CAS 100007-55-4

Etoposide glucuronide

Description:

Etoposide glucuronide is a metabolite of etoposide, a chemotherapeutic agent primarily used in the treatment of various cancers, including testicular cancer and small cell lung cancer. This compound is formed through the glucuronidation process, which is a phase II metabolic reaction that enhances the solubility of drugs for excretion. Etoposide glucuronide is characterized by its increased water solubility compared to its parent compound, facilitating renal excretion. The chemical structure features a glucuronic acid moiety linked to the etoposide molecule, which alters its pharmacokinetic properties. While etoposide acts by inhibiting topoisomerase II, leading to DNA damage and apoptosis in cancer cells, etoposide glucuronide is generally considered to be less pharmacologically active. Understanding the characteristics of etoposide glucuronide is important for assessing the metabolism and potential side effects of etoposide therapy, as well as for developing strategies to optimize cancer treatment regimens.

Formula: C₃₅H₄₀O₁₉

InChI: InChI=1S/C35H40O19/c1-11-46-9-20-30(50-11)25(38)27(40)34(51-20)52-28-14-7-17-16(48-10-49-17)6-13(14)21(22-15(28)8-47-33(22)43)12-4-18(44-2)29(19(5-12)45-3)53-35-26(39)23(36)24(37)31(54-35)32(41)42/h4-7,11,15,20-28,30-31,34-40H,8-10H2,1-3H3,(H,41,42)/t11-,15+,20-,21-,22+,23+,24+,25-,26-,27-,28-,30-,31+,34+,35-/m1/s1

InChI key: InChIKey=URCVASXWNJQAEH-HDWVWLDDSA-N

SMILES: O=C1[C@@]2([C@@H](C=3C([C@@H](O[C@@H]4O[C@]5([C@]([C@H](O)[C@H]4O)(O[C@H](C)OC5)[H])[H])[C@]2(CO1)[H])=CC6=C(C3)OCO6)C7=CC(OC)=C(O[C@@H]8O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]8O)C(OC)=C7)[H]

Synonyms:

• (2S,3S,4S,5R,6S)-6-(4-{(5R,5aR,8aR,9S)-9-[(7,8-dihydroxy-2-methylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)oxy]-6-oxo-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl}-2,6-dimethoxyphenoxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylate (non-preferred name)
• 4-(9-{[2-deoxy-4,6-O-(hydroxymethylidene)-2-methylhexopyranosyl]oxy}-6-oxo-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl)-2,6-dimethoxyphenyl hexopyranosiduronic acid
• 4-[(5R,5aR,8aR,9S)-9-[(4,6-O-(1R)-Ethylidene-β-<span class="text-smallcaps">D</smallcap>-glucopyranosyl)oxy]-5,5a,6,8,8a,9-hexahydro-6-oxofuro[3′,4′:6,7]naphtho[2,3-d]-1,3-dioxol-5-yl]-2,6-dimethoxyphenyl β-<smallcap>D</span>-glucopyranosiduronic acid
• Furo[3′,4′:6,7]naphtho[2,3-d]-1,3-dioxole, β-<span class="text-smallcaps">D</span>-glucopyranosiduronic acid deriv.
• Pyrano[3,2-d]-1,3-dioxin, β-<span class="text-smallcaps">D</span>-glucopyranosiduronic acid deriv.
• beta-D-Glucopyranosiduronic acid, 4-(9-((4,6-O-ethylidene-beta-D-glucopyranosyl)oxy)-5,5a,6,8,8a,9-hexahydro-6-oxofuro(3',4':6,7)naphtho(2,3-d)-1,3-diozol-5-yl)-2,6-dimethoxyphenyl, (5R-(5alpha,5abeta,8aalpha,9beta(R*)))-
• β-<span class="text-smallcaps">D</smallcap>-Glucopyranosiduronic acid, 4-[(5R,5aR,8aR,9S)-9-[(4,6-O-(1R)-ethylidene-β-<smallcap>D</span>-glucopyranosyl)oxy]-5,5a,6,8,8a,9-hexahydro-6-oxofuro[3′,4′:6,7]naphtho[2,3-d]-1,3-dioxol-5-yl]-2,6-dimethoxyphenyl
• β-<span class="text-smallcaps">D</smallcap>-Glucopyranosiduronic acid, 4-[9-[(4,6-O-ethylidene-β-<smallcap>D</span>-glucopyranosyl)oxy]-5,5a,6,8,8a,9-hexahydro-6-oxofuro[3′,4′:6,7]naphtho[2,3-d]-1,3-dioxol-5-yl]-2,6-dimethoxyphenyl, [5R-[5α,5aβ,8aα,9β(R*)]]-
• β-D-Glucopyranosiduronic acid, 4-[9-[(4,6-O-ethylidene-β-D-glucopyranosyl)oxy]-5,5a,6,8,8a,9-hexahydro-6-oxofuro[3′,4′:6,7]naphtho[2,3-d]-1,3-dioxol-5-yl]-2,6-dimethoxyphenyl, [5R-[5α,5aβ,8aα,9β(R*)]]-
• Etoposide glucuronide
• β-D-Glucopyranosiduronic acid, 4-[(5R,5aR,8aR,9S)-9-[(4,6-O-(1R)-ethylidene-β-D-glucopyranosyl)oxy]-5,5a,6,8,8a,9-hexahydro-6-oxofuro[3′,4′:6,7]naphtho[2,3-d]-1,3-dioxol-5-yl]-2,6-dimethoxyphenyl
• Furo[3′,4′:6,7]naphtho[2,3-d]-1,3-dioxole, β-D-glucopyranosiduronic acid deriv.
• Pyrano[3,2-d]-1,3-dioxin, β-D-glucopyranosiduronic acid deriv.

Etoposide Glucuronide

Controlled Product

CAS: 100007-55-4

Formula: C₃₅H₄₀O₁₉

Color and Shape: Neat

Molecular weight: 764.69

Ref: TR-E427700