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| CAS No.: | 98-96-4 |
|---|---|
| Name: | Pyrazinamide |
| Molecular Structure: | |
|
|
|
| Formula: | C5H5N3O |
| Molecular Weight: | 123.114 |
| Synonyms: | Pyrazinamide (TN);Pirazinamid;Pirazimida;D-50;T 165;Novamid;NCI-C01785;Pyrazineamide;MK 56;2-Carbamylpyrazine;D-50 (VAN);Pirazinamida [INN-Spanish];Pirazinamide [DCIT];PZA;2-Pyrazinecarboxamide;1/C5H5N3O/c6-5(9)4-3-7-1-2-8-4/h1-3H,(H2,6,9;Pyrazinamide (JP14/USP);5-25-04-00178 (Beilstein Handbook Reference);Prestwick_811;Zinamide;Pyrazinamidum [INN-Latin];PYZ;Pyrazinecarboxylic acid amide;Aldinamide;Pyrazinamide [BAN:INN:JAN];Unipyranamide;Pyrazinoic acid amide;DRG 0124;Aldinamid;Farmizina;Eprazin;pyrazine-2-carboxamide;Tebrazid;Pyrazine carboxylamide;Pyrazine carboxamide; |
| EINECS: | 202-717-6 |
| Density: | 1.301 g/cm3 |
| Melting Point: | 189-191 °C(lit.) |
| Boiling Point: | 357.4 °C at 760 mmHg |
| Flash Point: | 169.9 °C |
| Solubility: | 15 mg/mL in water |
| Appearance: | crystalline solid |
| Hazard Symbols: |
 F, C
|
| Risk Codes: | 11-34 |
| Safety: | 22-24/25-45-36/37/39-26-16 |
| PSA: | 68.87000 |
| LogP: | 0.27580 |
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(1H-benzo[d][1,2,3]triazol-1-yl)(pyrazin-2-yl)methanone
- 98-96-4
pyrazinamide
| Conditions | Yield |
|---|---|
| With ammonium hydroxide In tetrahydrofuran; ethanol at 20℃; for 4h; | 100% |
- 19847-12-2
2-pyrazine carbonitrile
- 98-96-4
pyrazinamide
| Conditions | Yield |
|---|---|
| With manganese(IV) oxide; silica gel In chlorobenzene for 5h; Heating; | 100% |
| With manganese(IV) oxide; water In isopropyl alcohol at 98℃; under 5171.62 Torr; for 0.0333333h; Catalytic behavior; Temperature; | 99% |
| With C34H38N6NiO2(2+)*2Cl(1-); water In isopropyl alcohol at 70℃; for 6h; Schlenk technique; Inert atmosphere; | 99% |
| Conditions | Yield |
|---|---|
| With ammonium hydroxide; air; V2O5#dotMoO3 at 390℃; | 95.2% |
| Stage #1: 2-Methylpyrazine With dihydrogen peroxide; iron(II) chloride at 30 - 50℃; for 4h; Stage #2: With ammonia at 50℃; for 7h; Reagent/catalyst; | 95% |
| Conditions | Yield |
|---|---|
| With ammonium hydroxide In water at 20℃; for 12h; | 95% |
| With ammonium cerium(IV) nitrate; urea for 0.0166667h; microwave irradiation; | 90% |
| Stage #1: 2-pyrazylcarboxylic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 25℃; for 1.5h; Inert atmosphere; Stage #2: With ammonium hydroxide In tetrahydrofuran at 0 - 25℃; for 0.166667h; Inert atmosphere; | 75% |
| Conditions | Yield |
|---|---|
| With dipotassium peroxodisulfate at 70℃; for 12h; | 86% |
| With sulfuric acid; dihydrogen peroxide; iron(II) sulfate at 60℃; for 4h; | 96 % Turnov. |
| With N-hydroxyphthalimide; ammonium cerium(IV) nitrate; trifluoroacetic acid at 70℃; for 6h; |
| Conditions | Yield |
|---|---|
| With ammonium hydroxide; air; antimony(III) trioxide; titanium(IV) oxide; molybdenum(VI) oxide at 440℃; Oxidation; ammonolysis; demethylation; | A 5% B 86% |
- 123-32-0
2,5-dimethyl-pyrazine
A
- 290-37-9
1,4-pyrazine
B
- 109-08-0
2-Methylpyrazine
C
- 98-96-4
pyrazinamide
D
- 41110-27-4
2,5-pyrazinedicarboxamide
| Conditions | Yield |
|---|---|
| With ammonium hydroxide; air; antimony(III) trioxide; titanium(IV) oxide; molybdenum(VI) oxide at 420℃; Oxidation; ammonolysis; demethylation; Further byproducts given; | A 10% B 2% C 76% D 6% |
| With ammonium hydroxide; air; antimony(III) trioxide; titanium(IV) oxide; molybdenum(VI) oxide at 400℃; Product distribution; Further Variations:; Catalysts; Temperatures; Oxidation; ammonolysis; demethylation; | A 10% B 15% C 33% D 5% |
| With ammonium hydroxide; air; antimony(III) trioxide; titanium(IV) oxide; molybdenum(VI) oxide at 380℃; Oxidation; ammonolysis; demethylation; Further byproducts given; | A 5% B 28% C 21% D 5% |
| Conditions | Yield |
|---|---|
| With 1H-imidazole; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; ammonium chloride; N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 90℃; for 3h; Sealed tube; | 74% |
- 19847-12-2
2-pyrazine carbonitrile
- 64-17-5
ethanol
A
- 98-96-4
pyrazinamide
B
- 1339045-85-0
ethyl pyrazine-2-carbimidate hydrochloride
C
- 6924-68-1
ethyl 2-pyrazinecarboxylate
| Conditions | Yield |
|---|---|
| With hydrogenchloride Cooling with ice; | A 30% B 65% C 5% |
- 123-32-0
2,5-dimethyl-pyrazine
A
- 290-37-9
1,4-pyrazine
B
- 98-96-4
pyrazinamide
C
- 5521-57-3
5‐methylpyrazine-2-carboxamide
D
- 41110-27-4
2,5-pyrazinedicarboxamide
| Conditions | Yield |
|---|---|
| With ammonium hydroxide; air; antimony(III) trioxide; titanium(IV) oxide; molybdenum(VI) oxide at 400℃; Oxidation; ammonolysis; demethylation; | A 2% B 5% C 32% D 51% |
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Chemistry
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IUPAC Name: Pyrazine-2-carboxamide
Molecular Formula: C5H5N3O
Molecular Weight: 123.11 g/mol
SMILES: c1(cnccn1)C(N)=O
InChI: InChI=1/C5H5N3O/c6-5(9)4-3-7-1-2-8-4/h1-3H,(H2,6,9)
EINECS: 202-717-6
Classification Code: Anti-Bacterial Agents; Anti-Infective Agents; Antibacterial [tuberculostatic]; Antitubercular agents; Drug / Therapeutic Agent; Human Data; Mutation data; Tumor data
Product Categories: Drug bulk; Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts; Pyrazines, Pyrimidines & Pyridazines; Antitubercular; Pyrazinamide; Pyrazines; Chloropyrazines, etc.; Amide; Heterocycles; Intermediates & Fine Chemicals; Pharmaceuticals; Pyrazines, Pyrimidines & Pyridazines
Index of Refraction: 1.577
Molar Refractivity: 31.36 cm3
Molar Volume: 94.5 cm3
Polarizability: 12.43×10-24 cm3
Surface Tension: 66.4 dyne/cm
Density: 1.301 g/cm3
Flash Point: 169.9 °C
Enthalpy of Vaporization: 60.28 kJ/mol
Boiling Point: 357.4 °C at 760 mmHg
Melting Point: 189-191 °C(lit.)
Water Solubility: 15 mg/mL
Vapour Pressure of Pyrazinamide (CAS NO.98-96-4): 2.74E-05 mmHg at 25 °C
Uses
Pyrazinamide is a drug used to treat tuberculosis. The drug is largely bacteriostatic, but can be bacteriocidal on actively replicating tuberculosis bacteria.
Toxicity Data With Reference
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| mouse | LD50 | intraperitoneal | 1680mg/kg (1680mg/kg) | Chemotherapia. Vol. 5, Pg. 39, 1962. | |
| mouse | LD50 | subcutaneous | 2973mg/kg (2973mg/kg) | Drugs in Japan Vol. -, Pg. 1038, 1995. | |
| mouse | LDLo | oral | 3gm/kg (3000mg/kg) | BEHAVIORAL: EXCITEMENT BEHAVIORAL: ATAXIA | American Review of Tuberculosis. Vol. 70, Pg. 423, 1954. |
| rat | LDLo | oral | 3gm/kg (3000mg/kg) | BEHAVIORAL: EXCITEMENT BEHAVIORAL: ATAXIA | American Review of Tuberculosis. Vol. 70, Pg. 423, 1954. |
| women | TDLo | oral | 10mg/kg (10mg/kg) | VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION | JAMA, Journal of the American Medical Association. Vol. 127, Pg. 1356, 1997. |
Safety Profile
Hazard Codes: 
F, 
C
Risk Statements: 11-34
R11:Highly flammable.
R34:Causes burns.
Safety Statements: 22-24/25-45-36/37/39-26-16
S22:Do not breathe dust.
S24/25:Avoid contact with skin and eyes.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S16:Keep away from sources of ignition.
WGK Germany: 3
RTECS of Pyrazinamide (CAS NO.98-96-4): UQ2275000
Specification
Pyrazinamide (CAS NO.98-96-4), its Synonyms are 2-Carbamylpyrazine ; 2-Pyrazinecarboxamide ; Aldinamid ; Aldinamide ; Eprazin ; Farmizina ; Pyrazinecarboxylic acid amide ; Pyrazinoic acid amide ; Tebrazid ; Unipyranamide ; Zinamide . It is white powder.