Temozolomide

Temozolomide
Clinical data
Trade names	Temodar, Temodal, Temcad, others
Other names	TMZ
AHFS/Drugs.com	Monograph
MedlinePlus	a601250
License data	EU EMA: by INN; US DailyMed: Temozolomide;
Pregnancy; category	AU: D;
Routes of; administration	By mouth, intravenous
ATC code	L01AX03 (WHO) ;
Legal status
Legal status	UK: POM (Prescription only); US: ℞-only; EU: Rx-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	almost 100%
Protein binding	15% (10–20%)
Metabolism	hydrolysis
Metabolites	3-methyl-(triazen-1-yl)imidazole-4-carboxamide (MTIC, the active species); temozolomide acid
Elimination half-life	1.8 hours
Excretion	mainly kidney
Identifiers
	IUPAC name 4-methyl-5-oxo-2,3,4,6,8-pentazabicyclo[4.3.0]nona-2,7,9-triene-9-carboxamide;
CAS Number	85622-93-1 ;
PubChem CID	5394;
IUPHAR/BPS	7301;
DrugBank	DB00853 ;
ChemSpider	5201 ;
UNII	YF1K15M17Y;
KEGG	D06067 ;
ChEBI	CHEBI:72564 ;
ChEMBL	ChEMBL810 ;
CompTox Dashboard (EPA)	DTXSID5043714 ;
ECHA InfoCard	100.158.652
Chemical and physical data
Formula	C6H6N6O2
Molar mass	194.154 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	212 °C (414 °F) (decomp.)
	SMILES O=C(c1ncn2C(=O)N(\N=N/c12)C)N;
	InChI InChI=1S/C6H6N6O2/c1-11-6(14)12-2-8-3(4(7)13)5(12)9-10-11/h2H,1H3,(H2,7,13) ; Key:BPEGJWRSRHCHSN-UHFFFAOYSA-N ;
	(what is this?) (verify)

Temozolomide, sold under the brand name Temodar among others, is an anticancer medication used to treat brain tumors such as glioblastoma and anaplastic astrocytoma.^[3]^[4] It is taken by mouth or via intravenous infusion.^[3]^[4]

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).^[4] 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.^[4]

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.^[3]^[5]^[6] Olaparib in combination with temozolomide demonstrated substantial clinical activity in relapsed small cell lung cancer.^[7] It is available as a generic medication.

^ "Temozolomide". Drugs.com. 4 May 2020. Archived from the original on 29 August 2021. Retrieved 7 May 2020.
^ "Temodal Capsules - Summary of Product Characteristics (SmPC)". (emc). 24 October 2019. Archived from the original on 20 September 2020. Retrieved 7 May 2020.
^ ^a ^b ^c ^d "Temodar- temozolomide capsule Temodar- temozolomide injection, powder, lyophilized, for solution". DailyMed. 31 January 2020. Archived from the original on 8 April 2021. Retrieved 7 May 2020.
^ ^a ^b ^c ^d ^e "Temodal EPAR". European Medicines Agency (EMA). 17 September 2018. Archived from the original on 22 October 2020. Retrieved 7 May 2020. Text was copied from this source which is copyright European Medicines Agency. Reproduction is authorized provided the source is acknowledged.
^ "Guidance on the use of temozolomide for the treatment of recurrent malignant glioma (brain cancer)" (PDF). 3 March 2016. Archived from the original on 11 July 2021. Retrieved 7 May 2020.
^ Sasmita AO, Wong YP, Ling AP (February 2018). "Biomarkers and therapeutic advances in glioblastoma multiforme". Asia-Pacific Journal of Clinical Oncology. 14 (1): 40–51. doi:10.1111/ajco.12756. PMID 28840962.
^ Farago AF, Yeap BY, Stanzione M, Hung YP, Heist RS, Marcoux JP, et al. (October 2019). "Combination Olaparib and Temozolomide in Relapsed Small-Cell Lung Cancer". Cancer Discovery. 9 (10): 1372–1387. doi:10.1158/2159-8290.CD-19-0582. PMC 7319046. PMID 31416802.

[1] "Temozolomide". Drugs.com. 4 May 2020. Archived from the original on 29 August 2021. Retrieved 7 May 2020.

[2] "Temodal Capsules - Summary of Product Characteristics (SmPC)". (emc). 24 October 2019. Archived from the original on 20 September 2020. Retrieved 7 May 2020.

[Temodar_FDA_label-3] "Temodar- temozolomide capsule Temodar- temozolomide injection, powder, lyophilized, for solution". DailyMed. 31 January 2020. Archived from the original on 8 April 2021. Retrieved 7 May 2020.

[Temodal_EPAR-4] "Temodal EPAR". European Medicines Agency (EMA). 17 September 2018. Archived from the original on 22 October 2020. Retrieved 7 May 2020. Text was copied from this source which is copyright European Medicines Agency. Reproduction is authorized provided the source is acknowledged.

[NICE-5] "Guidance on the use of temozolomide for the treatment of recurrent malignant glioma (brain cancer)" (PDF). 3 March 2016. Archived from the original on 11 July 2021. Retrieved 7 May 2020.

[6] Sasmita AO, Wong YP, Ling AP (February 2018). "Biomarkers and therapeutic advances in glioblastoma multiforme". Asia-Pacific Journal of Clinical Oncology. 14 (1): 40–51. doi:10.1111/ajco.12756. PMID 28840962.

[7] Farago AF, Yeap BY, Stanzione M, Hung YP, Heist RS, Marcoux JP, et al. (October 2019). "Combination Olaparib and Temozolomide in Relapsed Small-Cell Lung Cancer". Cancer Discovery. 9 (10): 1372–1387. doi:10.1158/2159-8290.CD-19-0582. PMC 7319046. PMID 31416802.

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