Sulfamoxole
Basic information
- CAS
729-99-7- Standard SMILES
Cc1nc(NS(=O)(=O)c2ccc(N)cc2)oc1C- InChIKey
CYFLXLSBHQBMFT-UHFFFAOYSA-N- Molecular formula
- C11H13N3O3S
- Average molar mass
- 267.31 g/mol
- Monoisotopic mass
- 267.06776246
Overview
Sulfamoxole is a sulfonamide antibiotic in which 4-aminobenzenesulfonic acid and 4,5-dimethyl-1,3-oxazol-2-amine have combined to form the sulfonamide bond. It has a role as an antimicrobial agent and a drug allergen. It is a sulfonamide, an oxazole and a sulfonamide antibiotic.
Names & identifiers
- Preferred name
- Sulfamoxole
- IUPAC
- 4-amino-N-(4,5-dimethyl-1,3-oxazol-2-yl)benzenesulfonamide
- English name
- SULFAMOXOL
- Molecular formula
- C11H13N3O3S
- Molecular weight
- 267.3
Names & synonyms
SULFAMOXOLE729-99-7SulfamoxolSulphamoxoleSulfamoxolumSulfadimethyloxazoleOxasulfaSulfuno4-Amino-N-(4,5-dimethyl-2-oxazolyl)benzenesulfonamide4,5-Dimethyl-2-sulfanilamidooxazole4-Amino-N-(4,5-dimethyl-1,3-oxazol-2-yl)benzenesulfonamideN1-(4,5-Dimethyl-2-oxazolyl)sulfanilamide
Show more names
NuprinSulfabutinSulfamoxol-d4Sulfamocol-D4SdmoSulfanosulfonoSulfune
2-(p-Aminobenzenesulfonamido)-4,5-dimethyloxazolep-Aminobenzenesulfonyl-2-amino-4,5-dimethyloxazoleDTXSID50236172-(p-Aminobenzolsulfonamido)-4,5-dimethyloxazolBenzenesulfonamide, 4-amino-N-(4,5-dimethyl-2-oxazolyl)-N(sup 1)-(4,5-Dimethyl-2-oxazolyl)sulfanilamideNSC-683535HGG82XE020
Database identifiers
- CAS
729-99-7- PubChem CID
- 12894
- DTXSID
DTXSID5023617- ChEMBL
CHEMBL2105399- ChEBI
Properties
Computed structural properties
- XLogP
- 1.3
- Topological polar surface area
- 107 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 3
- Heavy atoms
- 18
- Formal charge
- 0
- Complexity
- 373
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Antibiotics (Sulfonamide)
SpringerMaterials PropertiesFusion temperature
LogP0.2
Human DrugsPharmaceuticals
Melting Point185 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 197 · 197-199℃
- Boiling point
- 481 · 481.0±47.0 °C(Predicted)
- Density
- 1.3786 g/cm3 · 1.3786 g/cm3
- refractive index
- 1.663 · 1.6630 (estimate)
- storage temp.
- Refrigerator, Under Inert Atmosphere
- solubility
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P261, P272, P280, P302+P352, P321, P333+P317, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesSkin Sens. 1 (100%)
Safety data
- wgk
- 2
- rtecs
- WO9150000
- Toxicity
- LD50 in mice, rats (g/kg): >10.0, >12.5 orally; 1.80, ~2.50 i.p. (Lagler)
- risk_code
- 43
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 36/37
- Hazard statements
- H317
- Precautionary statements
- P261-P272-P280-P302+P352-P333+P313-P362+P364
Chemistry & industry
Pharmacology
ATC CodeJ - Antiinfectives for systemic use
Pharmacodynamics
Sulfamoxole is a sulfonamide antibiotic. The sulfonamides are synthetic bacteriostatic antibiotics with a wide spectrum against most gram-positive and many gram-negative organisms. However, many strains of an individual species may be resistant. Sulfonamides inhibit multiplication of bacteria by acting as competitive inhibitors of <i>p</i>-aminobenzoic acid in the folic acid metabolism cycle. Bacterial sensitivity is the same for the various sulfonamides, and resistance to one sulfonamide indicates resistance to all. Most sulfonamides are readily absorbed orally. However, parenteral administration is difficult, since the soluble sulfonamide salts are highly alkaline and irritating to the tissues. The sulfonamides are widely distributed throughout all tissues. High levels are achieved in pleural, peritoneal, synovial, and ocular fluids. Although these drugs are no longer used to treat meningitis, CSF levels are high in meningeal infections. Their antibacterial action is inhibited by pus.
Mechanism of Action
Sulfamoxole is a competitive inhibitor of the bacterial enzyme dihydropteroate synthetase. This enzyme is needed for the proper processing of para-aminobenzoic acid (PABA) which is essential for folic acid synthesis. The inhibited reaction is necessary in these organisms for the synthesis of folic acid.
MeSH Pharmacological ClassificationSubstances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection.
Cellular LocationsMembrane
Uses & manufacturing
Use ClassificationPharmaceuticals
Applications
Silversulfadiazine and Sulfamoxol are common drugs in treatment of bacterial disease.
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Compound notes
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