Name: Teniposide
SKU: 29767-20-2

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Basic Information

Molecular Structure:
CAS No.:	29767-20-2
Name:	Teniposide

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

Synthetic route

: 9-[(4,6-O-(thien-2-ylmethylidene-Β-D-glucopyranosyl)oxy)-5,8,9a,9-tetrahydro-5-(4-(5-nitrothien-2-yl)methoxy)3,5-dimethoxyphenyl]furo[3',4':6,7]naphtha[2,3-d]-1,3-dioxol-6(5aH)-one

: 29767-20-2
teniposide

Conditions

Conditions	Yield
G-values;

: 20898-85-5
(5-nitrothiophen-2-yl)methanol

: 29767-20-2
teniposide

: 9-[(4,6-O-(thien-2-ylmethylidene-Β-D-glucopyranosyl)oxy)-5,8,9a,9-tetrahydro-5-(4-(5-nitrothien-2-yl)methoxy)3,5-dimethoxyphenyl]furo[3',4':6,7]naphtha[2,3-d]-1,3-dioxol-6(5aH)-one

Conditions

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 18h;	38%

: 74786-64-4
1-(5-nitrothiophen-2-yl)ethan-1-ol

: 29767-20-2
teniposide

: 9-[(4,6-O-(thien-2-ylmethylidene-Β-D-glucopyranosyl)oxy)-5,8,8a,9-tetrahydro-5-(4-(1-(5-nitrothien-2-yl)ethoxy)-3,5-dimethoxyphenyl)]furo[3',4':6,7]naphtha[2,3-d]-1,3-dioxol-6(5aH)-one

Conditions

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate at 20℃; for 18h;	19%

: ((5-fluoro-benzothiazole-2-yl)thio)acetic acid

: 29767-20-2
teniposide

A: 2″-(((5-fluoro-benzothiazole-2-yl)thio)acetato)teniposide

B: 3″-(((5-fluoro-benzothiazole-2-yl)thio)acetato)teniposide

Conditions

Conditions	Yield
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%

...Expand

: ((5-fluoro-benzoxazole-2-yl)thio)acetic acid

: 29767-20-2
teniposide

A: 2″-(((5-fluoro-benzoxazole-2-yl)thio)acetato)teniposide

B: 3″-(((5-fluoro-benzoxazole-2-yl)thio)acetato)teniposide

Conditions

Conditions	Yield
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%

...Expand

: ((5-fluoro-benzoxazole-2-yl)thio)acetic acid

: 29767-20-2
teniposide

: 3″-(((5-fluoro-benzoxazole-2-yl)thio)acetato)teniposide

Conditions

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%

: ((5-fluoro-benzothiazole-2-yl)thio)acetic acid

: 29767-20-2
teniposide

: 3″-(((5-fluoro-benzothiazole-2-yl)thio)acetato)teniposide

Conditions

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%

: ((5-fluoro-benzothiazole-2-yl)thio)acetic acid

: 29767-20-2
teniposide

: 2",3"-(((di-(5-fluorobenzothiazole-2-yl)thio)acetato))teniposide

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 1.5h;	14%
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 0.5h; Molecular sieve;	14%

: ((5-fluoro-benzoxazole-2-yl)thio)acetic acid

: 29767-20-2
teniposide

: 2",3"-(((di-(5-fluorobenzoxazole-2-yl)thio)acetato))teniposide

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 1.5h;	12%

: ((5-fluoro-benzothiazole-2-yl)thio)acetic acid

: 29767-20-2
teniposide

: 2″-(((5-fluoro-benzoxazole-2-yl)thio)acetato)teniposide

Conditions

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;

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Specification

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 SO_x. 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.

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Specification