Raltitrexed

  • CAT Number: A000990
  • CAS Number: 112887-68-0
  • Molecular Formula: C21H22N4O6S
  • Molecular Weight: 458.49
  • Purity: ≥95%
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Raltitrexed, also known as ZD 1694, is an antimetabolite drug used in treatment of colorectal cancer since 1998. It may also be used in the treatment of malignant mesothelioma. It is an inhibitor of thymidylate synthase, and is manufactured by AstraZeneca. Raltitrexed is a quinazoline folate analogue with antineoplastic activity. After transport into cells via the reduced folate carrier, raltitrexed undergoes intracellular polyglutamation and blocks the folate-binding site of thymidylate synthase, thereby inhibiting tetrahydrofolate activity and DNA replication and repair and resulting in cytotoxicity.


Catalog Number A000990
CAS Number 112887-68-0
Synonyms

Tomudex; 112887-68-0; ZD1694; ZD-1694; ICI-D1694

Molecular Formula C21H22N4O6S
Purity ≥95%
Target DNA Synthesis
Solubility Soluble in DMSO > 10 mM
Storage -20°C
InChI 1S/C21H22N4O6S/c1-11-22-14-4-3-12(9-13(14)19(28)23-11)10-25(2)17-7-6-16(32-17)20(29)24-15(21(30)31)5-8-18(26)27/h3-4,6-7,9,15H,5,8,10H2,1-2H3,(H,24,29)(H,26,27)(H,30,31)(H,22,23,28)/t15-/m0/s1
InChIKey IVTVGDXNLFLDRM-HNNXBMFYSA-N
SMILES CC1=NC(=O)C2=C(N1)C=CC(=C2)CN(C)C3=CC=C(S3)C(=O)NC(CCC(=O)O)C(=O)O
Reference

1: Cui W, Fan W, Zhang Q, Wen J, Huang Y, Yang J, Li J, Wang Y. Comparison of two
transarterial chemoembolization regimens in patients with unresectable
hepatocellular carcinoma: raltitrexed plus oxaliplatin versus 5-fluorouracil plus
oxaliplatin. Oncotarget. 2017 Mar 16;8(45):79165-79174. doi:
10.18632/oncotarget.16298. eCollection 2017 Oct 3. PubMed PMID: 29108296; PubMed
Central PMCID: PMC5668029.
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2: Kim S, Bisch A, Montange D, Paillard MJ, Nguyen T, Jary M, Jacquin M,
Winkfield B, Borg C, Royer B. A simple and fast LC-MS/MS method with a very high
sensitivity for the measurement of raltitrexed in human plasma. J Chromatogr B
Analyt Technol Biomed Life Sci. 2017 Aug 15;1060:240-246. doi:
10.1016/j.jchromb.2017.06.021. Epub 2017 Jun 13. PubMed PMID: 28628839.
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3: Qiu C, Li Y, Liang X, Qi Y, Chen Y, Meng X, Zheng H, Xu Y, Cai S, Cai G, Liu
J. A study of peritoneal metastatic xenograft model of colorectal cancer in the
treatment of hyperthermic intraperitoneal chemotherapy with Raltitrexed. Biomed
Pharmacother. 2017 Aug;92:149-156. doi: 10.1016/j.biopha.2017.04.053. Epub 2017
May 20. PubMed PMID: 28535418.
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4: Guo JH, Zhang HY, Gao S, Zhang PJ, Li XT, Chen H, Wang XD, Zhu X. Hepatic
artery infusion with raltitrexed or 5-fluorouracil for colorectal cancer liver
metastasis. World J Gastroenterol. 2017 Feb 28;23(8):1406-1411. doi:
10.3748/wjg.v23.i8.1406. PubMed PMID: 28293087; PubMed Central PMCID: PMC5330825.
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5: Choi YM, Yeo HK, Park YW, Lee JY. Structural Analysis of Thymidylate Synthase
from Kaposi/’s Sarcoma-Associated Herpesvirus with the Anticancer Drug
Raltitrexed. PLoS One. 2016 Dec 9;11(12):e0168019. doi:
10.1371/journal.pone.0168019. eCollection 2016. PubMed PMID: 27936107; PubMed
Central PMCID: PMC5148040.
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6: Zhao C, Fan L, Qi F, Ou S, Yu L, Yi X, Ni B, Zheng Z, Lu J, Zhang C, Chen C,
Lu X, Cheng L, Hu T, Ma Y. Raltitrexed plus oxaliplatin-based transarterial
chemoembolization in patients with unresectable hepatocellular carcinoma.
Anticancer Drugs. 2016 Aug;27(7):689-94. doi: 10.1097/CAD.0000000000000371.
PubMed PMID: 27145327.
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7: Zhao H, Zhang Y, Sun J, Zhan C, Zhao L. Raltitrexed Inhibits HepG2 Cell
Proliferation via G0/G1 Cell Cycle Arrest. Oncol Res. 2016;23(5):237-48. doi:
10.3727/096504016X14562725373671. PubMed PMID: 27098147.

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8: Carreres-Prieto M, López-Sisamón D, Layos-Romero L. [Interstitial lung disease
induced by raltitrexed-oxaliplatin based chemotherapy for colorectal cancer: a
case report]. Farm Hosp. 2015 Mar 1;39(2):118-9. doi: 10.7399/fh.2015.39.2.8109.
Spanish. PubMed PMID: 25817092.
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9: Zhao P, Ding Z, Tang L, Zhou X. Preliminary investigation of intraperitoneal
raltitrexed in patients with gastric cancer. World J Surg Oncol. 2014 Dec
30;12:403. doi: 10.1186/1477-7819-12-403. PubMed PMID: 25547003; PubMed Central
PMCID: PMC4396911.
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10: Li XY, Liu L, Xie XM, Zhou C. The role of raltitrexed/cisplatin with
concurrent radiation therapy in treating advanced cervical cancer. Eur Rev Med
Pharmacol Sci. 2014 Nov;18(22):3491-6. PubMed PMID: 25491626.

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