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Sulfadimethoxine

Brand Name(s) in US

Sulfadimethoxine

CAS No.122-11-2
Chemical Name:Sulfadimethoxine
CBNumber:CB7333026
Molecular Formula:C12H14N4O4S
Formula Weight:310.33
MOL File:122-11-2.mol

Sulfadimethoxine Property

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 Solid
pka pKa 5.94(H2O t = 25.0±0.5 I = 0.2) (Uncertain)
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
FDA 21 CFR 556.640; 558.4
CAS DataBase Reference 122-11-2(CAS DataBase Reference)
FDA UNII 30CPC5LDEX
ATC code J01ED01
EPA Substance Registry System Sulfadimethoxine (122-11-2)
UNSPSC Code 41116107
NACRES NA.24

Safety

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)

NFPA 704:

	0
2		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordWarning
Hazard statements H302
Precautionary statements P264-P270-P301+P312-P501

Sulfadimethoxine Price More Price(6)

Brand: Sigma-Aldrich(India)
Product number: S7007
Product name : Sulfadimethoxine
Purity: 98.0 - 102.0%
Packaging: 10G
Price: ₹8822.38
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: S7007
Product name : Sulfadimethoxine
Purity: 98.0 - 102.0%
Packaging: 25G
Price: ₹16962.78
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: S7007
Product name : Sulfadimethoxine
Purity: 98.0 - 102.0%
Packaging: 100G
Price: ₹33276.05
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: PHR1448
Product name : Sulfadimethoxine
Purity: Pharmaceutical Secondary Standard; Certified Reference Material
Packaging: 500MG
Price: ₹9201.25
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: 46794
Product name : Sulfadimethoxine
Purity: VETRANAL?, analytical standard
Packaging: 250MG
Price: ₹5315.08
Updated: 2022/06/14
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Sulfadimethoxine Chemical Properties,Usage,Production

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.
Biological Activity Sulfonamide 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 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.