Teniposide

ChemicalBook > CAS DataBase List > Teniposide

Product Name: Teniposide
CAS No.: 29767-20-2
Chemical Name: Teniposide
Synonyms: etp;vehem;vm-26;Vumon;Eniposide;nsc122819;Teniposid;Tenoposide;nsc-122819;TENIPOSIDE
CBNumber: CB0455475
Molecular Formula: C32H32O13S
Formula Weight: 656.65
MOL File: 29767-20-2.mol

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Teniposide Property

Melting point:: 244-247°C
alpha: D20 -107° (9:1 chloroform/methanol)
Boiling point:: 650.86°C (rough estimate)
Density: 1.2568 (rough estimate)
refractive index: 1.5530 (estimate)
storage temp.: -20°C
solubility: DMSO: soluble10mg/mL, clear
pka: 10.13(at 25℃)
form: powder
color: white to beige
optical activity: [α]/D -100 to -115°, c = 1 in chloroform/methanol (9:1)
λmax: 283nm(MeOH)(lit.)
Merck: 14,9145
Stability:: Hygroscopic
CAS DataBase Reference: 29767-20-2(CAS DataBase Reference)
IARC: 2A (Vol. 76) 2000

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Safety

Hazard Codes: Xi,T
Risk Statements: 36/37/38-45
Safety Statements: 26-36-45-53
RIDADR: UN 2811 6.1 / PGIII
WGK Germany: 3
RTECS: KC0180000
HS Code: 29349990
Hazardous Substances Data: 29767-20-2(Hazardous Substances Data)
Toxicity: LD50 intraperitoneal in mouse: 29570ug/kg

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H341Suspected of causing genetic defects

H412Harmful to aquatic life with long lasting effects

Precautionary statements

P202Do not handle until all safety precautions have been read and understood.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P308+P313IF exposed or concerned: Get medical advice/attention.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: SML0609
Product name: Teniposide
Purity: ≥97% (HPLC)
Packaging: 10mg
Price: $74.1
Updated: 2024/03/01

Sigma-Aldrich

Product number: 1643736
Product name: Teniposide
Purity: United States Pharmacopeia (USP) Reference Standard
Packaging: 200mg
Price: $429
Updated: 2022/05/15

TCI Chemical

Product number: T3109
Product name: Teniposide
Purity: >98.0%(HPLC)
Packaging: 20mg
Price: $101
Updated: 2024/03/01

TCI Chemical

Product number: T3109
Product name: Teniposide
Purity: >98.0%(HPLC)
Packaging: 100mg
Price: $323
Updated: 2024/03/01

Cayman Chemical

Product number: 14425
Product name: Teniposide
Purity: ≥98%
Packaging: 10mg
Price: $32
Updated: 2024/03/01

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Teniposide Chemical Properties,Usage,Production

Chemical Properties

White Solid

Originator

Vehem,Sandoz,France,1976

Uses

Teniposide 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.

Uses

A labelled semi-synthetic derivative of Podophyllotoxin. Antineoplastic.

Uses

A semi-synthetic derivative of Podophyllotoxin. Antineoplastic.

Indications

Teniposide (VM-26, Vumon) is closely related to etoposide in structure, mechanisms of action and resistance, and adverse effects. It is more lipophilic and approximately threefold more potent than etoposide. Its major uses have been in pediatric cancers, particularly in acute lymphoblastic leukemias.

Definition

ChEBI: 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.

Manufacturing Process

10 ml of pure thiophene-2-aldehyde and 0.25 g of anhydrous zinc chloride are American Home Products Corporation; British Patent 1,022,642; March 16, 1966
American Home Products Corporation; British Patent 1,022,645; March 16, 1966
Bell, S.C.; British Patent 1,057,492; February 1, 1967; assigned to American Home Products Corporation

brand name

Vumon (Bristol-Myers Squibb).

Therapeutic Function

Antineoplastic

General Description

Teniposide 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.

Biochem/physiol Actions

Teniposide (VM-26) is a Topoisomerase II inhibitor with antitumor activity. Teniposide inhibits DNA synthesis by forming a complex with topoisomerase II and DNA, inducing breaks in double stranded DNA and preventing repair.

Clinical Use

Teniposide is used in combination with other agents for the treatment of refractory childhood acute lymphoblastic leukemia.

Safety Profile

Poison by intraperitoneal and subcutaneous routes. An experimental teratogen. Human systemic effects by ingestion and intravenous route: anorexia, nausea or vomiting, leukopenia, agranulocytosis and aplastic anemia of the blood, bone marrow changes, and hair changes. Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits very toxic fumes of SOx.

Synthesis

Teniposide, [5R-(5|á,5a|?,8a|á,9|?)]-9-[4,6-O-(2-thienylmethylene)-|?-D-glucopyranosyl)oxy]- 5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)furo[3,4: 6,7]-naphtho[2,3-d]-1,3-dioxol-6(5aH)-one (30.4.9), is basically synthesized by an analogous scheme from 4-benzyloxy-4-desmethylepipodophyllotoxin (30.4.6), which is esterified by 2,3,4,6- tetra-O-acetyl-|?-D-glucose in the presence of boron trifluoride etherate, giving a glycoside 30.4.7. The acetyl and benzyloxycarbonyl protecting groups in this molecule are removed by succesive use of zinc acetate and sodium methoxide, and then by subsequent hydrogen reduction, which forms the diol 30.4.8. The resulting diol is then transformed into the corresponding acetal 2-formylthiophene, which is the desired teniposide (30.4.9) .

storage

Store at -20°C

Teniposide Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Teniposide manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD

Product: Teniposide 29767-20-2
Price: US $0.00/Kg/Bag
Min. Order: 10g
Purity: 98%min
Supply Ability: 10kg
Release date: 2021-09-23

Zhuozhou Wenxi import and Export Co., Ltd

Product: Teniposide 29767-20-2
Price: US $15.00-10.00/KG
Min. Order: 1KG
Purity: 99%+ HPLC
Supply Ability: Monthly supply of 1 ton
Release date: 2021-08-11

Zhuozhou Wenxi import and Export Co., Ltd

Product: Teniposide 29767-20-2
Price: US $15.00-10.00/KG
Min. Order: 1KG
Purity: 99%+ HPLC
Supply Ability: Monthly supply of 1 ton
Release date: 2021-07-10

29767-20-2, TeniposideRelated Search:

Podophyllotoxin CHLOROPHOSPHONAZO III Centchroman Ethylparaben Methylparaben Ethyl 4-hydroxybenzoate,sodium salt Sodium methylparaben 4'-demethylepipodophyllotoxin-9 beta-glucopyranoside MATAIRESINOL 3,3-Diphenylpropionic acid 3,5-DIMETHOXYPHENYLPROPIONIC ACID 4'-Demethylepipodophyllotoxin 7-HYDROXY-1,2,3,4-TETRAHYDRO-NAPHTHALENE-2-CARBOXYLIC ACID 2-NAPHTHALENECARBOXYLIC ACID, 1,2,3,4-TETRAHYDRO-6-HYDROXY- 6-METHOXY-1,2,3,4-TETRAHYDRO-NAPHTHALENE-2-CARBOXYLIC ACID 3,3-Diphenylpropionic Acid Ethyl Ester (R)-4-(4-Methoxybenzyloxy)-1,2-butanediol (-)-HYDROXYMATAIRESINOL

(5R,5aα)-5α,8,8aβ,9β-Tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-9-[[4-O,6-O-[(R)-2-thienylmethylene]-β-D-glucopyranosyl]oxy]furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one

4'-Demethylepipodophyllotoxin-9-(4,6-O-2-thenylidene β-D-glucopyranoside)

4’-Demethylepipodophyllotoxin9-(4,6-o-2-thenylidene-

4'-Demethylepipodophyllotoxin thenylidene glucoside

Epipodophyllotoxin, 4'-demethyl-, 9-(4,6-o-2-thienylidene-.beta.-D-glucopyranoside)

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)-.beta.-D-glucopyranosyl]oxy]-, [5R-(5.alpha.,5A.beta.,8A.alpha.,9.beta.)]-

(10R,11R,15R,16S)-16-{[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-(thiophen-2-yl)-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl]oxy}-10-(4-hydroxy-3,5-diMethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1,3(7),8-trien-12-one

Teniposide(VuMon)

(10R,11R,15R,16R)-16-{[(4aR,7R,8R,8aS)-7,8-dihydroxy-2-(thiophen-2-yl)-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl]oxy}-10-(4-hydroxy-3,5-diMethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1(9),2,7-trien-12-one

(5R,5aR,8aR,9S)-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-9-[[4,6-O-[(R)-2-thienylmethylene]-β-D-glucopyranosyl]oxy]-furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one

4′-Dimethyl-9-(4,6-O-2-thenyid)-epipodophyllotoxin

Tenoposide

Eniposide

4’-demethylepipodophyllotoxin9-(4,6-o-2-thenylidene-beta-d-glucopyranoside)

4’-demethyl-epipodophyllotoxin-beta-d-thenylidene-glucosid

4’-demethyl-epipodophyllotoxin-beta-d-thenylidene-glucoside

4’-demethylepipodophyllotoxin-beta-d-thenylidineglucoside

5abeta,8aalpha,9beta(r*)]]-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-[5r-[5alph

dimethoxyphenyl)-9]]4-6-o-(2-thienylmethylene)-beta-d-glucopyranosyl]oxy]furo[

epipodophyllotoxin,4’-demethyl-,9-(4,6-o-2-thenylidene-beta-d-glucopyranoside

etp

eniposide, Vumon, VM-26

3’,4’:6,7]naphtho[2,3-d]-1,3-dioxol-6(5ah)-one

4’-demethyl1-o-(4,6-o,o-(2-thenylidene)-beta-d-glucopyranosyl)epipodophyllot

4’-demethyl1-o-(4,6-o,o-(2-thenylidene)-beta-d-glucopyranosyl)epipodophylloto

4’-demethylepipodophyllotoxin9-(4,6-o-2-thenylidene-bata-d-glucopyranoside.

nsc122819

nsc-122819

TENIPOSIDE

vehem

vm-26

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-[(R)-2-thienylmethylene]-b-D-glucopyranosyl]oxy]-, (5R,5aR,8aR,9S)-

[5R-[5alpha,5abeta,8aalpha,9beta(R*)]]-5,8,8a,9-Tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-9-[[4,6-O-(2-thienylmethylene)-beta-D-glucopyranosyl]oxy]-furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one

4'-Demethyl 1-O-(4,6-O,O-(2-thenylidene)-beta-D-glucopyranosyl)epipodophyllotoxin

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)-beta-D-glucopyranosyl)-oxy)-, (5R-(5alpha,5abeta,8aalpha,9beta(R*)))

Pipodophyllotoxin VM 26

Vumon

4'-Dimethylepipodophyllotoxin-9-(4,6-O-2-thenylidene)-b-D-glucopyranoside

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-[(R)-2-thienylmethylene]-β-D-glucopyranosyl]oxy]-, (5R,5aR,8aR,9S)-

Teniposide USP/EP/BP

Teniposide Impurity 2

Teniposide (1643736)

Methylguanidoacetic acid monohydrate

(5R,5aR,8aR,9S)-9-(((2R,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)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one

Teniposid

Teniposide (200 mg) (PLANNED TO BE DISCONTINUED)

4'-Dimethylepipodophyllotoxin-(4,6-O-2-thenylidene)-beta-D-glucopyranoside

Teniposide, 10 mM in DMSO

29767-20-2

29707-20-2

29767-20-7

C32H32O13S

C32H29D3O13S

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