Sulfadimethoxine
Synonym(s):4-Amino-N-(2,6-dimethoxy-4-pyrimidinyl)benzenesulfonamide;Sulfadimethoxine
- CAS NO.:122-11-2
- Empirical Formula: C12H14N4O4S
- Molecular Weight: 310.33
- MDL number: MFCD00057345
- EINECS: 204-523-7
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-20 11:41:24
What is Sulfadimethoxine?
Chemical properties
White Solid
Originator
Madribon,Roche,US,1958
The Uses of Sulfadimethoxine
Antibacterial.
The Uses of Sulfadimethoxine
Antibacterial.This compound is a contaminant of emerging concern (CECs).
Background
Sulfadimethoxine is a sulfonamide antibiotic. Sulfadimethoxine is used to treat many infections, including treatment of respiratory, urinary tract, enteric, and soft tissue infections. It is most frequently used in veterinary medicine, although it is approved in some countries for use in humans. Sulfadimethoxine inhibits bacterial synthesis of folic acid (pteroylglutamic acid) from para-aminobenzoic acid. Sulfadimethoxine is approved in Russia for use in humans, including children, and has been successfully used there for more than 35 years. It is widely available in Russia as an over-the-counter drug manufactured by a number of Russian pharmaceutical companies.
In the US, sulfadimethoxine is one of the products that have been withdrawn or removed from the market after being found to be unsafe or not effective.
Indications
For use in the treatment of infections.
Definition
ChEBI: A sulfonamide consisting of pyrimidine having methoxy substituents at the 2- and 6-positions and a 4-aminobenzenesulfonamido group at the 4-position.
Manufacturing Process
1.4 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 Function
Antibacterial
Pharmaceutical Applications
2,4-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.
Pharmacokinetics
Sulfadimethoxine has been shown to be effective against streptococci, klebsiella, proteus, shigella, staphylococci, escherichia, and salmonella.
Safety Profile
Moderately 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 Treatments
Sulfadimethoxine 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.
Metabolism
Not Available
Properties of Sulfadimethoxine
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 |
form | neat |
pka | pKa 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 |
CAS DataBase Reference | 122-11-2(CAS DataBase Reference) |
EPA Substance Registry System | Sulfadimethoxine (122-11-2) |
Safety information for Sulfadimethoxine
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H302:Acute toxicity,oral |
Precautionary Statement Codes |
P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P270:Do not eat, drink or smoke when using this product. P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. P501:Dispose of contents/container to..… |
Computed Descriptors for Sulfadimethoxine
Abamectin manufacturer
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