SULFADOXINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H14N4O4S
Molecular Weight	310.329
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=C(OC)C(NS(=O)(=O)C2=CC=C(N)C=C2)=NC=N1

InChI

InChIKey=PJSFRIWCGOHTNF-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18557slr015_fansidar_lbl.pdf | John E. Bennett, 'Mandell, Douglas, and Bennett's Principles and Practice of Infectious Diseases' (2014), p. 507, Retrieved from | https://books.google.es/books?id=73pYBAAAQBAJ&dq

Sulfadoxine is an antimalarial agent which, together with pyrimethamine, composes an FDA-approved drug, Fansidar. Sulfadoxine acts by inhibiting dihydropteroate synthase; it crosses the blood-brain barrier and achieves 30% to 60% of the plasma concentration.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Dihydropteroate synthetase 10 Target ID: CHEMBL2013 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18557slr015_fansidar_lbl.pdf	Inhibitor 8504		0.14 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Plasmodium falciparum malaria 63 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18557slr015_fansidar_lbl.pdf	Curative		Approved 8583	FANSIDAR Approved Use Fansidar is indicated for the treatment of acute, uncomplicated P. falciparum malaria for those patients in whom chloroquine resistance is suspected. Launch Date 1981

C_max

Value	Dose	Co-administered	Analyte	Population
71.7 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11419747/	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: PYRIMETHAMINE	PYRIMETHAMINE	SULFADOXINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
165.15 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23084093/	1500 mg single, oral dose: 1500 mg route of administration: Oral experiment type: SINGLE co-administered: PYRIMETHAMINE	PYRIMETHAMINE	SULFADOXINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
60 mg/L DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18557slr015_fansidar_lbl.pdf	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: PYRIMETHAMINE	PYRIMETHAMINE	SULFADOXINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
12394 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11419747/	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: PYRIMETHAMINE	PYRIMETHAMINE	SULFADOXINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
21761.02 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23084093/	1500 mg single, oral dose: 1500 mg route of administration: Oral experiment type: SINGLE co-administered: PYRIMETHAMINE	PYRIMETHAMINE	SULFADOXINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
155.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11419747/	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: PYRIMETHAMINE	PYRIMETHAMINE	SULFADOXINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
200 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18557slr015_fansidar_lbl.pdf	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: PYRIMETHAMINE	PYRIMETHAMINE	SULFADOXINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
10% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18557slr015_fansidar_lbl.pdf	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: PYRIMETHAMINE	PYRIMETHAMINE	SULFADOXINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
500 mg 3 times / day single, oral Recommended Dose: 500 mg, 3 times / day Route: oral Route: single Dose: 500 mg, 3 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18557slr015_fansidar_lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18557slr015_fansidar_lbl.pdf	Disc. AE: Stevens-Johnson syndrome... AEs leading to discontinuation/dose reduction: Stevens-Johnson syndrome Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18557slr015_fansidar_lbl.pdf
500 mg 3 times / day single, oral Recommended Dose: 500 mg, 3 times / day Route: oral Route: single Dose: 500 mg, 3 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18557slr015_fansidar_lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18557slr015_fansidar_lbl.pdf	Disc. AE: Toxic epidermal necrolysis, Stevens-Johnson syndrome... AEs leading to discontinuation/dose reduction: Toxic epidermal necrolysis Stevens-Johnson syndrome (grade 5) Toxic epidermal necrolysis (grade 5) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18557slr015_fansidar_lbl.pdf

AEs

AE	Significance	Dose	Population
Stevens-Johnson syndrome	Disc. AE	500 mg 3 times / day single, oral Recommended Dose: 500 mg, 3 times / day Route: oral Route: single Dose: 500 mg, 3 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18557slr015_fansidar_lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18557slr015_fansidar_lbl.pdf
Toxic epidermal necrolysis	Disc. AE	500 mg 3 times / day single, oral Recommended Dose: 500 mg, 3 times / day Route: oral Route: single Dose: 500 mg, 3 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18557slr015_fansidar_lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18557slr015_fansidar_lbl.pdf
Stevens-Johnson syndrome	grade 5 Disc. AE	500 mg 3 times / day single, oral Recommended Dose: 500 mg, 3 times / day Route: oral Route: single Dose: 500 mg, 3 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18557slr015_fansidar_lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18557slr015_fansidar_lbl.pdf
Toxic epidermal necrolysis	grade 5 Disc. AE	500 mg 3 times / day single, oral Recommended Dose: 500 mg, 3 times / day Route: oral Route: single Dose: 500 mg, 3 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18557slr015_fansidar_lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18557slr015_fansidar_lbl.pdf

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:9329	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9329
ChemicalBook	CB8171942	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB8171942
eMolecules	511843	https://www.emolecules.com/cgi-bin/more?vid=511843
MolPort	MolPort-003-850-341	https://www.molport.com/shop/molecule-link/MolPort-003-850-341
Selleck Chemicals	Sulfadoxine(Sulphadoxine)	http://www.selleckchem.com/products/Sulfadoxine(Sulphadoxine).html
ZINC	ZINC000000002094	http://zinc15.docking.org/substances/ZINC000000002094

PubMed

Title	Date	PubMed
Rationale and prospects of combination therapy as a strategy for delaying antimalarial drug resistance.	2001 Mar-Jun	12418672
Therapeutic efficacy of sulfadoxine-pyrimethamine in uncomplicated Plasmodium falciparum malaria 3 years after introduction in Mpumalanga.	2001 Nov	11847920
Failure of sulphadoxine-pyrimethamine in treating Plasmodium falciparum malaria in KwaZulu-Natal.	2001 Nov	11847918
Plasmodium falciparum: underestimation of dihydrofolate reductase and dihydropteroate synthase polymorphism in field samples: a technical shortcoming of nested PCR assays with mutation-specific primers.	2001 Nov	11846521
Plasmodium falciparum dihydrofolate reductase Val-16 and Thr-108 mutation associated with in vivo resistance to antifolate drug: a case study.	2001 Sep-Dec	12125519
Therapeutic efficacy of chloroquine and sulfadoxine/pyrimethamine against Plasmodium falciparum infection in Somalia.	2002	12378287
Therapeutic efficacy of sulfadoxine-pyrimethamine, amodiaquine and the sulfadoxine-pyrimethamine-amodiaquine combination against uncomplicated Plasmodium falciparum malaria in young children in Cameroon.	2002	12163917
[Which medication should be used to treat uncomplicated malaria when chloroquine becomes ineffective in Western Côte d'Ivoire?].	2002	12038180
A randomized comparison of chloroquine, amodiaquine and their combination with pyrimethamine-sulfadoxine in the treatment of acute, uncomplicated, Plasmodium falciparum malaria in children.	2002 Apr	12061970
Resistance of Plamodium falciparum to antimalarial drugs in Zaragoza (Antioquia, Colombia), 1998.	2002 Apr	12048572
Biofilm bacteria: formation and comparative susceptibility to antibiotics.	2002 Apr	11989739
[In vivo sensitivity of Plasmodium falciparum to amino-4-quinolines and sulfadoxine pyrimethamine in Agou (Ivory Coast)].	2002 Apr	11980332
Reversion of autoimmune lymphoproliferative syndrome with an antimalarial drug: preliminary results of a clinical cohort study and molecular observations.	2002 Apr	11918552
Treatment of imported malaria in an ambulatory setting: prospective study.	2002 Apr 13	11950734
Resistance to antimalarials.	2002 Aug	12200977
Determinants of treatment response to sulfadoxine-pyrimethamine and subsequent transmission potential in falciparum malaria.	2002 Aug 1	12142257
[Congenital toxoplasmosis: prevention in the pregnant woman and management of the neonate].	2002 Feb	11915504
High-performance liquid chromatographic assay for the simultaneous determination of sulfadoxine and pyrimethamine from whole blood dried onto filter paper.	2002 Feb 5	11863287
[Frequency of persistent or transitory serologic negative values in infants with congenital toxoplasmosis. Experience of the Reims Toxoplasmosis Group (1980-1997)].	2002 Feb 9	11878142
Do mutations in Plasmodium falciparum dihydropteroate synthase and dihydrofolate reductase confer resistance to sulfadoxine-pyrimethamine in Iran?	2002 Jan-Feb	11926005
An economic comparison of chloroquine and sulfadoxine-pyrimethamine as first-line treatment for malaria in South Africa: development of a model for estimating recurrent direct costs.	2002 Jan-Feb	11926003
Pyrimethamine-sulfadoxine resistance in Plasmodium falciparum must be delayed in Africa.	2002 Jul	12379946
The safety and efficacy of sulfadoxine-pyrimethamine, amodiaquine, and their combination in the treatment of uncomplicated Plasmodium falciparum malaria.	2002 Jul	12363058
Malaria: a rising incidence in the United States.	2002 Jul	12217468
The drug sensitivity and transmission dynamics of human malaria on Nias Island, North Sumatra, Indonesia.	2002 Jul	12194705
Sulfadoxine-pyrimethamine monotherapy in Tanzanian children gives rapid parasite clearance but slow fever clearance that is improved by chloroquine in combination therapy.	2002 Jul	12100442
Pharmacokinetics of sequential and simultaneous treatment with the combination chloroquine and sulfadoxine-pyrimethamine in acute uncomplicated Plasmodium falciparum malaria in the Philippines.	2002 Jul	12100441
Sulphadoxine/pyrimethamine: an appropriate first-line alternative for the treatment of uncomplicated falciparum malaria in Ghanaian children under 5 years of age.	2002 Jul	12100440
Physico-chemical studies on the charge-transfer complex formed between sulfadoxine and pyrimethamine with chloranilic acid.	2002 Jul 20	12093493
Molecular epidemiology of malaria in Cameroon. X. Evaluation of PFMDR1 mutations as genetic markers for resistance to amino alcohols and artemisinin derivatives.	2002 Jun	12224572
A high malaria reinfection rate in children and young adults living under a low entomological inoculation rate in a periurban area of Bamako, Mali.	2002 Mar	12139226
Seasonal malaria attack rates in infants and young children in northern Ghana.	2002 Mar	12139221
Intermittent malaria treatment as a component of the EPI (Expanded Programme on Immunization) schedule in Africa.	2002 Mar 15	11915124
African scientists discuss drug-resistant malaria.	2002 Mar 2	11888598
Clinical efficacy of chloroquine or sulfadoxine-pyrimethamine in children under five from south-western Uganda with uncomplicated falciparum malaria.	2002 Mar-Apr	12055815
Effectiveness of twice-weekly pyrimethamine-sulfadoxine as primary prophylaxis of Pneumocystis carinii pneumonia and toxoplasmic encephalitis in patients with advanced HIV infection.	2002 May	12072919
200 Gy sterilised Toxoplasma gondii tachyzoites maintain metabolic functions and mammalian cell invasion, eliciting cellular immunity and cytokine response similar to natural infection in mice.	2002 May 15	11972976
Intensity of malaria transmission, antimalarial-drug use and resistance in Uganda: what is the relationship between these three factors?	2002 May-Jun	12174786
Treatment of uncomplicated malaria in children in Guinea-Bissau with chloroquine, quinine, and sulfadoxine-pyrimethamine.	2002 May-Jun	12174785
Chloroquine and sulphadoxine-pyrimethamine efficacy for uncomplicated malaria treatment and haematological recovery in children in Bobo-Dioulasso, Burkina Faso during a 3-year period 1998-2000.	2002 Nov	12390597
Transcriptional analysis of genes encoding enzymes of the folate pathway in the human malaria parasite Plasmodium falciparum.	2002 Oct	12366841
Origin and dissemination of Plasmodium falciparum drug-resistance mutations in South America.	2002 Oct 1	12232841
Chlorproguanil-dapsone versus sulfadoxine-pyrimethamine for sequential episodes of uncomplicated falciparum malaria in Kenya and Malawi: a randomised clinical trial.	2002 Oct 12	12387962
Simultaneous spectrophotometric determination of sulfadoxine and pyrimethamine in pharmaceutical formulations.	2002 Oct 15	12367711
Pyrimethamine/sulfadoxine combination in the treatment of uncomplicated falciparum malaria: relation between dihydropteroate synthase/dihydrofolate reductase genotypes, sulfadoxine plasma levels, and treatment outcome.	2002 Sep	12408659
Monitoring the drug-sensitivity of Plasmodium falciparum in coastal towns in Madagascar by use of in vitro chemosensitivity and mutation detection tests.	2002 Sep	12375368
In vivo drug resistance of falciparum malaria in mining areas of Venezuela.	2002 Sep	12225503
A possible novel mechanism of opportunistic infection in systemic lupus erythematosus, based on a case of toxoplasmic encephalopathy.	2002 Sep	12209046
Intermittent administration of iron and sulfadoxine-pyrimethamine to control anaemia in Kenyan children: a randomised controlled trial.	2002 Sep 21	12354473
[Blackwater fever].	2002 Sep 7	12355996

Patents

Sample Use Guides

In Vivo Use Guide

Treatment: adults should take 2 to 3 tablets (each tablet contains 500 mg sulfadoxine and 25 mg pyrimethamine) taken as a single dose. Prevention: adults should take 1 tablet weekly or 2 tablets once every two weeks.

Route of Administration: Oral

In Vitro Use Guide

MIC99 value was found to be 30000 and 500000 ng/ml for FC27 strain of P. falciparum and K1 strain of P. falciparum, respectively when treated with sulfadoxine.

Name

Type

Language

J21.373J

Preferred Name

English

SULFADOXINE

Official Name

English

RO 4-4393

Code

English

FANSIDAR COMPONENT SULFADOXINE

Common Name

English

SULFADOXINE [WHO-IP]

Common Name

English

RO-44393

Code

English

SULPHADOXINE

Common Name

English

SULFADOXINE [USAN]

Common Name

English

SULFADOXINUM [WHO-IP LATIN]

Common Name

English

SULFADOXINE [JAN]

Common Name

English

SULFADOXINE [VANDF]

Common Name

English

SULFADOXINE [ORANGE BOOK]

Common Name

English

SULFADOXINE [MART.]

Common Name

English

SULFADOXINE [MI]

Common Name

English

SULFADOXIN

Common Name

English

NSC-759319

Code

English

WR-4073

Code

English

SULFADOXINE [USP-RS]

Common Name

English

sulfadoxine [INN]

Common Name

English

Sulfadoxine [WHO-DD]

Common Name

English

SULFADOXINE [USP MONOGRAPH]

Common Name

English

RO-4-4393

Code

English

FANASULF

Common Name

English

SULFADOXINE [EP MONOGRAPH]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000008048