Tegafur

Identification

Summary

Tegafur is an antineoplastic agent used in combination with other anticancer medications to treat advanced gastric and colorectal cancers.

Brand Names
Teysuno
Generic Name
Tegafur
DrugBank Accession Number
DB09256
Background

Tegafur (INN, BAN, USAN) is a prodrug of Fluorouracil (5-FU), an antineoplastic agent used as the treatment of various cancers such as advanced gastric and colorectal cancers. It is a pyrimidine analogue used in combination therapies as an active chemotherapeutic agent in conjunction with Gimeracil and Oteracil, or along with Fluorouracil as Tegafur-uracil. Tegafur is usually given in combination with other drugs that enhance the bioavailability of the 5-FU by blocking the enzyme responsible for its degradation, or serves to limit the toxicity of 5-FU by ensuring high concentrations of 5-FU at a lower dose of tegafur 5. When converted and bioactivated to 5-FU, the drug mediates an anticancer activity by inhibiting thymidylate synthase (TS) during the pyrimidine pathway involved in DNA synthesis. 5-FU is listed on the World Health Organization's List of Essential Medicines.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 200.169
Monoisotopic: 200.059720321
Chemical Formula
C8H9FN2O3
Synonyms
  • 1-(2-Tetrahydrofuryl)-5-fluorouracil
  • Tegafur
External IDs
  • MJF-12264

Pharmacology

Indication

Indicated for the treatment of cancer usually in combination with other biochemically modulating drugs.

Indicated in adults for the treatment of advanced gastric cancer when given in combination with Cisplatin 5.

Indicated for the first-line treatment of metastatic colorectal cancer with Uracil and calcium folinate 6.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatAdvanced gastric cancerRegimen in combination with: Oteracil (DB03209), Cisplatin (DB00515), Gimeracil (DB09257)••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Tegafur is an antineoplastic agent that belongs in the class of pyrimidine analogues. It interferes with the 2'-deoxythymidylate (DTMP) synthesis in the pyrimidine pathway, resulting in inhibition of DNA synthesis 4. In a phase III trial investigating the clinical efficacy of S-1 (tegafur/gimeracil/oteracil) in patients with advanced or recurrent gastric cancer, treatment resulted in a high response rate and was associated with a longer overall survival and longer progression-free survival rate when used in combination with cisplatin 1. In a meta analysis, triple combination therapy consisting of tegafur, gimeracil and oteracil showed longer survival times and well tolerance in patients with advanced gastric cancer 2. Tegafur and its active metabolites are potent myleosuppressive agents 5.

Mechanism of action

The transformation of 2'-deoxyurindylate (dUMP) to 2'-deoxythymidylate (dTMP) is essential in driving the synthesis of DNA and purines in cells 4. Thymidylate synthase catalyzes the conversion of dUMP to dTMP, which is a precursor of thymidine triphosphate (TTP), one of the four deoxyribonucleotides required for DNA synthesis 3. After administration into the body, tegafur is converted into the active antineoplastic metabolite, fluorouracil (5-FU). In tumour cells, 5-FU undergoes phosphorylation to form the active anabolites, including 5-fluorodeoxyuridine monophosphate (FdUMP) 5. FdUMP and reduced folate are bound to thymidylate synthase leading to formation of a ternary complex which inhibits DNA synthesis 5. In addition, 5-fluorouridine-triphosphate (FUTP) is incorporated into RNA causing disruption of RNA functions 5.

TargetActionsOrganism
AThymidylate synthase
inhibitor
Humans
Absorption

Tegafur displays a dose-proportional pharmacokinetic properties. Tegafur is rapidly and well absorbed into the systemic circulation, reaching the peak plasma concentration within 1 to 2 hours of administration 6.

Volume of distribution

The volume of distribution based on apparent volume of distribution and urinary excretion data of tegafur is 16 L/m^2 5.

Protein binding

Tegafur is 52.3% bound to serum proteins and 5-FU is 18.4% protein bound 5,6.

Metabolism

Hepatic CYP2A6 is the predominant enzyme that mediates 5-hydroxylation of tegafur to generate 5'-hydroxytegafur. This metabolite is unstable and undergoes spontaneous degradation to form 5-FU, which is an active antineoplastic agent that exerts a pharmacological action on tumours. 5-FU is rapidly metabolised by the liver enzyme dihydropyrimidine dehydrogenase (DPD) 3.

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Route of elimination

Following oral administration, about less 20% of total tegafur is excreted unchanged in the urine 6.

Half-life

The elimination half life of tegafur is approximately 11 hours 6.

Clearance

No pharmacokinetic data available.

Adverse Effects
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Toxicity

Oral LD50 value in rat, mouse and dog are 930mg/kg, 775mg/kg, and 34mg/kg, respectively MSDS. Continuous exposure to tegafur may cause physical defects in the developing embryo (teratogenesis).

Acute toxicity from the combination use of tegafur was associated with nausea, vomiting, diarrhoea, mucositis, gastrointestinal irritation, bleeding, bone marrow depression, and respiratory failure 5. Overdose may lead to fatal complications 6. In case of overdose, appropriate therapeutic and supportive medical interventions should be implemented.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Dihydropyrimidine dehydrogenase [NADP(+)]DPYD*2A(A;A) / (A;G)G > AADR Directly StudiedThe presence of this genotype in DPYD is associated with an increased risk of drug-related toxicity from tegafur therapy.Details
Dihydropyrimidine dehydrogenase [NADP(+)]DPYD*13(C;C) / (A;C)A > CADR Directly StudiedThe presence of this genotype in DPYD is associated with an increased risk of drug-related toxicity from tegafur therapy.Details
Dihydropyrimidine dehydrogenase [NADP(+)]---(A;A) / (A;T)T > AADR Directly StudiedThe presence of this genotype in DPYD may be associated with an increased risk of drug-related toxicity from tegafur therapy.Details
Dihydropyrimidine dehydrogenase [NADP(+)]DPYD*4(G;G) / (A:G)G > AADR Directly StudiedThe presence of this genotype in DPYD may be associated with an increased risk of drug-related toxicity from tegafur therapy.Details
Dihydropyrimidine dehydrogenase [NADP(+)]DPYD*5(G;G) / (A;G)A > GADR Directly StudiedThe presence of this genotype in DPYD may be associated with an increased risk of drug-related toxicity from tegafur therapy.Details
Dihydropyrimidine dehydrogenase [NADP(+)]DPYD*6(A;A) / (A;G)G > AADR Directly StudiedThe presence of this genotype in DPYD may be associated with an increased risk of drug-related toxicity from tegafur therapy.Details
Dihydropyrimidine dehydrogenase [NADP(+)]DPYD*9A(C;C) / (C;T)T > CADR Directly StudiedThe presence of this genotype in DPYD may be associated with an increased risk of drug-related toxicity from tegafur 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.
DrugInteraction
AbacavirAbacavir may decrease the excretion rate of Tegafur which could result in a higher serum level.
AbametapirThe serum concentration of Tegafur can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Tegafur can be increased when combined with Abatacept.
AbirateroneThe metabolism of Tegafur can be decreased when combined with Abiraterone.
AcalabrutinibThe metabolism of Tegafur can be decreased when combined with Acalabrutinib.
Food Interactions
  • Drink plenty of fluids. Drinking water is important to prevent dehydration when taking Teysuno.
  • Take on an empty stomach. Food does not impact the bioavailability of tegafur. Food does affect other ingredients in the combination product Teysuno. Take Teysuno at least 1 hour before or after eating.

Products

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International/Other Brands
Ai Yi (Hengrui) / ESUEEW AN T (Sawai Seiyaku) / Fimer (LKM) / Ftorafur (Grindeks) / Furil (Lotus Pharmaceuticals) / Futraful (Taiho) / Icarus (Koa Isei) / Lunacin (Sawai Seiyaku) / NKS-1 T (Nippon Kayaku) / Qi Xing (Hualu Pharmaceutical) / S-1 (Taiho) / Sterozine (Kotobuki Seiyaku) / Tefudex (Korea United Pharma) / Tegacin (Patron) / Tegracil (Shin Poong) / Teroful (Kwang Dong) / TS-1 (Toho Yakuhin) / TS-ONE (Taiho) / UFT (Merck) / Ufur (TTY) / Unitoral (Korea United Pharm) / Utefos (Mylan)
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
TeysunoTegafur (20 mg) + Gimeracil (5.8 mg) + Oteracil (15.8 mg)CapsuleOralNordic Group Bv2016-09-08Not applicableEU flag
TEYSUNOTegafur (20 mg) + Gimeracil (5.8 mg) + Oteracil (15.8 mg)CapsuleOralNordic Group Bv2014-07-08Not applicableItaly flag
TEYSUNOTegafur (15 mg) + Gimeracil (4.35 mg) + Oteracil (11.8 mg)CapsuleOralNordic Group Bv2014-07-08Not applicableItaly flag
TeysunoTegafur (15 mg) + Gimeracil (4.35 mg) + Oteracil (11.8 mg)CapsuleOralNordic Group Bv2016-09-08Not applicableEU flag
TeysunoTegafur (15 mg) + Gimeracil (4.35 mg) + Oteracil (11.8 mg)CapsuleOralNordic Group Bv2016-09-08Not applicableEU flag

Categories

ATC Codes
L01BC03 — TegafurL01BC53 — Tegafur, combinations
Drug Categories
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
Pyrimidones / Aryl fluorides / Hydropyrimidines / Vinylogous amides / Heteroaromatic compounds / Tetrahydrofurans / Lactams / Ureas / Oxacyclic compounds / Azacyclic compounds
show 6 more
Substituents
Aromatic heteromonocyclic compound / Aryl fluoride / Aryl halide / Azacycle / Halopyrimidine / Heteroaromatic compound / Hydrocarbon derivative / Hydropyrimidine / Lactam / Organic nitrogen compound
show 12 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
pyrimidines, organohalogen compound (CHEBI:32188)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
1548R74NSZ
CAS number
17902-23-7
InChI Key
WFWLQNSHRPWKFK-UHFFFAOYSA-N
InChI
InChI=1S/C8H9FN2O3/c9-5-4-11(6-2-1-3-14-6)8(13)10-7(5)12/h4,6H,1-3H2,(H,10,12,13)
IUPAC Name
5-fluoro-1-(oxolan-2-yl)-1,2,3,4-tetrahydropyrimidine-2,4-dione
SMILES
FC1=CN(C2CCCO2)C(=O)NC1=O

References

General References
  1. Tsuburaya A, Morita S, Kodera Y, Kobayashi M, Shitara K, Yamaguchi K, Yoshikawa T, Yoshida K, Yoshino S, Sakamoto J: A randomized phase II trial to elucidate the efficacy of capecitabine plus cisplatin (XP) and S-1 plus cisplatin (SP) as a first-line treatment for advanced gastric cancer: XP ascertainment vs. SP randomized PII trial (XParTS II). BMC Cancer. 2012 Jul 23;12:307. doi: 10.1186/1471-2407-12-307. [Article]
  2. Yang J, Zhou Y, Min K, Yao Q, Xu CN: S-1-based vs non-S-1-based chemotherapy in advanced gastric cancer: a meta-analysis. World J Gastroenterol. 2014 Sep 7;20(33):11886-93. doi: 10.3748/wjg.v20.i33.11886. [Article]
  3. Kohne CH, Peters GJ: UFT: mechanism of drug action. Oncology (Williston Park). 2000 Oct;14(10 Suppl 9):13-8. [Article]
  4. 55. (2012). In Rang and Dale's Pharmacology (7th ed., pp. 680-681). Edinburgh: Elsevier/Churchill Livingstone. [ISBN:978-0-7020-3471-8]
  5. European Medicines Agency (EMA): TEYSUNO (tegafur/gimeracil/oteracil) Summary of Product Characteristics [Link]
  6. UFT (uracil/tegafur) capsules_Product information [Link]
KEGG Drug
D01244
KEGG Compound
C12673
PubChem Compound
5386
PubChem Substance
310265158
ChemSpider
5193
RxNav
4582
ChEBI
32188
ChEMBL
CHEMBL20883
Wikipedia
Tegafur
MSDS
Download (242 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Unknown StatusTreatmentBreast Neoplasms / Neoadjuvant Therapies1
4Unknown StatusTreatmentUnresectable Pancreatic Cancer1
3Active Not RecruitingTreatmentGastric Cancer1
3CompletedTreatmentBreast Cancer2
3CompletedTreatmentCervical Cancer1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Capsule
Tablet, soluble
CapsuleOral
TabletOral
CapsuleOral100 mg
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)339.8-343.4MSDS
water solubilityPartly miscibleMSDS
Predicted Properties
PropertyValueSource
Water Solubility14.0 mg/mLALOGPS
logP-0.09ALOGPS
logP0.024Chemaxon
logS-1.2ALOGPS
pKa (Strongest Acidic)8.08Chemaxon
pKa (Strongest Basic)-4.3Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area58.64 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity44.5 m3·mol-1Chemaxon
Polarizability17.52 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - EI-BGC-MSsplash10-00di-9010000000-09f17e43065fd7cafc97
GC-MS Spectrum - CI-BGC-MSsplash10-0089-6900000000-0edac06a6aa07cfd4b9f
GC-MS Spectrum - CI-BGC-MSsplash10-0udi-2190000000-6638249408dce3b6c1ee
GC-MS Spectrum - CI-BGC-MSsplash10-014i-0090000000-dc47df1bb362c454d07d
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ul0-9200000000-ffa0c4846508da8a8a9d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0900000000-55f467b76a66cff12149
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9100000000-ef2a741ce278df8d68b7
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fef-9100000000-3aba796621401dd9c6de
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9100000000-2763748e38b133471567
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-9400000000-5be6590f1051b6940837
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-133.74132
predicted
DeepCCS 1.0 (2019)
[M+H]+137.5726
predicted
DeepCCS 1.0 (2019)
[M+Na]+146.95747
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Thymidylate synthase activity
Specific Function
Contributes to the de novo mitochondrial thymidylate biosynthesis pathway.
Gene Name
TYMS
Uniprot ID
P04818
Uniprot Name
Thymidylate synthase
Molecular Weight
35715.65 Da

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Curator comments
Data supporting this enzyme action are limited to in vitro studies.
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. 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]
  2. 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
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. 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]
  2. Backman JT, Filppula AM, Niemi M, Neuvonen PJ: Role of Cytochrome P450 2C8 in Drug Metabolism and Interactions. Pharmacol Rev. 2016 Jan;68(1):168-241. doi: 10.1124/pr.115.011411. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific 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. Const...
Gene Name
CYP2A6
Uniprot ID
P11509
Uniprot Name
Cytochrome P450 2A6
Molecular Weight
56501.005 Da
References
  1. Ikeda K, Yoshisue K, Matsushima E, Nagayama S, Kobayashi K, Tyson CA, Chiba K, Kawaguchi Y: Bioactivation of tegafur to 5-fluorouracil is catalyzed by cytochrome P-450 2A6 in human liver microsomes in vitro. Clin Cancer Res. 2000 Nov;6(11):4409-15. [Article]
  2. 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]
  3. Daigo S, Takahashi Y, Fujieda M, Ariyoshi N, Yamazaki H, Koizumi W, Tanabe S, Saigenji K, Nagayama S, Ikeda K, Nishioka Y, Kamataki T: A novel mutant allele of the CYP2A6 gene (CYP2A6*11 ) found in a cancer patient who showed poor metabolic phenotype towards tegafur. Pharmacogenetics. 2002 Jun;12(4):299-306. [Article]
  4. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
  5. UFT (uracil/tegafur) capsules_Product information [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
Gene Name
CYP2E1
Uniprot ID
P05181
Uniprot Name
Cytochrome P450 2E1
Molecular Weight
56848.42 Da
References
  1. 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
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. 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]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inducer
General Function
Serine-type endopeptidase inhibitor activity
Specific Function
Major thyroid hormone transport protein in serum.
Gene Name
SERPINA7
Uniprot ID
P05543
Uniprot Name
Thyroxine-binding globulin
Molecular Weight
46324.12 Da
References
  1. CYTOMEL (liothyronine) FDA label [File]

Drug created at October 26, 2015 16:26 / Updated at October 09, 2021 02:48