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98-96-4

Basic Information
CAS No.: 98-96-4
Name: Pyrazinamide
Article Data: 59
Molecular Structure:
Molecular Structure of 98-96-4 (Pyrazinamide)
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: FlammableF,CorrosiveC
Risk Codes: 11-34
Safety: 22-24/25-45-36/37/39-26-16
PSA: 68.87000
LogP: 0.27580
Synthetic route
306990-94-3

(1H-benzo[d][1,2,3]triazol-1-yl)(pyrazin-2-yl)methanone

98-96-4

pyrazinamide

Conditions
ConditionsYield
With ammonium hydroxide In tetrahydrofuran; ethanol at 20℃; for 4h;100%
19847-12-2

2-pyrazine carbonitrile

98-96-4

pyrazinamide

Conditions
ConditionsYield
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%
109-08-0

2-Methylpyrazine

98-96-4

pyrazinamide

Conditions
ConditionsYield
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%
98-97-5

2-pyrazylcarboxylic acid

98-96-4

pyrazinamide

Conditions
ConditionsYield
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%
290-37-9

1,4-pyrazine

98-96-4

pyrazinamide

Conditions
ConditionsYield
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;
123-32-0

2,5-dimethyl-pyrazine

A

98-96-4

pyrazinamide

B

41110-27-4

2,5-pyrazinedicarboxamide

Conditions
ConditionsYield
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
ConditionsYield
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%
56423-63-3

2-bromopyrazine

98-96-4

pyrazinamide

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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


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 cm
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: FlammableF, Corrosive
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.