, foamTopical
CapsuleOral10 MG
GelTopical500 mg
CreamTopical1 %
SuppositoryRectal20 MG
Capsule, coatedOral20 mg
SolutionParenteral200000 mg
Solution / dropsOphthalmic
CapsuleOral10 mg/1
CapsuleOral20 mg/1
GelTopical0.5 g
TabletOral
InjectionIntramuscular20 mg
InjectionIntramuscular40 mg
SolutionParenteral40 mg
SolutionIntramuscular40 mg
GelTopical5 mg/g
Capsule, coatedOral20.4 mg
Injection, solutionIntramuscular; Parenteral20 MG/ML
Injection, solutionIntramuscular; Parenteral20 MG/1ML
Tablet, solubleOral
SuppositoryRectal10 mg
TabletOral10 mg / cap
Capsule, liquid filledOral10 mg
GelTopical1 g
Capsule, liquid filledOral20 mg
CapsuleOral10 mg / cap
CapsuleOral20 mg / cap
SuppositoryRectal
InjectionIntramuscular20 mg/ml
InjectionIntramuscular
GelTopical500 mg/100g
GelTopical5 MG
Injection, solution
Powder, for solutionOral20 mg
SolutionIntramuscular20 mg
KitOral
CapsuleOral20 MG
Capsule, coatedOral2000000 mg
LiquidOphthalmic5 mg/1ml
Tablet, coatedOral20 mg
GelTopical0.5 %w/w
TabletOral10 mg
Tablet, film coated10 mg
Prices
Unit descriptionCostUnit
Piroxicam powder13.16USD g
Akten 3.5% drops7.5USD ml
Feldene 20 mg capsule4.93USD capsule
Feldene 10 mg capsule2.82USD capsule
Piroxicam 20 mg capsule2.69USD capsule
Pms-Piroxicam 20 mg Suppository1.82USD suppository
Piroxicam 10 mg capsule1.44USD capsule
Apo-Piroxicam 20 mg Capsule0.75USD capsule
Novo-Pirocam 20 mg Capsule0.75USD capsule
Nu-Pirox 20 mg Capsule0.75USD capsule
Apo-Piroxicam 10 mg Capsule0.43USD capsule
Gen-Piroxicam 10 mg Capsule0.43USD capsule
Novo-Pirocam 10 mg Capsule0.43USD capsule
Nu-Pirox 10 mg Capsule0.43USD capsule
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)198-200 °CPhysProp
water solubility23 mg/L (at 22 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP3.06AVDEEF,A (1997)
logS-4.16ADME Research, USCD
Caco2 permeability-4.45ADME Research, USCD
pKa6.3SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.143 mg/mLALOGPS
logP2.2ALOGPS
logP0.6Chemaxon
logS-3.4ALOGPS
pKa (Strongest Acidic)4.76Chemaxon
pKa (Strongest Basic)3.79Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area99.6 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity87.04 m3·mol-1Chemaxon
Polarizability32.27 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9898
Blood Brain Barrier-0.9659
Caco-2 permeable+0.8867
P-glycoprotein substrateSubstrate0.5786
P-glycoprotein inhibitor INon-inhibitor0.7285
P-glycoprotein inhibitor IINon-inhibitor0.7453
Renal organic cation transporterNon-inhibitor0.9437
CYP450 2C9 substrateSubstrate0.6437
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.7356
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorInhibitor0.9086
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8789
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8709
Ames testNon AMES toxic0.8767
CarcinogenicityNon-carcinogens0.7612
BiodegradationNot ready biodegradable0.923
Rat acute toxicity3.1545 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9589
hERG inhibition (predictor II)Non-inhibitor0.8311
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-MSsplash10-014i-3911000000-4ebab92e0a9daf942bf0
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-1000-1698000000-9bfc929b8cee2ec1d841
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-00dj-6911100000-64e355e5e08c884173b8
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-001i-0019000000-0d247806d6203409cc16
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-014j-0591000000-7d11d429795ac27fa093
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-000t-0910000000-42d97ebe5da8190aa202
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-001m-2900000000-32c34cd63ced296fee89
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00kf-5900000000-1d4473d813b920140b81
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00lr-0009000000-9e65aa6e4b407ea80734
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-000f-3984000000-e855ded4bfe08c600884
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-007c-3900000000-fb37337024398fe8044d
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-006t-9600000000-db1bff24de3a9b89b68d
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00r2-9200000000-22caea8b3219419be51f
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-01vk-6900000000-a75ce07d3bc58c9e773b
MS/MS Spectrum - , positiveLC-MS/MSsplash10-001i-5829000000-bfa87ed6f54b64fe3942
MS/MS Spectrum - , positiveLC-MS/MSsplash10-1000-1698000000-9bfc929b8cee2ec1d841
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00dj-6911100000-64e355e5e08c884173b8
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0209000000-66312a4c5e7f702984ce
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00xs-0920000000-1e8de22ac2ba9037c727
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-4901000000-83287769dc339ea0594f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0921000000-d3c644c7cb098d229bf7
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-4932000000-4925ea77f49ae99b46ee
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-02t9-4911000000-368394a5e9144fbdfdbf
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]-177.7012979
predicted
DarkChem Lite v0.1.0
[M-H]-178.3851979
predicted
DarkChem Lite v0.1.0
[M-H]-166.28563
predicted
DeepCCS 1.0 (2019)
[M+H]+177.6479979
predicted
DarkChem Lite v0.1.0
[M+H]+178.5391979
predicted
DarkChem Lite v0.1.0
[M+H]+168.64363
predicted
DeepCCS 1.0 (2019)
[M+Na]+177.8416979
predicted
DarkChem Lite v0.1.0
[M+Na]+178.5877979
predicted
DarkChem Lite v0.1.0
[M+Na]+174.73677
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
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. 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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [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
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. 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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Calvo AM, Zupelari-Goncalves P, Dionisio TJ, Brozoski DT, Faria FA, Santos CF: Efficacy of piroxicam for postoperative pain after lower third molar surgery associated with CYP2C8*3 and CYP2C9. J Pain Res. 2017 Jul 6;10:1581-1589. doi: 10.2147/JPR.S138147. eCollection 2017. [Article]
  2. Kim KA, Oh SO, Park PW, Park JY: Effect of probenecid on the pharmacokinetics of carbamazepine in healthy subjects. Eur J Clin Pharmacol. 2005 Jun;61(4):275-80. doi: 10.1007/s00228-005-0940-7. Epub 2005 May 25. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. 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. [Article]
  2. Du H, Wei Z, Yan Y, Xiong Y, Zhang X, Shen L, Ruan Y, Wu X, Xu Q, He L, Qin S: Functional Characterization of Human CYP2C9 Allelic Variants in COS-7 Cells. Front Pharmacol. 2016 Apr 25;7:98. doi: 10.3389/fphar.2016.00098. eCollection 2016. [Article]
  3. Flockhart Table of Drug Interactions [Link]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Bertucci C, Wainer IW: Improved chromatographic performance of a modified human albumin based stationary phase. Chirality. 1997;9(4):335-40. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
Molecular Weight
61815.78 Da
References
  1. 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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
Molecular Weight
59855.585 Da
References
  1. 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. [Article]
  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. [Article]
  3. Kusuhara H, Sekine T, Utsunomiya-Tate N, Tsuda M, Kojima R, Cha SH, Sugiyama Y, Kanai Y, Endou H: Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain. J Biol Chem. 1999 May 7;274(19):13675-80. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds.
Gene Name
SLC22A11
Uniprot ID
Q9NSA0
Uniprot Name
Solute carrier family 22 member 11
Molecular Weight
59970.945 Da
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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost.
Gene Name
SLCO2B1
Uniprot ID
O94956
Uniprot Name
Solute carrier organic anion transporter family member 2B1
Molecular Weight
76709.98 Da
References
  1. Karlgren M, Vildhede A, Norinder U, Wisniewski JR, Kimoto E, Lai Y, Haglund U, Artursson P: Classification of inhibitors of hepatic organic anion transporting polypeptides (OATPs): influence of protein expression on drug-drug interactions. J Med Chem. 2012 May 24;55(10):4740-63. doi: 10.1021/jm300212s. Epub 2012 May 15. [Article]

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