Basic information
- Standard SMILES
Cc1ccnc(NS(=O)(=O)c2ccc(N)cc2)n1- InChIKey
QPPBRPIAZZHUNT-UHFFFAOYSA-N- Molecular formula
- C11H12N4O2S
- Average molar mass
- 264.31 g/mol
- Monoisotopic mass
- 264.06809662
Overview
Sulfamerazine is a sulfonamide consisting of pyrimidine with a methyl substituent at the 4-position and a 4-aminobenzenesulfonamido group at the 2-position. It has a role as an antiinfective agent and a drug allergen. It is a sulfonamide, a member of pyrimidines and a sulfonamide antibiotic. It is functionally related to a sulfanilamide.
Names & identifiers
- Preferred name
- Sulfamerazine
- IUPAC
- 4-amino-N-(4-methylpyrimidin-2-yl)benzenesulfonamide
- English name
- Sulfamerazine
- Molecular formula
- C11H12N4O2S
- Molecular weight
- 264.3
Names & synonyms
sulfamerazine127-79-7SulphamerazineSulfamethyldiazineMesulfa4-amino-N-(4-methylpyrimidin-2-yl)benzenesulfonamidePercoccideBenzenesulfonamide, 4-amino-N-(4-methyl-2-pyrimidinyl)-SeptacilSeptosylSolumedin2-Sulfa-4-methylpyrimidine
Show more names
SMIA-310rp2632DEBENAL2643-RPMebacidRomezinRP 2632
N-(4-Methyl-2-pyrimidyl)sulfanilamide2-(Sulfanilamido)-4-methylpyrimidine2-(4-Aminobenzenesulfonamido)-4-methylpyrimidine4-Amino-N-(4-methyl-2-pyrimidinyl)-benzenesulfonamideDTXSID0023612(p-Aminobenzolsulfonyl)-2-amino-4-methylpyrimidin4-amino-N-(4-methylpyrimidin-2-yl)benzene-1-sulfonamideUR1SAB295F
Database identifiers
- CAS
127-79-7- PubChem CID
- 5325
- DTXSID
DTXSID0023612- ChEMBL
CHEMBL438- ChEBI
CHEBI:102130- UNII
- UR1SAB295F
- EC Number
- 204-866-2
- Nikkaji
- J5.402J
Properties
Computed structural properties
- XLogP
- 0.1
- Topological polar surface area
- 106 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 3
- Heavy atoms
- 18
- Formal charge
- 0
- Complexity
- 360
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Antibiotics (Sulfonamide)
SpringerMaterials PropertiesFusion temperature
LogP0.14
Solubility3.04e-01 g/L
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Animal Drugs
Active Ingredients (Sulfamerazine) -> FDA Greenbook
Pharmaceuticals -> Animal Drugs -> Approved in Taiwan
Melting Point236 °C
Physical DescriptionSolid
Collision Cross Section
156.3 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
154.8 Ų [M+H]+ [CCS Type: TW]
168.3 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with Waters Major Mix]
155.14 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
161.33 Ų [M-H]-
Physicochemical properties
- Melting point
- 234 · 234-238°C
- Boiling point
- 519.1 · 519.1±52.0 °C(Predicted)
- Density
- 1.3364 · 1.3364 (rough estimate)
- refractive index
- 1.644 · 1.6440 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- DMSO (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 2.29 · pKa 2.29(H2O t = 24.0 I = 0.5 (NaCl)) (Uncertain)
- color
- White to Off-White
- Water Solubility
- 202 mg/L · 202mg/L(20 ºC)
- Merck
- 14 · 14,8913
- BRN
- 249133 · 249133
- InChI
- 1S/C11H12N4O2S/c1-8-6-7-13-11(14-8)15-18(16,17)10-4-2-9(12)3-5-10/h2-7H,12H2,1H3,(H,13,14,15)
- InChIKey
- QPPBRPIAZZHUNT-UHFFFAOYSA-N
- SMILES
- Cc1ccnc(NS(=O)(=O)c2ccc(N)cc2)n1
- CAS DataBase Reference
- 127 · 127-79-7(CAS DataBase Reference)
- FDA 21 CFR
- 556.66 · 556.660; 558.4; 558.582
- FDA UNII
- 1 SAB295F · UR1SAB295F
- ATC code
- 6 BA06,J01ED07 · D06BA06,J01ED07
- NIST Chemistry Reference
- Sulfamerazine(127-79-7)
- EPA Substance Registry System
- 4 · Benzenesulfonamide, 4-amino-N-(4-methyl-2-pyrimidinyl)- (127-79-7)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302
- Precautionary statements
- 264 · P264-P270-P301+P312-P501
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36/37
- WGK Germany
- 2 · 2
- RTECS
- 750000 · WP0750000
- F
- 10 · 10
- TSCA
- TSCA listed
- HS Code
- 2935904000 · 2935904000
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 Oral · Acute Tox. 4 Oral
- Toxicity
- 50 oral · LD50 oral in mouse: 25gm/kg
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 2% (1 of 51) of reports.
Warning
H315 (94.1%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 51 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationSulfamerazine: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Other Safety InformationIMAP assessments - Benzenesulfonamide, 4-amino-N-(4-methyl-2-pyrimidinyl)-: Human health tier I assessment
Hazard Classes and CategoriesSkin Irrit. 2 (94.1%)
Safety data
- F
- 10
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- WP0750000
- hs_code
- 2935904000
- Toxicity
- LD50 oral in mouse: 25gm/kg
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36/37
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P264-P270-P301+P312-P501
Chemistry & industry
Pharmacology
ATC Code
D - Dermatologicals
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
QD - Dermatologicals
PharmacodynamicsSulfonamides act as competitive inhibitors of the enzyme dihydropteroate synthetase (DHPS), an enzyme involved in folate synthesis in bacteria.
Mechanism of Action
Sulfamerazine is a sulfonamide drug that inhibits bacterial synthesis of dihydrofolic acid by competing with para-aminobenzoic acid (PABA) for binding to dihydropteroate synthetase (dihydrofolate synthetase). Sulfamerazine is bacteriostatic in nature. Inhibition of dihydrofolic acid synthesis decreases the synthesis of bacterial nucleotides and DNA.
Metabolism/MetabolitesSulfamerazine has known human metabolites that include N(4)-Acetylsulfamerazine.
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Absorption, Distribution and ExcretionRapidly absorbed following oral administration.
Cellular LocationsExtracellular
Uses & manufacturing
Use Classification
Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients
Pharmaceuticals -> Animal Drugs -> Approved in Taiwan
General Manufacturing InformationBenzenesulfonamide, 4-amino-N-(4-methyl-2-pyrimidinyl)-: INACTIVE
Applications
UsesAntibacterial.This compound is a contaminant of emerging concern (CECs).
General DescriptionChemical structure: sulfonamide
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
国药集团化学试剂有限公司86-21-63210123 · [email protected]
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Additional notes
DefinitionChEBI: A sulfonamide consisting of pyrimidine with a methyl substituent at the 4-position and a 4-aminobenzenesulfonamido group at the 2-position.
Related reactions
1 records
Linked notes
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