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Sulfadoxine

Sulfadoxine structure

CAS No:
2447-57-6
Formula:
C12H14N4O4S
Chemical Name:
Sulfadoxine
Synonyms:
Benzenesulfonamide,4-amino-N-(5,6-dimethoxy-4-pyrimidinyl)-;Sulfanilamide,N1-(5,6-dimethoxy-4-pyrimidinyl)-;4-Amino-N-(5,6-dimethoxy-4-pyrimidinyl)benzenesulfonamide;Ro 4-4393;N1-5,6-Dimethoxy-4-pyrimidinylsulfanilamide;4,5-Dimethoxy-6-sulfanilamidopyrimidine;Fanasil;4-Sulfanilamido-5,6-dimethoxypyrimidine;Sulformetoxine;Sulforthodimethoxine;Sulforthomidine;WR 4073;Sulfadoxine;Sulformethoxine;Sanasil;Sulfadoxin;Sulformetoxin;Fanasulf;Orthosulfin;4-Amino-N-(5,6-dimethoxy-4-pyrimidinyl)benzensulfonamide;Sulfadimoxine
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

Sulfadoxine(Sulphadoxine) is a long acting sulfonamide that is used, usually in combination with other drugs, for respiratory, urinary tract and malarial infections.Target: AntiparasiticSulfadoxine(Sulphadoxine) is an ultra-long-lasting sulfonamide. Sulfadoxine is often used in combination with pyrimethamine to treat or prevent malaria. Both drugs are antifolates; they inhibit the production of enzymes involved in the synthesis of folic acid within the parasites. Either drug by itself is

Solid

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.|A long acting sulfonamide that is used, usually in combination with other drugs, for respiratory, urinary tract, and malarial infections.|Sulfadoxine is a Sulfonamide.|Sulfadoxine is a broad-spectrum sulfanilamide and a synthetic analog of para-aminobenzoic acid (PABA) with bacteriostatic and antimalarial properties. Sulfadoxine competes with PABA for the bacterial enzyme dihydropteroate synthase, thereby preventing the incorporation of PABA into dihydrofolic acid, the immediate precursor of folic acid. This leads to an inhibition of parasitic folic acid synthesis and de novo synthesis of purines and pyrimidines, ultimately resulting in cell growth arrest and cell death.

Sulfadoxine Basic Attributes

Molecular Weight：

310.33

Exact Mass：

310.33

EC Number：

219-504-9

UNII：

88463U4SM5

NSC Number：

759319

DSSTox ID：

DTXSID6023608

NCI Thesaurus Code：

C47735

HScode：

2935009090

Characteristics

PSA：

125

XLogP3：

0.7

Appearance：

white

Density：

1.4±0.1 g/cm3

Melting Point：

190-194 °C

Boiling Point：

522.8°C at 760 mmHg

Flash Point：

270.0±32.9 °C

Refractive Index：

1.623

Water Solubility：

Soluble in ethanol & ammonium hydroxide (9:1) at 20mg/ml

Storage Conditions：

2-8°C

Vapor Pressure：

5.01E-11mmHg at 25°C

Toxicity：

Oral-mouse LD50: 5200 mg/kg; intraperitoneal-mouse LD50: 2900 mg/kg

Flammability characteristics：

Flammable; burning produces toxic nitrogen oxides and sulfur oxide fumes

Collision Cross Section：

165.3 Å² [M+H]+ [CCS Type: TW, Method: Major Mix IMS/Tof Calibration Kit (Waters)]|166.2 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]|166.6 Å² [M+H]+ [CCS Type: TW]|169.1 Å² [M+H]+ [CCS Type: TW, Method: calibrated with Waters Major Mix]|177.8 Å² [M+Na]+ [CCS Type: TW, Method: calibrated with Waters Major Mix]|173.22 Å² [M-H]-

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

36/37/38

safety instructions：

RTECS Number：

DA9500000

Marks：

Storage features：

Warehouse ventilated, low temperature and dry

Precautionary statement(s)：

P305 + P351 + P338

Hazard Statements：

H315-H319-H335

GHS Classification：

|Warning|H315 (60%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P272, P273, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P333+P313, P337+P313, P362, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 135 companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Toxicity class：

moderately toxic

Drug Information

Drug Indication：

Sulfadoxine is used in combination with pyrimethamine for the treatment or prevention of malaria. It can also be used to treat various infections in livestock as well. Sulfadoxine and pyrimethamine is indicated for the treatment of Plasmodium falciparum malaria in those patients in whom chloroquine resistance is suspected.

Pharmacology：

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.

MeSH：

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) (See all compounds classified as Antimalarials.)|Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection. (See all compounds classified as Anti-Infective Agents.)|Substances capable of killing agents causing urinary tract infections or of preventing them from spreading. (See all compounds classified as Anti-Infective Agents, Urinary.)

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.

MeSH Entry Terms：

Fanasil

Sulfadoxine Use and Manufacturing

Uses

Used as an antibacterial

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Pharmaceuticals -> Animal Drugs -> Approved in Taiwan

Computed Properties

Molecular Weight:310.33
XLogP3:0.7
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:5
Exact Mass:310.07357611
Monoisotopic Mass:310.07357611
Topological Polar Surface Area:125
Heavy Atom Count:21
Complexity:420
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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