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Name	Pyrazinamide	EINECS	202-717-6
CAS No.	98-96-4	Density	1.301 g/cm³
PSA	68.87000	LogP	0.27580
Solubility	15 mg/mL in water	Melting Point	189-191 °C(lit.)
Formula	C₅H₅N₃O	Boiling Point	357.4 °C at 760 mmHg
Molecular Weight	123.114	Flash Point	169.9 °C
Transport Information	N/A	Appearance	crystalline solid
Safety	22-24/25-45-36/37/39-26-16	Risk Codes	11-34
Molecular Structure		Hazard Symbols	F,C
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;	Article Data	59

Pyrazinamide Synthetic route

: 306990-94-3
(1H-benzo[d][1,2,3]triazol-1-yl)(pyrazin-2-yl)methanone

: 98-96-4
pyrazinamide

Conditions

Conditions	Yield
With ammonium hydroxide In tetrahydrofuran; ethanol at 20℃; for 4h;	100%

: 19847-12-2
2-pyrazine carbonitrile

: 98-96-4
pyrazinamide

Conditions

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%

: 109-08-0
2-Methylpyrazine

: 98-96-4
pyrazinamide

Conditions

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%

: 98-97-5
2-pyrazylcarboxylic acid

: 98-96-4
pyrazinamide

Conditions

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%

: 290-37-9
1,4-pyrazine

: 77287-34-4, 77287-35-5, 60100-09-6
formamide

: 98-96-4
pyrazinamide

Conditions

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;

: 123-32-0
2,5-dimethyl-pyrazine

A: 98-96-4
pyrazinamide

B: 41110-27-4
2,5-pyrazinedicarboxamide

Conditions

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

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%

: 56423-63-3
2-bromopyrazine

: 15226-74-1, 61091-28-9, 61117-58-6
dicobalt octacarbonyl

: 98-96-4
pyrazinamide

Conditions

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

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

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%

Pyrazinamide Chemical Properties

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

Pyrazinamide Uses

Pyrazinamide is a drug used to treat tuberculosis. The drug is largely bacteriostatic, but can be bacteriocidal on actively replicating tuberculosis bacteria.

Pyrazinamide 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.

Pyrazinamide Safety Profile

Hazard Codes: F, Corrosive 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

Pyrazinamide 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.

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