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CAS NO.57-67-0
| Sulfaguanidine Basic information |
| Product Name: | Sulfaguanidine |
| Synonyms: | ((4-Aminophenyl)sulfonyl)guanidine;((p-Aminophenyl)sulfonyl)guanidine;1-((p-Aminophenyl)sulfonyl)guanidine;1-Amino-4-(([amino(imino)methyl]amino)sulfonyl)benzene;1-Sulfanilylguanidine;4-amino-n-(aminoiminomethyl)-benzenesulfonamid;4-amino-n-(diaminomethylene)-benzenesulfonamid;4-Amino-N-(diaminomethylene)benzenesulfonamide |
| CAS: | 57-67-0 |
| MF: | C7H10N4O2S |
| MW: | 214.24 |
| EINECS: | 200-345-9 |
| Product Categories: | Antibiotics for Research and Experimental Use;Biochemistry;Sulfonamides (Antibiotics for Research and Experimental Use);Antibacterial;Antibiotics;Antibiotics A to;Antibiotics N-SAntibiotics;Chemical Structure Class;Inhibits an EnzymeAntibiotics;Interferes with DNA SynthesisSpectrum of Activity;L - ZAntibiotics;Mechanism of Action;Sulfonamides;GANIDAN;pharmaceutical |
| Mol File: | 57-67-0.mol |
|
|
|
| Sulfaguanidine Chemical Properties |
| mp | 190-193°C |
| storage temp. | -20°C |
| Water Solubility | 1g/1000mL at 25 ºC |
| Merck | 8908 |
| 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 Information |
| 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 |
| MSDS Information |
| Provider | Language |
|---|---|
| SigmaAldrich | English |
| Sulfaguanidine Usage And Synthesis |
| 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. |
| Application |
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 |
| Usage | antibacterial |
| Usage | Sulfaguanidine is a sulfonamide based antibiotic drug with potential application in veterinary medicine. |
| Sulfaguanidine Preparation Products And Raw materials |
| Preparation Products | Sulfadiazine-->Robenidine hydrochloride-->Sulfamethazine-->Sulfameter |
| Raw materials | 4-Chloronitrobenzene-->Guanidine nitrate-->Sulfanilamide |
| Sulfaguanidine Basic information |
| Product Name: | Sulfaguanidine |
| Synonyms: | ((4-Aminophenyl)sulfonyl)guanidine;((p-Aminophenyl)sulfonyl)guanidine;1-((p-Aminophenyl)sulfonyl)guanidine;1-Amino-4-(([amino(imino)methyl]amino)sulfonyl)benzene;1-Sulfanilylguanidine;4-amino-n-(aminoiminomethyl)-benzenesulfonamid;4-amino-n-(diaminomethylene)-benzenesulfonamid;4-Amino-N-(diaminomethylene)benzenesulfonamide |
| CAS: | 57-67-0 |
| MF: | C7H10N4O2S |
| MW: | 214.24 |
| EINECS: | 200-345-9 |
| Product Categories: | Antibiotics for Research and Experimental Use;Biochemistry;Sulfonamides (Antibiotics for Research and Experimental Use);Antibacterial;Antibiotics;Antibiotics A to;Antibiotics N-SAntibiotics;Chemical Structure Class;Inhibits an EnzymeAntibiotics;Interferes with DNA SynthesisSpectrum of Activity;L - ZAntibiotics;Mechanism of Action;Sulfonamides;GANIDAN;pharmaceutical |
| Mol File: | 57-67-0.mol |
|
|
|
| Sulfaguanidine Chemical Properties |
| mp | 190-193°C |
| storage temp. | -20°C |
| Water Solubility | 1g/1000mL at 25 ºC |
| Merck | 8908 |
| 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 Information |
| 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 |
| MSDS Information |
| Provider | Language |
|---|---|
| SigmaAldrich | English |
| Sulfaguanidine Usage And Synthesis |
| 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. |
| Application |
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 |
| Usage | antibacterial |
| Usage | Sulfaguanidine is a sulfonamide based antibiotic drug with potential application in veterinary medicine. |
| Sulfaguanidine Preparation Products And Raw materials |
| Preparation Products | Sulfadiazine-->Robenidine hydrochloride-->Sulfamethazine-->Sulfameter |
| Raw materials | 4-Chloronitrobenzene-->Guanidine nitrate-->Sulfanilamide |