Basic information
- CAS
29767-20-2- Standard SMILES
COc1cc([C@@H]2c3cc4c(cc3[C@@H](O[C@@H]3O[C@@H]5COC(c6cccs6)O[C@H]5[C@H](O)[C@H]3O)[C@H]3COC(=O)[C@H]23)OCO4)cc(OC)c1O- InChIKey
NRUKOCRGYNPUPR-PSZSYXFXSA-N- Molecular formula
- C32H32O13S
- Average molar mass
- 656.7 g/mol
- Monoisotopic mass
- 656.15636224
Overview
Teniposide is a furonaphthodioxole that is a synthetic derivative of podophyllotoxin with anti-tumour activity; causes single- and double-stranded breaks in DNA and DNA-protein cross-links and prevents repair by topoisomerase II binding. It has a role as an antineoplastic agent and an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor. It is a beta-D-glucoside, a member of thiophenes, a member of phenols, an aromatic ether, a gamma-lactone, a furonaphthodioxole, a cyclic acetal and a monosaccharide derivative. It is functionally related to a podophyllotoxin.
Names & identifiers
- Preferred name
- Teniposidum
- IUPAC
- (5S,5aR,8aR,9R)-5-[[(4aR,6R,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
- English name
- Teniposide
- Molecular formula
- C32H32O13S
- Molecular weight
- 656.65
Names & synonyms
TeniposidumRefChem:1048736(5S,5aR,8aR,9R)-5-(((4aR,6R,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-oneTeniposidum [INN-Latin]Teniposido [INN-Spanish]SCHEMBL94844(5R,5aR,8aR,9S)-9-(((4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-(thiophen-2-yl)hexahydropyrano[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(5S,5aR,8aR,9R)-9-(4-hydroxy-3,5-dimethoxyphenyl)-8-oxo-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl 4,6-O-(2-thienylmethylene)-beta-D-glucopyranosideFuro[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)-.beta.-D-glucopyranosyl]oxy]-, (5R,5aR,8aR,9S)-etpvehemvm-26
Show more names
VumonEniposidensc122819
Properties
Computed structural properties
- XLogP
- 1.2
- Topological polar surface area
- 189 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 14
- Rotatable bonds
- 6
- Heavy atoms
- 46
- Formal charge
- 0
- Complexity
- 1,090
Experimental & physicochemical properties
LogP1.5
Solubility5.98e-02 g/L
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 244 · 244-247°C
- alpha
- 20 · D20 -107° (9:1 chloroform/methanol)
- Boiling point
- 650.86 °C · 650.86°C (rough estimate)
- Density
- 1.2568 · 1.2568 (rough estimate)
- refractive index
- 1.553 · 1.5530 (estimate)
- storage temp.
- -20 °C · -20°C
- solubility
- 10 mg/mL, · DMSO: soluble10mg/mL, clear
- pka
- 10.13 · 10.13(at 25℃)
- form
- powder
- color
- white to beige
- optical activity
- -100 to · [α]/D -100 to -115°, c = 1 in chloroform/methanol (9:1)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
Toxicity Summary
The mechanism of action appears to be related to the inhibition of type II topoisomerase activity since teniposide does not intercalate into DNA or bind strongly to DNA. Teniposide binds to and inhibits DNA topoisomerase II. The cytotoxic effects of teniposide are related to the relative number of double-stranded DNA breaks produced in cells, which are a reflection of the stabilization of a topoisomerase II-DNA intermediate.
Carcinogen Classification2A, probably carcinogenic to humans. (L135)
Safety data
- wgk
- 3
- rtecs
- KC0180000
- ridadr
- UN 2811 6.1 / PGIII
- hs_code
- 29349990
- Toxicity
- LD50 intraperitoneal in mouse: 29570ug/kg
- risk_code
- 36/37/38-45
- Signal word
- Warning
- Symbol(GHS)
- GHS08
- hazard_code
- Xi,T
- safety_code
- 26-36-45-53
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard statements
- H341-H412
- Hazard Classifications
- Carc. 1B
- Precautionary statements
- P202-P273-P280-P308+P313-P405-P501
- Hazardous Substances Data
- 29767-20-2(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Metabolism/MetabolitesRoute of Elimination: From 4% to 12% of a dose is excreted in urine as parent drug. Fecal excretion of radioactivity within 72 hours after dosing accounted for 0% to 10% of the dose.
Half Life: 5 hours
Cellular LocationsCytoplasm
Metabolite PathwaysTeniposide Action Pathway
Uses & manufacturing
UsesTeniposide is used for the treatment of refractory acute lymphoblastic leukaemia
Applications
UsesTeniposide is a podophyllotoxin derivative that causes dose-dependent single- and double-stranded breaks in DNA by inhibiting topoisomerase II. Its cytostatic effects are related to its ability to stabilize the DNA-topoisomerase II complex during DNA replication, inducing DNA damage and cellular apoptosis. Teniposide has been widely used in the treatment of various cancers including, small cell lung cancer, malignant lymphoma, breast cancer, oral squamous cell carcinoma, and acute lymphoblastic leukemia.
UsesA labelled semi-synthetic derivative of Podophyllotoxin. Antineoplastic.
UsesA semi-synthetic derivative of Podophyllotoxin. Antineoplastic.
General DescriptionTeniposide is available in 50-mg ampules with Cremophor ELfor IV administration in the treatment of acute lymphoblasticleukemia (ALL). The agent is more potent as an inhibitor oftopoisomerase II. The pharmacokinetics of teniposide issimilar to that of etoposide; however, the more lipophilic teniposideis more highly protein bound (99%) and less isexcreted unchanged in the urine (10%–20%). There is alsogreater overall metabolism of teniposide; however, CYP3A4-mediated conversion to the active catechol is slower comparedwith etoposide. Elimination occurs primarily in the urine witha terminal elimination half-life of 5 hours.
Related reactions
0 records
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Compound notes
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