CAS 117091-64-2

Etoposide phosphate

Description:

Etoposide phosphate is a prodrug of etoposide, primarily used in cancer treatment, particularly for testicular cancer and small cell lung cancer. It is a derivative of the podophyllotoxin family and functions as a topoisomerase II inhibitor, disrupting DNA replication and transcription, which ultimately leads to cell death. Etoposide phosphate is characterized by its phosphate ester group, which enhances its solubility and bioavailability compared to its parent compound, etoposide. Upon administration, it is rapidly converted to etoposide in the body, allowing for effective therapeutic action. The substance is typically administered intravenously and is known for its potential side effects, including myelosuppression, gastrointestinal disturbances, and hypersensitivity reactions. Its pharmacokinetics involve a distribution phase followed by elimination, with a half-life that can vary based on individual patient factors. Overall, etoposide phosphate represents an important option in the chemotherapeutic arsenal, particularly for patients requiring a more soluble form of etoposide.

Formula: C₂₉H₃₃O₁₆P

InChI: InChI=1S/C29H33O16P/c1-11-38-9-20-27(42-11)23(30)24(31)29(43-20)44-25-14-7-17-16(40-10-41-17)6-13(14)21(22-15(25)8-39-28(22)32)12-4-18(36-2)26(19(5-12)37-3)45-46(33,34)35/h4-7,11,15,20-25,27,29-31H,8-10H2,1-3H3,(H2,33,34,35)/t11-,15+,20-,21-,22+,23-,24-,25-,27-,29+/m1/s1

InChI key: InChIKey=LIQODXNTTZAGID-OCBXBXKTSA-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(OP(=O)(O)O)C(OC)=C7)[H]

Synonyms:

• (5R,5aR,8aR,9S)-5-[3,5-Dimethoxy-4-(phosphonooxy)phenyl]-9-[[4,6-O-(1R)-ethylidene-β-<span class="text-smallcaps">D</span>-glucopyranosyl]oxy]-5,8,8a,9-tetrahydrofuro[3′,4′:6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one
• (5R,5aR,8aR,9S)-9-{[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methylhexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy}-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one
• (5R,5aR,8aR,9S)-9-{[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-méthylhexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy}-5-(4-hydroxy-3,5-diméthoxyphényl)-5,8,8a,9-tétrahydrofuro[3',4':6,7]naphto[2,3-d][1,3]dioxol-6(5aH)-one
• (5S,5aR,8aR,9R)-9-(4-Hydroxy-3,5-dimethoxyphenyl)-8-oxo-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl 4,6-O-[(1R)-ethylidene]-beta-D-glucopyranoside
• 4'-Demethylepipodophyllotoxin ethylidene-.beta.-D-glucoside
• 4-[(5R,5aR)-9-({4,6-O-[(1R)-ethylidene]-beta-D-glucopyranosyl}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 phosphate
• 4-[(5R,5aR,8aR,9S)-9-({4,6-O-[(1R)-ethylidene]-beta-D-glucopyranosyl}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 dihydrogen phosphate
• 4′-Demethylepipodophyllotoxin 9-(4,6-O-ethylidene-beta-D-glucopyranoside)
• Bmy 40481
• Epeg
• Etopofos
• Etopophos
• Etoposide (JAN/USP)
• Etoposide (VP16)
• Etoposide 4′-phosphate
• Etoposide [USAN:BAN:INN:JAN]
• Furo[3′,4′:6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 5-[3,5-dimethoxy-4-(phosphonooxy)phenyl]-9-[(4,6-O-ethylidene-β-<span class="text-smallcaps">D</span>-glucopyranosyl)oxy]-5,8,8a,9-tetrahydro-, [5R-[5α,5aβ,8aα,9β(R*)]]-
• Furo[3′,4′:6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 5-[3,5-dimethoxy-4-(phosphonooxy)phenyl]-9-[[4,6-O-(1R)-ethylidene-β-<span class="text-smallcaps">D</span>-glucopyranosyl]oxy]-5,8,8a,9-tetrahydro-, (5R,5aR,8aR,9S)-
• Pyrano[3,2-d]-1,3-dioxin, furo[3′,4′:6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one deriv.
• Furo[3′,4′:6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 5-[3,5-dimethoxy-4-(phosphonooxy)phenyl]-9-[[4,6-O-(1R)-ethylidene-β-D-glucopyranosyl]oxy]-5,8,8a,9-tetrahydro-, (5R,5aR,8aR,9S)-
• (5R,5aR,8aR,9S)-5-[3,5-Dimethoxy-4-(phosphonooxy)phenyl]-9-[[4,6-O-(1R)-ethylidene-β-D-glucopyranosyl]oxy]-5,8,8a,9-tetrahydrofuro[3′,4′:6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one

Etoposide Phosphate

CAS: 117091-64-2

Other glycosides, natural or reproduced by synthesis, and their salts, ethers, esters and other derivatives

Formula: C₂₉H₃₃O₁₆P

Color and Shape: White Off-White Powder

Molecular weight: 668.15062

Ref: 45-1268819

Etoposide 4'-Phosphate

CAS: 117091-64-2

Etoposide 4'-Phosphate

Molecular weight: 668.54g/mol

Ref: 54-BIFK0022

Etoposide Phosphate

CAS: 117091-64-2

Etoposide Phosphate is a selective and orally active topoisomerase II inhibitor and anticancer chemotherapy drug that apoptosise, the p53, and G2/M

Formula: C₂₉H₃₃O₁₆P

Color and Shape: Solid

Molecular weight: 668.54

Ref: TM-T21303

Etoposide Phosphate (Etopophos)

CAS: 117091-64-2

Color and Shape: Neat

Ref: 86-MM3886.00

Etoposide Phosphate

CAS: 117091-64-2

Formula: C₂₉H₃₃O₁₆P

Molecular weight: 668.54

Ref: 4Z-E-5931

Etoposide phosphate

CAS: 117091-64-2

Topoisomerase II inhibitor; chemotherapeutic drug

Formula: C₂₉H₃₃O₁₆P

Purity: Min. 95%

Color and Shape: Powder

Molecular weight: 668.54 g/mol

Ref: 3D-FE57280

Etoposide Phosphate Diammonium Salt

Controlled Product

CAS: 117091-64-2

Applications A bioequivalent prodrug of the DNA topoisomerase II inhibitor Etoposide (E933750). Antineoplastic used in the treatment of a wide variety of hematological malignancies and solid tumors.
References Kaul, S. et al.: J. Clin. Pharmacol., 13, 2835 (1995); J. Pharmakin. Biopharmac., 24, 313 (1996); Brooks, D.J. et al.: Anti-Cancer Drugs, 6, 637 (1995);

Formula: C₂₉H₃₁O₁₆P•2NH₄

Color and Shape: Neat

Molecular weight: 668.54 + 2(34.06)

Ref: TR-E933755