Flutamide

Identification

Summary

Flutamide is an antiandrogen used for locally confined stage B2-C and D-2 metastatic prostate carcinoma.

Generic Name
Flutamide
DrugBank Accession Number
DB00499
Background

An antiandrogen with about the same potency as cyproterone in rodent and canine species.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 276.2118
Monoisotopic: 276.072176843
Chemical Formula
C11H11F3N2O3
Synonyms
  • 4'-nitro-3'-trifluoromethylisobutyranilide
  • Flutamid
  • Flutamida
  • Flutamide
  • Flutamidum
  • FTA
  • NFBA
  • Niftolid
  • Niftolide
  • α,α,α-trifluoro-2-methyl-4'-nitro-m-propionotoluidide
External IDs
  • SCH 13521
  • SCH-13521

Pharmacology

Indication

For the management of locally confined Stage B2-C and Stage D2 metastatic carcinoma of the prostate

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Flutamide is a nonsteroidal antiandrogen. In animal studies, flutamide demonstrates potent antiandrogenic effects. It exerts its antiandrogenic action by inhibiting androgen uptake and/or by inhibiting nuclear binding of androgen in target tissues or both. Prostatic carcinoma is known to be androgen-sensitive and responds to treatment that counteracts the effect of androgen and/or removes the source of androgen, e.g. castration. Elevations of plasma testosterone and estradiol levels have been noted following flutamide administration.

Mechanism of action

Flutamide is a nonsteroidal antiandrogen that blocks the action of both endogenous and exogenous testosterone by binding to the androgen receptor. In addition Flutamide is a potent inhibitor of testosterone-stimulated prostatic DNA synthesis. Moreover, it is capable of inhibiting prostatic nuclear uptake of androgen.

TargetActionsOrganism
AAndrogen receptor
antagonist
Humans
UAryl hydrocarbon receptor
agonist
Humans
UNuclear receptor subfamily 1 group I member 2Not AvailableHumans
Absorption

Rapidly and completely absorbed.

Volume of distribution

Not Available

Protein binding

94-96%

Metabolism

Flutamide is rapidly and extensively metabolized, with flutamide comprising only 2.5% of plasma radioactivity 1 hour after administration.

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Route of elimination

Flutamide and its metabolites are excreted mainly in the urine with only 4.2% of a single dose excreted in the feces over 72 hours.

Half-life

The plasma half-life for the alpha-hydroxylated metabolite of flutamide (an active metabolite) is approximately 6 hours.

Clearance

Not Available

Adverse Effects
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Toxicity

In animal studies with flutamide alone, signs of overdose included hypoactivity, piloerection, slow respiration, ataxia, and/or lacrimation, anorexia, tranquilization, emesis, and methemoglobinemia.

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
AbacavirFlutamide may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbametapirThe serum concentration of Flutamide can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Flutamide can be increased when combined with Abatacept.
AbirateroneThe serum concentration of Flutamide can be increased when it is combined with Abiraterone.
AcalabrutinibThe metabolism of Flutamide can be decreased when combined with Acalabrutinib.
AceclofenacAceclofenac may decrease the excretion rate of Flutamide which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Flutamide which could result in a higher serum level.
AcenocoumarolThe metabolism of Acenocoumarol can be decreased when combined with Flutamide.
AcetaminophenThe risk or severity of methemoglobinemia can be increased when Acetaminophen is combined with Flutamide.
AcetazolamideAcetazolamide may increase the excretion rate of Flutamide which could result in a lower serum level and potentially a reduction in efficacy.
Interactions
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Food Interactions
  • Take with or without food. The absorption is unaffected by food.

Products

Products
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Product Images
International/Other Brands
Andraxan (CSC) / Antipros (Medicamerc) / Curestat (Advanced Pharmaceutical) / Cytomid (Cipla) / Dedile (Ivax) / Drogenil (Bayer) / Elbat (Genepharm) / Etaconil (Nolver) / Farostat (Orion) / Flimutal (Cryopharma) / Flucinom (Merck Sharp & Dohme) / Flulem (Teva) / Odyne (Nippon Kayaku) / Prostadirex (Sanofi-Aventis) / Prostanon (Pharmachemie)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
EuflexTablet250 mgOralMerck Ltd.1984-12-312015-06-01Canada flag
EulexinCapsule125 mg/1OralMerck Sharp & Dohme Limited1989-01-272005-09-30US flag
FlutamideTablet250 mgOralPharmel Inc1998-12-012016-10-25Canada flag
FlutamideTablet250 mgOralPharmascience Inc1997-10-312016-10-28Canada flag
FlutamideTablet250 mgOralSchering Plough1996-12-312014-07-31Canada flag
FlutamideTablet250 mgOralAa Pharma Inc1998-10-08Not applicableCanada flag
Flutamide-250Tablet250 mg / tabOralPro Doc Limitee1999-02-222009-07-23Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Dom-flutamideTablet250 mg / tabOralDominion PharmacalNot applicableNot applicableCanada flag
FlutamideCapsule125 mg/1OralActavis Pharma, Inc.2011-07-282020-02-29US flag
FlutamideCapsule125 mg/1OralGenpharm Ulc2015-11-012015-11-30US flag
FlutamideCapsule125 mg/1OralEon Labs, Inc.2001-09-182011-08-31US flag
FlutamideCapsule125 mg/1OralPar Pharmaceutical, Inc.2006-01-26Not applicableUS flag
FlutamideCapsule125 mg/1OralCipla USA Inc.2016-09-21Not applicableUS flag
FlutamideCapsule125 mg/1OralBarr Laboratories2001-09-182011-08-31US flag
FlutamideCapsule125 mg/1OralGolden State Medical Supply, Inc.2001-09-18Not applicableUS flag
FlutamideCapsule125 mg/1OralTeva2001-09-192018-05-31US flag00172 4960 58 nlmimage10 af2dd78e
FlutamideCapsule125 mg/1OralPhysicians Total Care, Inc.2001-09-182004-06-30US flag

Categories

ATC Codes
L02BB01 — Flutamide
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as trifluoromethylbenzenes. These are organofluorine compounds that contain a benzene ring substituted with one or more trifluoromethyl groups.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Trifluoromethylbenzenes
Direct Parent
Trifluoromethylbenzenes
Alternative Parents
Nitrobenzenes / Anilides / Nitroaromatic compounds / N-arylamides / Secondary carboxylic acid amides / Propargyl-type 1,3-dipolar organic compounds / Organic oxoazanium compounds / Organopnictogen compounds / Organofluorides / Organic zwitterions
show 4 more
Substituents
Alkyl fluoride / Alkyl halide / Allyl-type 1,3-dipolar organic compound / Anilide / Aromatic homomonocyclic compound / C-nitro compound / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Hydrocarbon derivative
show 18 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
monocarboxylic acid amide, (trifluoromethyl)benzenes (CHEBI:5132)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
76W6J0943E
CAS number
13311-84-7
InChI Key
MKXKFYHWDHIYRV-UHFFFAOYSA-N
InChI
InChI=1S/C11H11F3N2O3/c1-6(2)10(17)15-7-3-4-9(16(18)19)8(5-7)11(12,13)14/h3-6H,1-2H3,(H,15,17)
IUPAC Name
2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide
SMILES
CC(C)C(=O)NC1=CC(=C(C=C1)[N+]([O-])=O)C(F)(F)F

References

Synthesis Reference

Jack Lawrence James, Louis Frank Molnar, Jr., Tania E. Toney-Parker, "Processes for preparing flutamide compounds and compounds prepared by such processes." U.S. Patent US 6,228,401, issued November, 1976.

US6228401
General References
  1. Link [Link]
Human Metabolome Database
HMDB0014642
KEGG Drug
D00586
KEGG Compound
C07653
PubChem Compound
3397
PubChem Substance
46508874
ChemSpider
3280
BindingDB
50131270
RxNav
4508
ChEBI
5132
ChEMBL
CHEMBL806
ZINC
ZINC000003812944
Therapeutic Targets Database
DAP000301
PharmGKB
PA449685
PDBe Ligand
HFT
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Flutamide
AHFS Codes
  • 10:00.00 — Antineoplastic Agents
FDA label
Download (413 KB)
MSDS
Download (55.8 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentPremenstrual Syndrome1
4CompletedTreatmentProstate Cancer1
4RecruitingSupportive CareProstatic Neoplasms1
3Active Not RecruitingTreatmentProstate Cancer5
3CompletedTreatmentAdenocarcinoma, Prostate1
3CompletedTreatmentProstate Cancer12
3CompletedTreatmentProstatic Neoplasms, Locally Advanced1
3RecruitingTreatmentAdenocarcinoma, Prostate / Metastatic Malignant Neoplasm in the Bone / Stage III Prostate Cancer AJCC v8 / Stage IIIA Prostate Cancer AJCC v8 / Stage IIIB Prostate Cancer AJCC v8 / Stage IIIC Prostate Cancer AJCC v8 / Stage IVA Prostate Cancer AJCC v81
3RecruitingTreatmentCastration Levels of Testosterone / Metastatic Prostatic Adenocarcinoma / Stage IV Prostate Cancer AJCC v8 / Stage IVA Prostate Cancer AJCC v8 / Stage IVB Prostate Cancer AJCC v81
3TerminatedTreatmentProstate Cancer3

Pharmacoeconomics

Manufacturers
  • Schering corp sub schering plough corp
  • Genpharm inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Par pharmaceutical inc
  • Sandoz inc
  • Watson laboratories inc
Packagers
  • Barr Pharmaceuticals
  • Cipla Ltd.
  • Eon Labs
  • Ivax Pharmaceuticals
  • Neuman Distributors Inc.
  • Par Pharmaceuticals
  • Pharmaceutical Utilization Management Program VA Inc.
  • Physicians Total Care Inc.
  • Salutas Pharma GmbH
  • Sandhills Packaging Inc.
  • Teva Pharmaceutical Industries Ltd.
  • Watson Pharmaceuticals
Dosage Forms
FormRouteStrength
Tablet, film coatedOral250 mg
CapsuleOral
TabletOral250 mg
CapsuleOral125 mg/1
TabletOral250 mg / tab
TabletOral
Tablet, film coatedOral
Tablet, coated
Prices
Unit descriptionCostUnit
Flutamide 125 mg capsule2.12USD 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)111.5-112.5Gold, E.H.; U.S. Patent 3,847,988; November 12, 1974; assigned to Schering Corp.
water solubility9.45 mg/LNot Available
logP3.35MORRIS,JJ ET AL. (1991)
Predicted Properties
PropertyValueSource
Water Solubility0.00566 mg/mLALOGPS
logP2.55ALOGPS
logP3.27ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)13.17ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area74.92 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity63.42 m3·mol-1ChemAxon
Polarizability23.2 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9948
Blood Brain Barrier+0.9655
Caco-2 permeable+0.7533
P-glycoprotein substrateNon-substrate0.8131
P-glycoprotein inhibitor INon-inhibitor0.8254
P-glycoprotein inhibitor IINon-inhibitor0.9428
Renal organic cation transporterNon-inhibitor0.9535
CYP450 2C9 substrateNon-substrate0.7927
CYP450 2D6 substrateNon-substrate0.8935
CYP450 3A4 substrateSubstrate0.568
CYP450 1A2 substrateInhibitor0.9108
CYP450 2C9 inhibitorNon-inhibitor0.6306
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorInhibitor0.8994
CYP450 3A4 inhibitorNon-inhibitor0.5924
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6574
Ames testNon AMES toxic0.5728
CarcinogenicityCarcinogens 0.6077
BiodegradationNot ready biodegradable0.9924
Rat acute toxicity2.5770 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9881
hERG inhibition (predictor II)Non-inhibitor0.8734
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-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-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-004i-0090000000-983edf51e9c479db69a5
MS/MS Spectrum - , positiveLC-MS/MSsplash10-004i-0190000000-df05faf7e38e6d6da203
MS/MS Spectrum - , positiveLC-MS/MSsplash10-004i-0290000000-cca4c08f2a9bb3fc6f57
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03di-2940000000-170008eb50a63f0664d0

Targets

Drugtargets
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Details
1. Androgen receptor
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Zinc ion binding
Specific Function
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription ...
Gene Name
AR
Uniprot ID
P10275
Uniprot Name
Androgen receptor
Molecular Weight
98987.9 Da
References
  1. Chang HC, Miyamoto H, Marwah P, Lardy H, Yeh S, Huang KE, Chang C: Suppression of Delta(5)-androstenediol-induced androgen receptor transactivation by selective steroids in human prostate cancer cells. Proc Natl Acad Sci U S A. 1999 Sep 28;96(20):11173-7. [Article]
  2. Martelli A, Campart GB, Carrozzino R, Ghia M, Mattioli F, Mereto E, Orsi P, Puglia CP: Evaluation of flutamide genotoxicity in rats and in primary human hepatocytes. Pharmacol Toxicol. 2000 Mar;86(3):129-34. [Article]
  3. Montalvo L, Carmena MJ, Solano RM, Clemente C, Roman ID, Sanchez-Chapado M, Prieto JC: Effect of flutamide-induced androgen-receptor blockade on adenylate cyclase activation through G-protein coupled receptors in rat prostate. Cell Signal. 2000 May;12(5):311-6. [Article]
  4. Pazos F, Sanchez-Franco F, Balsa JA, Escalada J, Palacios N, Cacicedo L: Mechanisms of reduced body growth in the pubertal feminized male rat: unbalanced estrogen and androgen action on the somatotropic axis. Pediatr Res. 2000 Jul;48(1):96-103. [Article]
  5. Shilling AD, Williams DE: The non-aromatizable androgen, dihydrotestosterone, induces antiestrogenic responses in the rainbow trout. J Steroid Biochem Mol Biol. 2000 Nov 15;74(4):187-94. [Article]
  6. Balk SP: Androgen receptor as a target in androgen-independent prostate cancer. Urology. 2002 Sep;60(3 Suppl 1):132-8; discussion 138-9. [Article]
  7. 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
Agonist
General Function
Transcription regulatory region dna binding
Specific Function
Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes...
Gene Name
AHR
Uniprot ID
P35869
Uniprot Name
Aryl hydrocarbon receptor
Molecular Weight
96146.705 Da
References
  1. Hu W, Sorrentino C, Denison MS, Kolaja K, Fielden MR: Induction of cyp1a1 is a nonspecific biomarker of aryl hydrocarbon receptor activation: results of large scale screening of pharmaceuticals and toxicants in vivo and in vitro. Mol Pharmacol. 2007 Jun;71(6):1475-86. Epub 2007 Feb 27. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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. Harmsen S, Meijerman I, Beijnen JH, Schellens JH: Nuclear receptor mediated induction of cytochrome P450 3A4 by anticancer drugs: a key role for the pregnane X receptor. Cancer Chemother Pharmacol. 2009 Jun;64(1):35-43. doi: 10.1007/s00280-008-0842-3. Epub 2008 Oct 7. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Kang P, Dalvie D, Smith E, Zhou S, Deese A: Identification of a novel glutathione conjugate of flutamide in incubations with human liver microsomes. Drug Metab Dispos. 2007 Jul;35(7):1081-8. doi: 10.1124/dmd.107.014860. Epub 2007 Apr 2. [Article]
  2. Shet MS, McPhaul M, Fisher CW, Stallings NR, Estabrook RW: Metabolism of the antiandrogenic drug (Flutamide) by human CYP1A2. Drug Metab Dispos. 1997 Nov;25(11):1298-303. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
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
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Wang B, Zhou SF: Synthetic and natural compounds that interact with human cytochrome P450 1A2 and implications in drug development. Curr Med Chem. 2009;16(31):4066-218. [Article]
  2. Shet MS, McPhaul M, Fisher CW, Stallings NR, Estabrook RW: Metabolism of the antiandrogenic drug (Flutamide) by human CYP1A2. Drug Metab Dispos. 1997 Nov;25(11):1298-303. [Article]
  3. Blobaum AL, Byers FW, Bridges TM, Locuson CW, Conn PJ, Lindsley CW, Daniels JS: A Screen of Approved Drugs Identifies the Androgen Receptor Antagonist Flutamide and Its Pharmacologically Active Metabolite 2-Hydroxy-Flutamide as Heterotropic Activators of Cytochrome P450 3A In Vitro and In Vivo. Drug Metab Dispos. 2015 Nov;43(11):1718-26. doi: 10.1124/dmd.115.064006. Epub 2015 Aug 11. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d 24-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
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 Da
References
  1. Rochat B, Morsman JM, Murray GI, Figg WD, McLeod HL: Human CYP1B1 and anticancer agent metabolism: mechanism for tumor-specific drug inactivation? J Pharmacol Exp Ther. 2001 Feb;296(2):537-41. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1B1
Uniprot ID
Q16678
Uniprot Name
Cytochrome P450 1B1
Molecular Weight
60845.33 Da
References
  1. Rochat B, Morsman JM, Murray GI, Figg WD, McLeod HL: Human CYP1B1 and anticancer agent metabolism: mechanism for tumor-specific drug inactivation? J Pharmacol Exp Ther. 2001 Feb;296(2):537-41. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Kang P, Dalvie D, Smith E, Zhou S, Deese A: Identification of a novel glutathione conjugate of flutamide in incubations with human liver microsomes. Drug Metab Dispos. 2007 Jul;35(7):1081-8. doi: 10.1124/dmd.107.014860. Epub 2007 Apr 2. [Article]
  2. Shet MS, McPhaul M, Fisher CW, Stallings NR, Estabrook RW: Metabolism of the antiandrogenic drug (Flutamide) by human CYP1A2. Drug Metab Dispos. 1997 Nov;25(11):1298-303. [Article]

Drug created on June 13, 2005 13:24 / Updated on May 15, 2021 12:14