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Cas Database

Name	Etoposide	EINECS	251-509-1
CAS No.	33419-42-0	Density	1.55 g/cm³
PSA	160.83000	LogP	1.33860
Solubility	DMSO: 30 mg/mL	Melting Point	236-251 °C(lit.)
Formula	C₂₉H₃₂O₁₃	Boiling Point	798.054 °C at 760 mmHg
Molecular Weight	588.565	Flash Point	263.603 °C
Transport Information	UN 3249	Appearance	White crystalline powder
Safety	53-45-36/37-26	Risk Codes	45-22-36/37/38
Molecular Structure		Hazard Symbols	T, Xi
Synonyms	Etoposide; 4'-Demethylepipodophyllotoxin 9-(4,6-O-Ethylidene-β-D-glucopyranoside); 4‘-Demethylepipodophyllotoxin 9-(4,6-O-ethylidene-β-D-glucopyranoside);	Article Data	31

Etoposide Synthetic route

: 217475-21-3
2''-3''-di-O-benzyletoposide

: 33419-42-0
etoposide

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In tetrahydrofuran at 20℃; under 2585.81 Torr; for 4h; Catalytic hydrogenation;	96.8%
With hydrogen; 5%-palladium/activated carbon In tetrahydrofuran at 20℃; under 2585.81 Torr; for 4h; Product distribution / selectivity; Buchi apparatus;	96.8%
With hydrogen; 5%-palladium/activated carbon In acetone at 20℃; under 2250.23 Torr; for 1h; Product distribution / selectivity;	93.3%
With hydrogen; Pd/C In tetrahydrofuran; methanol at 20℃; under 2585.81 Torr; for 3.5h; Product distribution / selectivity; Parr-shaker bottle;	92.5%

: 270928-23-9
Carbonic acid benzyl ester 4-[(5R,5aR,8aR,9S)-9-((2R,4aR,6R,7R,8S,8aR)-7,8-bis-benzyloxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl]-2,6-dimethoxy-phenyl ester

: 33419-42-0
etoposide

Conditions

Conditions	Yield
With hydrogen; trifluoroacetic acid; palladium on activated charcoal In methanol; ethyl acetate under 2585.81 Torr; for 12h; Hydrogenation;	85%

: 23363-35-1
4-demethylepipodophyllotoxin-7'-O-β-D-glucopyranoside

: 534-15-6
1,1-dimethoxyethane

: 33419-42-0
etoposide

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In nitromethane at 25℃; for 2h;	68%

: 105-57-7
diethyl acetal

: 134659-25-9
C57H47ClO18

: 33419-42-0
etoposide

Conditions

Conditions	Yield
With methanol; zinc diacetate; toluene-4-sulfonic acid 1.) sealed tube, 70 deg C, 12 h, 2.) MeCN, 0.5 h; Yield given. Multistep reaction;

: 92206-84-3
2,3-di-O-chloroacetyl-4:6-O-ethylidene-β-D-glucopuranose

: 92206-82-1, 112246-47-6
Chloro-acetic acid 4-((5S,5aS,9R)-9-hydroxy-6-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl)-2,6-dimethoxy-phenyl ester

A: 33419-42-0
etoposide

B: 112246-48-7
(5S,5aS,8aS,9R)-9-((2R,4aR,6R,7R,8R,8aS)-7,8-Dihydroxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-5-(4-hydroxy-3,5-dimethoxy-phenyl)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate; zinc diacetate 1.) CH2Cl2, 2.) reflux, MeOH; Yield given. Multistep reaction. Yields of byproduct given;

: 172138-90-8
Acetic acid 4-[(5R,5aR,8aR,9S)-9-((2R,4aR,6R,7R,8S,8aR)-7,8-diacetoxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl]-2,6-dimethoxy-phenyl ester

A: 33419-42-0
etoposide

B: (5R,6R,7R,8S)-8-((2R,4aR,6R,7R,8R,8aS)-7,8-Dihydroxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-5-(4-hydroxy-3,5-dimethoxy-phenyl)-7-hydroxymethyl-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester

C: etoposide

Conditions

Conditions	Yield
With zinc diacetate In methanol for 96h; Heating; Yield given;	A n/a B 1.5 g C n/a
With zinc diacetate In methanol for 96h; Heating; Yields of byproduct given;	A n/a B 1.5 g C n/a
With zinc diacetate In methanol for 96h; Heating; Yield given. Yields of byproduct given;	A n/a B 1.5 g C n/a

: 6559-91-7
4'-demethylepipodophyllotoxin

: 33419-42-0
etoposide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 81.9 percent / BF3*OEt2 / acetonitrile / 5 h / -10 °C 2: 96.8 percent / H2 / Pd/C / tetrahydrofuran / 4 h / 20 °C / 2585.81 Torr View Scheme
Multi-step reaction with 2 steps 1: BF3*OEt2 / acetonitrile / -10 °C 2: 96.8 percent / H2 / Pd/C / tetrahydrofuran / 4 h / 20 °C / 2585.81 Torr View Scheme
Multi-step reaction with 3 steps 1: 75 percent / BF3*Et2O / CH2Cl2 / 0.5 h / -20 °C 2: 70 percent / Zn(OAc)2, MeOH / 40 h / Heating 3: 68 percent / TsOH / nitromethane / 2 h / 25 °C View Scheme

: 4,6-O-ethylidene-2,3-O-dibenzyl-D-glucose

: 33419-42-0
etoposide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 81.9 percent / BF3*OEt2 / acetonitrile / 5 h / -10 °C 2: 96.8 percent / H2 / Pd/C / tetrahydrofuran / 4 h / 20 °C / 2585.81 Torr View Scheme
Multi-step reaction with 2 steps 1: BF3*OEt2 / acetonitrile / -10 °C 2: 96.8 percent / H2 / Pd/C / tetrahydrofuran / 4 h / 20 °C / 2585.81 Torr View Scheme

: 23363-33-9
4'-demethyl-4'-O-(benzoyloxycarbonyl)epipodophyllotoxin

: 33419-42-0
etoposide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 94 percent / BF3*OEt2 / CH2Cl2 / 1 h / 0 °C 2: m-CPBA / CH2Cl2 / 0.08 h / -78 °C 3: 74 percent / trifluoromethanesulfonic anhydride / CH2Cl2 / 5 h / -78 - -40 °C 4: 85 percent / H2; CF3COOH / Pd/C / ethyl acetate; methanol / 12 h / 2585.81 Torr View Scheme

: 270071-30-2
Carbonic acid benzyl ester 4-((5R,5aR,8aR,9S)-9-ethylsulfanyl-6-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl)-2,6-dimethoxy-phenyl ester

: 33419-42-0
etoposide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: m-CPBA / CH2Cl2 / 0.08 h / -78 °C 2: 74 percent / trifluoromethanesulfonic anhydride / CH2Cl2 / 5 h / -78 - -40 °C 3: 85 percent / H2; CF3COOH / Pd/C / ethyl acetate; methanol / 12 h / 2585.81 Torr View Scheme

Etoposide Specification

Etoposide, its cas register number is 33419-42-0. It also can be called (-)-Etoposide 4'-Demethylepipodophyllotoxin 9-(4,6-O-(R)-ethylidene-beta-D-glucopyranoside); 4'-Demethylepipodophyllotoxin 9-(4,6-O-ethylidene-beta-D-glucopyranoside); 4'-O-Demethyl-1-O-(4,6-O-ethylidene-beta-D-glucopyranosyl)epipodophyllotoxin; Etoposido is a white crystalline powder. Etoposide is a chemotherapy drug derived from a type of plant alkaloid known as a podophyllotoxin.

Physical properties about Etoposido are: (1)ACD/LogP: 0.275; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): 0.28; (4)ACD/LogD (pH 7.4): 0.27; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 33.62; (8)ACD/KOC (pH 7.4): 33.53; (9)#H bond acceptors: 13 ; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 8; (12)Index of Refraction: 1.662; (13)Molar Refractivity: 140.107 cm³; (14)Molar Volume: 378.5 cm³; (15)Polarizability: 55.543 10-24cm³; (16)Surface Tension: 76.4929962158203 dyne/cm; (17)Density: 1.555 g/cm³; (18)Flash Point: 263.603 °C; (19)Enthalpy of Vaporization: 121.702 kJ/mol; (20)Boiling Point: 798.054 °C at 760 mmHg

Uses of Etoposido: 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 often given in combination with other drugs. It is also sometimes used in a conditioning regimen prior to a bone marrow or blood stem cell transplant.

When you are using this chemical, please be cautious about it as the following:
1. Avoid exposure - obtain special instruction before use;
2. In case of accident or if you feel unwell, seek medical advice immediately (show label where possible);
3. Wear suitable protective clothing and gloves;
4. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;

You can still convert the following datas into molecular structure:|
(1)InChI=1S/C29H32O13/c1-11-36-9-20-27(40-11)24(31)25(32)29(41-20)42-26-14-7-17-16(38-10-39-17)6-13(14)21(22-15(26)8-37-28(22)33)12-4-18(34-2)23(30)19(5-12)35-3/h4-7,11,15,20-22,24-27,29-32H,8-10H2,1-3H3/t11-,15+,20?,21-,22+,24-,25-,26-,27-,29+/m1/s1; (2)InChIKey=VJJPUSNTGOMMGY-LBYSYZCZSA-N;
(3)SmilesC[C@@H]1OCC2[C@@H](O1)[C@@H]([C@H]([C@@H](O2)O[C@@H]3c4cc5c(cc4[C@H]([C@@H]6[C@@H]3COC6=O)c7cc(c(c(c7)OC)O)OC)OCO5)O)O

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
child	TDLo	intravenous	183mg/kg/2H-C (183mg/kg)	BEHAVIORAL: ATAXIA	Drug Intelligence and Clinical Pharmacy. Vol. 22, Pg. 41, 1988.
human	TDLo	intravenous	2630ug/kg/10D (2.63mg/kg)	BLOOD: AGRANULOCYTOSIS BLOOD: APLASTIC ANEMIA BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE	Cancer Vol. 34, Pg. 985, 1974.
human	TDLo	oral	16mg/kg/5D-I (16mg/kg)	BLOOD: AGRANULOCYTOSIS BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE BLOOD: APLASTIC ANEMIA	Cancer Vol. 34, Pg. 985, 1974.
man	TDLo	intravenous	57ug/kg/2M-C (.057mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES	Lancet. Vol. 341, Pg. 1353, 1993.
mouse	LD50	intraperitoneal	64mg/kg (64mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) SKIN AND APPENDAGES (SKIN): HAIR: OTHER GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH	Kiso to Rinsho. Clinical Report. Vol. 19, Pg. 3473, 1985.
mouse	LD50	intravenous	15070ug/kg (15.07mg/kg)		National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
mouse	LD50	oral	215mg/kg (215mg/kg)		National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
mouse	LD50	subcutaneous	143mg/kg (143mg/kg)		Drugs in Japan Vol. -, Pg. 190, 1990.
rabbit	LD50	intravenous	37mg/kg (37mg/kg)		Journal of Toxicological Sciences. Vol. 11(Suppl,
rabbit	LD50	oral	147mg/kg (147mg/kg)	SKIN AND APPENDAGES (SKIN): HAIR: OTHER GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"	Journal of Toxicological Sciences. Vol. 11(Suppl,
rat	LD50	intraperitoneal	39mg/kg (39mg/kg)	GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)	Kiso to Rinsho. Clinical Report. Vol. 19, Pg. 3473, 1985.
rat	LD50	intravenous	58mg/kg (58mg/kg)		Drugs in Japan Vol. -, Pg. 230, 1995.
rat	LD50	oral	1784mg/kg (1784mg/kg)		Kiso to Rinsho. Clinical Report. Vol. 19, Pg. 3473, 1985.
rat	LD50	oral	1784mg/kg (1784mg/kg)	GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)	Kiso to Rinsho. Clinical Report. Vol. 19, Pg. 3473, 1985.
rat	LD50	subcutaneous	> 200mg/kg (200mg/kg)		Drugs in Japan Vol. -, Pg. 190, 1990.
women	TDLo	intravenous	160ug/kg/3M-C (.16mg/kg)	LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)	Lancet. Vol. 341, Pg. 1353, 1993.

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