temozolomide

Also known as TMZ, methazolastone, 8-carbamoyl-3-methylimidazo(5,1-d)-1,2,3,5-tetrazin-4(3H)-one, 3,4-dihydro-3-methyl-4-oxoimidazo(5,1-d)-as-tetrazine-8-carboxamide, 3-methyl-4-oxo-3,4-dihydroimidazo(5,1-d)(1,2,3,5)tetrazine-8-carboxamide, 3,4-dihydro-3-methyl-4-oxoimidazo(5,1-d)-1,2,3,5-tetrazine-8-carboxamide

Temozolomide, sold under the brand name Temodar among others, is an anticancer medication used to treat brain tumors such as glioblastoma and anaplastic astrocytoma. It is taken by mouth or via intravenous infusion.

In the Vinony graph

Vinony's link graph records 367 inbound references to temozolomide, and connects out to chemotherapy, hydrolysis and glioblastoma.

It is catalogued under topics including Alkylating antineoplastic agents, Cancer treatments and Carboxamides.

Vinony links it to 29 Wikipedia language editions.

Key facts

Drug.Verifiedfields: changed
Drug.Watchedfields: changed
Drug.verifiedrevid: 477861554
Drug.image: Temozolomide structure.svg
Drug.image_class: skin-invert-image
Drug.width: 160
Drug.image2: Temozolomide-3D-spacefill.png
Drug.image_class2: bg-transparent
Drug.width2: 160
Drug.tradename: Temodar, Temodal, Temcad, others
Drug.MedlinePlus: a601250
Drug.licence_EU: yes
Drug.DailyMedID: Temozolomide
Drug.pregnancy_AU: D
Drug.routes_of_administration: By mouth, intravenous
Drug.ATC_prefix: L01
Drug.ATC_suffix: AX03
Drug.legal_UK: POM

via Wikipedia infobox

Chemical data

Formula: C6H6N6O2
Molecular weight: 194.15 g/mol
IUPAC name: 3-methyl-4-oxoimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide
SMILES: CN1C(=O)N2C=NC(=C2N=N1)C(=O)N
InChIKey: BPEGJWRSRHCHSN-UHFFFAOYSA-N
XLogP: -1.1
Polar surface area: 106 Å²
H-bond donors: 1
H-bond acceptors: 5
Formal charge: 0

via PubChem

Research

12,869 papers

Randomized Study of Temozolomide or Temozolomide and Capecitabine in Patients With Advanced Pancreatic Neuroendocrine Tumors (ECOG-ACRIN E2211).Journal of clinical oncology : official journal of the American Society of Clinical Oncology · 2023
Lomustine-temozolomide combination therapy versus standard temozolomide therapy in patients with newly diagnosed glioblastoma with methylated MGMT promoter (CeTeG/NOA-09): a randomised, open-label, phase 3 trial.Lancet (London, England) · 2019
Elucidating the mechanisms of Temozolomide resistance in gliomas and the strategies to overcome the resistance.Biochimica et biophysica acta. Reviews on cancer · 2021
Temozolomide versus standard 6-week radiotherapy versus hypofractionated radiotherapy in patients older than 60 years with glioblastoma: the Nordic randomised, phase 3 trial.The Lancet. Oncology · 2012
Temozolomide and flavonoids against glioma: from absorption and metabolism to exosomal delivery.Naunyn-Schmiedeberg's archives of pharmacology · 2024

via PubMed

Wikidata facts

Mass: 194.055

Show 4 more facts

chemical formula: C₆H₆N₆O₂
canonical SMILES: CN1C(=O)N2C=NC(=C2N=N1)C(=O)N
World Health Organisation international non-proprietary name: temozolomide
Commons category: Temozolomide

Sources (6)

via Wikidata · CC0

~11 min read

Encyclopedic overview

13 sections

Contents

Medical uses
Contraindications
Adverse effects
Interactions
Pharmacology
Mechanism of action
Pharmacokinetics
Chemical properties
History
Research
References
Further reading
External links

The most common side effects with temozolomide are nausea, vomiting, constipation, loss of appetite, alopecia (hair loss), headache, fatigue, convulsions (seizures), rash, neutropenia or lymphopenia (low white-blood-cell counts), and thrombocytopenia (low blood platelet counts). People receiving the solution for infusion may also have injection-site reactions, such as pain, irritation, itching, warmth, swelling and redness, as well as bruising.

Excerpted from Wikipedia’s “temozolomide” article, available under the CC BY-SA 4.0 licence.