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Sulfadoxine

Pharmacology and mechanism of action Indications Side effects Contraindications and precautions Interactions Preparations References
Sulfadoxine
Sulfadoxine
CAS No.
2447-57-6
Chemical Name:
Sulfadoxine
Synonyms
fanzil;wr4873;fanasil;ro4-4393;SULFADOXIN;SULFADOXINE;sulphadoxine;SulphodoxiMe;Sulfadimoxine;Sulformetoxine
CBNumber:
CB8171942
Molecular Formula:
C12H14N4O4S
Formula Weight:
310.33
MOL File:
2447-57-6.mol

Sulfadoxine Properties

Melting point:
190-194°C
Boiling point:
298°C (rough estimate)
Density 
1.4006 (rough estimate)
refractive index 
1.6270 (estimate)
storage temp. 
2-8°C
solubility 
Soluble in ethanol & ammonium hydroxide (9:1) at 20mg/ml
form 
powder
color 
white
Merck 
14,8906
BRN 
625453
SAFETY
  • Risk and Safety Statements
  • Hazard and Precautionary Statements (GHS)
Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  26
WGK Germany  2
RTECS  DA9500000
Toxicity LD50 in mice (microcrystals, mg/kg): 5200 orally, 2900 s.c., 2900 i.p. (Bhni)
Symbol(GHS):
Signal word: Warning
Hazard statements:
Code Hazard statements Hazard class Category Signal word Pictogram P-Codes
H315 Causes skin irritation Skin corrosion/irritation Category 2 Warning P264, P280, P302+P352, P321,P332+P313, P362
H319 Causes serious eye irritation Serious eye damage/eye irritation Category 2A Warning P264, P280, P305+P351+P338,P337+P313P
H335 May cause respiratory irritation Specific target organ toxicity, single exposure;Respiratory tract irritation Category 3 Warning
Precautionary statements:
P261 Avoid breathing dust/fume/gas/mist/vapours/spray.
P264 Wash hands thoroughly after handling.
P264 Wash skin thouroughly after handling.
P280 Wear protective gloves/protective clothing/eye protection/face protection.
P304+P340 IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P337+P313 IF eye irritation persists: Get medical advice/attention.
P405 Store locked up.

Sulfadoxine price More Price(14)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 31736 Sulfadoxin VETRANAL 2447-57-6 250mg $38.9 2018-11-20 Buy
Sigma-Aldrich 1626500 Sulfadoxine United States Pharmacopeia (USP) Reference Standard 2447-57-6 200mg $352.8 2018-11-20 Buy
TCI Chemical S0899 Sulfadoxin >98.0%(HPLC)(T) 2447-57-6 5g $41 2018-11-22 Buy
TCI Chemical S0899 Sulfadoxin >98.0%(HPLC)(T) 2447-57-6 25g $138 2018-11-22 Buy
Alfa Aesar J66268 Sulfadoxine 98% 2447-57-6 5g $34 2018-11-20 Buy

Sulfadoxine Chemical Properties,Uses,Production

Pharmacology and mechanism of action

The efficacy of sulphadoxine for the treatment of human malaria was first reported in 1964 [1]. Soon thereafter it was found that potentiation took place when sulphadoxine was combined with pyrimethamine for treatment of malaria and monotherapy was abandoned.
Malaria parasites synthesize their folate co-factors and cannot use dietary folic acid as the human host can. Sulphadoxine competes with para-aminobenzoic acid (PABA) for binding to the enzyme dihydropteroate synthetase in the synthesis of dihydropteroate which is an essential substance for the formation of folic acid [2]. It is active against asexual blood forms of P. falciparum but less active against other species. The action is too slow to be used alone for malaria treatment [3].

Indications

Sulphadoxine is used only in combination with pyrimethamine for the treatment of falciparum malaria. It should generally not be used for malaria prophylaxis except perhaps in long-term travellers who have previously tolerated the combination.
 

Side effects

Sulphadoxine is usually well tolerated. Vomiting, skin rashes, pruritus and haematological reactions such as haemolysis and leucopenia occur [4]. Hypersensitivity pneumonitis is reported[5, 6]. Cases of liver injury alone (hepatitis of hepatocellular, mixed hepatocellular, or aggressive type) or as part of a generalized allergic syndrome are well known[4, 6], and one case of fatal hepatic failure has also been reported [7].
Severe cutaneous adverse reactions (erythema multiforme, Stevens-Johnson syndrome, or toxic epidermal necrolysis) have been reported in persons taking prophylactic doses of sulphadoxine/pyrimethamine[6, 8]. Sulphadoxine has been incriminated as the most probable cause of these reactions. They all occurred within 7 weeks after start of prophylaxis.
The reported incidence was 1/5,000–8,000 users in USA and approximately 1/10,000 users in Sweden with fatality rates of 1/11,000–25,000 and 1/50,000, respectively. In Mozambique, when sulphadoxine was given alone in a single dose for cholera prophylaxis to 149,000 inhabitants, a total of 22 cases of Stevens-Johnson syndrome was seen with 3 deaths [9].
 

Contraindications and precautions

The drug or its combination should not be given to patients allergic to sulphonamides. It should not be used in persons with severe blood, kidney or liver diseases.
 

Interactions

Increased impairment of folic acid synthesis and consequent haematological adverse effects may occur if trimethoprim or its combination with sulphonamide is administered concurrently. Sulphadoxine potentiates the action of warfarin and thiopentone [10].
 

Preparations

Sulphadoxine combined with pyrimethamine.  • Fansidar® (Roche). Tablets (sulphadoxine 500 mg+pyrimethamine 25 mg), solution for intramuscular injection (sulphadoxine 200 mg/ml+pyrimethamine 10 mg/ml).
 

References

1. Laing ABG (1964). Antimalarial effect of sulphorthodimethoxine (Fanasil). BMJ, 2, 1439–1440.
2. The biology of malaria parasites. Technical Report Series no. 743 (1987). (Geneva: World Health Organization).
3. Chemotherapy of Malaria. Monograph series No. 27, 2nd edn, (1986), (Geneva: World Health Organization).
4. Hoigné R, Malinverni R, Sonntag R (1992). Sulfonomides, other folic acid antagonists and miscellaneous antibacterial drugs. In: Meyler’s Side Effects of Drugs, 12th edn, edited by M.N.G.Dukes (Amsterdam: Elsevier), pp. 715–722.
5. Svanbom M, Rombo L, Gustafsson L (1984). Unusual pulmonary reaction during short term prophylaxis with pyrimethamine-sulphadoxine (Fansidar). BMJ, 1, 1876.
6. Hellgren U, Rombo L, Berg B, Carlson J, Wiholm B-E (1987). Adverse reactions to sulphadoxinepyrimethamine in Swedish travellers: implications for prophylaxis. BMJ, 295, 365–366.
7. Zitelli BJ, Alexander J, Taylor S (1987). Fatal hepatic necrosis due to pyrimethamine-sulphadoxine (Fansidar). Ann Intern Med, 106, 393–395. 25. Miller KD, Lobel HO, Satriale RF, Kirutsky JN, Stern R, Campell CC (1986). Severe cutaneous reactions among American travellers using pyrimethamine-sulphadoxine (Fansidar) for malaria prophylaxis. Am J Trop Hyg, 35, 451–458.
8. Hernberg A (1985). Stevens-Johnson syndrome after mass prophylaxis with sulphadoxine for cholera in Mozambique. Lancet, 2, 1072–1073.
9. Sulfadoxine. Therapeutic Drugs, edited by Sir Colin Dollery (1991), (London: Churchill Livingstone), pp. S115–S119.

Chemical Properties

White Crystalline Solid

Uses

Used as an antibacterial

Definition

ChEBI: 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.

brand name

Fanasil (Hoffmann-LaRoche-International); Fanzil (Hoffmann-LaRoche).

Antimicrobial activity

Its antibacterial activity is relatively poor. Used alone it has a slow and uncertain effect against malaria parasites. Resistance of malaria parasites to the combination with pyrimethamine is common in many endemic areas.

Pharmaceutical Applications

An ultra-long-acting sulfonamide. It is no longer prescribed alone, but is used in combination with pyrimethamine as the antimalarial agent Fansidar. It is poorly soluble in water.

Pharmacokinetics

Oral absorption :Extensive
Cmax 500 mg oral: c. 60 mg/L after 3–4 h
Plasma half-life:c.6 days
Volume of distribution:0.13 L/kg
Plasma protein binding:94%
The extremely long half-life allows administration at weekly intervals. The acetyl metabolite has a similarly long half-life, but sulfadoxine is less extensively metabolized than many other sulfonamides.

Clinical Use

Sulfadoxine is used only in combination with pyrimethamine.

Side effects

Side effects are those common to the group. There have been many reports of Stevens–Johnson syndrome following its use and the combination with pyrimethamine is no longer recommended for the prophylaxis of malaria.

Sulfadoxine Preparation Products And Raw materials

Raw materials

Preparation Products


Sulfadoxine Suppliers

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View Lastest Price from Sulfadoxine manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2018-12-17 Sulfadoxine
2447-57-6
US $1.00 / kg 1kg 99% Customized career henan chemical co

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