Sulfamethazine

HCID 5327CAS 57-68-1
Substructure searchFind similar structures

Basic information

Standard SMILES
Cc1cc(C)nc(NS(=O)(=O)c2ccc(N)cc2)n1
InChIKey
ASWVTGNCAZCNNR-UHFFFAOYSA-N
Molecular formula
C12H14N4O2S
Average molar mass
278.33 g/mol
Monoisotopic mass
278.08374688

Names & identifiers

Preferred name
Sulfamethazine
IUPAC
4-amino-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide
English name
2-(4-Aminobenzenesulfonamido)-4,6-dimethylpyrimidine
Molecular formula
C12H14N4O2S
Molecular weight
278.33

Names & synonyms

sulfamethazineSulfadimidine57-68-1SulfadimerazineSulphamethazineSulfamezathineSulphadimidine4-amino-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamideSulfadimethylpyrimidineSulfadimezineSulfadimethyldiazineSulfadimesine
Show more names
SM2sulfametazinaSULFADIMIDINSULFAMETAZINEL-30SulfamidineSulfadimidine[1]
SulphamezathineSulphamidineSulfadineSulfamethiazineSulphamethasineAzolmetazinCremomethazineDimezathine

Database identifiers

CAS
57-68-1
PubChem CID
5327
DTXSID
DTXSID6021290
ChEMBL
CHEMBL446
ChEBI
CHEBI:102265
UNII
48U51W007F
EC Number
200-346-4
Nikkaji
J106.516E

Properties

Computed structural properties

XLogP
0.3
Topological polar surface area
106 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
6
Rotatable bonds
3
Heavy atoms
19

Physicochemical properties

Melting point
197 °C · 197 °C
Boiling point
294 °C · 294°C (rough estimate)
Density
1.2997 · 1.2997 (rough estimate)
refractive index
1.644 · 1.6440 (estimate)
storage temp.
2 · 2-8°C
solubility
50 mg/mL · acetone: soluble50mg/mL

Safety & regulation

Safety data

F
10
wgk
2
tsca
TSCA listed
rtecs
WO9275000
hs_code
29350090
Toxicity
LD50 i.p. in mice: 1.06 g/kg (Bobranski)

Chemistry & industry

Applications · 4 items

DescriptionSulfamethazine is an antibacterial sulfonamide. Like other sulfonamides, sulfamethazine is bacteriostatic, competitively inhibiting dihydropteroate synthase to block folate synthesis and inhibit growth and multiplication. Sulfamethazine is metabolized by cytochrome P450 isoforms and arylamine N-acetyltransferase 2 in a sex-dependent manner.

UsesSulfamethazine is an antibacterial.This compound is a contaminant of emerging concern (CECs).

General DescriptionSulfamethazine’splasma half-life is 7 hours. This compound is similar inchemical properties to sulfamerazine and sulfadiazine butdoes have greater water solubility than either. Its pKa is 7.2.Because it is more soluble in acid urine than sulfamerazineis, the possibility of kidney damage from use of the drug isdecreased. The human body appears to handle the drugunpredictably; hence, there is some disfavor to its use in thiscountry except in combination sulfa therapy (in trisulfapyrimidines,USP) and in veterinary medicine.

General DescriptionOdorless sticky, white or creamy-white crystalline powder. Slightly bitter taste. An antibacterial.

Upstream & downstream products

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]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]

Additional notes

DefinitionChEBI: A sulfonamide consisting of pyrimidine with methyl substituents at the 4- and 6-positions and a 4-aminobenzenesulfonamido group at the 2-position.

Related reactions

8 records
New reaction record

Linked notes

Loading…