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SML3519

Sigma-Aldrich

Exatecan

≥98% (HPLC)

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Synonym(s):
(1S,9S)-9-Ethyl-5-fluoro-9-hydroxy-4-methyl-10,13-dioxo-2,3,9,10,13,15-hexahydro-1H,12H-benzo[de]pyrano[3′,4′:6,7]indolizino[1,2-b]quinoline-1-amine, DX 8951
Empirical Formula (Hill Notation):
C24H22FN3O4
CAS Number:
171335-80-1
Molecular Weight:
435.45
MDL number:
MFCD00926120
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear (Warmed)

storage temp.

-10 to -25°C

SMILES string

O=C1N2C(C3=NC4=CC(F)=C(C(CC[C@@H]5N)=C4C5=C3C2)C)=CC6=C1COC([C@@]6(CC)O)=O

InChI

1S/C24H22FN3O4/c1-3-24(31)14-6-18-21-12(8-28(18)22(29)13(14)9-32-23(24)30)19-16(26)5-4-11-10(2)15(25)7-17(27-21)20(11)19/h6-7,16,31H,3-5,8-9,26H2,1-2H3/t16-,24-/m0/s1

InChI key

ZVYVPGLRVWUPMP-FYSMJZIKSA-N

Biochem/physiol Actions

Exatecan is a camptothecin (CPT) analog that exhibits a stronger topoisomerase-I inhibitory and antitumor activities and is highly effective against P-glycoprotein (P-gp) mediated multi-drug resistant cells. Several of the exatecan derivative based antibody-drug and peptide-drug conjugate payloads display high therapeutic indices universally across solid tumors.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H300,H340,H360F

Hazard Classifications

Acute Tox. 2 Oral - Muta. 1B - Repr. 1B

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

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Jie Chen et al.
Molecular medicine reports, 19(1), 477-489 (2018-11-16)
Unresectable advanced pancreatic cancer (APC) is a highly lethal malignancy. Although numerous chemotherapeutic regimens are available, evidence regarding the survival extension, the life quality improvement, the associated risks and occurrence rates of adverse effects, is required. The effects of 19
N Joto et al.
International journal of cancer, 72(4), 680-686 (1997-08-07)
We previously reported that DX-8951f, a novel water-soluble camptothecin analog, significantly inhibits the growth of various human and murine tumors in vitro and in vivo. The antitumor effects and topoisomerase I inhibitory activity of DX-8951f are stronger than those of
Ghassan K Abou-Alfa et al.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology, 24(27), 4441-4447 (2006-09-20)
Exatecan mesylate is a hexacyclic, water-soluble, topoisomerase-1 inhibitor. Exatecan has single-agent and combination activity with gemcitabine in advanced pancreatic cancer. A multicenter, randomized, phase III trial comparing exatecan plus gemcitabine versus gemcitabine alone in advanced pancreatic cancer was conducted. Eligibility

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