Sulfaguanidine Property

Melting point:

190-193°C

Boiling point:

426.1±47.0 °C(Predicted)

Density 

1.3916 (rough estimate)

refractive index 

1.6440 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

1 M HCl: soluble50mg/mL

form 

Powder

pka

pKa 2.37(H2O t = 37) (Uncertain)

color 

white to off-white

Water Solubility 

1g/1000mL at 25 ºC

Merck 

14,8908

BRN 

2695326

Stability:

Stable. Incompatible with strong oxidizing agents.

CAS DataBase Reference

57-67-0(CAS DataBase Reference)

NIST Chemistry Reference

Sulfaguanidine(57-67-0)

EPA Substance Registry System

Benzenesulfonamide, 4-amino-N-(aminoiminomethyl)- (57-67-0)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

RIDADR 

3249

WGK Germany 

3

RTECS 

WO8575000

F 

10

HazardClass 

6.1(b)

PackingGroup 

III

HS Code 

29350090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Sulfaguanidine Chemical Properties,Usage,Production

sulfanilamide drugs

Sulfa and Sulfaguanidine have been ever common sulfa drugs. Owing to its relative high toxicity, it is generally not used as the drug of first choice, now they, together with acetaminophen chloride are only used as the intermediates of the manufacturing of sulfa drugs.
Sulfaguanidine is used as sulfa drugs for the treatment of intestinal infections in the earliest time. The molecular structure of sulfaguanidine contains a strongly basic guanidine group with high dissociation property and low lipid solubility. Although there is certain amount which can be absorbed through the gut after oral administration, the amount is not enough to achieve an effective blood concentration, therefore not being used for systemic infections. However, it can be maintained at a high concentration in the intestines, mostly used for the treatment of bacterial infections in the digestive tract such as gastroenteritis and dysentery. When being used in combination with antibacterial synergist trimethoprim (TMP) or di-trimethoprim (DVD), its antibacterial effect was significantly enhanced.
Preparation methods:
1. the finished product of sulfaguanidine can be made through the melting of sulfa and guanidine nitrate in the soda and further vacuum condensation.
2. it can be alternatively made from the reaction between acesulfame chloride and guanidine nitrate in the mixed solution of acetone and water in the presence of sodium hydroxide.
3. take p-nitrobenzenesulfonyl chloride as raw material, go through catalytic hydrogenation reaction to produce p-amino benzenesulfonyl chloride and further ammoniation to generate sulfonamides, and then reacted with guanidine nitrate to obtain sulfaguanidine.
Drug interactions:
1. Simultaneous administration of urine alkaline drugs can enhance the solubility of this product in alkaline urine and increase the excretion.
2. Sulfaguanidine can’t be used in combination with 4-aminobenzoic acid which can replace this product to be absorbed by bacteria and is mutually antagonistic with each other. It is also not suitable to be used in combination with local anesthetics drugs containing the p-amino-benzoyl group such as procaine, tetracaine and so on.
3. for patients subjecting to administration of estrogen contraceptives, simultaneously prolonged administration can lead to a reduction of the reliability of Sulfaguanidine contraceptive and also increase the chance of non-menstrual bleeding.
4. being used in combination with the light-sensitive drug effect may cause photosensitive additive effect.
5. people subjecting to the treatment of goods have a high demand for vitamin K.
This information is edited by Xiongfeng Dai from Chemicalbook.

Chemical Properties

It appears as needle-like crystalline powder with the melting point being 190-193 ℃. 1g of this product can be dissolved in about 1000 ml of water at 25 ℃, dissolved in about 10 ml of water at 100 ℃. It is slightly soluble in ethanol or acetone and easily soluble in dilute hydrochloric acid. It is odorless and tasteless with its color deepened in the case of light.

Uses

1. It belongs to sulfa drugs and used for the treatment of bacillary dysentery and enteritis.
2. It can be used for the treatment of intestinal antibacterial infections such as bacterial dysentery enteritis and can also be used to prevent infection before bowel surgery.
3. It is the first-choice of drug for the treatment of leprosy, being suitable for the treatment of various types of leprosy and being able to alleviate the clinical symptoms. It can generally alleviate the mucosal lesions rapidly with the improvement of skin lesions occurring more slowly, with even slower rate in neuropathy, thereby leading to long course. It is easy to produce drug resistance and difficult to cure. In addition, it can also be used for the treatment of dermatitis herpetiformis, lupus, psoriasis, foot fungus disease and malaria. Its preparation is tablet.

Production methods

It can be made through the condensation between sulfa and guanidine nitrate.

Category

Toxic substances.

Toxicity grading

Poisoning.

Acute toxicity

Intraperitoneal-mouse LDL0: 500 mg/kg.

Flammability and hazardous characteristics

It is combustible with combustion producing toxic fumes of nitrogen oxides and sulfur oxides.

Storage characteristics

Treasury: ventilated, low-temperature and dry.

Extinguishing agent

Dry powder, foam, sand, carbon dioxide, water mist.

Chemical Properties

white powder

Originator

Sulfaguanidine,Lederle,US,1941

Uses

Sulfonamide antibacterial.

Uses

Sulfaguanidine is a sulfonamide based antibiotic drug with potential application in veterinary medicine.

Definition

ChEBI: Sulfaguanidine is a sulfonamide incorporating a guanidine moiety used to block the synthesis of folic acid; mostly used in veterinary medicine It has a role as an antiinfective agent.

Manufacturing Process

10 parts of guanidine hydrochloride (0.1 mol) was dissolved in 75 parts of water and the pH adjusted to 8 to 9. The solution was warmed to 50°C to 60°C and kept at this temperature while a slurry of 25 parts (0.113 mol) of pnitrobenzenesulfonyl chloride was added slowly with mechanical stirring. The pH was kept at 8 to 9 by the addition of 40% sodium hydroxide solution. At the end of the reaction the solution was cooled and filtered from the separated solid. The p-nitrobenzene sulfonyl guanidine was recrystallized from hot water.
5 parts (0.024 mol) of p-nitrobenzene sulfonyl guanidine was dissolved in 50 parts of boiling 95% alcohol and to the solution was added 0.5 part of concentrated hydrochloric acid. The solution was heated to reflux and 6 parts of iron dust was added. The suspension was refluxed for 3 hours, made basic with potassium carbonate, and filtered hot. The alcohol was evaporated off and the p-aminobenzene sulfonyl guanidine recrystallized from boiling water with the addition of decolorizing charcoal.

brand name

Aseptil-guanidina;Coliseptale;Devaguanil;Dirkan;Emerin;Ente-rivo simplex;Granidan;Guamide;Guanicil;Guanimycin;Guanowept;Guasept;Inorgan;Intestovet;Ordenol;Orgaguanidon;Resulfon;Ruocil;Sgd;S-guanidan;S-guanidine;Shigatox;Suganyl;Sulfacarbon;Sulfentidine;Sulfogua;Tetrawest;Trisulvet.

Therapeutic Function

Antimicrobial

World Health Organization (WHO)

Sulfaguanidine, a sulfonamide anti-infective agent, was introduced in 1941 for the treatment of bacterial infections. The importance of sulfonamides has subsequently decreased as a result of increasing bacterial resistance and their replacement by antibiotics which are generally more active and less toxic. The sulfonamides are known to cause serious adverse effects such as renal toxicity sometimes fatal exfoliative dermatitis and erythema multiforma and dangerous adverse reactions affecting blood formation such as agranulocytosis and haemolytic or aplastic anaemia. Although sulfaguanidine, which is poorly absorbed from the gastrointestinal tract, is no longer recommended in some countries, it continues to be used in others for the treatment of local intestinal infections, including bacterial dysentery, and for preoperative bowel preparation.

Pharmaceutical Applications

1-Sulfanilylguanidine. A poorly absorbed compound, less potent than succinylsulfathiazole but with similar uses. Blood concentrations of 15–40 mg/L have been found after single doses of 1–7 g. Excretion in the urine is rapid.

Safety Profile

Moderately toxic by intraperitoneal route. An experimental teratogen. Other experimental reproductive effects. See also SULFONATES. When heated to decomposition it emits very toxic fumes of SO, and NO,.

Purification Methods

Crystallise the antibacterial from hot water (7mL/g). [Beilstein 14 III 1970, 14 IV 2668.]