Sulfadoxine

HCID 17134

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

SULFADOXINE2447-57-6SulphadoxineSulfadoxinSulforthomidine4-amino-N-(5,6-dimethoxypyrimidin-4-yl)benzenesulfonamideSulphormethoxineSulfadoxinumSulfadoxinaFanzilRo 4-4393Benzenesulfonamide, 4-amino-N-(5,6-dimethoxy-4-pyrimidinyl)-
Show more names
4-AMINO-N-(5,6-DIMETHOXY-4-PYRIMIDINYL)BENZENESULFONAMIDESulfadimoxineSulfadumoxinewr4873fanasil
Fanasulf4-Sulfanilamido-5,6-dimethoxypyrimidineDTXSID6023608Ro-4-4393N'-(5,6-Dimethoxy-4-pyrimidyl)sulfanilamideRo-44393NSC-759319Sulformethoxine

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

Experimental & physicochemical properties

Drugs · 3 items

Pharmaceuticals -> Antibiotics

Pharmaceuticals -> Antibiotics (Sulfonamide)

Pharmaceuticals -> Listed in ZINC15

LogP · 2 items

0.70

0.7

Solubility2.96e-01 g/L
Human Drugs · 2 items

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Animal DrugsPharmaceuticals -> Animal Drugs -> Approved in Taiwan
Melting Point · 2 items

190-194 °C

190 - 194 °C

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

Safety & regulation

GHS classification

GHS Classification · 4 items

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

Other Safety InformationIMAP assessments - Benzenesulfonamide, 4-amino-N-(5,6-dimethoxy-4-pyrimidinyl)-: Environment tier I assessment
Hazard Classes and CategoriesSkin Irrit. 2 (57.7%)

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

Chemistry & industry

Pharmacology

ATC CodeQJ - Antiinfectives for systemic use
Pharmacodynamics · 1 item

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 · 1 item

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 · 5 items

88463U4SM5

SULFADOXINE

Established Pharmacologic Class [EPC] - Sulfonamide

Chemical Structure [CS] - Sulfonamides

Sulfadoxine is a Sulfonamide.

MeSH Pharmacological Classification · 3 items

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

Use ClassificationPharmaceuticals -> Animal Drugs -> Approved in Taiwan
Applications · 2 items

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

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]
Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]
Additional notes · 1 item

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

2 records

Compound notes

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