etoposide and its Impurities
Etoposide is used as a form of chemotherapy for cancers such as Kaposi’s sarcoma, Ewing's sarcoma, lung cancer, testicular cancer, lymphoma, nonlymphocytic leukemia, and glioblastoma multiforme. It is sold under the brand name Etopophos.. Reference standards of Etoposide API, and its pharmacopeial, non pharmacopeial impurities, and stable isotopes are listed below


Etoposide - Impurity N
(5R,5aR,8aR,9S)-9-[[4,6-O-[(R)-Ethylidene]-b-D-glucopyranosyl]oxy]-5-[4-[[(5R, 5aR,8aR,9S)-5-(4-hydroxy-3,5-dimethoxyphenyl)-6-oxo-5,5a,6,8,8a,9- hexahydroisobenzofuro[5,6-f][1,3]benzodioxol-9-yl]oxy]3,5-dimethoxyphenyl]-5,8, 8a,9-tetrahydroisobenzofuro-[5,6-f][1,3]benzodioxol-6(5aH)-one
Catalogue No.:PA 05 70140
CAS :
NA
Molecular Formula : C50H50O20
Molecular Weight : 970.92


Etoposide - Impurity O
(5R,5aR,8aR,9S)-9-[[2,3-Bis-O-(dichloroacetyl)-4,6-O-[(S)-ethylidene]-b-L- glucopyranosyl]oxy]-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9- tetrahydroisobenzofuro[5,6-f][1,3]benzodioxol-6(5aH)-one
Catalogue No.:PA 05 70150
CAS :
260974-95-6
Molecular Formula : C33H32Cl4O15
Molecular Weight : 810.41


Etoposide - Impurity R
(5R,5aR,8aR,9S)-9-[[4,6-O-[(1R)-Ethane-1,1-diyl]-β-D-glucopyranosyl]oxy]-5-[4-[[(5R,5aR,8aR,9R)-5-(4-hydroxy-3,5-dimethoxyphenyl)-6-oxo-5,5a,6,8,8a,9-hexahydro[2]benzofuro[5,6-f][1,3]benzodioxol-9-yl]oxy]-3,5-dimethoxyphenyl]-5,8,8a,9-tetrahydro[2]benzofuro[5,6-f][1,3]benzodioxol-6(5aH)-one
Catalogue No.:PA 05 70180
CAS :
149839-65-6
Molecular Formula : C50H50O20
Molecular Weight : 970.93


(5R,5aR,8aR,9R)-9-Hydroxy-5-(3-hydroxy-4,5-dimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one
(5R,5aR,8aR,9R)-9-Hydroxy-5-(3-hydroxy-4,5-dimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one
Catalogue No.:PA 05 70510
CAS :
54747-66-9
Molecular Formula : C21H20O8
Molecular Weight : 400.38


(5R,5aR,8aR,9R)-9-Hydroxy-5-(3,4,5-trihydroxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one
(5R,5aR,8aR,9R)-9-Hydroxy-5-(3,4,5-trihydroxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one
Catalogue No.:PA 05 70520
CAS :
NA
Molecular Formula : C19H16O8
Molecular Weight : 372.33


(5R,5aR)-5-(4-Hydroxy-3,5-dimethoxyphenyl)-5,8-dihydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one
(5R,5aR)-5-(4-Hydroxy-3,5-dimethoxyphenyl)-5,8-dihydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one
Catalogue No.:PA 05 70530
CAS :
2585189-83-7
Molecular Formula : C21H18O7
Molecular Weight : 382.37


Benzyl ((2R,4aR,6R,7R,8R,8aS)-6,8-dihydroxy-2-methylhexahydropyrano[3,2-d][1,3]dioxin-7-yl) Carbonate
Benzyl ((2R,4aR,6R,7R,8R,8aS)-6,8-dihydroxy-2-methylhexahydropyrano[3,2-d][1,3]dioxin-7-yl) Carbonate
Catalogue No.:PA 05 70540
CAS :
NA
Molecular Formula : C16H20O8
Molecular Weight : 340.33


Benzyl ((2R,4aR,6R,7R,8S,8aR)-6,7-dihydroxy-2-methylhexahydropyrano[3,2-d][1,3]dioxin-8-yl) Carbonate
Benzyl ((2R,4aR,6R,7R,8S,8aR)-6,7-dihydroxy-2-methylhexahydropyrano[3,2-d][1,3]dioxin-8-yl) Carbonate
Catalogue No.:PA 05 70550
CAS :
NA
Molecular Formula : C16H20O8
Molecular Weight : 340.33


Dibenzyl ((2R,4aR,6S,7R,8S,8aR)-7-hydroxy-2-methylhexahydropyrano[3,2-d][1,3]dioxine-6,8-diyl) bis(Carbonate)
Dibenzyl ((2R,4aR,6S,7R,8S,8aR)-7-hydroxy-2-methylhexahydropyrano[3,2-d][1,3]dioxine-6,8-diyl) bis(Carbonate)
Catalogue No.:PA 05 70560
CAS :
NA
Molecular Formula : C24H26O10
Molecular Weight : 474.46


Dibenzyl ((2R,4aR,6S,7R,8R,8aS)-8-hydroxy-2-methylhexahydropyrano[3,2-d][1,3]dioxine-6,7-diyl) bis(Carbonate)
Dibenzyl ((2R,4aR,6S,7R,8R,8aS)-8-hydroxy-2-methylhexahydropyrano[3,2-d][1,3]dioxine-6,7-diyl) bis(Carbonate)
Catalogue No.:PA 05 70570
CAS :
NA
Molecular Formula : C24H26O10
Molecular Weight : 474.46


Tribenzyl ((2R,4aR,6S,7R,8R,8aR)-2-methylhexahydropyrano[3,2-d][1,3]dioxine-6,7,8-triyl) Tricarbonate
Tribenzyl ((2R,4aR,6S,7R,8R,8aR)-2-methylhexahydropyrano[3,2-d][1,3]dioxine-6,7,8-triyl) Tricarbonate
Catalogue No.:PA 05 70580
CAS :
NA
Molecular Formula : C32H32O12
Molecular Weight : 608.6


Dibenzyl ((2R,4aR,6R,7R,8R,8aR)-6-hydroxy-2-methylhexahydropyrano[3,2-d][1,3]dioxine-7,8-diyl) bis(Carbonate)
Dibenzyl ((2R,4aR,6R,7R,8R,8aR)-6-hydroxy-2-methylhexahydropyrano[3,2-d][1,3]dioxine-7,8-diyl) bis(Carbonate)
Catalogue No.:PA 05 70590
CAS :
NA
Molecular Formula : C24H26O10
Molecular Weight : 474.46


Benzyl ((2R,4aR,6S,7R,8R,8aR)-6,7-bis((1-chlorovinyl)peroxy)-2-methylhexahydropyrano[3,2-d][1,3]dioxin-8-yl) Carbonate
Benzyl ((2R,4aR,6S,7R,8R,8aR)-6,7-bis((1-chlorovinyl)peroxy)-2-methylhexahydropyrano[3,2-d][1,3]dioxin-8-yl) Carbonate
Catalogue No.:PA 05 70600
CAS :
NA
Molecular Formula : C20H22Cl2O10
Molecular Weight : 493.29


Benzyl ((2R,4aR,6S,7R,8R,8aR)-6,8-bis((1-chlorovinyl)peroxy)-2-methylhexahydropyrano[3,2-d][1,3]dioxin-7-yl) Carbonate
Benzyl ((2R,4aR,6S,7R,8R,8aR)-6,8-bis((1-chlorovinyl)peroxy)-2-methylhexahydropyrano[3,2-d][1,3]dioxin-7-yl) Carbonate
Catalogue No.:PA 05 70610
CAS :
NA
Molecular Formula : C20H22Cl2O10
Molecular Weight : 493.29


Benzyl ((2R,4aR,6S,7R,8S,8aR)-8-((1-chlorovinyl)peroxy)-7-hydroxy-2-methylhexahydropyrano[3,2-d][1,3]dioxin-6-yl) Carbonate
Benzyl ((2R,4aR,6S,7R,8S,8aR)-8-((1-chlorovinyl)peroxy)-7-hydroxy-2-methylhexahydropyrano[3,2-d][1,3]dioxin-6-yl) Carbonate
Catalogue No.:PA 05 70620
CAS :
NA
Molecular Formula : C18H21ClO9
Molecular Weight : 416.81


Benzyl ((2R,4aR,6S,7R,8R,8aS)-7-((1-chlorovinyl)peroxy)-8-hydroxy-2-methylhexahydropyrano[3,2-d][1,3]dioxin-6-yl) Carbonate
Benzyl ((2R,4aR,6S,7R,8R,8aS)-7-((1-chlorovinyl)peroxy)-8-hydroxy-2-methylhexahydropyrano[3,2-d][1,3]dioxin-6-yl) Carbonate
Catalogue No.:PA 05 70630
CAS :
NA
Molecular Formula : C18H21ClO9
Molecular Weight : 416.81


(2R,4aR,6S,7R,8R,8aS)-6,7-bis((1-Chlorovinyl)peroxy)-2-methylhexahydropyrano[3,2-d][1,3]dioxin-8-ol
(2R,4aR,6S,7R,8R,8aS)-6,7-bis((1-Chlorovinyl)peroxy)-2-methylhexahydropyrano[3,2-d][1,3]dioxin-8-ol
Catalogue No.:PA 05 70640
CAS :
NA
Molecular Formula : C12H16Cl2O8
Molecular Weight : 359.15


(2R,4aR,6S,7R,8S,8aR)-6,8-bis((1-Chlorovinyl)peroxy)-2-methylhexahydropyrano[3,2-d][1,3]dioxin-7-ol
(2R,4aR,6S,7R,8S,8aR)-6,8-bis((1-Chlorovinyl)peroxy)-2-methylhexahydropyrano[3,2-d][1,3]dioxin-7-ol
Catalogue No.:PA 05 70650
CAS :
NA
Molecular Formula : C12H16Cl2O8
Molecular Weight : 359.15


(2R,4aR,6R,7R,8S,8aR)-8-((1-chlorovinyl)peroxy)-2-methylhexahydropyrano[3,2-d][1,3]dioxine-6,7-diol
(2R,4aR,6R,7R,8S,8aR)-8-((1-chlorovinyl)peroxy)-2-methylhexahydropyrano[3,2-d][1,3]dioxine-6,7-diol
Catalogue No.:PA 05 70660
CAS :
NA
Molecular Formula : C10H15ClO7
Molecular Weight : 282.67


(2R,4aR,6R,7R,8R,8aS)-7-((1-Chlorovinyl)peroxy)-2-methylhexahydropyrano[3,2-d][1,3]dioxine-6,8-diol
(2R,4aR,6R,7R,8R,8aS)-7-((1-Chlorovinyl)peroxy)-2-methylhexahydropyrano[3,2-d][1,3]dioxine-6,8-diol
Catalogue No.:PA 05 70670
CAS :
NA
Molecular Formula : C10H15ClO7
Molecular Weight : 282.67


(5R,5aR,8aR,9S)-9-((1-Chlorovinyl)peroxy)-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-((1-Chlorovinyl)peroxy)-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
Catalogue No.:PA 05 70680
CAS :
NA
Molecular Formula : C23H21ClO9
Molecular Weight : 476.86


(5R,5aR,8aR,9S)-9-((1-Chlorovinyl)peroxy)-5-(4-((1-chlorovinyl)peroxy)-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-((1-Chlorovinyl)peroxy)-5-(4-((1-chlorovinyl)peroxy)-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one
Catalogue No.:PA 05 70690
CAS :
NA
Molecular Formula : C25H22Cl2O10
Molecular Weight : 553.34


(5R,5aR,8aR,9S)-5-(4-((1-Chlorovinyl)peroxy)-3,5-dimethoxyphenyl)-9-(((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)oxy)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one
(5R,5aR,8aR,9S)-5-(4-((1-Chlorovinyl)peroxy)-3,5-dimethoxyphenyl)-9-(((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)oxy)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one
Catalogue No.:PA 05 70710
CAS :
NA
Molecular Formula : C31H33ClO14
Molecular Weight : 665.04


(4aR,6R,7R,8S,8aR)-6-Hydroxy-2-methylhexahydropyrano[3,2-d][1,3]dioxine-7,8-diyl bis(2,2-Dichloroacetate)
(4aR,6R,7R,8S,8aR)-6-Hydroxy-2-methylhexahydropyrano[3,2-d][1,3]dioxine-7,8-diyl bis(2,2-Dichloroacetate)
Catalogue No.:PA 05 0701001
CAS :
149403-65-6
Molecular Formula : C12H14Cl4O8
Molecular Weight : 428.04


Benzyl ((2R,4aR,6S,7R,8R,8aS)-7,8-dihydroxy-2-methylhexahydropyrano[3,2-d][1,3]dioxin-6-yl) carbonate
Benzyl ((2R,4aR,6S,7R,8R,8aS)-7,8-dihydroxy-2-methylhexahydropyrano[3,2-d][1,3]dioxin-6-yl) carbonate
Catalogue No.:PA 05 0701006
CAS :
89709-04-6
Molecular Formula : C16H20O8
Molecular Weight : 340.33


(5R,5aR,8aR,9R)-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,9R)-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
Catalogue No.:PA 05 0701005
CAS :
163959-36-2
Molecular Formula : C29H32O13
Molecular Weight : 588.56


Benzyl (4-((5R,5aR,8aR,9S)-9-(((benzyloxy)carbonyl)oxy)-6-oxo-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl)-2-hydroxy-6-methoxyphenyl) carbonate
Benzyl (4-((5R,5aR,8aR,9S)-9-(((benzyloxy)carbonyl)oxy)-6-oxo-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl)-2-hydroxy-6-methoxyphenyl) carbonate
Catalogue No.:PA 05 0701008
CAS :
NA
Molecular Formula : C36H30O12
Molecular Weight : 654.62


(5R,5aR,8aR,9S)-5-(4-(Benzyloxy)-3,5-dimethoxyphenyl)-9-hydroxy-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one
(5R,5aR,8aR,9S)-5-(4-(Benzyloxy)-3,5-dimethoxyphenyl)-9-hydroxy-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one
Catalogue No.:PA 05 0701009
CAS :
403642-80-8
Molecular Formula : C28H26O8
Molecular Weight : 490.51


Dibenzyl (5-((5R,5aR,8aR,9S)-9-hydroxy-6-oxo-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl)-3-methoxy-1,2-phenylene) bis(carbonate)
Dibenzyl (5-((5R,5aR,8aR,9S)-9-hydroxy-6-oxo-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl)-3-methoxy-1,2-phenylene) bis(carbonate)
Catalogue No.:PA 05 0701011
CAS :
866874-15-9
Molecular Formula : C36H30O12
Molecular Weight : 654.62


(5R,5aR,8aR,9S)-5-(3,4-Dihydroxy-5-methoxyphenyl)-9-hydroxy-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one
(5R,5aR,8aR,9S)-5-(3,4-Dihydroxy-5-methoxyphenyl)-9-hydroxy-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one
Catalogue No.:PA 05 0701012
CAS :
102306-97-8
Molecular Formula : C20H18O8
Molecular Weight : 386.36