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Sulfadimethoxine

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Sulfadimethoxine Basic information
Brand Name(s) in US
Product Name:Sulfadimethoxine
Synonyms:deposul;diasulfa;madroxin;madroxine;maxulvet;memcozine;metoxidon;n(sup1)-(2,6-dimethoxy-4-pyrimidinyl)-sulfanilamid
CAS:122-11-2
MF:C12H14N4O4S
MW:310.33
EINECS:204-523-7
Product Categories:MADRIBON;APIs;Antibiotics for Research and Experimental Use;Biochemistry;Sulfonamides (Antibiotics for Research and Experimental Use);Amines;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
Mol File:122-11-2.mol
Sulfadimethoxine Structure
Sulfadimethoxine Chemical Properties
Melting point 200 °C
Boiling point 265.5°C (rough estimate)
density 1.4006 (rough estimate)
refractive index 1.6270 (estimate)
storage temp. Keep in dark place,Inert atmosphere,2-8°C
solubility NH4OH 1 M: 50 mg/mL, clear, faintly yellow
pkapKa 5.94(H2O t = 25.0±0.5 I = 0.2) (Uncertain)
form Solid
color White to Off-White
Water Solubility 46.3mg/L(37 ºC)
Merck 14,8905
BRN 306856
Major Applicationforensics and toxicology
pharmaceutical (small molecule)
InChIInChI=1S/C12H14N4O4S/c1-19-11-7-10(14-12(15-11)20-2)16-21(17,18)9-5-3-8(13)4-6-9/h3-7H,13H2,1-2H3,(H,14,15,16)
InChIKeyZZORFUFYDOWNEF-UHFFFAOYSA-N
SMILESC1(S(NC2C=C(OC)N=C(OC)N=2)(=O)=O)=CC=C(N)C=C1
CAS DataBase Reference122-11-2(CAS DataBase Reference)
EPA Substance Registry SystemSulfadimethoxine (122-11-2)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38-43
Safety Statements 26-36/37-24/25-23
RIDADR 3249
WGK Germany 3
RTECS WO9030000
8
HazardClass 6.1(b)
PackingGroup III
HS Code 29350090
Storage Class11 - Combustible Solids
Hazard ClassificationsAcute Tox. 4 Oral
ToxicityLD50 orally in mice: >10 g/kg (Seki)
MSDS Information
ProviderLanguage
Sulfadimethoxine English
SigmaAldrich English
Sulfadimethoxine Usage And Synthesis
Brand Name(s) in USAlbon, Bactrovet, and generic
Chemical PropertiesWhite Solid
OriginatorMadribon,Roche,US,1958
UsesAntibacterial.This compound is a contaminant of emerging concern (CECs).
DefinitionChEBI: A sulfonamide consisting of pyrimidine having methoxy substituents at the 2- and 6-positions and a 4-aminobenzenesulfonamido group at the 4-position.
Manufacturing Process1.4 g of 4-phenylsulfonyl-2,6-dimethoxypyrimidine and 4 g of sodium sulfanilamide (both dried over potassium hydroxide) were very finely ground and heated in an oil bath for 10 hours at 120°C (inside temperature). The reaction mixture was taken up in 30 ml of water and treated with 3 ml of 2 N sodium hydroxide solution. After standing for one hour at 0°C, the turbid solution was filtered and the filtrate was made alkaline with sodium carbonate. After again standing for one hour at 0°C, the precipitate was filtered off (1.9 g of regenerated sulfanilamide) and the filtrate was neutralized with acetic acid, whereupon crystallization resulted. The isolated crystals of 4-sulfanilamido- 2,6-dimethoxypyrimidine weighed 1.3 g (84% of theory), melting point 190°C to 196°C.
Therapeutic FunctionAntibacterial
Pharmaceutical Applications2,4-Dimethoxy-6-sulfanilamido-1,3-diazine. A rapidly absorbed compound with a long half-life (38–40 h) and a high degree of protein binding (98%). Renal clearance is very slow, and daily dosage maintains adequate plasma levels.
Biological ActivitySulfonamide antibiotic th at blocks the synthesis of dihydrofolic acid by inhibiting the enzyme dihydropteroate synthase.
Mode of Action: Inhibits folic acid synthesis in prokaryotes.
Anti-microbial Spectrum: Gram positive, Gram negative, Chlamydia
Mode of Resistance: Alteration of dihydropteroate synthase or alternative pathway for folic acid synthesis.
Mechanism of action The mechanism of action of sulfadimethoxine centres on its ability to inhibit bacterial folic acid synthesis. Folic acid, or folate, is essential for synthesising nucleotides, which are the building blocks of DNA. Sulfadimethoxine acts as a competitive inhibitor of the enzyme dihydropteroate synthase (DHPS). DHPS is crucial for converting para-aminobenzoic acid (PABA) into dihydropteroate, a precursor in folate synthesis. By inhibiting DHPS, sulfadimethoxine prevents the conversion of PABA to dihydropteroate, thereby halting the production of folic acid. Without folic acid, bacteria cannot synthesize the nucleotides necessary for DNA replication, resulting in bacteriostasis – the inhibition of bacterial growth and multiplication. This action is particularly effective against rapidly dividing bacterial cells, making sulfadimethoxine a potent antibacterial agent.
Side effectsCommon but usually not serious side effects include: Reduced appetite, vomiting, loose stools (diarrhea).
Side effects that may be serious orindicate a serious problem:
Dry eye syndrome (keratoconjunctivitis sicca; KCS). Before your dog takes this drug, your veterinarian will wantto measure your dog’s tear production. Signs of dry eye include redness or discharge from the eyes or increased blinking. Difficulty urinating or straining to urinate; blood in urine.
Skin conditions: Sores, skin that appears to be burned, severe itching, loss of fur.
Increased thirst and urination.
Swelling of face.
Lack of energy or appetite, tiredness, fever.
Difficulty walking. Yellowing of the gums or whites of the eyes (jaundice).
Safety ProfileModerately toxic by intraperitoneal, intravenous, and subcutaneous routes. An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of SOx and NOx.
Veterinary Drugs and TreatmentsSulfadimethoxine injection and tablets are approved for use in dogs and cats for respiratory, genitourinary, enteric and soft tissue infections caused by susceptible organisms. Sulfadimethoxine is used in the treatment of coccidiosis in dogs although not approved for this indication.
In horses, sulfadimethoxine injection is approved for the treatment of respiratory infections caused by Streptococcus equi.
In cattle, the drug is approved for treating shipping fever complex, calf diphtheria, bacterial pneumonia and foot rot caused by susceptible organisms.
In poultry, sulfadimethoxine is added to drinking water to treat coccidiosis, fowl cholera, and infectious coryza.
References[1] Patent: CN107325057, 2017, A. Location in patent: Paragraph 0027; 0028; 0035; 0036; 0040; 0041; 0045; 0046
[2] Monatshefte fuer Chemie, 1956, vol. 87, p. 136,142
Sulfadimethoxine Preparation Products And Raw materials
Raw materials2-Amino-4,6-dimethoxypyrimidine-->4-(Acetylamino)-N-(2,6-dimethoxy-4-pyrimidinyl)benzenesulfonamide
Tag:Sulfadimethoxine(122-11-2) Related Product Information
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