Temozolomide

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.

Temozolomide
Clinical data
Trade namesTemodar, Temodal, Temcad, others
Other namesTMZ
AHFS/Drugs.comMonograph
MedlinePlusa601250
License data
Pregnancy
category
  • AU: D
Routes of
administration
By mouth, intravenous
ATC code
Legal status
Legal status
  • UK: POM (Prescription only)
  • US: WARNINGRx-only
  • EU: Rx-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailabilityalmost 100%
Protein binding15% (10–20%)
Metabolismhydrolysis
Metabolites3-methyl-(triazen-1-yl)imidazole-4-carboxamide (MTIC, the active species); temozolomide acid
Elimination half-life1.8 hours
Excretionmainly kidney
Identifiers
  • 4-methyl-5-oxo-2,3,4,6,8-pentazabicyclo[4.3.0]nona-2,7,9-triene-9-carboxamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.158.652
Chemical and physical data
FormulaC6H6N6O2
Molar mass194.154 g·mol−1
3D model (JSmol)
Melting point212 °C (414 °F) (decomp.)
  • O=C(c1ncn2C(=O)N(\N=N/c12)C)N
  • InChI=1S/C6H6N6O2/c1-11-6(14)12-2-8-3(4(7)13)5(12)9-10-11/h2H,1H3,(H2,7,13) Y
  • Key:BPEGJWRSRHCHSN-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

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.

Temozolomide is an alkylating agent used to treat serious brain cancers; most commonly as second-line treatments for astrocytoma and as the first-line treatment for glioblastoma. Olaparib in combination with temozolomide demonstrated substantial clinical activity in relapsed small cell lung cancer. It is available as a generic medication.

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