Sulfaguanidine

Sulfaguanidine Basic information
sulfanilamide drugs Chemical Properties Uses Production methods Category Toxicity grading Acute toxicity Flammability and hazardous characteristics Storage characteristics Extinguishing agent
Product Name:Sulfaguanidine
Synonyms:4-Amino-N-(aminoiminomethyl)benzenesulfonamide 4-Amino-N-guanylbenzenesulfonamide 4-Amino-N-amidinobenzenesulfonamide 4-Aminobenzenesulfonylguanidine;GUAMIDE;BIO-FARMA BF003097;LABOTEST-BB LT00059386;AKOS BBB/022;Sulfaguanidine (guanidine);α-sarcoglycan;50DAG
CAS:57-67-0
MF:C7H10N4O2S
MW:214.24
EINECS:200-345-9
Product Categories:GANIDAN;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;pharmaceutical;57-67-0
Mol File:57-67-0.mol
Sulfaguanidine Structure
Sulfaguanidine Chemical Properties
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
pkapKa 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 Reference57-67-0(CAS DataBase Reference)
NIST Chemistry ReferenceSulfaguanidine(57-67-0)
EPA Substance Registry SystemBenzenesulfonamide, 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
10
HazardClass 6.1(b)
PackingGroup III
HS Code 29350090
MSDS Information
ProviderLanguage
SigmaAldrich English
Sulfaguanidine Usage And Synthesis
sulfanilamide drugsSulfa 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 PropertiesIt 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.
Uses1. 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 methodsIt can be made through the condensation between sulfa and guanidine nitrate.
CategoryToxic substances.
Toxicity gradingPoisoning.
Acute toxicityIntraperitoneal-mouse LDL0: 500 mg/kg.
Flammability and hazardous characteristicsIt is combustible with combustion producing toxic fumes of nitrogen oxides and sulfur oxides.
Storage characteristicsTreasury: ventilated, low-temperature and dry.
Extinguishing agentDry powder, foam, sand, carbon dioxide, water mist.
Chemical Propertieswhite powder
OriginatorSulfaguanidine,Lederle,US,1941
UsesSulfonamide antibacterial.
UsesSulfaguanidine is a sulfonamide based antibiotic drug with potential application in veterinary medicine.
DefinitionChEBI: 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 Process10 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 nameAseptil-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 FunctionAntimicrobial
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 Applications1-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 ProfileModerately 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 MethodsCrystallise the antibacterial from hot water (7mL/g). [Beilstein 14 III 1970, 14 IV 2668.]
N-(4-(N-(2,5-DIMETHOXYPHENYL)-N-(N-(4,6-DIMETHYLPYRIMIDIN-2-YL)CARBAMIMIDOYL)SULFAMOYL)PHENYL)ACETAMIDE TIMTEC-BB SBB002953 TIMTEC-BB SBB006047 Acetamide, N-(4-(((((((5-(3,5-dinitrophenyl)-1,3,4-thiadiazol-2-yl)ami no)iminomethyl)amino)iminomethyl)amino)sulfonyl)-2-methylphenyl)-, mon ohydrochloride 4-AMINO-N-{(5Z)-5-[2-(4-NITROPHENYL)-2-OXOETHYLIDENE]-4-OXO-4,5-DIHYDRO-1H-IMIDAZOL-2-YL}BENZENESULFONAMIDE BIO-FARMA BF003882 BIO-FARMA BF003723 4-AMINO-N-{(5Z)-5-[2-(4-CHLOROPHENYL)-2-OXOETHYLIDENE]-4-OXO-4,5-DIHYDRO-1H-IMIDAZOL-2-YL}BENZENESULFONAMIDE 4-AMINO-N-{(5Z)-5-[2-(4-METHYLPHENYL)-2-OXOETHYLIDENE]-4-OXO-4,5-DIHYDRO-1H-IMIDAZOL-2-YL}BENZENESULFONAMIDE BIO-FARMA BF003769 4-AMINO-N-{(5Z)-5-[2-(4-BROMOPHENYL)-2-OXOETHYLIDENE]-4-OXO-4,5-DIHYDRO-1H-IMIDAZOL-2-YL}BENZENESULFONAMIDE TIMTEC-BB SBB006056 TIMTEC-BB SBB006054 ([AMINO(IMINO)METHYL]AMINO)(4-([(E)-3-(4-FLUOROPHENYL)-3-OXO-1-PROPENYL]AMINO)PHENYL)DIOXO-LAMBDA6-SULFANE Acetamide, N-(4-(((imino((imino((5-(4-methoxyphenyl)-1,3,4-thiadiazol- 2-yl)amino)methyl)amino)methyl)amino)sulfonyl)-2-methylphenyl)-, monoh ydrochloride TIMTEC-BB SBB006049 TIMTEC-BB SBB006434 SULFAGUANIDINE MONOHYDRATE,SULFAGUANIDINE MONOHYDRATE VETRANAL,250

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