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85622-93-1

Basic Information
CAS No.: 85622-93-1
Name: Temozolomide
Article Data: 33
Molecular Structure:
Molecular Structure of 85622-93-1 (Temozolomide)
Formula: C6H6N6O2
Molecular Weight: 194.153
Synonyms: 3,4-Dihydro-3-methyl-4-oxoimidazo(5,1-d)-as-tetrazine-8-carboxamide;CCRG 81045;Temozolodida [Spanish];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-oxo-;3-methyl-2-oxo-1,3,4,5,8-pentazabicyclo[4.3.0]nona-4,6,8-triene-7-carboxamide;MB 39831;Methazolastone;Temozolomide [BAN:INN];Imidazo(5,1-d)(1,2,3,5)tetrazine-8-carboxamide, 3,4-dihydro-3-methyl-4-oxo-;Temodal;3-Methyl-4-oxo-3,4-dihydroimidazo(5,1-d)(1,2,3,5)tetrazine-8-carboxamide;Temozolomidum [Latin];8-Carbamoyl-3-methylimidazo(5,1-d)-1,2,3,5-tetrazin-4(3H)-one;
EINECS: 630-358-9
Density: 1.97 g/cm3
Melting Point: 212 °C dec.
Boiling Point: 526.6 °C at 760 mmHg
Flash Point: 272.3 °C
Appearance: Off-white to light-pink crystalline solid
Hazard Symbols: ToxicT, IrritantXi
Risk Codes: 45-46-60-61-22-36/37/38
Safety: 24/25-45-36/37-26-53
PSA: 108.17000
LogP: -1.37780
Synthetic route
624-83-9

methyl isocyanate

7008-85-7

5-diazoimidazole-4-carboxamide

85622-93-1

temozolomide

Conditions
ConditionsYield
In dichloromethane at 25℃; for 480h;98%
In 1,4-dioxane at 50℃;76.5%
In dimethyl sulfoxide at 25℃;

ethyl 3,4-dihydro-3-methyl-4-oxoimidazo[5,1-d]-1,2,3,5-tetrazine-8-carboxylate

85622-93-1

temozolomide

Conditions
ConditionsYield
With ammonium hydroxide; copper(II) sulfate at 100℃; for 6h; Reagent/catalyst; Temperature;92%

8-carbamoyl-3-methyl-imidazo[5,1-d]-1,2,3,5-tetrazin-4(3H)-one hydrochloride

85622-93-1

temozolomide

Conditions
ConditionsYield
With Lewatit Mono Plus MP-64 In acetone at 60 - 63℃; styrene-divinylbenzene (macroporous); Purification / work up;90.3%
With acetic acid In water; acetone for 0.166667h; Purification / work up; Heating / reflux;88%
With acetic acid In water; acetonitrile at 60 - 63℃; for 0.166667h; Purification / work up;86.7%
With acetic acid In tetrahydrofuran; water for 0.166667h; Purification / work up; Heating / reflux;70%

5-{3-methyl-3-[(phenyloxy)carbonyl]triazen-1-yl}imidazole-4-carboxamide

85622-93-1

temozolomide

Conditions
ConditionsYield
In methanol; acetone at 20℃; for 1h; UV-irradiation;79%

8-carbamoyl-3-trimethylsilylmethylimidazo<5,1-d>-1,2,3,5-tetrazin-4(3H)-one

85622-93-1

temozolomide

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In acetic acid; acetonitrile at 25℃; for 24h;78%
With tetrabutyl ammonium fluoride; acetic acid In acetonitrile at 25℃;78%
188612-53-5

5-amino-N1-methyl-1H-imidazole-1,4-dicarboxamide

85622-93-1

temozolomide

Conditions
ConditionsYield
Stage #1: 5-amino-N1-methyl-1H-imidazole-1,4-dicarboxamide With lithium chloride hydrate; acetic acid In water at 20℃; for 0.5h;
Stage #2: With iodine; sodium nitrite In water at -10 - 20℃; for 3h;
76%
Stage #1: 5-amino-N1-methyl-1H-imidazole-1,4-dicarboxamide With acetic acid; lithium bromide In water at 20℃; for 1h;
Stage #2: With sodium nitrite In water at -10 - 20℃; for 6h;
Stage #3: With sodium thiosulfate In water for 0.333333h; Product distribution / selectivity;
64%
Stage #1: 5-amino-N1-methyl-1H-imidazole-1,4-dicarboxamide With sodium nitrite In water at 0℃; for 0.333333h;
Stage #2: With tartaric acid In water at 0 - 60℃; for 4h;
47%
442534-20-5

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

85622-93-1

temozolomide

Conditions
ConditionsYield
With sulfuric acid at 15 - 20℃; for 3h;52%
188612-53-5

5-amino-N1-methyl-1H-imidazole-1,4-dicarboxamide

A

85622-93-1

temozolomide

B

4656-86-4

2-Azahypoxanthine

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrite at 5 - 25℃;A 35%
B 15%
1161825-88-2

3-N-hydroxymethyl temozolomide

74-88-4

methyl iodide

85622-93-1

temozolomide

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile22%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 25℃;22%
157467-00-0

(8-Carbamoyl-4-oxo-imidazo[5,1-d][1,2,3,5]tetrazin-3-yl)-acetic acid 2-thioxo-2H-pyridin-1-yl ester

85622-93-1

temozolomide

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In N,N-dimethyl-formamide at 25℃; Irradiation; Yield given;
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In N,N-dimethyl-formamide for 0.5h; Ambient temperature; Irradiation; Yield given;
Downstream Products
113942-30-6
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    Temozolomide CAS No.:85622-93-1 Name: Temozolomide Synonyms: 4-Methyl-5-oxo-2,3,4,6,8-pentazabicyclo[4.3.0]nona-2,7,9-triene-9-carboxamide Molecular Structure Molecular Formula: C6H6N6O2 Molecular Weight

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    85622-93-1 Temozolomide

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    Product Name: Temozolomide Synonyms: 4-methyl-5-oxo-2,3,4,6,8-pentazabicyclo[4.3.0]nona-2,7,9-triene-9-carboxamide;TEMOZOLOMIDE;1-d)(1,2,3,5)tetrazine-8-carboxamide,3,4-dihydro-3-methyl-4-oxo-imidazo(;3,4-dihydro-3-methyl-4-oxoimidazo(

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    Temozolomide Supplier CAS:85622-93-1 Molecularformula: C6H6N6O2 Purity: 99% min Appearance: White or light yellow powder Appearance:White powder Storage:RT. Package:25kg bag Application:Metabolism Drug; Carcino-Chemotherapeutic Drug;Anti

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Chemistry

IUPAC Name: 3-Methyl-4-oxoimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide   
Synonyms of Temozolomide (CAS NO.85622-93-1): 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 ; 8-Carbamoyl-3-methylimidazo(5,1-d)-1,2,3,5-tetrazin-4(3H)-one
CAS NO: 85622-93-1
Molecular formula: C6H6N6O2
Molar weight: 194.15
Molecular Structure:
H bond acceptors: 8
H bond donors: 2
Freely Rotating Bonds: 1
Polar Surface Area: 83.16 Å2
Index of Refraction: 1.895
Molar Refractivity: 45.6 cm3
Molar Volume: 98.3 cm3
Surface Tension: 105 dyne/cm
Density: 1.97 g/cm3
Flash Point: 272.3 °C
Enthalpy of Vaporization: 80.1 kJ/mol
Boiling Point: 526.6 °C at 760 mmHg
Vapour Pressure: 3.53E-11 mmHg at 25°C
Storage temp: 2-8°C 
Melting Point: 212°C dec.
Appearance: Off-White to Light-Pink Crystalline Solid
Product Categories of Temozolomide (CAS NO.85622-93-1): Active Pharmaceutical Ingredients;Antineoplastic;Intermediates & Fine Chemicals;Pharmaceuticals;Antitumour

Uses

 Temozolomide (CAS NO.85622-93-1) can be used in treatment of Grade IV astrocytoma. Methylation damages the DNA and triggers the death of tumor cells,temozolomide's ability to alkylate/methylate DNA, which most often occurs at the N-7 or O-6 positions of guanine residues for the therapeutic benefit of temozolomide depends .

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LDLo intraperitoneal 125mg/kg (125mg/kg)   Cancer Research. Vol. 47, Pg. 5846, 1987.

Safety Profile

Safety Information about Temozolomide (CAS NO.85622-93-1):
Hazard Codes:  T,  Xi
The Risk Statements: 45-46-60-61-22-36/37/38
45: May cause cancer 
46: May cause heritable genetic damage 
60: May impair fertility 
61: May cause harm to the unborn child 
36/37/38: Irritating to eyes, respiratory system and skin 
The Safety Statements: 24/25-45-36/37-26-53
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 
45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)  
53: Avoid exposure - obtain special instruction before use 
24/25: Avoid contact with skin and eyes 
36/37: Wear suitable protective clothing and gloves 

Analytical Methods

Laboratory studies and clinical trials are investigating whether it might be possible to further increase the anticancer potency of temozolomide by combining it with other pharmacologic agents.