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Sulfadoxine
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Systematic (IUPAC) name |
4-Amino-N-(5,6-dimethoxy-4-pyrimidinyl)benzenesulfonamide |
Clinical data |
AHFS/Drugs.com |
International Drug Names |
Identifiers |
CAS Registry Number
|
2447-57-6 Y |
ATCvet code
|
QJ01EQ13 |
PubChem |
CID: 17134 |
DrugBank |
DB01299 N |
ChemSpider |
16218 N |
UNII |
88463U4SM5 N |
KEGG |
D00580 Y |
ChEMBL |
CHEMBL1539 N |
NIAID ChemDB |
007816 |
Chemical data |
Formula |
C12H14N4O4S |
Molecular mass
|
310.33 g/mol |
SMILES
- COC1=C(N=CN=C1OC)NS(=O)(=O)C2=CC=C(C=C2)N
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N (what is this?) (verify) |
Sulfadoxine (also spelled sulphadoxine) is an ultra-long-lasting sulfonamide previously used in combination with pyrimethamine to treat or prevent malaria.[1] Due to high levels of resistance, its use is no longer recommended routinely.[2] It is also used, usually in combination with other drugs, to treat or prevent various infections in livestock.[3]
It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system.[4]
Contents
- 1 Mechanism of action
- 2 Synthesis
- 3 See also
- 4 References
Mechanism of action
Sulfadoxine competitively inhibits dihydropteroate synthase, interfering with folate synthesis.
Synthesis
Sulfadoxine synthesis:
U.S. Patent 3,132,139 BE 618639 [5][6]
See also
- Sulfadoxine/pyrimethamine
References
- ^ Medical Treatment - Sulphadoxine and Pyrimethamine.
- ^ Matondo SI, Temba GS, Kavishe AA et al. (2014). "High levels of sulphadoxine-pyrimethamine resistance Pfdhfr-Pfdhps quintuple mutations: a cross sectional survey of six regions in Tanzania.". Malar J 13: 152. doi:10.1186/1475-2875-13-152. PMC 3998221. PMID 24751352.
- ^ http://en.scientificcommons.org/19483411.
- ^ "WHO Model List of EssentialMedicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014.
- ^ Bretschneider, H.; Richter, W.; Kl�Tzer, W. (1965). "Synthesen des 4-Sulfanilamido-5,6-dimethoxypyrimidins". Monatshefte f�r Chemie 96 (6): 1661. doi:10.1007/BF01185885. edit
- ^ Gr�Ssner, A.; Montavon, M.; Schnider, O. (1965). "Disubstituierte 4-Sulfanilamido-pyrimidine". Monatshefte f�r Chemie 96 (6): 1677. doi:10.1007/BF01185886. edit
Antibacterials: nucleic acid inhibitors (J01E, J01M)
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Antifolates
(inhibits
purine metabolism,
thereby inhibiting
DNA and RNA synthesis) |
DHFR inhibitor |
- 2,4-Diaminopyrimidine
- Brodimoprim
- Diaveridine
- Iclaprim†
- Ormetoprim
- Trimethoprim#
- Tetroxoprim
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Sulfonamides
(DHPS inhibitor) |
Short-
acting |
- Sulfaisodimidine
- Sulfamethizole
- Sulfadimidine
- Sulfapyridine
- Sulfafurazole
- Sulfanilamide
- Sulfathiazole
- Sulfathiourea
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Intermediate-
acting |
- Sulfamethoxazole
- Sulfadiazine#
- Sulfamoxole
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Long-
acting |
- Sulfadimethoxine
- Sulfadoxine
- Sulfalene
- Sulfametomidine
- Sulfametoxydiazine
- Sulfamethoxypyridazine
- Sulfaperin
- Sulfamerazine
- Sulfaphenazole
- Sulfamazone
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Other/ungrouped |
- Sulfacetamide
- Sulfadicramide
- Sulfametrole
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Combinations |
- Trimethoprim/sulfamethoxazole#
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Topoisomerase
inhibitors/
quinolones/
(inhibits
DNA replication) |
1st g. |
- Cinoxacin‡
- Flumequine
- Nalidixic acid
- Oxolinic acid
- Pipemidic acid
- Piromidic acid
- Rosoxacin
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Fluoro-
quinolones |
2nd g. |
- Ciprofloxacin#
- Enoxacin‡
- Fleroxacin‡
- Lomefloxacin
- Nadifloxacin
- Ofloxacin
- Norfloxacin
- Pefloxacin
- Rufloxacin
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3rd g. |
- Balofloxacin
- Grepafloxacin‡
- Levofloxacin
- Pazufloxacin
- Sparfloxacin‡
- Temafloxacin‡
- Tosufloxacin
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4th g. |
- Besifloxacin
- Clinafloxacin†
- Garenoxacin
- Gemifloxacin
- Moxifloxacin
- Gatifloxacin‡
- Sitafloxacin
- Trovafloxacin‡/Alatrofloxacin‡
- Prulifloxacin
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Vet. |
- Danofloxacin
- Difloxacin
- Enrofloxacin
- Ibafloxacin
- Marbofloxacin
- Orbifloxacin
- Pradofloxacin
- Sarafloxacin
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Related (DG) |
- Aminocoumarins: Novobiocin
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Anaerobic DNA
inhibitors |
Nitro- imidazole derivatives |
- Metronidazole#
- Tinidazole
- Ornidazole
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Nitrofuran derivatives |
- Nitrofurantoin#
- Furazolidone‡
- Nifurtoinol
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RNA synthesis |
Rifamycins/
RNA polymerase |
- Rifampicin#
- Rifabutin
- Rifapentine
- Rifaximin
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
Index of bacterial disease
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Description |
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Disease |
- Gram-positive firmicutes
- Gram-positive actinobacteria
- Gram-negative proteobacteria
- Gram-negative non-proteobacteria
- Cholera
- Tuberculosis
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Treatment |
- Antibiotics
- cell wall
- nucleic acid
- mycobacteria
- protein synthesis
- other
- Antibodies
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UpToDate Contents
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English Journal
- Comparative assessment on the prevalence of mutations in the Plasmodium falciparum drug-resistant genes in two different ecotypes of Odisha state, India.
- Kar NP1, Chauhan K1, Nanda N1, Kumar A2, Carlton JM3, Das A4.
- Infection, genetics and evolution : journal of molecular epidemiology and evolutionary genetics in infectious diseases.Infect Genet Evol.2016 Jul;41:47-55. doi: 10.1016/j.meegid.2016.03.014. Epub 2016 Mar 15.
- Considering malaria as a local and focal disease, epidemiological understanding of different ecotypes of malaria can help in devising novel control measures. One of the major hurdles in malaria control lies on the evolution and dispersal of the drug-resistant malaria parasite, Plasmodium falciparum.
- PMID 26988711
- Low-grade sulfadoxine-pyrimethamine resistance in Plasmodium falciparum parasites from Lubango, Angola.
- Kaingona-Daniel EP1,2,3,4, Gomes LR1,2,4, Gama BE1,5, Almeida-de-Oliveira NK1,2,4, Fortes F6,4, Ménard D7, Daniel-Ribeiro CT1,2,4, Ferreira-da-Cruz MF8,9,10.
- Malaria journal.Malar J.2016 Jun 7;15(1):309.
- BACKGROUND: Malaria is a major parasitic disease, affecting millions of people in endemic areas. Plasmodium falciparum parasites are responsible for the most severe cases and its resistance to anti-malarial drugs is notorious. This is a possible obstacle to the effectiveness of intermittent preventi
- PMID 27267365
- Decrease of microscopic Plasmodium falciparum infection prevalence during pregnancy following IPTp-SP implementation in urban cities of Gabon.
- Bouyou-Akotet MK1, Mawili-Mboumba DP2, Kendjo E3, Moutandou Chiesa S4, Tshibola Mbuyi ML3, Tsoumbou-Bakana G5, Zong J5, Ambounda N6, Kombila M2.
- Transactions of the Royal Society of Tropical Medicine and Hygiene.Trans R Soc Trop Med Hyg.2016 Jun 6. [Epub ahead of print]
- BACKGROUND: Six years after the implementation of intermittent preventive treatment in pregnancy (IPTp) with sulfadoxine-pyrimethamine (SP) in Gabon, its impact on placental malaria and pregnancy outcomes remains unknown.METHODS: Age, gestational data, use of IPTp-SP and birth weight were recorded d
- PMID 27268713
Japanese Journal
- Impact of Artemisinin-Based Combination Therapy on Falciparum Malaria in Urban Kolkata: A Clinic-Based Report
- Saha Pabitra,Ganguly Swagata,Dutta Soma,Kundu Pratip K.,Bera Dilip K.,Basu Nandita,Maji Ardhendu K.
- Japanese Journal of Infectious Diseases 68(4), 321-323, 2015
- … specifically artesunate + sulfadoxine-pyrimethamine) has been implemented for uncomplicated falciparum malaria since 2010. …
- NAID 130005088794
- Community-based scheduled screening and treatment of malaria in pregnancy for improved maternal and infant health in The Gambia, Burkina Faso and Benin: study protocol for a randomized controlled trial
- Scott Susana,Mens Petra F,Tinto Halidou,Nahum Alain,Ruizendaal Esmée,Pagnoni Franco,Peeters Grietens Koen,Kendall Lindsay,Bojang Kalifa,Schallig Henk,D'Alessandro Umberto
- Trials 15, 340, 2014-08-28
- … The secondary objectives are to determine the protective efficacy of CSST on maternal anaemia, maternal peripheral infection, low birth weight, selection of sulfadoxine-pyrimethamine (SP) resistance markers, and on antenatal clinic (ANC) attendance and coverage of intermittent preventive treatment during pregnancy (IPTp-SP).Methods/design: This is a multi-centre cluster-randomised controlled trial involving three countries with varying malaria endemicity; …
- NAID 120005477056
Related Links
- のサプライヤーのリストを取得する Sulfadoxine と同等の製品を ... Chemos GmbH ためのサプライヤです Sulfadoxine. 我々は1,3,5,7-Tetramethylpyrrometheneの販売人である。 Chemosは、化学、生化学、実験装置の世界的な ...
- Sulfadoxine/pyrimethamine Combination of Sulfadoxine Sulfonamide Pyrimethamine Antiparasitic Clinical data Trade names Fansidar Licence data US FDA: link Pregnancy cat. C (AU) C (US) Legal status Prescription Only (S4) (AU) POM ...
Related Pictures
★リンクテーブル★
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- 関
- pyrimethamine