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Tegafur (INN, BAN, USAN) is a chemotherapeutic fluorouracil prodrug used in the treatment of cancers. It is a component of the combination drug tegafur/uracil. When metabolised, it becomes 5-fluorouracil.^[1]

Medical uses

As a prodrug to 5-FU it is used in the treatment of the following cancers:^[2]

Stomach (when combined with gimeracil and oteracil)
Breast (with uracil)
Gallbladder
Lung (specifically adenocarcinoma, typically with uracil)
Colorectal (usually when combined with gimeracil and oteracil)
Head and neck
Liver (with uracil)^[3]

Pancreatic

It is often given in combination with drugs that alter its bioavailability and toxicity such as gimeracil, oteracil or uracil.^[2] These agents achieve this by inhibiting the enzyme dihydropyrimidine dehydrogenase (uracil/gimeracil) or orotate phosphoribosyltransferase (oteracil).^[2]

Adverse effects

The major side effects of tegafur are similar to fluorouracil and include myelosuppression, central neurotoxicity and gastrointestinal toxicity (especially diarrhoea).^[2] Gastrointestinal toxicity is the dose-limiting side effect of tegafur.^[2] Central neurotoxicity is more common with tegafur than with fluorouracil.^[2]

Mechanism of action

It is a prodrug to fluorouracil which is a thymidylate synthase inhibitor.^[2]

Pharmacokinetics

It is metabolised into fluorouracil by CYP2A6.^[4]^[5]

Interactive pathway map

Click on genes, proteins and metabolites below to link to respective articles. ^{[§ 1]}

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Fluorouracil (5-FU) Activity edit

^ The interactive pathway map can be edited at WikiPathways: "FluoropyrimidineActivity_WP1601".

References

^ El Sayed, YM; Sadée, W (1983). "Metabolic activation of R,S-1-(tetrahydro-2-furanyl)-5-fluorouracil (ftorafur) to 5-fluorouracil by soluble enzymes". Cancer Research 43 (9): 4039–44. PMID 6409396.
^ ^a ^b ^c ^d ^e ^f ^g Sweetman, S, ed. (14 November 2011). "Martindale: The Complete Drug Reference". Pharmaceutical Press. Retrieved 12 February 2014.
^ Ishikawa, T (14 May 2008). "Chemotherapy with enteric-coated tegafur/uracil for advanced hepatocellular carcinoma." (PDF). World Journal of Gastroenterology : WJG 14 (18): 2797–2801. doi:10.3748/wjg.14.2797. PMC 2710718. PMID 18473401.
^ Nakayama, T; Noguchi, S (January 2010). "Therapeutic usefulness of postoperative adjuvant chemotherapy with Tegafur-Uracil (UFT) in patients with breast cancer: focus on the results of clinical studies in Japan." (PDF). The Oncologist 15 (1): 26–36. doi:10.1634/theoncologist.2009-0255. PMC 3227888. PMID 20080863.
^ Matt, P; van Zwieten-Boot, B; Calvo Rojas, G; Ter Hofstede, H; Garcia-Carbonero, R; Camarero, J; Abadie, E; Pignatti, F (October 2011). "The European Medicines Agency review of Tegafur/Gimeracil/Oteracil (Teysuno™) for the treatment of advanced gastric cancer when given in combination with cisplatin: summary of the Scientific Assessment of the Committee for medicinal products for human use (CHMP)." (PDF). The Oncologist 16 (10): 1451–1457. doi:10.1634/theoncologist.2011-0224. PMC 3228070. PMID 21963999. Cite uses deprecated parameters (help)

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UpToDate Contents

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1. 転移性大腸癌に対する全身化学療法：終了した臨床試験 systemic chemotherapy for metastatic colorectal cancer completed clinical trials
2. 高齢患者における切除結腸癌に対する補助化学療法 adjuvant therapy for resected colon cancer in elderly patients
3. 切除可能非小細胞肺癌における全身補助化学療法 adjuvant systemic therapy in resectable non small cell lung cancer
4. 直腸癌に対する術前補助化学放射線療法および放射線療法 neoadjuvant chemoradiotherapy and radiotherapy for rectal cancer
5. 化学療法剤の腸管毒性 enterotoxicity of chemotherapeutic agents

English Journal

Prognostic significance of adverse events associated with preoperative radiotherapy for rectal cancer.

Ishihara S, Watanabe T, Akahane T, Shimada R, Horiuchi A, Shibuya H, Hayama T, Yamada H, Nozawa K, Igaki H, Matsuda K.SourceDepartment of Surgery, Teikyo University, 2-11-1, Kaga, Itabashi-ku, Tokyo, 173-8605, Japan, sochan31@hotmail.com.
International journal of colorectal disease.Int J Colorectal Dis.2011 Jul;26(7):911-7. Epub 2011 Feb 22.
PMID 21340716

An Open-Label, Multicenter, Three-Stage, Phase II Study of S-1 in Combination with Cisplatin as First-Line Therapy for Patients with Advanced Non-small Cell Lung Cancer.

Sandler A, Graham C, Baggstrom M, Herbst R, Zergebel C, Saito K, Jones D.Source*Oregon Health and Science University, Portland, Oregon; †Charleston Cancer Center, Charleston, South Carolina; ‡Washington University School of Medicine, St. Louis, Missouri; §M. D. Anderson Cancer Center, Houston, Texas; ∥Taiho Pharma USA, Princeton, New Jersey; and ¶University of New Mexico, Albuquerque, New Mexico.
Journal of thoracic oncology : official publication of the International Association for the Study of Lung Cancer.J Thorac Oncol.2011 Jun 13. [Epub ahead of print]
PMID 21673602

Japanese Journal

第59回日本泌尿器科学会中部総会シンポジウム「泌尿器科抗癌化学療法 : 最新レジメンの有効性と安全性｣―司会の言葉―

原勲,元雄良治
泌尿器科紀要 57(3), 151-152, 2011-03-31
… We dealt with uracil and tegafur (UFT) therapy which has been widely used in Japan. …
NAID 120003001362

ホルモン不応性前立腺癌に対するドセタキセル/UFT療法

島崎猛夫,宮澤克人,森山学,田中達朗,佐藤到,中谷直喜,中島日出夫,久保杏奈,鈴木孝治,元雄良治
泌尿器科紀要 57(3), 163-166, 2011-03-31
… This study was undertaken to assess the feasibility of docetaxel in combination with UFT (a combination of tegafur and uracil) in Japanese patients with HRPC. …
NAID 120003001359

Related Pictures

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リンク元

「テガフール」

Tegafur
Systematic (IUPAC) name
	(RS)-5-Fluoro-1-(tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione
Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy cat.	D (AU)
Legal status	Prescription Only (S4) (AU) POM (UK)
Routes	Oral
Pharmacokinetic data
Half-life	3.9-11 hours
Identifiers
CAS number	17902-23-7
ATC code	L01BC03
PubChem	CID 288216
ChemSpider	254191
UNII	1548R74NSZ
KEGG	D01244
ChEMBL	CHEMBL20883
Synonyms	5-fluoro-1-(oxolan-2-yl)pyrimidine-2,4-dione
Chemical data
Formula	C8H9FN2O3
Mol. mass	200.16 g/mol
	SMILES FC=1C(=O)NC(=O)N(C=1)[C@@H]2OCCC2;
	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)/t6-/m1/s1 ; Key:WFWLQNSHRPWKFK-ZCFIWIBFSA-N ;
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　　[★]

英: tegafur
ラ: tegafurum
商: サンフラール、フェンタール、イカルス、ステロジン、ティーエスワン、テフシール、フトラフール、ユーエフティ、ルナシン
関: ティーエスワン

[WikiPathways-6] The interactive pathway map can be edited at WikiPathways: "FluoropyrimidineActivity_WP1601".

[1] El Sayed, YM; Sadée, W (1983). "Metabolic activation of R,S-1-(tetrahydro-2-furanyl)-5-fluorouracil (ftorafur) to 5-fluorouracil by soluble enzymes". Cancer Research 43 (9): 4039–44. PMID 6409396.

[MD-2] ^ ^a ^b ^c ^d ^e ^f ^g Sweetman, S, ed. (14 November 2011). "Martindale: The Complete Drug Reference". Pharmaceutical Press. Retrieved 12 February 2014.

[3] Ishikawa, T (14 May 2008). "Chemotherapy with enteric-coated tegafur/uracil for advanced hepatocellular carcinoma." (PDF). World Journal of Gastroenterology : WJG 14 (18): 2797–2801. doi:10.3748/wjg.14.2797. PMC 2710718. PMID 18473401.

[4] Nakayama, T; Noguchi, S (January 2010). "Therapeutic usefulness of postoperative adjuvant chemotherapy with Tegafur-Uracil (UFT) in patients with breast cancer: focus on the results of clinical studies in Japan." (PDF). The Oncologist 15 (1): 26–36. doi:10.1634/theoncologist.2009-0255. PMC 3227888. PMID 20080863.

[5] Matt, P; van Zwieten-Boot, B; Calvo Rojas, G; Ter Hofstede, H; Garcia-Carbonero, R; Camarero, J; Abadie, E; Pignatti, F (October 2011). "The European Medicines Agency review of Tegafur/Gimeracil/Oteracil (Teysuno™) for the treatment of advanced gastric cancer when given in combination with cisplatin: summary of the Scientific Assessment of the Committee for medicinal products for human use (CHMP)." (PDF). The Oncologist 16 (10): 1451–1457. doi:10.1634/theoncologist.2011-0224. PMC 3228070. PMID 21963999. Cite uses deprecated parameters (help)

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