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

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

InChI

InChI=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)

InChIKey

ZZORFUFYDOWNEF-UHFFFAOYSA-N

SMILES

C1(S(NC2C=C(OC)N=C(OC)N=2)(=O)=O)=CC=C(N)C=C1

CAS DataBase Reference

122-11-2(CAS DataBase Reference)

EPA Substance Registry System

Sulfadimethoxine (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

F 

8

HazardClass 

6.1(b)

PackingGroup 

III

HS Code 

29350090

Toxicity

LD50 orally in mice: >10 g/kg (Seki)

MSDS

• Language:English Provider:Sulfadimethoxine
• Language:English Provider:SigmaAldrich

Sulfadimethoxine Usage And Synthesis

Brand Name(s) in US

Albon, Bactrovet, and generic

Chemical Properties

White Solid

Originator

Madribon,Roche,US,1958

Uses

Antibacterial.This compound is a contaminant of emerging concern (CECs).

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.

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 effects

Common 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 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.

Sulfadimethoxine(122-11-2)Related Product Information

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