Explore a selection of our essential drug information below, or:
Identification
- Summary
Fluorouracil is a pyrimidine analog used to treat basal cell carcinomas, and as an injection in palliative cancer treatment.
- Brand Names
- Actikerall, Carac, Efudex, Fluoroplex, Tolak
- Generic Name
- Fluorouracil
- DrugBank Accession Number
- DB00544
- Background
A pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the thymidylate synthetase conversion of deoxyuridylic acid to thymidylic acid.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Fluorouracil (DB00544)
- Weight
- Average: 130.0772
Monoisotopic: 130.017855555 - Chemical Formula
- C4H3FN2O2
- Synonyms
- 5-Fluoracil
- 5-Fluoropyrimidine-2,4-dione
- 5-Fluorouracil
- 5-Fluracil
- 5-FU
- Fluoro Uracil
- Fluorouracil
- Fluorouracilo
- Fluorouracilum
- Fluouracil
- External IDs
- NSC-19893
- RO 2-9757
Pharmacology
- Indication
For the topical treatment of multiple actinic or solar keratoses. In the 5% strength it is also useful in the treatment of superficial basal cell carcinomas when conventional methods are impractical, such as with multiple lesions or difficult treatment sites. Fluorouracil injection is indicated in the palliative management of some types of cancer, including colon, esophageal, gastric, rectum, breast, biliary tract, stomach, head and neck, cervical, pancreas, renal cell, and carcinoid.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Actinic keratoses •••••••••••• Treatment of Breast cancer •••••••••••• Treatment of Colon cancer •••••••••••• Treatment of Gastric cancer •••••••••••• Treatment of Pancreatic cancer •••••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Fluorouracil is an antineoplastic anti-metabolite. Anti-metabolites masquerade as purine or pyrimidine - which become the building blocks of DNA. They prevent these substances from becoming incorporated into DNA during the "S" phase (of the cell cycle), stopping normal development and division. Fluorouracil blocks an enzyme which converts the cytosine nucleotide into the deoxy derivative. In addition, DNA synthesis is further inhibited because Fluorouracil blocks the incorporation of the thymidine nucleotide into the DNA strand.
- Mechanism of action
The precise mechanism of action has not been fully determined, but the main mechanism of fluorouracil is thought to be the binding of the deoxyribonucleotide of the drug (FdUMP) and the folate cofactor, N5–10-methylenetetrahydrofolate, to thymidylate synthase (TS) to form a covalently bound ternary complex. This results in the inhibition of the formation of thymidylate from uracil, which leads to the inhibition of DNA and RNA synthesis and cell death. Fluorouracil can also be incorporated into RNA in place of uridine triphosphate (UTP), producing a fraudulent RNA and interfering with RNA processing and protein synthesis.
Target Actions Organism ATelomerase reverse transcriptase other/unknownHumans ADihydropyrimidine dehydrogenase [NADP(+)] inhibitorHumans AThymidylate synthase inhibitorYeast ADNA incorporation into and destabilizationHumans ARNA incorporation into and destabilizationHumans AThymidylate synthase other/unknownHumans - Absorption
28-100%
- Volume of distribution
Not Available
- Protein binding
8-12%
- Metabolism
Hepatic. The catabolic metabolism of fluorouracil results in degradation products ( e.g., CO2, urea and α-fluoro-ß-alanine) which are inactive.
- Route of elimination
Seven percent to 20% of the parent drug is excreted unchanged in the urine in 6 hours; of this over 90% is excreted in the first hour. The remaining percentage of the administered dose is metabolized, primarily in the liver.
- Half-life
10-20 minutes
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
LD50=230mg/kg (orally in mice)
- Pathways
Pathway Category Capecitabine Action Pathway Drug action Fluorouracil Action Pathway Drug action Capecitabine Metabolism Pathway Drug metabolism Fluorouracil Metabolism Pathway Drug metabolism - Pharmacogenomic Effects/ADRs
Interacting Gene/Enzyme Allele name Genotype(s) Defining Change(s) Type(s) Description Details Thymidylate synthase TSER*2 Not Available (CCGCGCCACTTCGCCTGCCTCCGTCCCG)2/3/4 ADR Directly Studied Patients with this genotype have increased risk of severe neutropenia or severe diarrhea with [drug; fluorouracil]. Details Dihydropyrimidine dehydrogenase [NADP(+)] --- (G;G) / (A;G) C allele / G allele ADR Directly Studied Patients with this genotype have reduced metabolism of fluorouracil and increased risk of toxicity. Details Glutathione S-transferase P --- (A;A) / (A;G) A allele ADR Directly Studied Patients with this genotype have increased risk of toxicity with fluorouracil Details Dihydropyrimidine dehydrogenase [NADP(+)] --- (A;A) / (A;G) A allele ADR Directly Studied Patients with this genotype have reduced metabolism of fluorouracil and increased risk of toxicity. Details Dihydropyrimidine dehydrogenase [NADP(+)] --- (A;A) / (A;T) T > A ADR Directly Studied Patients with this genotype have reduced metabolism of fluorouracil and increased risk of toxicity. Details Dihydropyrimidine dehydrogenase [NADP(+)] DPYD*2A (A;A) / (A;G) G > A ADR Directly Studied The presence of this genotype in DPYD is associated with an increased risk of drug-related toxicity from fluorouracil therapy. Details Dihydropyrimidine dehydrogenase [NADP(+)] DPYD*13 (C;C) / (A;C) A > C ADR Directly Studied The presence of this genotype in DPYD is associated with an increased risk of drug-related toxicity from fluorouracil therapy. Details Dihydropyrimidine dehydrogenase [NADP(+)] --- (A;A) / (A;T) T > A ADR Directly Studied The presence of this genotype in DPYD is associated with an increased risk of drug-related toxicity from fluorouracil therapy. Details Dihydropyrimidine dehydrogenase [NADP(+)] DPYD*4 (G;G) / (A:G) G > A ADR Directly Studied The presence of this genotype in DPYD may be associated with an increased risk of drug-related toxicity from fluorouracil therapy. Details Dihydropyrimidine dehydrogenase [NADP(+)] DPYD*5 (G;G) / (A;G) A > G ADR Directly Studied The presence of this genotype in DPYD may be associated with an increased risk of drug-related toxicity from fluorouracil therapy. Details Dihydropyrimidine dehydrogenase [NADP(+)] DPYD*6 (A;A) / (A;G) G > A ADR Directly Studied The presence of this genotype in DPYD may be associated with an increased risk of drug-related toxicity from fluorouracil therapy. Details Dihydropyrimidine dehydrogenase [NADP(+)] DPYD*9A (C;C) / (C;T) T > C ADR Directly Studied The presence of this genotype in DPYD may be associated with an increased risk of drug-related toxicity from fluorouracil therapy. 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Fluorouracil can be increased when it is combined with Abametapir. Abatacept The metabolism of Fluorouracil can be increased when combined with Abatacept. Abciximab The risk or severity of bleeding can be increased when Abciximab is combined with Fluorouracil. Abemaciclib Abemaciclib may decrease the excretion rate of Fluorouracil which could result in a higher serum level. Abiraterone The metabolism of Fluorouracil can be decreased when combined with Abiraterone. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Fluorouracil sodium PM476L7O8G 14787-18-9 XLBUSGPKSVRQSF-UHFFFAOYSA-M - International/Other Brands
- Carzonal (Tobishi) / Efudix (Meda) / Efurix (Valeant) / Ftoruracil (Verofarm)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Adrucil Solution 50 mg / mL Intravenous Pfizer Italia S.R.L. 1995-12-31 2004-04-08 Canada 
Adrucil Inj 50mg/ml Liquid 500 mg / 10 mL Intravenous Adria Laboratories Of Canada Ltd. 1978-12-31 1996-09-10 Canada Carac Cream 5 mg/1g Topical Bausch Health, Canada Inc. 2013-06-28 Not applicable US 
Carac Cream 5 mg/1g Topical Dermik Laboratories 2000-10-27 2015-11-30 US Efudex Cream 5 % w/w Topical Bausch Health, Canada Inc. 1975-12-31 Not applicable Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Adrucil Injection, solution 5 g/100mL Intravenous Teva Parenteral Medicines, Inc. 2003-10-01 2020-10-31 US Adrucil Injection, solution 2.5 g/50mL Intravenous Teva Parenteral Medicines, Inc. 2003-10-01 2020-10-31 US Adrucil Injection, solution 50 mg/1mL Intravenous Teva Parenteral Medicines, Inc. 2003-10-01 2020-10-31 US Fluorouracil Solution 20 mg/1mL Topical Taro Pharmaceuticals U.S.A., Inc. 2003-11-05 Not applicable US Fluorouracil Injection, solution 50 mg/1mL Intravenous Sandoz S.P.A. 2008-09-10 2014-10-07 US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Actikerall Fluorouracil (0.5 % w/w) + Salicylic acid (10 % w/w) Solution Topical Cipher Pharmaceuticals Inc. 2016-02-19 Not applicable Canada ACTIKERALL Fluorouracil (5 MG/G) + Salicylic acid (100 MG/G) Solution Topical Almirall Hermal Gmbh 2017-09-27 Not applicable Italy 
Actikerall 5 mg/g + 100 mg/g Lösung zur Anwendung auf der Haut Fluorouracil (5 mg/g) + Salicylic acid (100 mg/g) Solution Cutaneous Almirall Hermal Gmbh 2011-09-16 Not applicable Austria 
Verrumal - Lösung zur äußerlichen Anwendung Fluorouracil (5 mg) + Salicylic acid (100 mg) Solution Topical Almirall Hermal Gmbh 1999-11-15 Not applicable Austria VERRUMAL SOLUTION Fluorouracil (0.5 g/100g) + Dimethyl sulfoxide (8 g/100g) + Salicylic acid (10 g/100g) Solution Topical ZUELLIG PHARMA SDN. BHD. 2020-09-08 Not applicable Malaysia 
- Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Fluorac Fluorouracil (5 g/100g) + Diclofenac sodium (1 g/100g) Cream Topical Burke Therapeutics, LLC 2015-01-22 2015-09-14 US Verrunex Fluorouracil (0.5 g/0.5g) + Salicylic acid (1.2 g/1.2g) Kit Topical Accumix Pharmaceuticals 2014-12-15 2015-07-17 US
Categories
- ATC Codes
- L01BC52 — Fluorouracil, combinations
- L01BC — Pyrimidine analogues
- L01B — ANTIMETABOLITES
- L01 — ANTINEOPLASTIC AGENTS
- L — ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
- Drug Categories
- Antimetabolites
- Antineoplastic Agents
- Antineoplastic and Immunomodulating Agents
- BCRP/ABCG2 Substrates
- Cardiotoxic antineoplastic agents
- Cytochrome P-450 CYP1A2 Substrates
- Cytochrome P-450 CYP1A2 Substrates with a Narrow Therapeutic Index
- Cytochrome P-450 CYP2A6 Substrates
- Cytochrome P-450 CYP2A6 Substrates with a Narrow Therapeutic Index
- Cytochrome P-450 CYP2C8 Substrates
- Cytochrome P-450 CYP2C8 Substrates with a Narrow Therapeutic Index
- Cytochrome P-450 CYP2C9 Inhibitors
- Cytochrome P-450 CYP2C9 Inhibitors (strength unknown)
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Drugs causing inadvertant photosensitivity
- Fluoropyrimidines
- Fluorouracil and prodrugs
- Immunologic Factors
- Immunosuppressive Agents
- Misc. Skin and Mucous Membrane Agents
- Moderate Risk QTc-Prolonging Agents
- Myelosuppressive Agents
- Narrow Therapeutic Index Drugs
- Noxae
- Nucleic Acid Synthesis Inhibitors
- Nucleoside Metabolic Inhibitor
- Photosensitizing Agents
- Pyrimidine Analogues
- Pyrimidines
- Pyrimidinones
- QTc Prolonging Agents
- Thyroxine-binding globulin inducers
- Toxic Actions
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as halopyrimidines. These are aromatic compounds containing a halogen atom linked to a pyrimidine ring. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Diazines
- Sub Class
- Pyrimidines and pyrimidine derivatives
- Direct Parent
- Halopyrimidines
- Alternative Parents
- Hydroxypyrimidines / Aryl fluorides / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Organofluorides / Hydrocarbon derivatives
- Substituents
- Aromatic heteromonocyclic compound / Aryl fluoride / Aryl halide / Azacycle / Halopyrimidine / Heteroaromatic compound / Hydrocarbon derivative / Hydroxypyrimidine / Organic nitrogen compound / Organic oxygen compound
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- organofluorine compound, nucleobase analogue (CHEBI:46345) / a uracil analogue (CPD0-1327)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- U3P01618RT
- CAS number
- 51-21-8
- InChI Key
- GHASVSINZRGABV-UHFFFAOYSA-N
- InChI
- InChI=1S/C4H3FN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)
- IUPAC Name
- 5-fluoro-1,2,3,4-tetrahydropyrimidine-2,4-dione
- SMILES
- FC1=CNC(=O)NC1=O
References
- Synthesis Reference
Leroy B. Townsend, Robert A. Earl, Steven J. Manning, "Method of synthesizing 1-(tetrahydro-2-furanyl)-5-fluorouracil." U.S. Patent US3960864, issued October, 1969.
US3960864- General References
- Longley DB, Harkin DP, Johnston PG: 5-fluorouracil: mechanisms of action and clinical strategies. Nat Rev Cancer. 2003 May;3(5):330-8. [Article]
- Petty RD, Cassidy J: Novel fluoropyrimidines: improving the efficacy and tolerability of cytotoxic therapy. Curr Cancer Drug Targets. 2004 Mar;4(2):191-204. [Article]
- External Links
- Human Metabolome Database
- HMDB0014684
- KEGG Drug
- D00584
- KEGG Compound
- C07649
- PubChem Compound
- 3385
- PubChem Substance
- 46508557
- ChemSpider
- 3268
- BindingDB
- 50340677
- 4492
- ChEBI
- 46345
- ChEMBL
- CHEMBL185
- ZINC
- ZINC000038212689
- Therapeutic Targets Database
- DAP000829
- PharmGKB
- PA128406956
- PDBe Ligand
- URF
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Fluorouracil
- PDB Entries
- 1h7x / 1rxc / 1upf / 3kvr / 3kvv / 3nai / 3nbq / 4e1v / 4o0o / 4txn … show 13 more
- FDA label
- Download (378 KB)
- MSDS
- Download (74 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Active Not Recruiting Not Available Borderline Resectable Pancreatic Adenocarcinoma / Chemotherapy Effects / Pancreatic Adenocarcinoma Locally Advanced / Post-pancreatectomy 1 somestatus stop reason just information to hide Not Available Active Not Recruiting Treatment Esophageal Cancer 1 somestatus stop reason just information to hide Not Available Approved for Marketing Not Available Hepatocellular Carcinoma / Injury; Blood Vessel, Hepatic, Artery 1 somestatus stop reason just information to hide Not Available Approved for Marketing Not Available Pancreatic Cancer 1 somestatus stop reason just information to hide Not Available Completed Not Available Actinic Keratosis (AK) 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Sanofi aventis us llc
- Valeant pharmaceuticals international
- Allergan herbert skin care div allergan inc
- Spear pharmaceuticals inc
- Taro pharmaceutical industries ltd
- Pharmacia and upjohn co
- Teva parenteral medicines inc
- Abic ltd
- Abraxis pharmaceutical products
- App pharmaceuticals llc
- Bedford laboratories div ben venue laboratories inc
- Bioniche pharma usa llc
- Ebewe pharma ges mbh nfg kg
- Marchar laboratories inc ltd
- Smith and nephew solopak div smith and nephew
- Watson laboratories inc
- Elorac inc
- Taro pharmaceuticals usa inc
- Packagers
- Allergan Inc.
- Amcol Health and Beauty Solutions
- APP Pharmaceuticals
- APPD
- Baxter International Inc.
- Bigmar Bioren Pharmaceuticals Sa
- Contract Pharm
- Creative Cosmetics Inc.
- Dermik Labs
- Dispensing Solutions
- Ebewe Pharma
- Generamedix Inc.
- Hospira Inc.
- Intas Pharmaceuticals Ltd.
- Legacy Pharmaceuticals Packaging LLC
- Medisca Inc.
- Oceanside Pharmaceuticals Incorporated
- Pharmacia Inc.
- Physicians Total Care Inc.
- Sanofi-Aventis Inc.
- Sicor Pharmaceuticals
- Solco Healthcare US LLC
- Spear Dermatology Products Inc.
- Synerx Pharma LLC
- Taro Pharmaceuticals USA
- Teva Pharmaceutical Industries Ltd.
- Valeant Ltd.
- Dosage Forms
Form Route Strength Injection Parenteral 10000 mg Injection, solution Parenteral 5000 mg Injection Parenteral 500 mg Ointment Topical 5 g Injection, solution Intravenous 1000 mg/20ml Injection, solution Intravenous 500 mg/m10mL Injection, solution Intravenous 250 mg/5mL Injection, solution 1000 mg/20ml Injection, solution, concentrate Intravenous Injection, solution Parenteral 5000 mg/100ml Solution Parenteral 1000 mg Injection, solution 5000 mg/100ml Solution Cutaneous Liquid Intravenous 500 mg / 10 mL Cream Topical 5 mg/1g Injection Intravenous 25 mg Injection 50 MG/ML Injection Injection Intra-arterial; Intravenous 50 MG/ML Injection, solution Intra-arterial; Intravenous 500 mg/10ml Cream Topical 2 g/40g Cream Topical 5 % w/w Solution Topical 0.5 g/10mL Solution Topical 1.25 g/10mL Ointment Topical Cream Topical 5 % Cream Topical 0.5000 g Solution Intravenous 500.000 mg Solution Intravenous 250 mg/5ml Solution Intravenous 500 mg/10ml Injection, solution Intravenous 50 MG/ML Cream Topical 5 g Cream Topical Capsule Injection, solution Intravenous Cream Topical 10 mg/1g Cream Topical 1 % Cream Topical 50 mg/1g Injection 50 mg Injection 50 mg/10ml Injection Intravenous 2.5 g/50mL Injection, solution Intravenous 2.5 g/50mL Injection, solution Intravenous 5 g/100mL Injection, solution Intravenous 50 mg/1mL Solution Topical 20 mg/1mL Solution Topical 50 mg/1mL Injection Parenteral 5000 MG/100ML Injection Parenteral 1000 MG/20ML Injection Parenteral 500 MG/10ML Injection, solution Parenteral Liquid Intravenous 50 mg / mL Injection, solution 50 mg/1ml Solution Intravenous 0.5 g / 10 mL Solution Intravenous 1000 mg / 20 mL Solution Intravenous 250 mg / 5 mL Solution Intravenous 5 g / 100 mL Solution Intravenous 50 mg / mL Solution Intravenous 500 mg / 10 mL Solution Intravenous 5000 mg / 100 mL Injection Intravenous 50 mg/ml Injection, solution Intra-arterial; Intravenous 50 mg/ml Injection Intravenous 25 mg/ml Solution Intravenous 50 mg/1ml Injection, solution Parenteral 50 MG/ML Injection, solution Parenteral 1000 MG Solution Intravenous 1000 mg/20ml Injection, solution Intravenous; Parenteral Injection, solution Solution Intravenous Solution Injection, solution Intra-arterial Injection, solution Intravenous 500 mg/10ml Injection, solution Intravenous; Parenteral 250 MG/ML Injection, solution Intravenous; Parenteral 500 MG/10ML Injection, solution Parenteral 1 G/20ML Injection, solution Parenteral 250 MG/5ML Injection, solution Parenteral 5 G/100ML Injection, solution Parenteral 500 MG/10ML Solution Intravenous 250 mg Solution Intravenous 500 mg Solution Parenteral 50 mg Solution Parenteral 25 mg Solution Intravenous 5000000 mg Injection Intravenous 1000 mg/20mL Injection Intravenous Cream Topical 5.000 g Solution Intravenous 250.000 mg Solution Parenteral 500 mg Cream Topical 5.0000 g Solution Intrauterine 250.00 mg Tablet, film coated Oral 500 mg Solution Intravenous 50 mg Cream Topical 0.04 g/1g Cream Topical 4 % w/w Cream Topical 40 mg/1g Cream Topical Solution Intravenous 250.00 mg Solution Topical 8 g/100g Kit Topical Solution 50 mg/1ml Solution Topical - Prices
Unit description Cost Unit Efudex 5% Cream 40 gm Tube 478.39USD tube Fluoroplex 1% Cream 30 gm Tube 268.61USD tube Fluorouracil 5% Cream 40 gm Tube 249.98USD tube Carac 0.5% Cream 30 gm Tube 209.77USD tube Efudex 5% Solution 10ml Bottle 136.51USD bottle Fluorouracil 5% Solution 10ml Bottle 115.78USD bottle Fluorouracil 2% Solution 10ml Bottle 78.63USD bottle Efudex 5% cream 10.28USD g Fluorouracil 5% cream 9.62USD g Fluorouracil powder 8.45USD g Fluoroplex 1% cream 7.85USD g Carac cream 6.43USD g Efudex 50 mg/g Cream 0.9USD g Fluorouracil 50 mg/ml Solution 0.52USD ml Adrucil 50 mg/ml vial 0.4USD ml Fluorouracil 5000 mg/100 ml 0.28USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US6670335 No 2003-12-30 2021-06-02 US US7169401 No 2007-01-30 2023-07-18 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 282-283 Heidelberger, C. and Duschinsky, R.; US. Patent 2,802,005; August 6, 1957. Heidelberger, C. and Duschinsky, R.; U.S.Patent 2,885,396; May 5, 1959. water solubility 1.11E+004 mg/L (at 22 °C) BURR,A & BUNDGAARD,H (1985) logP -0.89 HANSCH,C ET AL. (1995) logS -1.07 ADME Research, USCD pKa 8.02 SANGSTER (1994) - Predicted Properties
Property Value Source Water Solubility 5.86 mg/mL ALOGPS logP -0.58 ALOGPS logP -0.66 Chemaxon logS -1.4 ALOGPS pKa (Strongest Acidic) 7.18 Chemaxon pKa (Strongest Basic) -8 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 58.2 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 26.17 m3·mol-1 Chemaxon Polarizability 9.46 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9605 Blood Brain Barrier + 0.9791 Caco-2 permeable - 0.7583 P-glycoprotein substrate Non-substrate 0.7752 P-glycoprotein inhibitor I Non-inhibitor 0.8991 P-glycoprotein inhibitor II Non-inhibitor 1.0 Renal organic cation transporter Non-inhibitor 0.9053 CYP450 2C9 substrate Non-substrate 0.7898 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Non-substrate 0.7558 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9658 CYP450 2D6 inhibitor Non-inhibitor 0.9361 CYP450 2C19 inhibitor Non-inhibitor 0.9688 CYP450 3A4 inhibitor Non-inhibitor 0.9661 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9839 Ames test Non AMES toxic 0.8941 Carcinogenicity Non-carcinogens 0.9288 Biodegradation Not ready biodegradable 0.922 Rat acute toxicity 2.2529 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9685 hERG inhibition (predictor II) Non-inhibitor 0.9325
Spectra
- Mass Spec (NIST)
- Download (7.93 KB)
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 115.8284263 predictedDarkChem Lite v0.1.0 [M-H]- 115.8855263 predictedDarkChem Lite v0.1.0 [M-H]- 115.8201263 predictedDarkChem Lite v0.1.0 [M-H]- 118.47958 predictedDeepCCS 1.0 (2019) [M-H]- 115.8284263 predictedDarkChem Lite v0.1.0 [M-H]- 115.8855263 predictedDarkChem Lite v0.1.0 [M-H]- 115.8201263 predictedDarkChem Lite v0.1.0 [M-H]- 118.47958 predictedDeepCCS 1.0 (2019) [M+H]+ 116.9228263 predictedDarkChem Lite v0.1.0 [M+H]+ 116.8946263 predictedDarkChem Lite v0.1.0 [M+H]+ 116.9253263 predictedDarkChem Lite v0.1.0 [M+H]+ 121.56781 predictedDeepCCS 1.0 (2019) [M+H]+ 116.9228263 predictedDarkChem Lite v0.1.0 [M+H]+ 116.8946263 predictedDarkChem Lite v0.1.0 [M+H]+ 116.9253263 predictedDarkChem Lite v0.1.0 [M+H]+ 121.56781 predictedDeepCCS 1.0 (2019) [M+Na]+ 116.6899263 predictedDarkChem Lite v0.1.0 [M+Na]+ 116.5913263 predictedDarkChem Lite v0.1.0 [M+Na]+ 116.6398263 predictedDarkChem Lite v0.1.0 [M+Na]+ 130.12488 predictedDeepCCS 1.0 (2019) [M+Na]+ 116.6899263 predictedDarkChem Lite v0.1.0 [M+Na]+ 116.5913263 predictedDarkChem Lite v0.1.0 [M+Na]+ 116.6398263 predictedDarkChem Lite v0.1.0 [M+Na]+ 130.12488 predictedDeepCCS 1.0 (2019)
Targets
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Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Other/unknown
- General Function
- Telomerase is a ribonucleoprotein enzyme essential for the replication of chromosome termini in most eukaryotes. Active in progenitor and cancer cells. Inactive, or very low activity, in normal somatic cells. Catalytic component of the teleromerase holoenzyme complex whose main activity is the elongation of telomeres by acting as a reverse transcriptase that adds simple sequence repeats to chromosome ends by copying a template sequence within the RNA component of the enzyme. Catalyzes the RNA-dependent extension of 3'-chromosomal termini with the 6-nucleotide telomeric repeat unit, 5'-TTAGGG-3'. The catalytic cycle involves primer binding, primer extension and release of product once the template boundary has been reached or nascent product translocation followed by further extension. More active on substrates containing 2 or 3 telomeric repeats. Telomerase activity is regulated by a number of factors including telomerase complex-associated proteins, chaperones and polypeptide modifiers. Modulates Wnt signaling. Plays important roles in aging and antiapoptosis
- Specific Function
- DNA binding
- Gene Name
- TERT
- Uniprot ID
- O14746
- Uniprot Name
- Telomerase reverse transcriptase
- Molecular Weight
- 126995.435 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Involved in pyrimidine base degradation (PubMed:1512248). Catalyzes the reduction of uracil and thymine (PubMed:1512248). Also involved the degradation of the chemotherapeutic drug 5-fluorouracil (PubMed:1512248)
- Specific Function
- 4 iron, 4 sulfur cluster binding
- Gene Name
- DPYD
- Uniprot ID
- Q12882
- Uniprot Name
- Dihydropyrimidine dehydrogenase [NADP(+)]
- Molecular Weight
- 111400.32 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Yeast
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Not Available
- Specific Function
- FMN binding
- Gene Name
- TMP1
- Uniprot ID
- P12461
- Uniprot Name
- Thymidylate synthase
- Molecular Weight
- 35996.01 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Yes
Incorporation into and destabilization
References
- Wyatt MD, Wilson DM 3rd: Participation of DNA repair in the response to 5-fluorouracil. Cell Mol Life Sci. 2009 Mar;66(5):788-99. doi: 10.1007/s00018-008-8557-5. [Article]
- Ghoshal K, Jacob ST: An alternative molecular mechanism of action of 5-fluorouracil, a potent anticancer drug. Biochem Pharmacol. 1997 Jun 1;53(11):1569-75. [Article]
- Longley DB, Harkin DP, Johnston PG: 5-fluorouracil: mechanisms of action and clinical strategies. Nat Rev Cancer. 2003 May;3(5):330-8. [Article]
- Petty RD, Cassidy J: Novel fluoropyrimidines: improving the efficacy and tolerability of cytotoxic therapy. Curr Cancer Drug Targets. 2004 Mar;4(2):191-204. [Article]
- Singh V, Brecik M, Mukherjee R, Evans JC, Svetlikova Z, Blasko J, Surade S, Blackburn J, Warner DF, Mikusova K, Mizrahi V: The complex mechanism of antimycobacterial action of 5-fluorouracil. Chem Biol. 2015 Jan 22;22(1):63-75. doi: 10.1016/j.chembiol.2014.11.006. Epub 2014 Dec 24. [Article]
Yes
Incorporation into and destabilization
References
- Wyatt MD, Wilson DM 3rd: Participation of DNA repair in the response to 5-fluorouracil. Cell Mol Life Sci. 2009 Mar;66(5):788-99. doi: 10.1007/s00018-008-8557-5. [Article]
- Ghoshal K, Jacob ST: An alternative molecular mechanism of action of 5-fluorouracil, a potent anticancer drug. Biochem Pharmacol. 1997 Jun 1;53(11):1569-75. [Article]
- Longley DB, Harkin DP, Johnston PG: 5-fluorouracil: mechanisms of action and clinical strategies. Nat Rev Cancer. 2003 May;3(5):330-8. [Article]
- Petty RD, Cassidy J: Novel fluoropyrimidines: improving the efficacy and tolerability of cytotoxic therapy. Curr Cancer Drug Targets. 2004 Mar;4(2):191-204. [Article]
- Singh V, Brecik M, Mukherjee R, Evans JC, Svetlikova Z, Blasko J, Surade S, Blackburn J, Warner DF, Mikusova K, Mizrahi V: The complex mechanism of antimycobacterial action of 5-fluorouracil. Chem Biol. 2015 Jan 22;22(1):63-75. doi: 10.1016/j.chembiol.2014.11.006. Epub 2014 Dec 24. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Other/unknown
- General Function
- Catalyzes the reductive methylation of 2'-deoxyuridine 5'-monophosphate (dUMP) to thymidine 5'-monophosphate (dTMP), using the cosubstrate, 5,10- methylenetetrahydrofolate (CH2H4folate) as a 1-carbon donor and reductant and contributes to the de novo mitochondrial thymidylate biosynthesis pathway
- Specific Function
- folic acid binding
- Gene Name
- TYMS
- Uniprot ID
- P04818
- Uniprot Name
- Thymidylate synthase
- Molecular Weight
- 35715.65 Da
References
- Formentini A, Sander S, Denzer S, Straeter J, Henne-Bruns D, Kornmann M: Thymidylate synthase expression in resectable and unresectable pancreatic cancer: role as predictive or prognostic marker? Int J Colorectal Dis. 2007 Jan;22(1):49-55. Epub 2006 Mar 15. [Article]
- Huang CL, Yokomise H, Fukushima M, Kinoshita M: Tailor-made chemotherapy for non-small cell lung cancer patients. Future Oncol. 2006 Apr;2(2):289-99. [Article]
- Fernandez-Contreras ME, Sanchez-Prudencio S, Sanchez-Hernandez JJ, Garcia de Paredes ML, Gisbert JP, Roda-Navarro P, Gamallo C: Thymidylate synthase expression pattern, expression level and single nucleotide polymorphism are predictors for disease-free survival in patients of colorectal cancer treated with 5-fluorouracil. Int J Oncol. 2006 May;28(5):1303-10. [Article]
- Garcia V, Garcia JM, Pena C, Silva J, Dominguez G, Hurtado A, Alonso I, Rodriguez R, Provencio M, Bonilla F: Thymidylate synthase messenger RNA expression in plasma from patients with colon cancer: prognostic potential. Clin Cancer Res. 2006 Apr 1;12(7 Pt 1):2095-100. [Article]
- Ploylearmsaeng SA, Fuhr U, Jetter A: How may anticancer chemotherapy with fluorouracil be individualised? Clin Pharmacokinet. 2006;45(6):567-92. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Rustum YM: Thymidylate synthase: a critical target in cancer therapy? Front Biosci. 2004 Sep 1;9:2467-73. [Article]
- Singh V, Brecik M, Mukherjee R, Evans JC, Svetlikova Z, Blasko J, Surade S, Blackburn J, Warner DF, Mikusova K, Mizrahi V: The complex mechanism of antimycobacterial action of 5-fluorouracil. Chem Biol. 2015 Jan 22;22(1):63-75. doi: 10.1016/j.chembiol.2014.11.006. Epub 2014 Dec 24. [Article]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Involved in pyrimidine base degradation (PubMed:1512248). Catalyzes the reduction of uracil and thymine (PubMed:1512248). Also involved the degradation of the chemotherapeutic drug 5-fluorouracil (PubMed:1512248)
- Specific Function
- 4 iron, 4 sulfur cluster binding
- Gene Name
- DPYD
- Uniprot ID
- Q12882
- Uniprot Name
- Dihydropyrimidine dehydrogenase [NADP(+)]
- Molecular Weight
- 111400.32 Da
References
- Ho DH, Townsend L, Luna MA, Bodey GP: Distribution and inhibition of dihydrouracil dehydrogenase activities in human tissues using 5-fluorouracil as a substrate. Anticancer Res. 1986 Jul-Aug;6(4):781-4. [Article]
- Keizer HJ, De Bruijn EA, Tjaden UR, De Clercq E: Inhibition of fluorouracil catabolism in cancer patients by the antiviral agent (E)-5-(2-bromovinyl)-2'-deoxyuridine. J Cancer Res Clin Oncol. 1994;120(9):545-9. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Catalyzes the reversible phosphorylytic cleavage of uridine to uracil and ribose-1-phosphate which can then be utilized as carbon and energy sources or in the rescue of pyrimidine bases for nucleotide synthesis (PubMed:7488099). Shows broad substrate specificity and can also accept deoxyuridine and other analogous compounds (Probable)
- Specific Function
- deoxyuridine phosphorylase activity
- Gene Name
- UPP1
- Uniprot ID
- Q16831
- Uniprot Name
- Uridine phosphorylase 1
- Molecular Weight
- 33934.005 Da
References
- Yan R, Wan L, Pizzorno G, Cao D: Uridine phosphorylase in breast cancer: a new prognostic factor? Front Biosci. 2006 Sep 1;11:2759-66. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Catalyzes the reversible phosphorylytic cleavage of uridine to uracil and ribose-1-phosphate which can then be utilized as carbon and energy sources or in the rescue of pyrimidine bases for nucleotide synthesis (PubMed:12849978, PubMed:21855639). Shows broad substrate specificity and can also accept deoxyuridine and other analogous compounds (PubMed:12849978)
- Specific Function
- deoxyuridine phosphorylase activity
- Gene Name
- UPP2
- Uniprot ID
- O95045
- Uniprot Name
- Uridine phosphorylase 2
- Molecular Weight
- 35526.93 Da
References
- Yan R, Wan L, Pizzorno G, Cao D: Uridine phosphorylase in breast cancer: a new prognostic factor? Front Biosci. 2006 Sep 1;11:2759-66. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity
- Specific Function
- arachidonic acid epoxygenase activity
- Gene Name
- CYP2A6
- Uniprot ID
- P11509
- Uniprot Name
- Cytochrome P450 2A6
- Molecular Weight
- 56517.005 Da
References
- Yamamiya I, Yoshisue K, Ishii Y, Yamada H, Yoshida K: Enantioselectivity in the cytochrome P450-dependent conversion of tegafur to 5-fluorouracil in human liver microsomes. Pharmacol Res Perspect. 2013 Oct;1(1):e00009. doi: 10.1002/prp2.9. Epub 2013 Oct 23. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:11093772, PubMed:14559847, PubMed:15766564, PubMed:19965576, PubMed:7574697). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:11093772, PubMed:14559847, PubMed:15766564, PubMed:19965576, PubMed:7574697). Primarily catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) with a preference for the last double bond (PubMed:15766564, PubMed:19965576, PubMed:7574697). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes all trans-retinoic acid toward its 4-hydroxylated form (PubMed:11093772). Displays 16-alpha hydroxylase activity toward estrogen steroid hormones, 17beta-estradiol (E2) and estrone (E1) (PubMed:14559847). Plays a role in the oxidative metabolism of xenobiotics. It is the principal enzyme responsible for the metabolism of the anti-cancer drug paclitaxel (taxol) (PubMed:26427316)
- Specific Function
- arachidonic acid epoxygenase activity
- Gene Name
- CYP2C8
- Uniprot ID
- P10632
- Uniprot Name
- Cytochrome P450 2C8
- Molecular Weight
- 55824.275 Da
References
- Komatsu T, Yamazaki H, Shimada N, Nakajima M, Yokoi T: Roles of cytochromes P450 1A2, 2A6, and 2C8 in 5-fluorouracil formation from tegafur, an anticancer prodrug, in human liver microsomes. Drug Metab Dispos. 2000 Dec;28(12):1457-63. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Catalyzes the conversion of 5,10-methylenetetrahydrofolate to 5-methyltetrahydrofolate, a cosubstrate for homocysteine remethylation to methionine (PubMed:29891918). Represents a key regulatory connection between the folate and methionine cycles (Probable)
- Specific Function
- FAD binding
- Gene Name
- MTHFR
- Uniprot ID
- P42898
- Uniprot Name
- Methylenetetrahydrofolate reductase (NADPH)
- Molecular Weight
- 74595.895 Da
References
- Scartozzi M, Maccaroni E, Giampieri R, Pistelli M, Bittoni A, Del Prete M, Berardi R, Cascinu S: 5-Fluorouracil pharmacogenomics: still rocking after all these years? Pharmacogenomics. 2011 Feb;12(2):251-65. doi: 10.2217/pgs.10.167. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Catalyzes the reductive methylation of 2'-deoxyuridine 5'-monophosphate (dUMP) to thymidine 5'-monophosphate (dTMP), using the cosubstrate, 5,10- methylenetetrahydrofolate (CH2H4folate) as a 1-carbon donor and reductant and contributes to the de novo mitochondrial thymidylate biosynthesis pathway
- Specific Function
- folic acid binding
- Gene Name
- TYMS
- Uniprot ID
- P04818
- Uniprot Name
- Thymidylate synthase
- Molecular Weight
- 35715.65 Da
References
- Scartozzi M, Maccaroni E, Giampieri R, Pistelli M, Bittoni A, Del Prete M, Berardi R, Cascinu S: 5-Fluorouracil pharmacogenomics: still rocking after all these years? Pharmacogenomics. 2011 Feb;12(2):251-65. doi: 10.2217/pgs.10.167. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Bifunctional enzyme catalyzing the last two steps of de novo pyrimidine biosynthesis, orotate phosphoribosyltransferase (OPRT), which converts orotate to orotidine-5'-monophosphate (OMP), and orotidine-5'-monophosphate decarboxylase (ODC), the terminal enzymatic reaction that decarboxylates OMP to uridine monophosphate (UMP)
- Specific Function
- identical protein binding
- Gene Name
- UMPS
- Uniprot ID
- P11172
- Uniprot Name
- Uridine 5'-monophosphate synthase
- Molecular Weight
- 52221.075 Da
References
- Link [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Catalyzes the formation of phosphoribosylamine from phosphoribosylpyrophosphate (PRPP) and glutamine
- Specific Function
- 4 iron, 4 sulfur cluster binding
- Gene Name
- PPAT
- Uniprot ID
- Q06203
- Uniprot Name
- Amidophosphoribosyltransferase
- Molecular Weight
- 57398.52 Da
References
- Link [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- Curator comments
- Data is limited to a in vitro study.
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:19965576, PubMed:9435160). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:19965576, PubMed:9435160). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:11555828, PubMed:12865317). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2 (PubMed:11555828, PubMed:12865317). Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). May act as a major enzyme for all-trans retinoic acid biosynthesis in the liver. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (PubMed:10681376). Primarily catalyzes stereoselective epoxidation of the last double bond of polyunsaturated fatty acids (PUFA), displaying a strong preference for the (R,S) stereoisomer (PubMed:19965576). Catalyzes bisallylic hydroxylation and omega-1 hydroxylation of PUFA (PubMed:9435160). May also participate in eicosanoids metabolism by converting hydroperoxide species into oxo metabolites (lipoxygenase-like reaction, NADPH-independent) (PubMed:21068195). Plays a role in the oxidative metabolism of xenobiotics. Catalyzes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin (PubMed:14725854). Metabolizes caffeine via N3-demethylation (Probable)
- Specific Function
- aromatase activity
- Gene Name
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58406.915 Da
References
- Komatsu T, Yamazaki H, Shimada N, Nakajima M, Yokoi T: Roles of cytochromes P450 1A2, 2A6, and 2C8 in 5-fluorouracil formation from tegafur, an anticancer prodrug, in human liver microsomes. Drug Metab Dispos. 2000 Dec;28(12):1457-63. [Article]
- Yamazaki H, Komatsu T, Takemoto K, Shimada N, Nakajima M, Yokoi T: Rat cytochrome p450 1A and 3A enzymes involved in bioactivation of tegafur to 5-fluorouracil and autoinduced by tegafur in liver microsomes. Drug Metab Dispos. 2001 Jun;29(6):794-7. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- May have a role in maintaining the integrity of the blood vessels. Has growth promoting activity on endothelial cells, angiogenic activity in vivo and chemotactic activity on endothelial cells in vitro
- Specific Function
- 1,4-alpha-oligoglucan phosphorylase activity
- Gene Name
- TYMP
- Uniprot ID
- P19971
- Uniprot Name
- Thymidine phosphorylase
- Molecular Weight
- 49954.965 Da
References
- Scartozzi M, Maccaroni E, Giampieri R, Pistelli M, Bittoni A, Del Prete M, Berardi R, Cascinu S: 5-Fluorouracil pharmacogenomics: still rocking after all these years? Pharmacogenomics. 2011 Feb;12(2):251-65. doi: 10.2217/pgs.10.167. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids and steroids (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:15766564, PubMed:19965576, PubMed:7574697, PubMed:9866708). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Exhibits low catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes bisallylic hydroxylation and hydroxylation with double-bond migration of polyunsaturated fatty acids (PUFA) (PubMed:9435160, PubMed:9866708). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan (PubMed:25994031)
- Specific Function
- (R)-limonene 6-monooxygenase activity
- Gene Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- Gunes A, Coskun U, Boruban C, Gunel N, Babaoglu MO, Sencan O, Bozkurt A, Rane A, Hassan M, Zengil H, Yasar U: Inhibitory effect of 5-fluorouracil on cytochrome P450 2C9 activity in cancer patients. Basic Clin Pharmacol Toxicol. 2006 Feb;98(2):197-200. doi: 10.1111/j.1742-7843.2006.pto_304.x. [Article]
- Brown MC: An adverse interaction between warfarin and 5-fluorouracil: A case report and review of the literature. Chemotherapy. 1999 Sep-Oct;45(5):392-5. doi: 10.1159/000007230. [Article]
- Gilbar PJ, Brodribb TR: Phenytoin and fluorouracil interaction. Ann Pharmacother. 2001 Nov;35(11):1367-70. doi: 10.1345/aph.1A051. [Article]
- Karadag O, Babaoglu MO, Altundag K, Elkiran T, Yasar U, Bozkurt A: 5-Fluorouracil-induced coronary spasm: may inhibition of hyperpolarization factors produced by CYP2C enzymes be the cause? Oncology. 2004;66(6):510-1. doi: 10.1159/000079506. [Article]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- General Function
- Binds water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs (Probable). Its main function is the regulation of the colloidal osmotic pressure of blood (Probable). Major zinc transporter in plasma, typically binds about 80% of all plasma zinc (PubMed:19021548). Major calcium and magnesium transporter in plasma, binds approximately 45% of circulating calcium and magnesium in plasma (By similarity). Potentially has more than two calcium-binding sites and might additionally bind calcium in a non-specific manner (By similarity). The shared binding site between zinc and calcium at residue Asp-273 suggests a crosstalk between zinc and calcium transport in the blood (By similarity). The rank order of affinity is zinc > calcium > magnesium (By similarity). Binds to the bacterial siderophore enterobactin and inhibits enterobactin-mediated iron uptake of E.coli from ferric transferrin, and may thereby limit the utilization of iron and growth of enteric bacteria such as E.coli (PubMed:6234017). Does not prevent iron uptake by the bacterial siderophore aerobactin (PubMed:6234017)
- Specific Function
- antioxidant activity
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Albumin
- Molecular Weight
- 69365.94 Da
References
- Sulkowska A, Bojko B, Rownicka J, Sulkowski W: Competition of drugs to serum albumin in combination therapy. Biopolymers. 2004 Jun 15;74(3):256-62. [Article]
- Bertucci C, Ascoli G, Uccello-Barretta G, Di Bari L, Salvadori P: The binding of 5-fluorouracil to native and modified human serum albumin: UV, CD, and 1H and 19F NMR investigation. J Pharm Biomed Anal. 1995 Aug;13(9):1087-93. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inducer
- General Function
- Major thyroid hormone transport protein in serum
- Specific Function
- serine-type endopeptidase inhibitor activity
- Gene Name
- SERPINA7
- Uniprot ID
- P05543
- Uniprot Name
- Thyroxine-binding globulin
- Molecular Weight
- 46324.12 Da
References
- CYTOMEL (liothyronine) FDA label [File]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Functions as a Na(+)-independent bidirectional multispecific transporter (PubMed:11327718, PubMed:18216183, PubMed:21446918, PubMed:28945155). Contributes to the renal and hepatic elimination of endogenous organic compounds from the systemic circulation into the urine and bile, respectively (PubMed:11327718, PubMed:25904762). Capable of transporting a wide range of purine and pyrimidine nucleobases, nucleosides and nucleotides, with cGMP, 2'deoxyguanosine and GMP being the preferred substrates (PubMed:11327718, PubMed:18216183, PubMed:26377792, PubMed:28945155). Functions as a pH- and chloride-independent cGMP bidirectional facilitative transporter that can regulate both intracellular and extracellular levels of cGMP and may be involved in cGMP signaling pathways (PubMed:18216183, PubMed:26377792). Mediates orotate/glutamate bidirectional exchange and most likely display a physiological role in hepatic release of glutamate into the blood (PubMed:21446918). Involved in renal secretion and possible reabsorption of creatinine (PubMed:25904762, PubMed:28945155). Able to uptake prostaglandin E2 (PGE2) and may contribute to PGE2 renal excretion (Probable). Also transports alpha-ketoglutarate and urate (PubMed:11327718, PubMed:26377792). Apart from the orotate/glutamate exchange, the counterions for the uptake of other SLC22A7/OAT2 substrates remain to be identified (PubMed:26377792)
- Specific Function
- alpha-ketoglutarate transmembrane transporter activity
- Gene Name
- SLC22A7
- Uniprot ID
- Q9Y694
- Uniprot Name
- Solute carrier family 22 member 7
- Molecular Weight
- 60025.025 Da
References
- Kobayashi Y, Ohshiro N, Sakai R, Ohbayashi M, Kohyama N, Yamamoto T: Transport mechanism and substrate specificity of human organic anion transporter 2 (hOat2 [SLC22A7]). J Pharm Pharmacol. 2005 May;57(5):573-8. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Uniporter involved in the facilitative transport of nucleosides and nucleobases, and contributes to maintaining their cellular homeostasis (PubMed:10722669, PubMed:10755314, PubMed:12527552, PubMed:14759222, PubMed:15037197, PubMed:17379602, PubMed:21795683, PubMed:26406980, PubMed:27995448, PubMed:35790189, PubMed:8986748). Functions as a Na(+)-independent transporter (PubMed:8986748). Involved in the transport of nucleosides such as adenosine, guanosine, inosine, uridine, thymidine and cytidine (PubMed:10722669, PubMed:10755314, PubMed:12527552, PubMed:14759222, PubMed:15037197, PubMed:17379602, PubMed:26406980, PubMed:8986748). Also transports purine nucleobases (hypoxanthine, adenine, guanine) and pyrimidine nucleobases (thymine, uracil) (PubMed:21795683, PubMed:27995448). Mediates basolateral nucleoside uptake into Sertoli cells, thereby regulating the transport of nucleosides in testis across the blood-testis barrier (By similarity). Regulates inosine levels in brown adipocytes tissues (BAT) and extracellular inosine levels, which controls BAT-dependent energy expenditure (PubMed:35790189)
- Specific Function
- adenine transmembrane transporter activity
- Gene Name
- SLC29A1
- Uniprot ID
- Q99808
- Uniprot Name
- Equilibrative nucleoside transporter 1
- Molecular Weight
- 50218.805 Da
References
- Tsujie M, Nakamori S, Nakahira S, Takahashi Y, Hayashi N, Okami J, Nagano H, Dono K, Umeshita K, Sakon M, Monden M: Human equilibrative nucleoside transporter 1, as a predictor of 5-fluorouracil resistance in human pancreatic cancer. Anticancer Res. 2007 Jul-Aug;27(4B):2241-9. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Broad substrate specificity ATP-dependent transporter of the ATP-binding cassette (ABC) family that actively extrudes a wide variety of physiological compounds, dietary toxins and xenobiotics from cells (PubMed:11306452, PubMed:12958161, PubMed:19506252, PubMed:20705604, PubMed:28554189, PubMed:30405239, PubMed:31003562). Involved in porphyrin homeostasis, mediating the export of protoporphyrin IX (PPIX) from both mitochondria to cytosol and cytosol to extracellular space, it also functions in the cellular export of heme (PubMed:20705604, PubMed:23189181). Also mediates the efflux of sphingosine-1-P from cells (PubMed:20110355). Acts as a urate exporter functioning in both renal and extrarenal urate excretion (PubMed:19506252, PubMed:20368174, PubMed:22132962, PubMed:31003562, PubMed:36749388). In kidney, it also functions as a physiological exporter of the uremic toxin indoxyl sulfate (By similarity). Also involved in the excretion of steroids like estrone 3-sulfate/E1S, 3beta-sulfooxy-androst-5-en-17-one/DHEAS, and other sulfate conjugates (PubMed:12682043, PubMed:28554189, PubMed:30405239). Mediates the secretion of the riboflavin and biotin vitamins into milk (By similarity). Extrudes pheophorbide a, a phototoxic porphyrin catabolite of chlorophyll, reducing its bioavailability (By similarity). Plays an important role in the exclusion of xenobiotics from the brain (Probable). It confers to cells a resistance to multiple drugs and other xenobiotics including mitoxantrone, pheophorbide, camptothecin, methotrexate, azidothymidine, and the anthracyclines daunorubicin and doxorubicin, through the control of their efflux (PubMed:11306452, PubMed:12477054, PubMed:15670731, PubMed:18056989, PubMed:31254042). In placenta, it limits the penetration of drugs from the maternal plasma into the fetus (By similarity). May play a role in early stem cell self-renewal by blocking differentiation (By similarity)
- Specific Function
- ABC-type xenobiotic transporter activity
- Gene Name
- ABCG2
- Uniprot ID
- Q9UNQ0
- Uniprot Name
- Broad substrate specificity ATP-binding cassette transporter ABCG2
- Molecular Weight
- 72313.47 Da
References
- Yuan J, Lv H, Peng B, Wang C, Yu Y, He Z: Role of BCRP as a biomarker for predicting resistance to 5-fluorouracil in breast cancer. Cancer Chemother Pharmacol. 2009 May;63(6):1103-10. doi: 10.1007/s00280-008-0838-z. Epub 2008 Sep 27. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- ATP-dependent transporter of the ATP-binding cassette (ABC) family that binds and hydrolyzes ATP to enable active transport of various substrates including many drugs, toxicants and endogenous compound across cell membranes (PubMed:10359813, PubMed:11581266, PubMed:15083066). Transports glucuronide conjugates such as bilirubin diglucuronide, estradiol-17-beta-o-glucuronide and GSH conjugates such as leukotriene C4 (LTC4) (PubMed:11581266, PubMed:15083066). Transports also various bile salts (taurocholate, glycocholate, taurochenodeoxycholate-3-sulfate, taurolithocholate- 3-sulfate) (By similarity). Does not contribute substantially to bile salt physiology but provides an alternative route for the export of bile acids and glucuronides from cholestatic hepatocytes (By similarity). May contribute to regulate the transport of organic compounds in testes across the blood-testis-barrier (Probable). Can confer resistance to various anticancer drugs, methotrexate, tenoposide and etoposide, by decreasing accumulation of these drugs in cells (PubMed:10359813, PubMed:11581266)
- Specific Function
- ABC-type bile acid transporter activity
- Gene Name
- ABCC3
- Uniprot ID
- O15438
- Uniprot Name
- ATP-binding cassette sub-family C member 3
- Molecular Weight
- 169341.14 Da
References
- Hagmann W, Jesnowski R, Faissner R, Guo C, Lohr JM: ATP-binding cassette C transporters in human pancreatic carcinoma cell lines. Upregulation in 5-fluorouracil-resistant cells. Pancreatology. 2009;9(1-2):136-44. doi: 10.1159/000178884. Epub 2008 Dec 13. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- ATP-dependent transporter of the ATP-binding cassette (ABC) family that actively extrudes physiological compounds and xenobiotics from cells. Transports a range of endogenous molecules that have a key role in cellular communication and signaling, including cyclic nucleotides such as cyclic AMP (cAMP) and cyclic GMP (cGMP), bile acids, steroid conjugates, urate, and prostaglandins (PubMed:11856762, PubMed:12523936, PubMed:12835412, PubMed:12883481, PubMed:15364914, PubMed:15454390, PubMed:16282361, PubMed:17959747, PubMed:18300232, PubMed:26721430). Mediates the ATP-dependent efflux of glutathione conjugates such as leukotriene C4 (LTC4) and leukotriene B4 (LTB4) too. The presence of GSH is necessary for the ATP-dependent transport of LTB4, whereas GSH is not required for the transport of LTC4 (PubMed:17959747). Mediates the cotransport of bile acids with reduced glutathione (GSH) (PubMed:12523936, PubMed:12883481, PubMed:16282361). Transports a wide range of drugs and their metabolites, including anticancer, antiviral and antibiotics molecules (PubMed:11856762, PubMed:12105214, PubMed:15454390, PubMed:17344354, PubMed:18300232). Confers resistance to anticancer agents such as methotrexate (PubMed:11106685)
- Specific Function
- 15-hydroxyprostaglandin dehydrogenase (NAD+) activity
- Gene Name
- ABCC4
- Uniprot ID
- O15439
- Uniprot Name
- ATP-binding cassette sub-family C member 4
- Molecular Weight
- 149525.33 Da
References
- Hagmann W, Jesnowski R, Faissner R, Guo C, Lohr JM: ATP-binding cassette C transporters in human pancreatic carcinoma cell lines. Upregulation in 5-fluorouracil-resistant cells. Pancreatology. 2009;9(1-2):136-44. doi: 10.1159/000178884. Epub 2008 Dec 13. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- ATP-dependent transporter of the ATP-binding cassette (ABC) family that actively extrudes physiological compounds, and xenobiotics from cells. Mediates ATP-dependent transport of endogenous metabolites such as cAMP and cGMP, folic acid and N-lactoyl-amino acids (in vitro) (PubMed:10893247, PubMed:12637526, PubMed:12695538, PubMed:15899835, PubMed:17229149, PubMed:25964343). Acts also as a general glutamate conjugate and analog transporter that can limit the brain levels of endogenous metabolites, drugs, and toxins (PubMed:26515061). Confers resistance to the antiviral agent PMEA (PubMed:12695538). Able to transport several anticancer drugs including methotrexate, and nucleotide analogs in vitro, however it does with low affinity, thus the exact role of ABCC5 in mediating resistance still needs to be elucidated (PubMed:10840050, PubMed:12435799, PubMed:12695538, PubMed:15899835). Acts as a heme transporter required for the translocation of cytosolic heme to the secretory pathway (PubMed:24836561). May play a role in energy metabolism by regulating the glucagon-like peptide 1 (GLP-1) secretion from enteroendocrine cells (By similarity)
- Specific Function
- ABC-type xenobiotic transporter activity
- Gene Name
- ABCC5
- Uniprot ID
- O15440
- Uniprot Name
- ATP-binding cassette sub-family C member 5
- Molecular Weight
- 160658.8 Da
References
- Hagmann W, Jesnowski R, Faissner R, Guo C, Lohr JM: ATP-binding cassette C transporters in human pancreatic carcinoma cell lines. Upregulation in 5-fluorouracil-resistant cells. Pancreatology. 2009;9(1-2):136-44. doi: 10.1159/000178884. Epub 2008 Dec 13. [Article]
Drug created at June 13, 2005 13:24 / Updated at October 21, 2024 12:35