Basic information
- CAS
2447-57-6- Standard SMILES
COc1ncnc(NS(=O)(=O)c2ccc(N)cc2)c1OC- InChIKey
PJSFRIWCGOHTNF-UHFFFAOYSA-N- Molecular formula
- C12H14N4O4S
- Average molar mass
- 310.33 g/mol
- Monoisotopic mass
- 310.07357593
Overview
Sulfadoxine is a sulfonamide consisting of pyrimidine having methoxy substituents at the 5- and 6-positions and a 4-aminobenzenesulfonamido group at the 4-position. In combination with the antiprotozoal pyrimethamine (CHEBI:8673) it is used as an antimalarial. It has a role as an antibacterial drug and an antimalarial. It is a sulfonamide and a member of pyrimidines.
Names & identifiers
- Preferred name
- Sulfadoxine
- IUPAC
- 4-amino-N-(5,6-dimethoxypyrimidin-4-yl)benzenesulfonamide
- English name
- Sulfadoxine
- Molecular formula
- C12H14N4O4S
- Molecular weight
- 310.33
Names & synonyms
Show more names
Database identifiers
- CAS
2447-57-6- PubChem CID
- 17134
- DTXSID
DTXSID6023608- ChEMBL
CHEMBL1539、CHEMBL244800- ChEBI
CHEBI:9329- UNII
- 88463U4SM5
- EC Number
- 219-504-9
- Nikkaji
- J21.373J
Properties
Computed structural properties
- XLogP
- 0.7
- Topological polar surface area
- 125 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 5
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 419
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Antibiotics (Sulfonamide)
Pharmaceuticals -> Listed in ZINC15
LogP
0.70
0.7
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Melting Point
190-194 °C
190 - 194 °C
Collision Cross Section
165.3 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]
166.2 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
172.96 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
166.6 Ų [M+H]+ [CCS Type: TW]
169.1 Ų [M+H]+ [CCS Type: TW; Method: calibrated with Waters Major Mix]
173.22 Ų [M-H]-
Physicochemical properties
- Melting point
- 190 · 190-194°C
- Boiling point
- 298 °C · 298°C (rough estimate)
- Density
- 1.4006 · 1.4006 (rough estimate)
- refractive index
- 1.627 · 1.6270 (estimate)
- storage temp.
- Keep in dark place,Inert atmosphere,Room temperature
- solubility
- Soluble in ethanol & ammonium hydroxide (9:1) at 20mg/ml
- form
- powder
- pka
- 6.16 · 6.16±0.50(Predicted)
- color
- white
- Water Solubility
- 209.8 mg/L · 209.8mg/L(temperature not stated)
- Merck
- 14 · 14,8906
- BRN
- 625453 · 625453
- BCS Class
- 3 · 3/1
- Major Application
- clinical testing
- InChI
- 1S/C12H14N4O4S/c1-19-10-11(14-7-15-12(10)20-2)16-21(17,18)9-5-3-8(13)4-6-9/h3-7H,13H2,1-2H3,(H,14,15,16)
- InChIKey
- PJSFRIWCGOHTNF-UHFFFAOYSA-N
- SMILES
- COc1ncnc(NS(=O)(=O)c2ccc(N)cc2)c1OC
- FDA UNII
- 88463 U4SM5 · 88463U4SM5
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07,GHS09
- Signal word
- Warning
- Hazard statements
- 317 · H317-H411
- Precautionary statements
- 261 · P261-P272-P273-P280-P302+P352-P333+P313
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26
- WGK Germany
- 2 · 2
- RTECS
- 9500000 · DA9500000
- HS Code
- 29350090 · 29350090
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 Skin · Aquatic Chronic 2Skin Sens. 1
- Toxicity
- 50 in · LD50 in mice (microcrystals, mg/kg): 5200 orally, 2900 s.c., 2900 i.p. (Bhni)
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (57.7%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P272, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 130 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 2
- rtecs
- DA9500000
- hs_code
- 29350090
- Toxicity
- LD50 in mice (microcrystals, mg/kg): 5200 orally, 2900 s.c., 2900 i.p. (Bhni)
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07,GHS09
- hazard_code
- Xi
- safety_code
- 26
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H317-H411
- Hazard Classifications
- Aquatic Chronic 2Skin Sens. 1
- Precautionary statements
- P261-P272-P273-P280-P302+P352-P333+P313
Chemistry & industry
Pharmacology
Pharmacodynamics
Sulfadoxine helps inhibit the enzyme dihydropteroate synthetase which is an enzyme necessary in the conversion of PABA to folic acid. As folic acid is vital to the synthesis, repair, and methylation of DNA which is vital to cell growth in Plasmodium falciparum. With this vital nutrient lacking, the parasite has difficulty in reproducing.
Mechanism of Action
Sulfadoxine is a sulfa drug, often used in combination with pyrimethamine to treat malaria. This medicine may also be used to prevent malaria in people who are living in, or will be traveling to, an area where there is a chance of getting malaria. Sulfadoxine targets Plasmodium dihydropteroate synthase and dihydrofolate reductase. Sulfa drugs or Sulfonamides are antimetabolites. They compete with para-aminobenzoic acid (PABA) for incorporation into folic acid. The action of sulfonamides exploits the difference between mammal cells and other kinds of cells in their folic acid metabolism. All cells require folic acid for growth. Folic acid (as a vitamin) diffuses or is transported into human cells. However, folic acid cannot cross bacterial (and certain protozoan) cell walls by diffusion or active transport. For this reason bacteria must synthesize folic acid from p-aminobenzoic acid.
FDA Pharmacological Classification
88463U4SM5
SULFADOXINE
Established Pharmacologic Class [EPC] - Sulfonamide
Chemical Structure [CS] - Sulfonamides
Sulfadoxine is a Sulfonamide.
MeSH Pharmacological Classification
Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection.
Substances capable of killing agents causing urinary tract infections or of preventing them from spreading.
Agents used in the treatment of malaria. They are usually classified on the basis of their action against plasmodia at different stages in their life cycle in the human. (From AMA, Drug Evaluations Annual, 1992, p1585)
Uses & manufacturing
Applications
DescriptionSulfadoxin is a sulfonamide antibiotic that inhibits dihydropteroate synthetase (DHPS), an enzyme involved in folic acid synthesis. Sulfadoxin competes with 4-aminobenzoate (PABA), the native substrate of DHPS, and inhibits PABA incorporation into folic acid. Folate is essential for purine and pyrimidine synthesis, therefore, sulfadoxin has antiproliferative activity in non-resistant P. falciparum. Sulfadoxin inhibits growth of P. falciparum in vitro, but potency varies between non-resistant (IC50 = 4 ng/ml) and resistant strains (IC50 = 3,970 ng/ml).
UsesUsed as an antibacterial.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
Additional notes
DefinitionChEBI: A sulfonamide consisting of pyrimidine having methoxy substituents at the 5- and 6-positions and a 4-aminobenzenesulfonamido group at the 4-position. In combination with the antiprotozoal pyrimethamine (CHEBI:8673) it is used as an antimalarial.
Related reactions
Compound notes
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