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2''-3''-di-O-benzyletoposide
etoposide
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% |
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
etoposide
Conditions | Yield |
---|---|
With hydrogen; trifluoroacetic acid; palladium on activated charcoal In methanol; ethyl acetate under 2585.81 Torr; for 12h; Hydrogenation; | 85% |
4-demethylepipodophyllotoxin-7'-O-β-D-glucopyranoside
1,1-dimethoxyethane
etoposide
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In nitromethane at 25℃; for 2h; | 68% |
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; |
2,3-di-O-chloroacetyl-4:6-O-ethylidene-β-D-glucopuranose
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
etoposide
B
(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 | Yield |
---|---|
With boron trifluoride diethyl etherate; zinc diacetate 1.) CH2Cl2, 2.) reflux, MeOH; Yield given. Multistep reaction. Yields of byproduct given; |
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
etoposide
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 |
4'-demethylepipodophyllotoxin
etoposide
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 |
etoposide
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 |
4'-demethyl-4'-O-(benzoyloxycarbonyl)epipodophyllotoxin
etoposide
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 |
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
etoposide
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, 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. |