Sulfamethoxazole
SMX · SULPHAMETHOXAZOLE · SMZ · Sulfamethoxazol · Co-trimoxazole · Bactrim · Septra · N1-(5-METHYLISOXAZOL-3-YL)SULFANILAMIDE
Identifiers & Physical Properties
| CAS No. | 144930-01-8 |
|---|---|
| Molecular formula | C10H11N3O3S |
| Average molar mass | 253.28 g/mol |
| Monoisotopic mass | 253.05211239 g/mol |
| SMILES | Cc1cc(NS(=O)(=O)c2ccc(N)cc2)no1 |
| InChIKey | JLKIGFTWXXRPMT-UHFFFAOYSA-N |
| PubChem CID | 5329 |
| ChEMBL | CHEMBL443 |
| ChEBI | CHEBI:9332 |
| EC No. | 211-963-3 |
| DTXSID | DTXSID8026064 |
Chemical & Physical Properties
| XLogP | 0.9 |
|---|---|
| Topological polar surface area | 107 |
| Hydrogen bond donors | 2 |
| Hydrogen bond acceptors | 6 |
| Rotatable bonds | 3 |
| Heavy atoms | 17 |
| Formal charge | 0 |
| Complexity | 346 |
| Melting point | 166 °C |
| Boiling point | 482℃ |
| Density | 1.3915 (rough estimate) |
| Refractive index | 1.6630 (estimate) |
| Flash point | >110°(230°F) |
| Storage conditions | Keep in dark place,Inert atmosphere,Room temperature |
| Solubility | Practically insoluble in water, freely soluble in acetone, sparingly soluble in ethanol (96 per cent). It dissolves in dilute solutions of sodium hydroxide and in dilute acids.Soluble in ethanol or acetone. Very slightly soluble in water |
| pKa (acidity coefficient) | pKa 5.60±0.05 (Uncertain) |
| Physical state | Solid |
| Color | White to Pale Yellow |
| Sensitivity | Light Sensitive |
| Merck | 14,8918 |
| BRN | 6732984 |
| Henry's law constant | 1.5×107 mol/(m3Pa) at 25℃, HSDB (2015) |
| BCS Class | 2,4 |
| Stability | Stable, but light sensitive. Incompatible with strong oxidizing agents. |
| Major applications | forensics and toxicologypharmaceutical (small molecule) |
| InChI | 1S/C10H11N3O3S/c1-7-6-10(12-16-7)13-17(14,15)9-4-2-8(11)3-5-9/h2-6H,11H2,1H3,(H,12,13) |
| InChIKey | JLKIGFTWXXRPMT-UHFFFAOYSA-N |
| SMILES | Cc1cc(NS(=O)(=O)c2ccc(N)cc2)no1 |
| CAS DataBase Reference | 723-46-6(CAS DataBase Reference) |
| EWG's Food Scores | 1-3 |
| NCI Dictionary of Cancer Terms | co-trimoxazole |
| FDA UNII | JE42381TNV |
| NCI Drug Dictionary | Bactrim |
| ATC code | J01EC01 |
| NIST Chemistry Reference | Sulfanilamide, n1-(5-methyl-3-isoxazolyl)-(723-46-6) |
| IARC | 3 (Vol. Sup 7, 79) 2001 |
| EPA Substance Registry System | Sulfamethoxazole (723-46-6) |
| UNSPSC Code | 41116107 |
| NACRES | NA.24 |
| GHS pictogram | GHS07,GHS08 |
| Signal word | Warning |
| GHS hazard statements | H317-H361d |
| GHS precautionary statements | P201-P280-P302+P352-P308+P313 |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Faceshields, Gloves |
| Hazard symbols | Xi,Xn |
| Risk statements (R) | 36/37/38-43-22 |
| Safety statements (S) | 26-36-36/37/39-22 |
| Water hazard class (WGK) | 2 |
| RTECS number | WP0700000 |
| TSCA inventory status | TSCA listed |
| Hazard class | IRRITANTAquatic Chronic 2Repr. 2 |
| Customs code | 29350090 |
| Storage class | 11 - Combustible Solids |
| Hazardous substances data | 723-46-6(Hazardous Substances Data) |
| Toxicity | LD50 orally in mice: 3662 mg/kg (Yamamoto) |
Safety & Regulations
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Faceshields, Gloves |
|---|---|
| Water hazard class (WGK) | 2 |
| TSCA inventory status | TSCA listed |
| RTECS number | WP0700000 |
| Customs code | 29350090 |
| Toxicity | LD50 orally in mice: 3662 mg/kg (Yamamoto) |
| Risk statements (R) | 36/37/38-43-22 |
| Signal word | Warning |
| GHS pictogram | GHS07,GHS08 |
| Hazard symbols | Xi,Xn |
| Safety statements (S) | 26-36-36/37/39-22 |
| Hazard class | IRRITANTAquatic Chronic 2Repr. 2 |
| Storage class | 11 - Combustible Solids |
| GHS hazard statements | H317-H361d |
| GHS precautionary statements | P201-P280-P302+P352-P308+P313 |
| Hazardous substances data | 723-46-6(Hazardous Substances Data) |
Applications & Uses
Uses
As an antimicrobial agent, it is particularly effective in treating Staphylococcus aureus and E. coli. It is mainly used for the treatment of fowl cholera. It can be used as anti-infective drug and can be used for the treatment and prevention of acute and chronic urinary tract infections, respiratory infections, intestinal infections, Salmonella infections, children acute otitis media, and meningitis.
Description
Like sulfisoxazole, this drug is effective in treating infections caused by streptococci, gonococci, pneumococci, staphylococci as well as colon bacillus. Unlike sulfisoxazole, only about 70% of it binds with proteins in the plasma after oral administration, and it diffuses mostly to tissues and tissue fluids. However, since it is removed much slower than sulfisoxazole, it does not require frequent administration and is also the drug of choice for many systemic infections. Moreover, it is an ingredient of a combined drug named bactrim, biseptol, and so on (which will be examined later on), which has a fixed correlation with trimethoprim. Synonyms of this drug are gantanol, sinomin, sulfisomezole, and others.
Uses
antibacterial, antipneumocystis
Uses
An antibacterial drug. Sulfonamide antibiotic that blocks the synthesis of dihydrofolic acid by inhibiting the enzyme dihydropteroate synthase.This compound is a contaminant of emerging concern (CECs).
General Description
Sulfamethoxazole’s plasma half-life is 11 hours. Sulfamethoxazole is a sulfonamide drug closely relatedto sulfisoxazole in chemical structure and antimicrobial activity.It occurs as a tasteless, odorless, almost white crystallinepowder. The solubility of sulfamethoxazole in the pHrange of 5.5 to 7.4 is slightly lower than that of sulfisoxazole but higher than that of sulfadiazine, sulfamerazine, or sulfamethazine.Following oral administration, sulfamethoxazole is notabsorbed as completely or as rapidly as sulfisoxazole, andits peak blood level is only about 50% as high.
General Description
Crystals or white powder.