Identification

Name
Phenylbutazone
Accession Number
DB00812  (APRD00409, DB08343)
Type
Small Molecule
Groups
Approved, Vet approved
Description

A drug that has anti-inflammatory, antipyretic, and analgesic activities. It is especially effective in the treatment of ankylosing spondylitis. It also is useful in rheumatoid arthritis and Reiter's syndrome (investigational indication). Although phenylbutazone is effective in gouty arthritis, risk/benefit considerations indicate that this drug should not be employed for this disease. (From AMA Drug Evaluations Annual, 1994, p1822)

Structure
Thumb
Synonyms
  • 3,5-Dioxo-1,2-diphenyl-4-n-butylpyrazolidine
  • 4-BUTYL-1,2-diphenyl-pyrazolidine-3,5-dione
  • 4-n-Butyl-1,2-diphenyl-3,5-pyrazolidinedione
  • Fenilbutazona
  • Phenbutazone
  • Phenylbutazon
  • Phenylbutazone
  • Phenylbutazonum
External IDs
G-13871 / NSC-25134 / USAF Ge-15
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo Phenylbutazone Tab 100mgTablet100 mgOralApotex Corporation1976-12-312009-09-18Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Novo-butazone Tab 100mgTablet100 mgOralNovopharm Limited1976-12-312005-08-10Canada
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Alka Phenyl TabPhenylbutazone (100 mg) + Aluminum hydroxide (100 mg) + Magnesium Trisilicate (150 mg)TabletOralDuchesnay Inc.1978-12-311997-08-11Canada
Alka Phenylbutazone TabPhenylbutazone (100 mg) + Aluminum hydroxide (100 mg) + Magnesium Trisilicate (150 mg)TabletOralPro Doc Limitee1974-12-311997-08-14Canada
Phenylone Plus TabPhenylbutazone (100 mg) + Aluminum hydroxide (100 mg) + Magnesium Trisilicate (150 mg)TabletOralMedic Laboratory LtÉe1978-12-311996-09-09Canada
International/Other Brands
Azolid
Categories
UNII
GN5P7K3T8S
CAS number
50-33-9
Weight
Average: 308.3743
Monoisotopic: 308.152477894
Chemical Formula
C19H20N2O2
InChI Key
VYMDGNCVAMGZFE-UHFFFAOYSA-N
InChI
InChI=1S/C19H20N2O2/c1-2-3-14-17-18(22)20(15-10-6-4-7-11-15)21(19(17)23)16-12-8-5-9-13-16/h4-13,17H,2-3,14H2,1H3
IUPAC Name
4-butyl-1,2-diphenylpyrazolidine-3,5-dione
SMILES
CCCCC1C(=O)N(N(C1=O)C1=CC=CC=C1)C1=CC=CC=C1

Pharmacology

Indication

For the treatment of backache and ankylosing spondylitis

Pharmacodynamics

Phenylbutazone is a synthetic, pyrazolone derivative. It is a nonhormonal anti-inflammatory, antipyretic compound useful in the management of inflammatory conditions. The apparent analgesic effect is probably related mainly to the compound's anti-inflammatory properties and arise from its ability to reduce production of prostaglandin H and prostacyclin. Prostaglandins act on a variety of cells such as vascular smooth muscle cells causing constriction or dilation, on platelets causing aggregation or disaggregation and on spinal neurons causing pain. Prostacylcin causes vascular constriction platelet disaggregation

Mechanism of action

Phenylbutazone binds to and inactivates prostaglandin H synthase and prostacyclin synthase through peroxide (H2O2) mediated deactivation. The reduced production of prostaglandin leads to reduced inflammation of the surrounding tissues.

TargetActionsOrganism
AProstaglandin G/H synthase 2
inhibitor
Human
AProstacyclin synthase
inhibitor
Human
AProstaglandin G/H synthase 1
inhibitor
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

Oral, LD50 = 238 mg/kg (mouse); Oral, LD50 = 781 mg/kg (rabbit); Oral, LD50 = 245 mg/kg (rat); Oral, LD50 = 375 mg/kg (rat)

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Phenylbutazone Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of gastrointestinal bleeding can be increased when Phenylbutazone is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of gastrointestinal bleeding can be increased when Phenylbutazone is combined with (S)-Warfarin.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be increased when combined with Phenylbutazone.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be increased when combined with Phenylbutazone.
5-androstenedioneThe metabolism of 5-androstenedione can be increased when combined with Phenylbutazone.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be increased when combined with Phenylbutazone.
AbacavirPhenylbutazone may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbciximabThe risk or severity of bleeding and hemorrhage can be increased when Phenylbutazone is combined with Abciximab.
AbemaciclibThe metabolism of Abemaciclib can be increased when combined with Phenylbutazone.
AbirateroneThe metabolism of Phenylbutazone can be decreased when combined with Abiraterone.
Food Interactions
  • Take with food to reduce irritation. Avoid alcohol.

References

Synthesis Reference

Dieter Rahtz, Henning Koch, Erich Gerhards, "Hydroxy phenylbutazone derivatives and their preparation." U.S. Patent US3968219, issued January, 1971.

US3968219
General References
Not Available
External Links
Human Metabolome Database
HMDB0014950
KEGG Drug
D00510
KEGG Compound
C07440
PubChem Compound
4781
PubChem Substance
46507038
ChemSpider
4617
ChEBI
48574
ChEMBL
CHEMBL101
Therapeutic Targets Database
DAP000974
PharmGKB
PA450932
HET
P1Z
Wikipedia
Phenylbutazone
ATC Codes
M01AA01 — PhenylbutazoneM01BA01 — Phenylbutazone and corticosteroidsM02AA01 — Phenylbutazone
PDB Entries
2bxc / 2bxp / 2bxq / 2w98
MSDS
Download (73.1 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
  • Sanofi aventis us llc
  • Novartis pharmaceuticals corp
  • Ivax pharmaceuticals inc
  • Mutual pharmaceutical co inc
  • Sandoz inc
  • Watson laboratories inc
Packagers
  • C.O. Truxton Inc.
  • Jaapharm Canada Inc.
  • Medisca Inc.
Dosage forms
FormRouteStrength
TabletOral
TabletOral100 mg
Prices
Unit descriptionCostUnit
Phenylbutazone powder1.16USD g
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)105 °CPhysProp
water solubility47.5 mg/L (at 30 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP3.16SANGSTER (1994)
logS-3.81ADME Research, USCD
pKa4.5SERJEANT,EP & DEMPSEY,B (1979)
Predicted Properties
PropertyValueSource
Water Solubility0.144 mg/mLALOGPS
logP2.81ALOGPS
logP4.14ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)5.13ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.62 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity88.76 m3·mol-1ChemAxon
Polarizability34.15 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9931
Caco-2 permeable+0.6185
P-glycoprotein substrateNon-substrate0.7632
P-glycoprotein inhibitor INon-inhibitor0.5423
P-glycoprotein inhibitor IIInhibitor0.5596
Renal organic cation transporterNon-inhibitor0.866
CYP450 2C9 substrateNon-substrate0.6378
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.5439
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorInhibitor0.5752
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.5968
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5233
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.7995
BiodegradationNot ready biodegradable0.9881
Rat acute toxicity2.7753 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9469
hERG inhibition (predictor II)Non-inhibitor0.892
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (9.03 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0a4i-0009000000-f8e4cda83d45cc4ca59b
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0a4i-0549000000-2907029e48d9c65ae00e
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-001i-2910000000-bb1ac78907a0338c7dc6
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-000x-6900000000-4f14a2268cc3ae06d3e5
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0006-9400000000-d5012ae523568dc8e63c
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0006-9100000000-2af914d40adc6817f026
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0006-9000000000-1b11164dde00c44d0ffe
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0006-9000000000-3b304315d58e9e8f6984
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-00kf-9000000000-b6387c41c12a5abb6d4b
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0009000000-bde0ac035aafd4e337f2
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0006-0092000000-e77e2c9ca9127d3ecff9
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4l-0196000000-6d31987fe09f0949a98d
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-016r-0190000000-6b839462a4e745d1fc0d
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00vi-0290000000-c78339fd5994808afb08
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-0109000000-c3cb4b19bc15bf87c709
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03kl-2921000000-02a08606b3d2e3c8c702
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-01vo-5910000000-1e1a7cd346204d8387aa
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0006-9700000000-b87550cf5df8c862c64a
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00kf-9500000000-222c301c8bf7fa8c9490
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-05mp-9400000000-435ce3b2edce024cf240
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0694-9300000000-6da14f0b017841074aae
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0v01-9200000000-7f2a34538722ab3db398
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0udi-9100000000-9da3ad0823a2792e46cb
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4i-2947000000-a91a724d8272a5a71f97

Taxonomy

Description
This compound belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Not Available
Direct Parent
Benzene and substituted derivatives
Alternative Parents
Pyrazolidinones / 1,3-dicarbonyl compounds / Carboxylic acid hydrazides / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
Monocyclic benzene moiety / Pyrazolidinone / 1,3-dicarbonyl compound / Pyrazolidine / Carboxylic acid hydrazide / Azacycle / Organoheterocyclic compound / Carboxylic acid derivative / Organic oxide / Organopnictogen compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
pyrazolidines (CHEBI:48574)

Targets

Kind
Protein
Organism
Human
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. Arifah AK, Lees P: Pharmacodynamics and pharmacokinetics of phenylbutazone in calves. J Vet Pharmacol Ther. 2002 Aug;25(4):299-309. [PubMed:12213119]
  2. Takada Y, Bhardwaj A, Potdar P, Aggarwal BB: Nonsteroidal anti-inflammatory agents differ in their ability to suppress NF-kappaB activation, inhibition of expression of cyclooxygenase-2 and cyclin D1, and abrogation of tumor cell proliferation. Oncogene. 2004 Dec 9;23(57):9247-58. [PubMed:15489888]
  3. Beretta C, Garavaglia G, Cavalli M: COX-1 and COX-2 inhibition in horse blood by phenylbutazone, flunixin, carprofen and meloxicam: an in vitro analysis. Pharmacol Res. 2005 Oct;52(4):302-6. [PubMed:15939622]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Prostaglandin-i synthase activity
Specific Function
Catalyzes the isomerization of prostaglandin H2 to prostacyclin (= prostaglandin I2).
Gene Name
PTGIS
Uniprot ID
Q16647
Uniprot Name
Prostacyclin synthase
Molecular Weight
57103.385 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Reed GA, Griffin IO, Eling TE: Inactivation of prostaglandin H synthase and prostacyclin synthase by phenylbutazone. Requirement for peroxidative metabolism. Mol Pharmacol. 1985 Jan;27(1):109-14. [PubMed:3917545]
  4. Marnett LJ, Siedlik PH, Ochs RC, Pagels WR, Das M, Honn KV, Warnock RH, Tainer BE, Eling TE: Mechanism of the stimulation of prostaglandin H synthase and prostacyclin synthase by the antithrombotic and antimetastatic agent, nafazatrom. Mol Pharmacol. 1984 Sep;26(2):328-35. [PubMed:6434940]
  5. Tobin T, Chay S, Kamerling S, Woods WE, Weckman TJ, Blake JW, Lees P: Phenylbutazone in the horse: a review. J Vet Pharmacol Ther. 1986 Mar;9(1):1-25. [PubMed:3517382]
Kind
Protein
Organism
Human
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. 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. Zitova A, Hynes J, Kollar J, Borisov SM, Klimant I, Papkovsky DB: Analysis of activity and inhibition of oxygen-dependent enzymes by optical respirometry on the LightCycler system. Anal Biochem. 2010 Feb 15;397(2):144-51. doi: 10.1016/j.ab.2009.10.029. Epub 2009 Oct 20. [PubMed:19849999]
  2. Beretta C, Garavaglia G, Cavalli M: COX-1 and COX-2 inhibition in horse blood by phenylbutazone, flunixin, carprofen and meloxicam: an in vitro analysis. Pharmacol Res. 2005 Oct;52(4):302-6. [PubMed:15939622]
  3. Morton AJ, Campbell NB, Gayle JM, Redding WR, Blikslager AT: Preferential and non-selective cyclooxygenase inhibitors reduce inflammation during lipopolysaccharide-induced synovitis. Res Vet Sci. 2005 Apr;78(2):189-92. [PubMed:15563928]

Enzymes

Details
1. Cytochrome P450 2C9
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
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
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]
  2. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
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. 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

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
Molecular Weight
61815.78 Da
References
  1. 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]
  2. Uwai Y, Saito H, Inui K: Interaction between methotrexate and nonsteroidal anti-inflammatory drugs in organic anion transporter. Eur J Pharmacol. 2000 Dec 1;409(1):31-6. [PubMed:11099697]
  3. 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]
Kind
Protein
Organism
Human
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. 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]
Kind
Protein
Organism
Human
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. 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]

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 04:50