Teniposide | 29767-20-2

Teniposide Properties

Melting point	244-247°C
Boiling point	650.86°C (rough estimate)
alpha	D20 -107° (9:1 chloroform/methanol)
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)
FDA UNII	957E6438QA
NCI Dictionary of Cancer Terms	teniposide
NCI Drug Dictionary	teniposide
ATC code	L01CB02
Proposition 65 List	Teniposide
IARC	2A (Vol. 76) 2000

SAFETY

Risk and Safety Statements

Symbol(GHS)

GHS08

Signal word

Warning

Hazard statements

H341-H412

Precautionary statements

P202-P273-P280-P308+P313-P405-P501

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

Toxicity

LD50 intraperitoneal in mouse: 29570ug/kg

NFPA 704

	0
2		0

Teniposide price More Price(42)

Manufacturer	Product number	Product description	CAS number	Packaging	Price	Updated	Buy
Sigma-Aldrich	SML0609	Teniposide ≥97% (HPLC)	29767-20-2	10mg	$74.1	2024-03-01	Buy
Sigma-Aldrich	1643736	Teniposide United States Pharmacopeia (USP) Reference Standard	29767-20-2	200mg	$429	2022-05-15	Buy
TCI Chemical	T3109	Teniposide >98.0%(HPLC)	29767-20-2	20mg	$101	2024-03-01	Buy
TCI Chemical	T3109	Teniposide >98.0%(HPLC)	29767-20-2	100mg	$323	2024-03-01	Buy
Cayman Chemical	14425	Teniposide ≥98%	29767-20-2	10mg	$32	2024-03-01	Buy

Product number	Packaging	Price	Buy
SML0609	10mg	$74.1	Buy
1643736	200mg	$429	Buy
T3109	20mg	$101	Buy
T3109	100mg	$323	Buy
14425	10mg	$32	Buy

Teniposide Chemical Properties,Uses,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 semi-synthetic derivative of Podophyllotoxin. Antineoplastic.

Uses

A labelled semi-synthetic derivative of Podophyllotoxin. Antineoplastic.

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.

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.

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) .

Synthesis_29767-20-2

storage

Store at -20°C

Teniposide Preparation Products And Raw materials

Raw materials

4'-demethylepipodophyllotoxin-9 beta-glucopyranoside 2-Thiophenecarboxaldehyde

Preparation Products

Teniposide Suppliers

Global( 219)Suppliers

Supplier	Tel	Email	Country	ProdList	Advantage
career henan chemical co	+86-0371-86658258	sales@coreychem.com	China	29914	58
Nanjing Dolon Biotechnology Co.,Ltd.	18905173768	sales@dolonchem.com	CHINA	2972	58
Hubei Jusheng Technology Co.,Ltd.	18871490254	linda@hubeijusheng.com	CHINA	28180	58
Xiamen AmoyChem Co., Ltd	+86-592-6051114 +8618959220845	sales@amoychem.com	China	6387	58
Hubei xin bonus chemical co. LTD	86-13657291602	linda@hubeijusheng.com	CHINA	22968	58
BOC Sciences	+1-631-485-4226	inquiry@bocsci.com	United States	19553	58
Chongqing Chemdad Co., Ltd	+86-023-61398051 +8613650506873	sales@chemdad.com	China	39916	58
CONIER CHEM AND PHARMA LIMITED	+8618523575427	sales@conier.com	China	49391	58
Shaanxi Dideu Medichem Co. Ltd	+86-29-87569266 15319487004	1015@dideu.com	China	2263	58
TargetMol Chemicals Inc.	+1-781-999-5354 +1-00000000000	marketing@targetmol.com	United States	19892	58

Supplier	Advantage
career henan chemical co	58
Nanjing Dolon Biotechnology Co.,Ltd.	58
Hubei Jusheng Technology Co.,Ltd.	58
Xiamen AmoyChem Co., Ltd	58
Hubei xin bonus chemical co. LTD	58
BOC Sciences	58
Chongqing Chemdad Co., Ltd	58
CONIER CHEM AND PHARMA LIMITED	58
Shaanxi Dideu Medichem Co. Ltd	58
TargetMol Chemicals Inc.	58

View Lastest Price from Teniposide manufacturers

Update time	Product	Price	Min. Order	Purity	Supply Ability	Manufacturer
2021-09-29	Teniposide 29767-20-2	US $0.00 / Kg/Bag	10g	98%min	10kg	WUHAN FORTUNA CHEMICAL CO., LTD
2021-08-12	Teniposide 29767-20-2	US $15.00-10.00 / KG	1KG	99%+ HPLC	Monthly supply of 1 ton	Zhuozhou Wenxi import and Export Co., Ltd
2021-07-13	Teniposide 29767-20-2	US $15.00-10.00 / KG	1KG	99%+ HPLC	Monthly supply of 1 ton	Zhuozhou Wenxi import and Export Co., Ltd

Teniposide
29767-20-2
US $0.00 / Kg/Bag
98%min
WUHAN FORTUNA CHEMICAL CO., LTD

Teniposide
29767-20-2
US $15.00-10.00 / KG
99%+ HPLC
Zhuozhou Wenxi import and Export Co., Ltd

Teniposide
29767-20-2
US $15.00-10.00 / KG
99%+ HPLC
Zhuozhou Wenxi import and Export Co., Ltd

Teniposide Spectrum

Teniposide(29767-20-2)¹HNMR

29767-20-2(Teniposide)Related Search:

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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

1of4

(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 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 eniposide, Vumon, 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]-β-D-glucopyranosyl]oxy]-, (5R,5aR,8aR,9S)- Teniposide USP/EP/BP Teniposide Impurity 2 Teniposide (1643736) Methylguanidoacetic acid monohydrate etp (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) (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 29767-20-2 29707-20-2 29767-20-7 C32H32O13S C32H29D3O13S Carbohydrates & Derivatives Chiral Reagents Heterocycles Intermediates & Fine Chemicals Pharmaceuticals Isotope Labelled Compounds