Basic information
- Standard SMILES
Cc1cc(NS(=O)(=O)c2ccc(N)cc2)no1- InChIKey
JLKIGFTWXXRPMT-UHFFFAOYSA-N- Molecular formula
- C10H11N3O3S
- Average molar mass
- 253.28 g/mol
- Monoisotopic mass
- 253.05211239
Names & identifiers
- Preferred name
- Sulfamethoxazole
- IUPAC
- 4-amino-N-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide
- English name
- Sulfamethoxazole
- Molecular formula
- C10H11N3O3S
- Molecular weight
- 253.28
Names & synonyms
Show more names
Database identifiers
- CAS
144930-01-8、144993-89-5、723-46-6- PubChem CID
- 5329
- DTXSID
DTXSID8026064- ChEMBL
CHEMBL443- ChEBI
CHEBI:9332- UNII
- JE42381TNV
- EC Number
- 211-963-3、656-929-2
- Nikkaji
- J4.525J
Properties
Computed structural properties
- XLogP
- 0.9
- Topological polar surface area
- 107 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 3
- Heavy atoms
- 17
- Formal charge
- 0
- Complexity
- 346
Physicochemical properties
- Melting point
- 166 °C · 166 °C
- Boiling point
- 482 ℃ · 482℃
- Density
- 1.3915 · 1.3915 (rough estimate)
- refractive index
- 1.663 · 1.6630 (estimate)
- Flash point
- 110 ° · >110°(230°F)
- storage temp.
- 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.
- pka
- 5.6 · pKa 5.60±0.05 (Uncertain)
- form
- Solid
- color
- White to Pale Yellow
- Water Solubility
- Soluble in ethanol or acetone. Very slightly soluble in water
- Sensitive
- Light Sensitive
- Merck
- 14 · 14,8918
- BRN
- 6732984 · 6732984
- Henry's Law Constant
- 1.5 · 1.5×107 mol/(m3Pa) at 25℃, HSDB (2015)
- BCS Class
- 2 · 2,4
- Stability
- Stable, but light sensitive. Incompatible with strong oxidizing agents.
- Major Application
- 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 · 723-46-6(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1-3
- NCI Dictionary of Cancer Terms
- co-trimoxazole
- FDA UNII
- 42381 TNV · JE42381TNV
- NCI Drug Dictionary
- Bactrim
- ATC code
- 1 EC01 · J01EC01
- NIST Chemistry Reference
- 1 · Sulfanilamide, n1-(5-methyl-3-isoxazolyl)-(723-46-6)
- IARC
- 3 · 3 (Vol. Sup 7, 79) 2001
- EPA Substance Registry System
- Sulfamethoxazole (723-46-6)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07,GHS08
- Signal word
- Warning
- Hazard statements
- 317 · H317-H361d
- Precautionary statements
- 201 · P201-P280-P302+P352-P308+P313
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- Hazard Codes
- Xi,Xn
- Risk Statements
- 36 · 36/37/38-43-22
- Safety Statements
- 26 · 26-36-36/37/39-22
- WGK Germany
- 2 · 2
- RTECS
- 700000 · WP0700000
- TSCA
- TSCA listed
- HazardClass
- IRRITANT
- HS Code
- 29350090 · 29350090
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 Repr · Aquatic Chronic 2Repr. 2
- Hazardous Substances Data
- 723 · 723-46-6(Hazardous Substances Data)
- Toxicity
- 50 orally · LD50 orally in mice: 3662 mg/kg (Yamamoto)
Safety & regulation
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- WP0700000
- hs_code
- 29350090
- Toxicity
- LD50 orally in mice: 3662 mg/kg (Yamamoto)
- risk_code
- 36/37/38-43-22
- Signal word
- Warning
- Symbol(GHS)
- GHS07,GHS08
- hazard_code
- Xi,Xn
- safety_code
- 26-36-36/37/39-22
- hazard_class
- IRRITANT
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H317-H361d
- Hazard Classifications
- Aquatic Chronic 2Repr. 2
- Precautionary statements
- P201-P280-P302+P352-P308+P313
- Hazardous Substances Data
- 723-46-6(Hazardous Substances Data)
Chemistry & industry
Applications
UsesAs 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.
DescriptionLike 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.
Usesantibacterial, antipneumocystis
UsesAn 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 DescriptionSulfamethoxazole’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 DescriptionCrystals or white powder.
Upstream & downstream products
Upstream raw materials
Suppliers50 total
Additional notes
DefinitionChEBI: An isoxazole (1,2-oxazole) compound having a methyl substituent at the 5-position and a 4-aminobenzenesulfonamido group at the 3-position.
Related reactions
Linked notes
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