57-67-0 Usage
Description
Sulfaguanidine is a sulfonamide-based antibiotic drug that belongs to the class of sulfa drugs. It is characterized by its needle-like crystalline powder form with a melting point of 190-193°C. Sulfaguanidine is odorless and tasteless, with its color deepening upon exposure to light. It is slightly soluble in ethanol or acetone and easily soluble in dilute hydrochloric acid. Being a toxic substance, it is used primarily for its antibacterial properties and is available under various brand names such as Aseptil-guanidina, Coliseptale, Devaguanil, and many others.
Uses
1. Used in Human Medicine:
Sulfaguanidine is used as an antibacterial agent for the treatment of various intestinal infections, including bacillary dysentery and enteritis. It is also utilized as a preventive measure against infection before bowel surgery. Additionally, it is the first-choice drug for the treatment of leprosy, alleviating clinical symptoms and improving mucosal and skin lesions, although the rate of improvement in neuropathy is slower, leading to a longer treatment course. Sulfaguanidine is also prescribed for conditions like dermatitis herpetiformis, lupus, psoriasis, foot fungus disease, and malaria. Its common preparation form is a tablet.
2. Used in Veterinary Medicine:
Sulfaguanidine has potential applications in veterinary medicine as a sulfonamide antibacterial, serving a similar purpose as in human medicine for treating bacterial infections in animals.
3. Used in Pharmaceutical Industry:
In the pharmaceutical industry, Sulfaguanidine is used as an active pharmaceutical ingredient (API) for the development of various medications targeting the aforementioned conditions. Its chemical properties make it suitable for formulation into different dosage forms, such as tablets, which facilitate its administration and absorption.
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 lookchem.
Production methods
It can be made through the condensation between sulfa and guanidine nitrate.
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.
Originator
Sulfaguanidine,Lederle,US,1941
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.
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 57-67-0 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 7 respectively; the second part has 2 digits, 6 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 57-67:
(4*5)+(3*7)+(2*6)+(1*7)=60
60 % 10 = 0
So 57-67-0 is a valid CAS Registry Number.
InChI:InChI=1/C7H10N4O2S/c8-5-1-3-6(4-2-5)14(12,13)11-7(9)10/h1-4H,8H2,(H4,9,10,11)
57-67-0Relevant articles and documents
Industrial method for the preparation of p-aminobenzenesulfonylguanidine (sulgin)
Skurydina,Pleshakov,Kuznetsova,Trifonova
, p. 352 - 353 (1977)
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Method for synthesizing sulphaguanidine
-
Paragraph 0017; 0018, (2016/10/31)
The invention discloses a method for synthesizing sulphaguanidine. According to the method, sulfonamide and guanidine hydrochloride are used as raw materials and are catalyzed by iodide to synthesize sulphaguanidine in one step. The method has the advantages of short process route and little environment pollution.
Novel method for synthesis of sulphaguanidine
Singh, Vikram,Kaushik
experimental part, p. 645 - 648 (2012/05/04)
The microwave-enhanced synthesis of sulphaguanidine is achieved rapidly and in good yield via the step-wise reaction of cyanamide with sulphonamide in the presence of acidic alumina or montmorillonite clays (KSF and K10).