Temozolomide Acid

Base Information

• Chemical Name: Temozolomide Acid
• CAS No.: 113942-30-6
• Molecular Formula: C6H5 N5 O3
• Molecular Weight: 195.137
• Hs Code.: 2933990090
• European Community (EC) Number: 679-519-5
• UNII: M35A7FW55W
• ChEMBL ID: CHEMBL4228794
• DSSTox Substance ID: DTXSID40150614
• Nikkaji Number: J1.420.003G
• Wikidata: Q27283423
• Mol file: 113942-30-6.mol

Synonyms:Temozolomide Acid;113942-30-6;3-Methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxylic acid;Temozolomide-8-carboxylic Acid;3-methyl-4-oxoimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxylic acid;M35A7FW55W;MFCD12032160;3-Methyl-4-oxo-3,4-dihydroimidazo(5,1-d)(1,2,3,5)tetrazine-8-carboxylic acid;Imidazo(5,1-d)-1,2,3,5-tetrazine-8-carboxylic acid, 3,4-dihydro-3-methyl-4-oxo-;Imidazo[5,1-d]-1,2,3,5-tetrazine-8-carboxylic acid, 3,4-dihydro-3-methyl-4-oxo-;C6H5N5O3;UNII-M35A7FW55W;3,4-Dihydro-3-methyl-4-oxoimidazo[5,1-d]-1,2,3,5-tetrazine-8-carboxylic Acid;3-Methyl-4-oxo-8-imidazolo[5,1-d][1,2,3,5]tetrazinecarboxylic acid;Temozolomide acid;Temozolomide-8-carboxylic acid;Temozolomide Impurity B;3-Methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxylic Acid (Temozolomide Acid);TMZATMZA;TMZA?;Temozolomide impurity, temozolomide acid- [USP];SCHEMBL892401;CHEMBL4228794;DTXSID40150614;AKOS016009153;CS-W019112;3-Methyl-4-oxo-3,4-dihydroimidazo[5,1-d]-[1,2,3,5]tetrazine-8-carboxylic acid;AC-28362;AS-16968;SY113164;FT-0674846;T3686;TEMOZOLOMIDE IMPURITY B [EP IMPURITY];A894295;W-200540;Q27283423;TEMOZOLOMIDE IMPURITY, TEMOZOLOMIDE ACID- [USP IMPURITY];3-Methyl-4-oxo-3,4-dihydro-imidazo[5,1-d][1,2,3,5]tetrazine-8-carboxylic acid;3-Methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxylicacid;3-Methyl-4-oxo-3 pound not4-dihydroimidazo[5 pound not1-d][1 pound not2 pound not3 pound not5]tetrazine-8-carboxylic acid

Chemical Property of Temozolomide Acid

Chemical Property:

• Melting Point: 166-168°C
• Boiling Point: 487.7±37.0 °C(Predicted)
• PKA: 2.88±0.20(Predicted)
• PSA: 102.38000
• Density: 1.97±0.1 g/cm3(Predicted)
• LogP: -1.47880
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 195.03923904
• Heavy Atom Count: 14
• Complexity: 317

Purity/Quality:

98%,99%, ^*data from raw suppliers

Temozolomide Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C(=O)N2C=NC(=C2N=N1)C(=O)O
• Uses: A metabolite of Temozolomide (T017775) as antitumor agent.

Technology Process of Temozolomide Acid

There total 2 articles about Temozolomide Acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

temozolomide (85622-93-1) → 3-methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrahydro-8-carboxylic acid (113942-30-6)

Guidance literature:

With sulfuric acid; sodium nitrite;

DOI:10.1016/S0223-5234(01)01331-9

Reference yield: 98.6%

8-carbamoyl-3-methylimidazo[5,1-d]-1,2,3,5-tetrazine-4(3H)-one → 3-methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrahydro-8-carboxylic acid (113942-30-6)

Guidance literature:

With sulfuric acid; sodium nitrite; In water; at 0 - 20 ℃; for 17h;

Reference yield: 88.0%

mafenide hydrochloride (138-37-4) + 3-methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrahydro-8-carboxylic acid (113942-30-6) → 3-methyl-4-oxo-N-(4-sulfamoylbenzyl)-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide

Guidance literature:

With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1016/j.ejmech.2016.10.037

upstream raw materials:

temozolomide

Downstream raw materials:

(6R,7R)-2-(allyloxy)carbonyl-7-phenylacetamido-3-cephem-3-methyl 3-methyl-4-oxoimidazo[5,1-d][1,2,3,5]tetrazin-8-carboxylate

(6R,7R)-2-(allyloxy)carbonyl-7-phenoxyacetamido-3-cephem-3-methyl 3-methyl-4-oxoimidazo[5,1-d][1,2,3,5]tetrazin-8-carboxylate

3-methyl-4-oxo-N-phenyl-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide

N'-benzoyl-3-methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carbohydrazide

Refernces

• 1、 Clemente, Nausicaa,Ferrara, Benedetta,Gigliotti, Casimiro Luca,Boggio, Elena,Capucchio, Maria Teresa,Biasibetti, Elena,Schiffer, Davide,Mellai, Marta,Annovazzi, Laura,Cangemi, Luigi,Muntoni, Elisabetta,Miglio, Gianluca,Dianzani, Umberto,Battaglia, Luigi,Dianzani, Chiara. "Solid lipid nanoparticles carrying temozolomide for melanoma treatment. Preliminary in vitro and in vivo studies". . . Retrieved 2018.
• 2、 -. "IMIDAZOTETRAZINE COMPOUNDS". Page/Page column 39. . Retrieved 2020/03/02.
• 3、 Ingham, Oliver,Shervington, Amal,Shervington, Leroy. "A novel series of phenolic temozolomide (TMZ) esters with 4 to 5-fold increased potency, compared to TMZ, against glioma cells irrespective of MGMT expression". . p. 17561 - 17570. Retrieved 2020/06/19.