sulfadimethoxine

Small moleculeexperimental

Sulfadimethoxine is a sulfonamide antibacterial 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 and is available as an over-the-counter drug manufactured by a number of Russian pharmaceutical companies. In USA and Europe sulfadimethoxine is approved in a veterinary medicinal products. ANADA was approved by FDA in US in 1997 as an Over the Counter medicine for treatment of bovine respiratory disease complex (shipping fever complex) and bacterial pneumonia associated with Pasteurella Spp. Sensitive to sulfadimethoxine; necrotic pododermatitis (foot rot) and calf diphtheria caused by Fusobacterium necrophorum (Sphaerophorus necrophorus) sensitive to sulfadimethoxine. Bioequivalence for this generic animal drug, Sulfadimethoxine Injection 40%, was established by demonstration of chemical equivalence to the pioneer product, Hoffmann-La Roche's Albon® Injection 40% (NADA 041-245). — NCATS

Clinical trial activity

0 trials · 0 clinical orgs · 0 marketing orgs

Phase 1
0
Phase 2
0
Phase 3
0
Phase 4
0

Indications

Mechanism of action

  • folP inhibitor

    Bacteria and some protozoa are unable to obtain folic acid from the environment, and must synthesize it by converting PABA (para-aminobenzoate) to dihydropteroate using the enzyme dihydropteroate synthase. Sulfadimethoxine, being structurally similar to PABA, acts as a competitive inhibitor. It binds to the enzyme's active site and prevents the synthesis of folic acid from progressing. Folic acid is necessary for these organisms to produce nucleic acids, which are required for cell division. Thus, it has a microbiostatic effect rather than a microbiocidal one, and has the strongest effect in the beginning stages of an infection, when the pathogen is rapidly dividing.

Chemistry & pharmacology

Loading structure…

SMILES

COC1=NC(OC)=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=C1
Mol. weight
310.329 g/mol
Lipinski Ro5
Pass
Rule of 3
No
Chirality
Achiral Molecule
Inorganic
No
Polymer
No

Oral

No

Parenteral

No

Topical

No

Sources

Also known as

  • 2,4-dimethoxy-6-sulfanilamido-1,3-diazine
  • 2,4-dimethoxy-6-sulfanilamido-1,3-diazine
  • 2,6-dimethoxy-4-(p-aminobenzenesulfonamido)pyrimidine
  • 2,6-dimethoxy-4-(p-aminobenzenesulfonamido)pyrimidine
  • 2,6-dimethoxy-4-sulfanilamidopyrimidine
  • 2,6-dimethoxy-4-sulfanilamidopyrimidine
  • 4-amino-n-(2,6-dimethoxy-4-pyrimidinyl)benzenesulfonamide
  • 4-amino-n-(2,6-dimethoxy-4-pyrimidinyl)benzenesulfonamide
  • 4-amino-n-(2,6-dimethyl-4-pyrimidinyl)benzenesulfonamide
  • 4-amino-n-(2,6-dimethyl-4-pyrimidinyl)benzenesulfonamide
  • 6-sulfanilamido-2,4-dimethoxypyrimidine
  • 6-sulfanilamido-2,4-dimethoxypyrimidine
  • abcid (tn)
  • abcid (tn)
  • agribon (tn)
  • agribon (tn)
  • madribon
  • madribon
  • n(1)-(2,6-dimethoxy-4-pyrimidinyl)sulfanilamide
  • n(1)-(2,6-dimethoxy-4-pyrimidinyl)sulfanilamide
  • neostreptal
  • suldixine
  • sulfabon
  • sulfadimethoxin
  • sulfadimethoxine
  • sulfadimethoxine
  • sulfadimethoxine
  • sulfadimethoxine
  • sulfadimethoxine
  • sulfadimethoxine
  • sulfadimethoxine
  • sulfadimethoxine
  • sulfadimethoxinum
  • sulfadimethoxinum
  • sulfadimethoxydiazin
  • sulfadimethoxydiazine
  • sulfadimethoxydiazine
  • sulfadimetoxin
  • sulfadimetoxina
  • sulfadimetoxina
  • sulfadimetoxine
  • sulfadimoxine
  • sulphadimethoxine
  • sulphadimethoxine
  • sulphadimethoxine