Sulfamethoxazole

HCID 5329CAS 144930-01-8

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

sulfamethoxazole723-46-6GantanolSulphamethoxazoleSulfisomezoleSulfamethoxazol4-Amino-N-(5-methyl-3-isoxazolyl)benzenesulfonamideRadonilSinominSulfamethylisoxazole4-amino-N-(5-methylisoxazol-3-yl)benzenesulfonamideSulfamethalazole
Show more names
SMXSMZCo-trimoxazoleBactrimSeptraN1-(5-METHYLISOXAZOL-3-YL)SULFANILAMIDETribSeptrin
Azo-gantanolUrobakSulfamethoxizoleGantanol-DSRo 4-2130SulfametoxazolGamazole3-Sulfanilamido-5-methylisoxazole

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

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

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)

Chemistry & industry

Applications · 6 items

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.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

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

3 records

Linked notes

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