57-67-0 Usage
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.
Chemical Properties
Different sources of media describe the Chemical Properties of 57-67-0 differently. You can refer to the following data:
1. 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.
2. white powder
Uses
Different sources of media describe the Uses of 57-67-0 differently. You can refer to the following data:
1. 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.
2. Sulfonamide antibacterial.
3. Sulfaguanidine is a sulfonamide based antibiotic drug with potential application in veterinary medicine.
Production methods
It can be made through the condensation between sulfa and guanidine nitrate.
Category
Toxic substances.
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.
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.]
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.
Synthesis and acrosin inhibitory activity of substituted 4-amino-N-(diaminomethylene) benzenesulfonamide derivatives
Ding, Lili,Zhu, Ju,Zheng, Canhui,Sheng, Chunquan,Qi, Jingjing,Liu, Xuefei,Han, Guangqian,Zhao, Juntao,Lv, Jiaguo,Zhou, Youjun
supporting information; scheme or table, p. 6674 - 6677 (2011/12/04)
A series of new substituted 4-amino-N-(diaminomethylene) benzenesulfonamides were synthesized and their in vitro acrosin inhibitory activities were evaluated. Most of the compounds showed potent acrosin inhibitory activities with compounds 4o and 4p being significantly more potent than the control compound N-alpha-tosyl-l-lysyl-chloromethyl-ketone (TLCK). The compounds provide a new scaffold for the development of acrosin inhibitory agents.
