Brand Name(s) in US
ChemicalBook > CAS DataBase List > Sulfadimethoxine

Sulfadimethoxine

Brand Name(s) in US
Product Name
Sulfadimethoxine
CAS No.
122-11-2
Chemical Name
Sulfadimethoxine
Synonyms
SULPHADIMETHOXINE;Sulfadimethoxine base;sulfadimethoxin;symbio;sulfadimetoxin;abcid;albon;fuxal;sudine;Dosmin
CBNumber
CB7333026
Molecular Formula
C12H14N4O4S
Formula Weight
310.33
MOL File
122-11-2.mol
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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
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)
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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)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
PHR1448
Product name
Sulfadimethoxine
Purity
Pharmaceutical Secondary Standard; Certified Reference Material
Packaging
500mg
Price
$105
Updated
2024/03/01
Sigma-Aldrich
Product number
1626001
Product name
Sulfadimethoxine
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$228.6
Updated
2024/03/01
TCI Chemical
Product number
S0359
Product name
Sulfadimethoxine
Purity
>98.0%(HPLC)(T)
Packaging
25g
Price
$81
Updated
2024/03/01
Cayman Chemical
Product number
28827
Product name
Sulfadimethoxine
Packaging
25g
Price
$70
Updated
2024/03/01
Cayman Chemical
Product number
28827
Product name
Sulfadimethoxine
Packaging
50g
Price
$109
Updated
2024/03/01
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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.

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 Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Sulfadimethoxine manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Sulfadimethoxine base 122-11-2
Price
US $0.00/kg
Min. Order
100kg
Purity
98%-102; USP40
Supply Ability
5 tons
Release date
2022-05-07
Hebei Chuanghai Biotechnology Co,.LTD
Product
Sulfadimethoxine 122-11-2
Price
US $5.00-2.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10000kg
Release date
2024-08-21
Weijer International Trade (Hebei) Co., Ltd
Product
Sulfadimethoxine 122-11-2
Price
US $80.00/KG
Min. Order
1KG
Purity
>99%
Supply Ability
20tons
Release date
2023-03-15

122-11-2, SulfadimethoxineRelated Search:

Sulfachoropyrazine sodium Sulfachloropyridazine sodium SULFACHLOROPYRIDAZINE Phenazine methosulfate Silver sulfadiazine N-(5-CHLORO-3-PYRAZINE)-4-AMINOBENZENESULFONAININO Sulfamethoxypyridazine 1,1-Dimethoxyethane Sulfalen Dimethoxymethane Sulfadiazine SULFADIMETHOXINE SODIUM SALT,Sodium sulfadimethoxine SULFADIMETHOXINE-D4 Sulfamethazine sodium salt Sulfamethazine Sulfaguanidine Sulfabenzamide 4-(Acetylamino)-N-(2,6-dimethoxy-4-pyrimidinyl)benzenesulfonamide

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  • n(sup1)-(2,6-dimethoxy-4-pyrimidinyl)sulfanilamide
  • neostrepal
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  • Sulphanyl acid N-(2,6-dimethoxypyrimidin-4-yl) amide
  • 2,4-Dimethoxy-6-sulfanilamido-1,3-pyrimidine
  • 4-(p-Aminobenzenesulfonamido)-2,6-dimethoxypyrimidine
  • 4-Sulfa-2,6-dimethoxypyrimidine
  • 6-Sulfanilamido-2,4-dimethoxy-1,3-diazine
  • Dosmin
  • Lastin
  • Sulfadimethoxine (200 mg)G0D2490.998mg/mg(ai)
  • Sulfadimethoxine (200 mg)
  • SULPHADIMETHOXINE BP 88,USP 25
  • Sulfadimethoxine (base and/or unspecified salts)
  • 4-azanyl-N-(2,6-dimethoxypyrimidin-4-yl)benzenesulfonamide
  • Sulfadimethoxine Solution, 100ppm
  • Sulfadimethoxine solution,1000ppm
  • Sulfadimethoxine for peak identification
  • 2,4-dimethoxy-6-sulfanilamido-1,3-diazine
  • 2,6-dimethoxy-4-(p-aminobenzenesulfonamido)pyrimidine
  • 2,6-dimethoxy-4-sulfanilamidopyrimidine
  • 4-amino-n-(2,6-dimethoxy-4-pyrimidinyl)-benzenesulfonamid
  • abcid
  • agribon
  • albon
  • arnosulfan
  • bactrovet
  • Agribon(TM)
  • diasulfyl
  • dimetazina
  • dimethoxysulfadiazine
  • dorisul
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  • madribon
  • madrigid
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