144-74-1

Basic information

• Product Name: Sulfathiazole sodium
• Synonyms: (n(sup1)-2-thiazolylsulfanilamido)-sodiu;2-sulfanilamidothiazolesodiumsalt;4-amino-n-2-thiazolyl-benzenesulfonamidmonosodiumsalt;monosodium2-sulfanilamidothiazole;n(sup1)-2-thiazolylsulfanilamidesodiumsalt;n(sup1)-2-thiazolyl-sulfanilamidmonosodiumsalt;n(sup1)-2-thiazolyl-sulfanilamidn(sup1)-sodiumderiv.;sodium2-sulfanilamidothiazole
• CAS NO: 144-74-1
• Molecular Formula: C₉H₈N₃O₂S₂*Na
• Molecular Weight: 277.3
• EINECS: 205-638-5
• Product Categories: pharmaceutical
• Mol File: 144-74-1.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 479.5 °C at 760 mmHg
• Flash Point: 243.8 °C
• Appearance: white to off-white/
• Vapor Pressure: 2.35E-09mmHg at 25°C
• Solubility: H2O: soluble50mg/mL
• BRN: 3802297
• CAS DataBase Reference: Sulfathiazole sodium(CAS DataBase Reference)
• NIST Chemistry Reference: Sulfathiazole sodium(144-74-1)
• EPA Substance Registry System: Sulfathiazole sodium(144-74-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25-23
• WGK Germany: 2
• RTECS: WP2450000
• F: 10
• Hazardous Substances Data: 144-74-1(Hazardous Substances Data)

Usage

Uses

Sulfathiazole sodium salt is a competitive inhibitor of bacterial para-aminobenzoic acid (PABA). It can also be used in biological study of thermotherapy and sulfonamide antibiotics deciphered Cyanobacteria and Proteobacteria microbiome in huanglongbing-affected Citrus paradise and Citrus limon.

General Description

Chemical structure: sulfonamide

Biochem/physiol Actions

Sulfathiazole is a sulfonamide antibiotic that blocks the synthesis of dihydrofolic acid by inhibiting the enzyme dihydropteroate synthase. Sulfathiazole is a competitive inhibitor of bacterial para-aminobenzoic acid (PABA), which is required for bacterial synthesis of folic acid. It is active against Gram positive bacteria, Gram negative bacteria and Chlamydia. Mode of resistance is via the alteration of dihydropteroate synthase or alternative pathway for folic acid synthesis.

InChI:InChI=1/C9H8N3O2S2.Na/c10-7-1-3-8(4-2-7)16(13,14)12-9-11-5-6-15-9;/h1-6H,10H2;/q-1;+1

Synthetic route

iron(III) chloride + sulfathiazole sodium (144-74-1) → C27H24FeN9O6S6

Conditions	Yield
at 20℃;	97%

copper (II)-fluoride + sulfathiazole sodium (144-74-1) → Cu2(sulfathiazolato)4 (72446-92-5)

Conditions	Yield
In methanol pptn. on addn. of Cu-salt to warm soln. of 2 equiv. ligand (stirring); collection (filtration), drying; elem. anal.;	90%

cobalt(II) chloride hexahydrate + sulfathiazole sodium (144-74-1) → Co(II)(sulfathiazolate)2(H2O)4 + Co(II)(sulfathiazolate)2(H2O)3

Conditions	Yield
In water aq. soln. of CoCl2 was added to 2.2 equiv. of S-compd. in H2O, stirring at room temp.; standing for 4 d, solid was centrifuged off, washed with H2O several times, dried (vac., away from light), elem. anal.; liq. was stood for 7-12 d, crystals were centrifuged off, washed with H2O several times, dried (vac., away from light), elem. anal.;	A 88.6% B 88%

sulfathiazole sodium (144-74-1) + methyl 4-(4-chlorophenyl)-2,4-dioxobutanoate (39757-35-2) → (2Z)-2-hydroxy-4-oxo-N-{4-[(1,3-thiazol-2-yl)sulfamoyl]phenyl}-4-(4-chlorophenyl)but-2-eneamide

Conditions	Yield
In acetic acid for 0.333333h; Reflux;	78%

cadmium(II) perchlorate hydrate + water (7732-18-5) + sulfathiazole sodium (144-74-1) → C18H24CdN6O8S4

Conditions	Yield
In methanol for 4h; Reflux;	60%

(E)-3-(4-methoxyphenyl)propenoyl chloride (34446-64-5, 42996-84-9) + sulfathiazole sodium (144-74-1) → p-methoxycinnamoyl sulfathiazole

Conditions	Yield
With pyridine In tetrahydrofuran for 25.5h; Cooling with ice;	55%

phthalic anhydride (85-44-9) + sulfathiazole sodium (144-74-1) → Cremothalidine (85-73-4)

Conditions	Yield
at 85 - 150℃; Kinetics;

sulfathiazole sodium (144-74-1) + chlorothio-trichloro-methane (594-42-3) → 4-amino-N-thiazol-2-yl-N-trichloromethylsulfanyl-benzenesulfonamide (103501-32-2)

Conditions	Yield
In benzene Heating;

methanol (67-56-1) + sulfathiazole sodium (144-74-1) + ascorbic acid (50-81-7) → compound C15H15N3O7S2

sulfathiazole sodium (144-74-1) + dimethyl sulfate (77-78-1) + aqueous NaOH → sulfanilic acid-<3-methyl-3H-thiazol-2-ylidenamide>

diazomethane (186581-53-3, 908094-01-9) + diethyl ether (60-29-7) + sulfathiazole sodium (144-74-1) → 4-amino-N-methyl-N-(thiazol-2-yl)benzenesulfonamide (51203-19-1) + sulfanilic acid-<3-methyl-3H-thiazol-2-ylidenamide>

sulfathiazole sodium (144-74-1) + copper(II) nitrate → Cu2(sulfathiazolato)4 (72446-92-5)

Conditions	Yield
In not given

sulfathiazole sodium (144-74-1) + copper(II) perchlorate → Cu2(sulfathiazolato)4 (72446-92-5)

Conditions	Yield
In not given

sulfathiazole sodium (144-74-1) + copper dichloride → Cu2(sulfathiazolato)4 (72446-92-5)

Conditions	Yield
In not given

sulfathiazole sodium (144-74-1) + cadmium(II) chloride (10108-64-2) → Cd(H2NC6H4SO2N(C3H2NS))2 (156187-43-8, 146597-11-7)

Conditions	Yield
In water dropwise addn. of metal chloride soln. to 10 % stoich. excess of ligand salt at 90°C (pptn.), heating for 1 h on water bath; filtration, washing (H2O, alcohol), drying (110-115°C); elem. anal.;

sulfathiazole sodium (144-74-1) + cobalt(II) chloride (7646-79-9) → Co(H2NC6H4SO2N(C3H2NS))2 (67077-81-0)

Conditions	Yield
In water dropwise addn. of metal chloride soln. to 10 % stoich. excess of ligand salt at 90°C (pptn.), heating for 1 h on water bath; filtration, washing (H2O, alcohol), drying (110-115°C); elem. anal.;

sulfathiazole sodium (144-74-1) + palladium dichloride → Pd(H2NC6H4SO2N(C3H2NS))2 (156187-42-7)

Conditions	Yield
In water dropwise addn. of metal chloride soln. to 10 % stoich. excess of ligand salt at 90°C (pptn.), heating for 1 h on water bath; filtration, washing (H2O, alcohol), drying (110-115°C); elem. anal.;

cetylpyridinium chloride (123-03-5) + sulfathiazole sodium (144-74-1) → cetylpyridinium sulfathiazole

Conditions	Yield
With methanol at 20℃; for 3h;

3,4,5-triacetoxybenzoyl chloride (70475-59-1) + sulfathiazole sodium (144-74-1) → N-(sulfathiazole)-3,4,5-triacetoxybenzamide

Conditions	Yield
With pyridine In tetrahydrofuran Cooling with ice;

water (7732-18-5) + nickel(II) acetate tetrahydrate (6018-89-9) + sulfathiazole sodium (144-74-1) → 4C9H8N3O2S2(1-)*2Ni(2+)*3H2O

Conditions	Yield
for 2h;

water (7732-18-5) + cobalt(II) diacetate tetrahydrate (6147-53-1) + sulfathiazole sodium (144-74-1) → Co(II)(sulfathiazolate)2(H2O)3

Conditions	Yield
for 72h; Sealed tube;

water (7732-18-5) + cobalt(II) diacetate tetrahydrate (6147-53-1) + sulfathiazole sodium (144-74-1) → 4C9H8N3O2S2(1-)*Co(2+)*10H2O*2Na(1+)

Conditions	Yield
at 40℃; Sealed tube;

Downstream Products

• 156187-42-7 Pd(H₂NC₆H₄SO₂N(C₃H₂NS))2 
• 67077-81-0 Co(H₂NC₆H₄SO₂N(C₃H₂NS))2 
• 146597-11-7 Cd(H₂NC₆H₄SO₂N(C₃H₂NS))2 
• 72446-92-5 Cu₂(sulfathiazolato)4 
• 85-73-4 Cremothalidine 

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