29767-20-2 Usage
Description
Teniposide, also known as Vumon, is a semi-synthetic derivative of podophyllotoxin with potent anti-neoplastic and anti-tumor activity. It is a white solid available in 50-mg ampules with Cremophor EL for intravenous administration, primarily used in the treatment of acute lymphoblastic leukemia (ALL). Teniposide exerts its cytostatic effects by inhibiting topoisomerase II, causing dose-dependent singleand double-stranded breaks in DNA, and stabilizing the DNA-topoisomerase II complex during DNA replication, which leads to DNA damage and cellular apoptosis.
Uses
Used in Oncology:
Teniposide is used as an antineoplastic agent for the treatment of various cancers, including small cell lung cancer, malignant lymphoma, breast cancer, oral squamous cell carcinoma, and acute lymphoblastic leukemia. It is particularly effective due to its ability to inhibit topoisomerase II, leading to DNA damage and apoptosis in cancer cells.
Used in Drug Development:
As a promising pharmaceutical candidate, Teniposide is also used in the development of novel drug delivery systems to enhance its applications and efficacy against cancer cells. Researchers are exploring the use of various organic and metallic nanoparticles as carriers for Teniposide delivery, aiming to improve its delivery, bioavailability, and therapeutic outcomes.
Chemical Properties:
Teniposide is a furonaphthodioxole derivative with the chemical properties of a white solid. It is more lipophilic than some other related compounds, leading to higher protein binding (99%) and less excretion unchanged in the urine (10%–20%). The pharmacokinetics of Teniposide is similar to that of etoposide, but with a slower CYP3A4-mediated conversion to the active catechol. Elimination of Teniposide primarily occurs in the urine, with a terminal elimination half-life of 5 hours.
Brand Name:
The brand name for Teniposide is Vumon, which is manufactured by Bristol-Myers Squibb.
Originator
Vehem,Sandoz,France,1976
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,
1966American Home Products Corporation; British Patent 1,022,645; March 16,
1966Bell, S.C.; British Patent 1,057,492; February 1, 1967; assigned to American
Home Products Corporation
Therapeutic Function
Antineoplastic
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-(5α,5aβ,8aα,9β)]-9-[4,6-O-(2-thienylmethylene)-β-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-β-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) .
Check Digit Verification of cas no
The CAS Registry Mumber 29767-20-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,9,7,6 and 7 respectively; the second part has 2 digits, 2 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 29767-20:
(7*2)+(6*9)+(5*7)+(4*6)+(3*7)+(2*2)+(1*0)=152
152 % 10 = 2
So 29767-20-2 is a valid CAS Registry Number.
29767-20-2Relevant articles and documents
Preparation method of etoposide, teniposide and analogs of etoposide and teniposide
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Paragraph 0106; 0107; 0108; 0120; 0121; 0122, (2017/01/02)
The invention discloses a preparation method of etoposide, teniposide and analogs of etoposide and teniposide. The preparation method includes the following steps of 1, selective protection of 4'domethylpodophyllotoxin4'hydroxy; 2, introduction of 4 hydroxy hydroxyl; 3, removal of a protecting group. The method is mild in reaction condition and environmentally friendly, and the yield and purity of the products are high.
