Deruxtecan
Deruxtecan, a topoisomerase I inhibitor, is an exatecan derivative (DX-8951 derivative) with a cleavable pepetide linker and a maleimide group. The maleimide group in Deruxtecan can react with antibody to form antibody-drug conguates (ADC) such as Trastuzumab deruxtecan (DS-8201a), which is a HER2-targeting antibody–drug conjugate. DS-8201a significantly suppressed tumor growth in an immunocompetent mouse model with human HER2-expressing CT26.WT (CT26.WThHER2) cells. DS-8201a was approved in 2019.
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Chemical Information
| Name | Deruxtecan |
|---|---|
| Iupac Chemical Name | Glycinamide, N-[6-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-1-oxohexyl]glycylglycyl-L-phenylalanyl-N-[[2-[[(1S,9S)-9-ethyl-5-fluoro-2,3,9,10,13,15-hexahydro-9-hydroxy-4-methyl-10,13-dioxo-1H,12Hbenzo[de]pyrano[3',4':6,7]indolizino[1,2-b]quinolin-1-yl]amino]-2-oxoethoxy]methyl]- |
| Synonyms | Deruxtecan, Trastuzumab deruxtecan; DS-8201a; DS8201a; DS 8201a; exatecan derivative; DX-8951 derivative; DX 8951; DX8951; |
| Molecular Formula | C52H56FN9O13 |
| Molecular Weight | 1034.05 |
| Smile | CC[C@@]1(O)C(OCC2=C1C=C3N(C2=O)CC(C3=NC4=CC(F)=C5C)=C6C4=C5CC[C@@H]6NC(COCNC(CNC([C@@H](NC(CNC(CNC(CCCCCN7C(C=CC7=O)=O)=O)=O)=O)CC8=CC=CC=C8)=O)=O)=O)=O |
| InChiKey | WXNSCLIZKHLNSG-MCZRLCSDSA-N |
| InChi | InChI=1S/C52H56FN9O13/c1-3-52(73)33-19-38-48-31(24-62(38)50(71)32(33)25-75-51(52)72)47-35(14-13-30-28(2)34(53)20-36(60-48)46(30)47)58-43(67)26-74-27-57-41(65)22-56-49(70)37(18-29-10-6-4-7-11-29)59-42(66)23-55-40(64)21-54-39(63)12-8-5-9-17-61-44(68)15-16-45(61)69/h4,6-7,10-11,15-16,19-20,35,37,73H,3,5,8-9,12-14,17-18,21-27H2,1-2H3,(H,54,63)(H,55,64)(H,56,70)(H,57,65)(H,58,67)(H,59,66)/t35-,37-,52-/m0/s1 |
| CAS Number | 1599440-13-7 |
| Related CAS |
Ordering Information
| Packaging | Price | Availability | Purity | Shipping Time |
|---|---|---|---|---|
| Bulk | Enquiry | Enquiry | Enquiry |
| Formulation | Solid powder |
|---|---|
| Purity | 98% Min. |
| Storage | Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years). |
| Solubility | Soluble in DMSO |
| Handling | |
| Shipping Condition | Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs. |
| HS Code |
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| Mechanism | |
| Cell study | |
| Animal study | |
| Clinical study |
1: Takegawa N, Tsurutani J, Kawakami H, Yonesaka K, Kato R, Haratani K, Hayashi H, Takeda M, Nonagase Y, Maenishi O, Nakagawa K. [fam-] trastuzumab deruxtecan, antitumor activity is dependent on HER2 expression level rather than on HER2 amplification. Int J Cancer. 2019 May 14. doi: 10.1002/ijc.32408. [Epub ahead of print] PubMed PMID: 31087550.
2: Shitara K, Iwata H, Takahashi S, Tamura K, Park H, Modi S, Tsurutani J, Kadowaki S, Yamaguchi K, Iwasa S, Saito K, Fujisaki Y, Sugihara M, Shahidi J, Doi T. Trastuzumab deruxtecan (DS-8201a) in patients with advanced HER2-positive gastric cancer: a dose-expansion, phase 1 study. Lancet Oncol. 2019 Jun;20(6):827-836. doi: 10.1016/S1470-2045(19)30088-9. Epub 2019 Apr 29. Erratum in: Lancet Oncol. 2019 May 10;:. PubMed PMID: 31047804.
3: Tamura K, Tsurutani J, Takahashi S, Iwata H, Krop IE, Redfern C, Sagara Y, Doi T, Park H, Murthy RK, Redman RA, Jikoh T, Lee C, Sugihara M, Shahidi J, Yver A, Modi S. Trastuzumab deruxtecan (DS-8201a) in patients with advanced HER2-positive breast cancer previously treated with trastuzumab emtansine: a dose-expansion, phase 1 study. Lancet Oncol. 2019 Jun;20(6):816-826. doi: 10.1016/S1470-2045(19)30097-X. Epub 2019 Apr 29. Erratum in: Lancet Oncol. 2019 May 10;:. PubMed PMID: 31047803.
4: Rinnerthaler G, Gampenrieder SP, Greil R. HER2 Directed Antibody-Drug-Conjugates beyond T-DM1 in Breast Cancer. Int J Mol Sci. 2019 Mar 5;20(5). pii: E1115. doi: 10.3390/ijms20051115. Review. PubMed PMID: 30841523; PubMed Central PMCID: PMC6429068.
5: Nakada T, Sugihara K, Jikoh T, Abe Y, Agatsuma T. The Latest Research and Development into the Antibody-Drug Conjugate, [fam-] Trastuzumab Deruxtecan (DS-8201a), for HER2 Cancer Therapy. Chem Pharm Bull (Tokyo). 2019;67(3):173-185. doi: 10.1248/cpb.c18-00744. Review. PubMed PMID: 30827997.
6: Bartsch R, Bergen E. ASCO 2018: highlights in HER2-positive metastatic breast cancer. Memo. 2018;11(4):280-283. doi: 10.1007/s12254-018-0441-x. Epub 2018 Oct 11. Review. PubMed PMID: 30595754; PubMed Central PMCID: PMC6280772.
7: Nagai Y, Oitate M, Shiozawa H, Ando O. Comprehensive preclinical pharmacokinetic evaluations of trastuzumab deruxtecan (DS-8201a), a HER2-targeting antibody-drug conjugate, in cynomolgus monkeys. Xenobiotica. 2019 Sep;49(9):1086-1096. doi: 10.1080/00498254.2018.1531158. Epub 2019 Jan 4. PubMed PMID: 30351177.
8: Lote H, Valeri N, Chau I. HER2 inhibition in gastro-oesophageal cancer: A review drawing on lessons learned from breast cancer. World J Gastrointest Oncol. 2018 Jul 15;10(7):159-171. doi: 10.4251/wjgo.v10.i7.159. Review. PubMed PMID: 30079142; PubMed Central PMCID: PMC6068859.
9: Trastuzumab Deruxtecan Targets HER2+ Cancers. Cancer Discov. 2018 Aug;8(8):OF5. doi: 10.1158/2159-8290.CD-NB2018-083. Epub 2018 Jun 27. PubMed PMID: 29950345.
10: Iwata TN, Ishii C, Ishida S, Ogitani Y, Wada T, Agatsuma T. A HER2-Targeting Antibody-Drug Conjugate, Trastuzumab Deruxtecan (DS-8201a), Enhances Antitumor Immunity in a Mouse Model. Mol Cancer Ther. 2018 Jul;17(7):1494-1503. doi: 10.1158/1535-7163.MCT-17-0749. Epub 2018 Apr 27. PubMed PMID: 29703841.
11: Doi T, Shitara K, Naito Y, Shimomura A, Fujiwara Y, Yonemori K, Shimizu C, Shimoi T, Kuboki Y, Matsubara N, Kitano A, Jikoh T, Lee C, Fujisaki Y, Ogitani Y, Yver A, Tamura K. Safety, pharmacokinetics, and antitumour activity of trastuzumab deruxtecan (DS-8201), a HER2-targeting antibody-drug conjugate, in patients with advanced breast and gastric or gastro-oesophageal tumours: a phase 1 dose-escalation study. Lancet Oncol. 2017 Nov;18(11):1512-1522. doi: 10.1016/S1470-2045(17)30604-6. Epub 2017 Oct 13. PubMed PMID: 29037983.
Chemical Structure
