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Sulfadiazine

description Chemical Properties Pharmacological effects Pharmacokinetics Indications Side effects Uses
Sulfadiazine
Sulfadiazine structure
CAS No.
68-35-9
Chemical Name:
Sulfadiazine
Synonyms
a306;A-306;SD-Na;rp2616;DIAZYL;Diazin;Trisem;Adiazin;RP 2616;s.n.112
CBNumber:
CB4166214
Molecular Formula:
C10H10N4O2S
Formula Weight:
250.28
MOL File:
68-35-9.mol

Sulfadiazine Properties

Melting point:
253 °C (dec.)(lit.)
Density 
1.3780 (rough estimate)
refractive index 
1.6440 (estimate)
storage temp. 
0-6°C
solubility 
Soluble in dimethyl sulfoxide.
pka
pKa 2.21(H2O t = 25 I = 0.5 (NaCl)) (Uncertain)
form 
powder
color 
white
Merck 
14,8903
BRN 
6733588
CAS DataBase Reference
68-35-9(CAS DataBase Reference)
NIST Chemistry Reference
Sulfadiazine(68-35-9)
EPA Substance Registry System
Benzenesulfonamide, 4-amino-N-2-pyrimidinyl-(68-35-9)
SAFETY
  • Risk and Safety Statements
  • Hazard and Precautionary Statements (GHS)
Hazard Codes  Xn,Xi
Risk Statements  22-36/37/38-42/43-43-42
Safety Statements  26-36
RIDADR  3249
WGK Germany  3
RTECS  WP1925000
10
TSCA  Yes
HazardClass  6.1(b)
PackingGroup  III
HS Code  29335990
Symbol(GHS):
Signal word: Danger
Hazard statements:
Code Hazard statements Hazard class Category Signal word Pictogram P-Codes
H302 Harmful if swallowed Acute toxicity,oral Category 4 Warning P264, P270, P301+P312, P330, P501
H315 Causes skin irritation Skin corrosion/irritation Category 2 Warning P264, P280, P302+P352, P321,P332+P313, P362
H317 May cause an allergic skin reaction Sensitisation, Skin Category 1 Warning P261, P272, P280, P302+P352,P333+P313, P321, P363, P501
H319 Causes serious eye irritation Serious eye damage/eye irritation Category 2A Warning P264, P280, P305+P351+P338,P337+P313P
H334 May cause allergy or asthma symptoms or breathing difficulties if inhaled Sensitisation, respiratory Category 1 Danger P261, P285, P304+P341, P342+P311,P501
H335 May cause respiratory irritation Specific target organ toxicity, single exposure;Respiratory tract irritation Category 3 Warning
Precautionary statements:
P261 Avoid breathing dust/fume/gas/mist/vapours/spray.
P280 Wear protective gloves/protective clothing/eye protection/face protection.
P284 Wear respiratory protection.
P304+P340 IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P342+P311 IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P405 Store locked up.

Sulfadiazine price More Price(18)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 35033 Sulfadiazine VETRANAL , analytical standard 68-35-9 100mg $44 2018-11-13 Buy
Sigma-Aldrich 1625009 Sulfadiazine United States Pharmacopeia (USP) Reference Standard 68-35-9 200mg $348 2018-11-13 Buy
TCI Chemical S0579 Sulfadiazine >99.0%(HPLC)(T) 68-35-9 25g $39 2018-11-22 Buy
Alfa Aesar A12370 Sulfadiazine, 99% 68-35-9 50g $17 2018-11-13 Buy
Alfa Aesar A12370 Sulfadiazine, 99% 68-35-9 250g $56.8 2018-11-13 Buy

Sulfadiazine Chemical Properties,Uses,Production

description

Sulfadiazine is an oral sulfonamide anti-bacterial agent. it is a synthetic pyrimidinyl sulfonamide derivative, The chemical classification of sulfadiazine is Sulfonamides.The sulfonamides are synthetic bacteriostatic antibiotics with a wide spectrum against most gram-positive and many gram-negative organisms. However, many strains of an individual species may be resistant. Sulfonamides inhibit multiplication of bacteria by acting as competitive inhibitors of p-aminobenzoic acid in the folic acid metabolism cycle. Bacterial sensitivity is the same for the various sulfonamides, and resistance to one sulfonamide indicates resistance to all. Most sulfonamides are readily absorbed orally. However, parenteral administration is difficult, since the soluble sulfonamide salts are highly alkaline and irritating to the tissues. The sulfonamides are widely distributed throughout all tissues. High levels are achieved in pleural, peritoneal, synovial, and ocular fluids. Although these drugs are no longer used to treat meningitis, CSF levels are high in meningeal infections. Their antibacterial action is inhibited by pus.
Sulfadiazine is used in combination with pyrimethamine to treat toxoplasmosis in patients with acquired immunodeficiency syndrome and in newborns with congenital infections.

Chemical Properties

It is White or white-like crystal or powder and is odorless and tasteless. It gradually becomes dark upon exposure to light. It is insoluble in water, soluble in boiling water (1:60), slightly soluble in ethanol and acetone and insoluble in chloroform and ether. It is easily soluble in dilute hydrochloric acid, sodium hydroxide solution or ammonia solution. Its melting point is 252~256 ℃ (decomposition occurs at the same time). Its sodium salt is a white crystalline powder and is odorless with slightly bitter taste. Its sodium salt gradually turns to brown color up exposure to light. When being subject to long-term storage in the moist air, it can slowly absorb carbon dioxide and precipitate out sulfadiazine. It is soluble in water, slightly soluble in ethanol, but insoluble in chloroform and ether. Its 10% aqueous solution has a pH of 9.5 to 10.5.

Pharmacological effects

Sulfadiazine hemolytic has inhibitory effect on various kinds of microorganisms including streptococcus, staphylococcus, meningococcus, pneumococcus, Neisseria gonorrhoeae, Escherichia coli, Shigella and other sensitive bacteria as well as Chlamydia trachomatis, actinomycetes, Plasmodium, Toxoplasma gondii and Star Nocardia. The antibacterial activity of this product is similar as that of sulfasuccinamide. But in recent years, there are increased reports regarding the bacterial resistance to this product, especially in Streptococcus, Neisseria and Enterobacteriaceae. Sulfa-class belongs to broad-spectrum antibacterial agents. The molecular structure of sulfadiazine is similar as that of the amino benzoic acid (PABA), and can compete with PABA for acting on the dihydrofolate synthetase inside bacterial cells, thereby preventing the biosynthesis of folic acid (essential for bacteria) using PABA as the raw material and further reducing the amount of metabolically active folate, which is a indispensible material for bacterial synthesis of purines, thymidine and deoxyribonucleic acid (DNA) and thereby inhibiting the growth and reproduction of bacteria.

Pharmacokinetics

This product can be easily absorbed after oral administration (more than 70% of the administrated drug can be absorbed), but with the absorption rate being relative slow. After a single oral dose of 2g, the plasma concentration reaches peak after 3~6 hours with the peak of free plasma concentration being about 30~60μg/ml. After drug absorption, it widely distributed in body tissue and pleural fluid, peritoneal fluid, synovial fluid, aqueous humor, saliva, sweat, urine and bile. The drug is easy to penetrate through the blood-brain barrier as well as being able to enter into the breast milk and penetrate through the placental barrier. When there is no meningeal inflammation, cerebrospinal fluid drug concentration is about 50% of the plasma concentration. While the value can be 50% to 80% when there is meningeal inflammation.
The drug has a low plasma protein binding rate which is around 38% to 48%. The elimination life for patients of normal renal function is about 10 hours while it can be as long as 34 hours for patients with kidney failure. Sulfadiazine drug is mainly deactivated in the liver through acetylation metabolism, followed by deactivation upon binding to the glucuronide in the liver. The drug is primarily excreted through glomerular filtration. Within 48 to 72 hours after administration of the drug, around 60% to 85% of administrated drug is excreted form urine. In addition, there is still a small amount of drugs being able to be discharged through feces, milk, and bile. Hemodialysis can partially clear the drug. However, peritoneal dialysis can’t effectively remove the drugs.

Indications

Sulfa drugs belong to broad-spectrum antibiotic. However, because of the resistance of many current clinical common pathogens to this class of drugs, it is only used for treating the infection caused by sensitive bacteria and other kinds of susceptible pathogens.
Sulfadiazine (not including the FDC of this drug together with trimethoprim) has its main indications as follows:
1. Used for prevention and treating the meningococcal meningitis caused by sensitive Meningococcal.
2. When being used in combination with trimethoprim, it can be used for treating the otitis media and other kinds of soft tissue infection caused sensitive Haemophilus influenzae, Streptococcus pneumoniae and other kinds of Streptococcus.
3. Used for treating disease related to star nocardia.
4. Used as the adjuvant drug assisting in the treatment of chloroquine-resistant falciparum malaria.
5. Used as the secondary-choice drug for treatment of Chlamydia trachomatis-induced urethritis and cervicitis.
6. Used as the secondary-choice drug for treatment of neonatal inclusion conjunctivitis caused by Chlamydia trachomatis.

Side effects

1. it can cause kidney damage. This product has a low acetylation ratio. This product and its acetylated compound has a low solubility in the urine and is easily subject to crystal precipitation upon a acidic urine, doing harm to the renal tubular as well as the epithelial cells of other urinary tract and causing crystallization of urine, hematuria, proteinuria, and even urine retention or uremia in severe cases.
2. hematopoietic system reactions include neutropenia, acute hemolytic anemia, aplastic anemia, and thrombocytopenia purpura.
3. gastrointestinal reactions include nausea and vomiting. Occasionally: jaundice, liver and spleen. For newborns, premature children, it can cause jaundice, and even kernicterus.
4. urinary system damage: As the prototype of sulfonamides and acesulfame are primarily subject to renal excretion and thus have higher concentrations in the urine. Upon acidic urine, its solubility decreases and can be crystallized and precipitated in renal tubules, renal pelvis, ureter or bladder, causing crystallization of urine, hematuria, proteinuria, dysuria, oliguria and even urine retention.
5. allergic reactions: commonly include rash, drug fever and even exfoliative dermatitis, erythema multiforme exudativum in severe cases. This often occurs during the 7 to 10 days after the medication. Photosensitive dermatitis has also been reported.

Uses

It is excellent kinds of sulfa drugs with strong antibacterial activity, good efficacy, rapid absorption, slow excretion rate and high plasma concentration. It is clinically used for treating upper respiratory tract infection, Meningococcal meningitis, otitis media, boils carbuncle, puerperal fever, urinary tract infections and acute dysentery and so on.
It is a sulfa-type drug which is used for the treatment of infection caused by hemolytic streptococcus, pneumococcus, meningococcis, Neisseria gonorrhea, and E. coli.
It is a sulfa drug with antibacterial effect and convergence effect.

Chemical Properties

White to slightly yellow crystalline pow

Uses

Sulfonamide antibacterial.

Uses

DMSO soluble potent immunosuppressant, neuroprotective neuroregenerative, in vitro T cell proliferation blocker. disrupts calcineurin-mediated signal transduction in T lymphocytes

Definition

ChEBI: A sulfonamide consisting of pyrimidine with a 4-aminobenzenesulfonamido group at the 2-position.

brand name

Coco-Diazine (Lilly); Eskadiazine (SmithKline Beecham).

Antimicrobial activity

Sulfadiazine is somewhat more active than other sulphonamides.

General Description

Sulfadiazine’s plasma half-life is 17 hours. It is a white,odorless crystalline powder soluble in water to the extentof 1:8,100 at 37°C and 1:13,000 at 25°C, in human serumto the extent of 1:620 at 37°C, and sparingly soluble in alcoholand acetone. It is readily soluble in dilute mineralacids and bases. Its pKa is 6.3.

Pharmaceutical Applications

Sulfadiazine is almost insoluble in water and unstable on exposure to light. It is administered orally or, as the sodium salt, by intravenous injection. It is a component of several multi-ingredient preparations. Its low solubility in urine led to its general replacement by other compounds. The intravenous solution is highly alkaline and should not be given by any other route.

Pharmacokinetics

Oral absorption: Very good
Cmax 3 g oral: c. 50 mg/L after 3–4 h
Plasma half-life :7–12 h
Volume of distribution: 0.36 L/kg
Plasma protein binding: c. 40%
Absorption and distribution
Adequate blood concentrations are easily achieved and maintained after oral administration. It is well distributed and penetrates in therapeutic concentrations into the CSF, but because of resistance it is no longer the drug of choice in meningitis. It crosses the placenta and enters breast milk to achieve concentrations around 20% of plasma levels.
Metabolism and excretion
Sulfadiazine is subject to acetylation in the liver. The acetyl derivative lacks antibacterial activity and is excreted more slowly (half-life 8–18 h). Parent compound and metabolite are both excreted mainly by glomerular filtration.

Clinical Use

Urinary tract infection
Nocardiasis
Chancroid
Toxoplasmosis (in combination with pyrimethamine)
Meningococcal infections
Prophylaxis of rheumatic fever

Side effects

In addition to side effects common to the group, sulfadiazine inhibits the metabolism of phenytoin. The risk of crystalluria can be reduced by high fluid intake and alkalization of the urine.

Safety Profile

Poison by intravenous route. Moderately toxic by ingestion and intraperitoneal routes. Human systemic effects by ingestion: hematuria, anuria, general anesthesia, gastrointestinal effects. Experimental teratogenic and reproductive effects. When heated to decomposition it emits very toxic fumes of NOx and SOx.

Sulfadiazine Preparation Products And Raw materials

Raw materials

Preparation Products


Sulfadiazine Suppliers

Global( 292)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Shenzhen Sendi Biotechnology Co.Ltd.
0755-23311925 18102838259
0755-23311925 Abel@chembj.com CHINA 3203 55
Henan DaKen Chemical CO.,LTD.
+86-371-55531817
info@dakenchem.com CHINA 21968 58
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 20680 55
Mainchem Co., Ltd.
+86-0592-6210733
+86-0592-6210733 sales@mainchem.com CHINA 32457 55
Hubei XinRunde Chemical Co., Ltd.
+8615102730682; +8618874586545
02783214688 bruce@xrdchem.cn CHINA 541 55
Hefei TNJ Chemical Industry Co.,Ltd.
86-0551-65418684 18949823763
86-0551-65418684 info@tnjchem.com China 1730 55
Xiamen AmoyChem Co., Ltd
+86 (0)592-605 1114
sales@amoychem.com CHINA 6374 58
Chemwill Asia Co.,Ltd.
86-21-51086038
86-21-51861608 chemwill_asia@126.com;sales@chemwill.com;chemwill@hotmail.com;chemwill@gmail.com CHINA 24001 58
Hubei Jusheng Technology Co.,Ltd.
86-188-71490254
peter@hubeijusheng.com CHINA 20095 58
Hebei Chisure Biotechnology Co., Ltd.
+8613292893290
+8613292893290 Nancy@SpeedGainpharma.com CHINA 1020 58

View Lastest Price from Sulfadiazine manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2018-08-20 Sulfadiazine
68-35-9
US $1.00 / KG 1G 98% 100KG career henan chemical co
2018-09-27 CAS 68-35-9 Sulfadiazine
68-35-9
US $10.00 / G 10G 99% 10MT Hubei XinRunde Chemical Co., Ltd.

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