Temozolomide

An orally administered antineoplastic alkylating agent used primarily for the treatment of glioblastoma and other selected malignant gliomas. Temozolomide undergoes spontaneous conversion at physiological pH to the active intermediate MTIC, which generates a reactive methylating species that modifies DNA, particularly at the O6 and N7 positions of guanine. These lesions impair DNA replication and promote tumor cell death. Temozolomide crosses the blood–brain barrier and is commonly administered with radiotherapy for newly diagnosed glioblastoma. Tumor MGMT promoter methylation is an important predictor of treatment response

$Compound Structure$

CAS Number: 85622-93-1

Molecular Mass: 194.15 g/mol

Formula: C₆H₆N₆O₂

Smiles: Cn1nnc2c(C(N)=O)ncn2c1=O

Synonymes:

Temozolomide, temozolomide, 85622-93-1, Methazolastone, Temodar, Temodal, 3-methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide, Temozolamide, CCRG-81045, Sch 52365, Temozolomidum, Sch-52365, NSC 362856, NSC-362856, temozolomida, M&B 39831, M&B-39831, CCRIS 8996, 3,4-dihydro-3-methyl-4-oxoimidazo[5,1-d]-1,2,3,5-tetrazine-8-carboxamide, MB 39831, M & B 39831, 8-Carbamoyl-3-methylimidazo(5,1-d)-1,2,3,5-tetrazin-4(3H)-one, BRN 5547136, M-39831, 3,4-Dihydro-3-methyl-4-oxoimidazo(5,1-d)-1,2,3,5-tetrazine-8-carboxamide, 3-Methyl-4-oxo-3,4-dihydroimidazo(5,1-d)(1,2,3,5)tetrazine-8-carboxamide, YF1K15M17Y, DTXSID5043714, 3,4-Dihydro-3-methyl-4-oxoimidazo(5,1-d)-as-tetrazine-8-carboxamide, Mk-7365, NSC362856, 3-methyl-4-oxoimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide, 3-methyl-4-oxo-3H,4H-imidazo[4,3-d][1,2,3,5]tetrazine-8-carboxamide, DTXCID3023714, CHEBI:72564, temomedac, Imidazo(5,1-d)(1,2,3,5)tetrazine-8-carboxamide, 3,4-dihydro-3-methyl-4-oxo-, 8-CARBAMOYL-3-METHYLIMIDAZO[5,1-D]-1,2,3,5-TETRAZIN-4(3H)-ONE, Temcad, 3-methyl-4-oxoimidazo(5,1-d)(1,2,3,5)tetrazine-8-carboxamide, TMZ Bioshuttle, 3,4-Dihydro-3-methyl-4-oxoimidazo[5,1-d]-as-tetrazine-8-carboxamide, 3-methyl-4-oxo-3H,4H-imidazo(4,3-d)(1,2,3,5)tetrazine-8-carboxamide, TMZA-HE, RefChem:389304, M and B 39831, CCRG81045, L01AX03, M&B39831, RP-46161, Imidazo(5,1-d)-1,2,3,5-tetrazine-8-carboxamide, 3, 4-dihydro-3-methyl-4-oxo-, 630-358-9, Temozolomidum [Latin], Temozolodida [Spanish], CCRG 81045, C6H6N6O2, MFCD00866492, CHEMBL810, Imidazo[5,1-d]-1,2,3,5-tetrazine-8-carboxamide, 3,4-dihydro-3-methyl-4-oxo-, MLS002701861, NCGC00167429-01, Temozolodida, TMZ, 3-Methyl-4-oxo-3,4-dihydroimidazo-[5,1-d][1,2,3,5]tetrazine-8-carboxamide, 3-Methyl-4-oxo-3,4-dihydro-imidazo[5,1-d][1,2,3,5]tetrazine-8-carboxylic acid amide, SMR000466338, Temodal (TN), Temodar (TN), CAS-85622-93-1, Temozolomide, VETRANAL(TM), analytical standard, SR-01000759347, UNII-YF1K15M17Y, Methazolastone, , Temodal, , Temozolomide [USAN:INN:BAN], Temozolomide CRS, IMIDAZO(5,1-D)-1,2,3,5-TETRAZINE-8-CARBOXAMIDE, 3,4-DIHYDRO-3-METHYL-4-OXO-, Temozolomide (Standard), TEMOZOLOMIDE [MI], TEMOZOLOMIDE [INN], TEMOZOLOMIDE [JAN], Temodar (TN) (Schering), TEMOZOLOMIDE [USAN], SCHEMBL3739, TEMOZOLOMIDE [VANDF], TEMOZOLOMIDE [MART.], MLS000759447, MLS001424028, BIDD:GT0204, TEMOZOLOMIDE [USP-RS], TEMOZOLOMIDE [WHO-DD], GTPL7301, orb1309506, TEMOZOLOMIDE [EMA EPAR], Temozolomide - Bio-X trade mark, Temozolomide (JP18/USAN/INN), Temozolomide, >=98% (HPLC), GLXC-02560, HMS2051O12, HMS2090B08, HMS2232N13, HMS3264I14, HMS3269P05, HMS3372K13, HMS3393O12, HMS3413D06, HMS3654N05, HMS3677D06, HMS3713H16, HMS5079A21, Pharmakon1600-01502289, TEMOZOLOMIDE [ORANGE BOOK], TEMOZOLOMIDE [EP MONOGRAPH], 3-methyl-4-oxo-imidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide, ALBB-021358, TEMOZOLOMIDE [USP MONOGRAPH], Tox21_112433, AC-758, BDBM50034562, DL-190, EBC-00562, HY-17364R, MSK159181, NSC759883, s1237, STK623541, 3-Methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetraazine-8-carboxamide, 3-methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide., AKOS005557098, Tox21_112433_1, CCG-100870, CS-0943, DB00853, FT28027, KS-1216, NC00120, NSC-759883, NCGC00167429-02, NCGC00167429-04, NCGC00167429-05, BP-25388, BT164447, HY-17364, NCI60_003316, SY013764, Temozolomide 100 microg/mL in Acetonitrile, NS00004198, SW197500-4, D06067, EN300-122324, AB00639915-06, AB00639915-08, AB00639915-09, AB00639915_10, AB00639915_11, F079436, Q425088, SR-01000759347-4, SR-01000759347-5, BRD-K32107296-001-04-5, BRD-K32107296-001-14-4, BRD-K32107296-001-15-1, BRD-K32107296-001-16-9, Z1201620684, 3-methyl-4-oxoimidazo [5,1-d] [1,2,3,5] tetrazine-8-carboxamide, Temozolomide, United States Pharmacopeia (USP) Reference Standard, 3-METHYL-4-OXO-8-IMIDAZOLO[5,1-D][1,2,3,5]TETRAZINECARBOXAMIDE, 3-Methyl-8-aminocarbonyl-imidazo[5,1-d]-1,2,3,5-tetrazin-4(3H)-one, Imidazo[5,2,3,5-tetrazine-8-carboxamide, 3,4-dihydro-3-methyl-4-oxo-, {Imidazo[5,1-d]-1,2,3,5-tetrazine-8-carboxamide,} 3, 4-dihydro-3-methyl-4-oxo-, 3,4-dihydro-3-methyl-4-oxo-imidazo[5,1-d]-1,2,3,5-tetrazine-8-carboxamide, 3,4-Dihydro-3-methyl-4-oxo-imidazo[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, Pharmaceutical Secondary Standard, Certified Reference Material, 3-Methyl-4-oxo-3,4-dihydro-imidazo[5,1-d][1,2,3,5]tetrazine-8-carboxylic acid amide (Temozolomide), 3-Methyl-4-oxo-3,4-dihydro-imidazo[5,1-d][1,2,3,5]tetrazine-8-carboxylic acid amide(Temozolomide)

Bioactivity: Antineoplastic alkylating agent; DNA-methylating prodrug that generates the active intermediate MTIC

Solubility in Different Solvents

Solvent	Temperature [K]	Crystal form	Solubility [mg/mL]	Reference
1-Propanol	273.15	-	0.1134	[112]
1-Propanol	278.15	-	0.1458	[112]
1-Propanol	283.15	-	0.1834	[112]
1-Propanol	288.15	-	0.2257	[112]
1-Propanol	293.15	-	0.2765	[112]
1-Propanol	298.15	-	0.3369	[112]
1-Propanol	303.15	-	0.4026	[112]
1-Propanol	308.15	-	0.4795	[112]
1-Propanol	313.15	-	0.5758	[112]
1-Propanol	318.15	-	0.685	[112]
Ethanol	273.15	-	0.2238	[112]
Ethanol	278.15	-	0.2669	[112]
Ethanol	283.15	-	0.3187	[112]
Ethanol	288.15	-	0.3828	[112]
Ethanol	293.15	-	0.4513	[112]
Ethanol	298.15	-	0.5287	[112]
Ethanol	303.15	-	0.6201	[112]
Ethanol	308.15	-	0.7351	[112]
Ethanol	313.15	-	0.8743	[112]
Ethanol	318.15	-	1.011	[112]
Ethyl acetate	273.15	-	0.1637	[112]
Ethyl acetate	278.15	-	0.2016	[112]
Ethyl acetate	283.15	-	0.2416	[112]
Ethyl acetate	288.15	-	0.2885	[112]
Ethyl acetate	293.15	-	0.3439	[112]
Ethyl acetate	298.15	-	0.4051	[112]
Ethyl acetate	303.15	-	0.465	[112]
Ethyl acetate	308.15	-	0.5379	[112]
Ethyl acetate	313.15	-	0.6163	[112]
Ethyl acetate	318.15	-	0.7114	[112]
Isopropanol	273.15	-	0.0571	[112]
Isopropanol	278.15	-	0.0694	[112]
Isopropanol	283.15	-	0.0873	[112]
Isopropanol	288.15	-	0.1087	[112]
Isopropanol	293.15	-	0.1312	[112]
Isopropanol	298.15	-	0.161	[112]
Isopropanol	303.15	-	0.196	[112]
Isopropanol	308.15	-	0.2349	[112]
Isopropanol	313.15	-	0.2889	[112]
Isopropanol	318.15	-	0.3519	[112]
Methanol	273.15	-	0.8551	[112]
Methanol	278.15	-	1.058	[112]
Methanol	283.15	-	1.31	[112]
Methanol	288.15	-	1.578	[112]
Methanol	293.15	-	1.872	[112]
Methanol	298.15	-	2.189	[112]
Methanol	303.15	-	2.539	[112]
Methanol	308.15	-	2.925	[112]
Methanol	313.15	-	3.37	[112]
Methanol	318.15	-	3.898	[112]

Molecule 3D descriptors

Descriptor	Value
PMI1	303.4440
PMI2	1032.7069
PMI3	1332.9306
NPR1	0.2277
NPR2	0.7748
RadiusOfGyration	2.6218
InertialShapeFactor	0.0026
Eccentricity	0.9737
Asphericity	0.4722
SpherocityIndex	0.0247
PBF	0.0894