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CAS No.: | 29767-20-2 |
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Name: | Teniposide |
Molecular Structure: | |
Formula: | C32H32O13S |
Molecular Weight: | 656.664 |
Synonyms: | Epipodophyllotoxin,4'-demethyl-, 9-(4,6-O-2-thenylidene-b-D-glucopyranoside) (8CI);Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one,5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-9-[[4,6-O-(2-thienylmethylene)-b-D-glucopyranosyl]oxy]-, [5R-[5a,5ab,8aa,9b(R*)]]-;EPT;NSC 122819;S 122819;Tenoposide;VM 26;Vehem;Vehem-Sandoz;Vumon; |
EINECS: | 249-831-2 |
Density: | 1.59 g/cm3 |
Melting Point: | 274 - 277oC |
Boiling Point: | 864.3 °C at 760 mmHg |
Flash Point: | 476.5 °C |
Appearance: | white or off-white crystalline powder |
Hazard Symbols: | Xi |
Risk Codes: | 36/37/38 |
Safety: | 26-36 |
PSA: | 189.07000 |
LogP: | 2.75290 |
teniposide
Conditions | Yield |
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G-values; |
(5-nitrothiophen-2-yl)methanol
teniposide
Conditions | Yield |
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With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 18h; | 38% |
1-(5-nitrothiophen-2-yl)ethan-1-ol
teniposide
Conditions | Yield |
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With triphenylphosphine; diethylazodicarboxylate at 20℃; for 18h; | 19% |
teniposide
Conditions | Yield |
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With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 8h; | A 15% B 17% |
teniposide
Conditions | Yield |
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With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 8h; | A 150 mg B 15% |
teniposide
Conditions | Yield |
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With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 5h; | 15% |
teniposide
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 5h; | 15% |
teniposide
Conditions | Yield |
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With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 1.5h; | 14% |
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 0.5h; Molecular sieve; | 14% |
teniposide
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 1.5h; | 12% |
teniposide
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 5h; |
The IUPAC Name of EPT is (5S,5aR,8aR,9R)-5-[[(4aR,7R,8R,8aS)-7,8-dihydroxy-2-thiophen-2-yl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one. With the CAS registry number 29767-20-2 and EINECS 249-831-2, it is also named as Teniposide. The product's category is Active Pharmaceutical Ingredients. When heated to decomposition it emits very toxic fumes of SOx. Additioanlly, this chemical should be sealed in the container and stored in the cool and dry place.
The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.71; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): 1.71; (4)ACD/LogD (pH 7.4): 1.71; (5)ACD/BCF (pH 5.5): 11.81; (6)ACD/BCF (pH 7.4): 11.78; (7)ACD/KOC (pH 5.5): 203.76; (8)ACD/KOC (pH 7.4): 203.18; (9)#H bond acceptors: 13; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 9; (12)Polar Surface Area: 156.07 Å2; (13)Index of Refraction: 1.697; (14)Molar Refractivity: 158.33 cm3; (15)Molar Volume: 410.8 cm3; (16)Surface Tension: 82.4 dyne/cm; (17)Enthalpy of Vaporization: 131.6 kJ/mol; (18)Vapour Pressure: 7.18E-32 mmHg at 25°C; (19)Rotatable Bond Count: 6; (20)Tautomer Count: 4; (21)Exact Mass: 656.156362; (22)MonoIsotopic Mass: 656.156362; (23)Topological Polar Surface Area: 189; (24)Heavy Atom Count: 46; (25)Complexity: 1090.
Uses of EPT: It is a chemotherapeutic medication mainly used in the treatment of childhood acute lymphocytic leukemia (ALL). Because it inhibits DNA synthesis by forming a complex with topoisomerase II and DNA. When used with other chemotherapeutic agents for the treatment of ALL, EPT results in severe myelosuppression.
When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing.
People can use the following data to convert to the molecule structure.
1. SMILES:O=C1OC[C@H]8[C@H]1[C@H](c2cc(OC)c(O)c(OC)c2)c4cc3OCOc3cc4[C@H]8O[C@@H]7O[C@H]5[C@@H](OC(OC5)c6sccc6)[C@H](O)[C@H]7O
2. InChI:InChI=1/C32H32O13S/c1-37-19-6-13(7-20(38-2)25(19)33)23-14-8-17-18(42-12-41-17)9-15(14)28(16-10-39-30(36)24(16)23)44-32-27(35)26(34)29-21(43-32)11-40-31(45-29)22-4-3-5-46-22/h3-9,16,21,23-24,26-29,31-35H,10-12H2,1-2H3/t16-,21+,23+,24-,26+,27+,28+,29+,31?,32-/m0/s1
The following are the toxicity data which has been tested.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
human | TDLo | intravenous | 26mg/kg/10D-I (26mg/kg) | BLOOD: AGRANULOCYTOSIS BLOOD: APLASTIC ANEMIA BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE | Cancer Vol. 34, Pg. 985, 1974. |
human | TDLo | intravenous | 132mg/kg/7W-I (132mg/kg) | GASTROINTESTINAL: NAUSEA OR VOMITING BLOOD: LEUKOPENIA | Cancer Treatment Reports. Vol. 63, Pg. 7, 1979. |
human | TDLo | oral | 9579mg/kg (9579mg/kg) | BEHAVIORAL: ANOREXIA (HUMAN GASTROINTESTINAL: NAUSEA OR VOMITING SKIN AND APPENDAGES (SKIN): HAIR: OTHER | European Journal of Cancer. Vol. 14, Pg. 1395, 1978. |
mouse | LD50 | intraperitoneal | 29570ug/kg (29.57mg/kg) | National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986, | |
mouse | LD50 | subcutaneous | 31560ug/kg (31.56mg/kg) | National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986, | |
rat | LD17 | intraperitoneal | 50mg/kg (50mg/kg) | Cancer Treatment Reports. Vol. 60, Pg. 1127, 1976. | |
rat | LDLo | intravenous | 15mg/kg (15mg/kg) | LUNGS, THORAX, OR RESPIRATION: DYSPNEA GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" BLOOD: LEUKOPENIA | Proceedings of the European Society of Toxicology. Vol. 17, Pg. 171, 1976. |