U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of SULFADOXINE

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
Targets

Targets

Primary TargetPharmacologyConditionPotency
0.14 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
71.7 μg/mL
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered: PYRIMETHAMINE
SULFADOXINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
165.15 mg/L
1500 mg single, oral
dose: 1500 mg
route of administration: Oral
experiment type: SINGLE
co-administered: PYRIMETHAMINE
SULFADOXINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
60 mg/L
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered: PYRIMETHAMINE
SULFADOXINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
12394 μg × h/mL
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered: PYRIMETHAMINE
SULFADOXINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
21761.02 mg × h/L
1500 mg single, oral
dose: 1500 mg
route of administration: Oral
experiment type: SINGLE
co-administered: PYRIMETHAMINE
SULFADOXINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
155.8 h
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered: PYRIMETHAMINE
SULFADOXINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
200 h
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered: PYRIMETHAMINE
SULFADOXINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
10%
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered: PYRIMETHAMINE
SULFADOXINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse 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:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Disc. AE: Stevens-Johnson syndrome...
AEs leading to
discontinuation/dose reduction:
Stevens-Johnson syndrome
Sources:
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:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
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:
AEs

AEs

AESignificanceDosePopulation
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:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
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:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
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:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
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:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
PubMed

PubMed

TitleDatePubMed
Rationale and prospects of combination therapy as a strategy for delaying antimalarial drug resistance.
2002-11-07
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.
2002-11
Simultaneous spectrophotometric determination of sulfadoxine and pyrimethamine in pharmaceutical formulations.
2002-10-15
Chlorproguanil-dapsone versus sulfadoxine-pyrimethamine for sequential episodes of uncomplicated falciparum malaria in Kenya and Malawi: a randomised clinical trial.
2002-10-12
Origin and dissemination of Plasmodium falciparum drug-resistance mutations in South America.
2002-10-01
Transcriptional analysis of genes encoding enzymes of the folate pathway in the human malaria parasite Plasmodium falciparum.
2002-10
Intermittent administration of iron and sulfadoxine-pyrimethamine to control anaemia in Kenyan children: a randomised controlled trial.
2002-09-21
[Blackwater fever].
2002-09-07
Pyrimethamine/sulfadoxine combination in the treatment of uncomplicated falciparum malaria: relation between dihydropteroate synthase/dihydrofolate reductase genotypes, sulfadoxine plasma levels, and treatment outcome.
2002-09
Monitoring the drug-sensitivity of Plasmodium falciparum in coastal towns in Madagascar by use of in vitro chemosensitivity and mutation detection tests.
2002-09
In vivo drug resistance of falciparum malaria in mining areas of Venezuela.
2002-09
A possible novel mechanism of opportunistic infection in systemic lupus erythematosus, based on a case of toxoplasmic encephalopathy.
2002-09
Intensity of malaria transmission, antimalarial-drug use and resistance in Uganda: what is the relationship between these three factors?
2002-08-15
Treatment of uncomplicated malaria in children in Guinea-Bissau with chloroquine, quinine, and sulfadoxine-pyrimethamine.
2002-08-15
Determinants of treatment response to sulfadoxine-pyrimethamine and subsequent transmission potential in falciparum malaria.
2002-08-01
Resistance to antimalarials.
2002-08
Plasmodium falciparum dihydrofolate reductase Val-16 and Thr-108 mutation associated with in vivo resistance to antifolate drug: a case study.
2002-07-20
Physico-chemical studies on the charge-transfer complex formed between sulfadoxine and pyrimethamine with chloranilic acid.
2002-07-20
Pyrimethamine-sulfadoxine resistance in Plasmodium falciparum must be delayed in Africa.
2002-07
The safety and efficacy of sulfadoxine-pyrimethamine, amodiaquine, and their combination in the treatment of uncomplicated Plasmodium falciparum malaria.
2002-07
Malaria: a rising incidence in the United States.
2002-07
The drug sensitivity and transmission dynamics of human malaria on Nias Island, North Sumatra, Indonesia.
2002-07
Sulfadoxine-pyrimethamine monotherapy in Tanzanian children gives rapid parasite clearance but slow fever clearance that is improved by chloroquine in combination therapy.
2002-07
Pharmacokinetics of sequential and simultaneous treatment with the combination chloroquine and sulfadoxine-pyrimethamine in acute uncomplicated Plasmodium falciparum malaria in the Philippines.
2002-07
Sulphadoxine/pyrimethamine: an appropriate first-line alternative for the treatment of uncomplicated falciparum malaria in Ghanaian children under 5 years of age.
2002-07
Clinical efficacy of chloroquine or sulfadoxine-pyrimethamine in children under five from south-western Uganda with uncomplicated falciparum malaria.
2002-06-12
Molecular epidemiology of malaria in Cameroon. X. Evaluation of PFMDR1 mutations as genetic markers for resistance to amino alcohols and artemisinin derivatives.
2002-06
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.
2002-05-15
Effectiveness of twice-weekly pyrimethamine-sulfadoxine as primary prophylaxis of Pneumocystis carinii pneumonia and toxoplasmic encephalitis in patients with advanced HIV infection.
2002-05
Treatment of imported malaria in an ambulatory setting: prospective study.
2002-04-13
Do mutations in Plasmodium falciparum dihydropteroate synthase and dihydrofolate reductase confer resistance to sulfadoxine-pyrimethamine in Iran?
2002-04-03
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.
2002-04-03
A randomized comparison of chloroquine, amodiaquine and their combination with pyrimethamine-sulfadoxine in the treatment of acute, uncomplicated, Plasmodium falciparum malaria in children.
2002-04
Resistance of Plamodium falciparum to antimalarial drugs in Zaragoza (Antioquia, Colombia), 1998.
2002-04
Biofilm bacteria: formation and comparative susceptibility to antibiotics.
2002-04
[In vivo sensitivity of Plasmodium falciparum to amino-4-quinolines and sulfadoxine pyrimethamine in Agou (Ivory Coast)].
2002-04
Reversion of autoimmune lymphoproliferative syndrome with an antimalarial drug: preliminary results of a clinical cohort study and molecular observations.
2002-04
Intermittent malaria treatment as a component of the EPI (Expanded Programme on Immunization) schedule in Africa.
2002-03-15
African scientists discuss drug-resistant malaria.
2002-03-02
A high malaria reinfection rate in children and young adults living under a low entomological inoculation rate in a periurban area of Bamako, Mali.
2002-03
Seasonal malaria attack rates in infants and young children in northern Ghana.
2002-03
[Frequency of persistent or transitory serologic negative values in infants with congenital toxoplasmosis. Experience of the Reims Toxoplasmosis Group (1980-1997)].
2002-02-09
High-performance liquid chromatographic assay for the simultaneous determination of sulfadoxine and pyrimethamine from whole blood dried onto filter paper.
2002-02-05
[Congenital toxoplasmosis: prevention in the pregnant woman and management of the neonate].
2002-02
Therapeutic efficacy of chloroquine and sulfadoxine/pyrimethamine against Plasmodium falciparum infection in Somalia.
2002
Therapeutic efficacy of sulfadoxine-pyrimethamine, amodiaquine and the sulfadoxine-pyrimethamine-amodiaquine combination against uncomplicated Plasmodium falciparum malaria in young children in Cameroon.
2002
[Which medication should be used to treat uncomplicated malaria when chloroquine becomes ineffective in Western Côte d'Ivoire?].
2002
Therapeutic efficacy of sulfadoxine-pyrimethamine in uncomplicated Plasmodium falciparum malaria 3 years after introduction in Mpumalanga.
2001-11
Failure of sulphadoxine-pyrimethamine in treating Plasmodium falciparum malaria in KwaZulu-Natal.
2001-11
Plasmodium falciparum: underestimation of dihydrofolate reductase and dihydropteroate synthase polymorphism in field samples: a technical shortcoming of nested PCR assays with mutation-specific primers.
2001-11
Patents

Sample Use Guides

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
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
EP   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
INN   USAN  
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
Created by admin on Wed Apr 02 08:33:14 GMT 2025 , Edited by admin on Wed Apr 02 08:33:14 GMT 2025
NDF-RT N0000008048
Created by admin on Wed Apr 02 08:33:14 GMT 2025 , Edited by admin on Wed Apr 02 08:33:14 GMT 2025
WHO-ESSENTIAL MEDICINES LIST 6.5.3.1 (SUL/PYR)
Created by admin on Wed Apr 02 08:33:14 GMT 2025 , Edited by admin on Wed Apr 02 08:33:14 GMT 2025
WHO-VATC QJ01EW13
Created by admin on Wed Apr 02 08:33:14 GMT 2025 , Edited by admin on Wed Apr 02 08:33:14 GMT 2025
NDF-RT N0000175880
Created by admin on Wed Apr 02 08:33:14 GMT 2025 , Edited by admin on Wed Apr 02 08:33:14 GMT 2025
LIVERTOX NBK548044
Created by admin on Wed Apr 02 08:33:14 GMT 2025 , Edited by admin on Wed Apr 02 08:33:14 GMT 2025
NDF-RT N0000008048
Created by admin on Wed Apr 02 08:33:14 GMT 2025 , Edited by admin on Wed Apr 02 08:33:14 GMT 2025
WHO-VATC QJ01EQ13
Created by admin on Wed Apr 02 08:33:14 GMT 2025 , Edited by admin on Wed Apr 02 08:33:14 GMT 2025
Code System Code Type Description
MERCK INDEX
m10308
Created by admin on Wed Apr 02 08:33:14 GMT 2025 , Edited by admin on Wed Apr 02 08:33:14 GMT 2025
PRIMARY Merck Index
PUBCHEM
17134
Created by admin on Wed Apr 02 08:33:14 GMT 2025 , Edited by admin on Wed Apr 02 08:33:14 GMT 2025
PRIMARY
DRUG BANK
DB01299
Created by admin on Wed Apr 02 08:33:14 GMT 2025 , Edited by admin on Wed Apr 02 08:33:14 GMT 2025
PRIMARY
SMS_ID
100000083266
Created by admin on Wed Apr 02 08:33:14 GMT 2025 , Edited by admin on Wed Apr 02 08:33:14 GMT 2025
PRIMARY
RS_ITEM_NUM
1626500
Created by admin on Wed Apr 02 08:33:14 GMT 2025 , Edited by admin on Wed Apr 02 08:33:14 GMT 2025
PRIMARY
EVMPD
SUB10700MIG
Created by admin on Wed Apr 02 08:33:14 GMT 2025 , Edited by admin on Wed Apr 02 08:33:14 GMT 2025
PRIMARY
DRUG CENTRAL
2503
Created by admin on Wed Apr 02 08:33:14 GMT 2025 , Edited by admin on Wed Apr 02 08:33:14 GMT 2025
PRIMARY
ECHA (EC/EINECS)
219-504-9
Created by admin on Wed Apr 02 08:33:14 GMT 2025 , Edited by admin on Wed Apr 02 08:33:14 GMT 2025
PRIMARY
MESH
D013413
Created by admin on Wed Apr 02 08:33:14 GMT 2025 , Edited by admin on Wed Apr 02 08:33:14 GMT 2025
PRIMARY
WIKIPEDIA
SULFADOXINE
Created by admin on Wed Apr 02 08:33:14 GMT 2025 , Edited by admin on Wed Apr 02 08:33:14 GMT 2025
PRIMARY
INN
2061
Created by admin on Wed Apr 02 08:33:14 GMT 2025 , Edited by admin on Wed Apr 02 08:33:14 GMT 2025
PRIMARY
EPA CompTox
DTXSID6023608
Created by admin on Wed Apr 02 08:33:14 GMT 2025 , Edited by admin on Wed Apr 02 08:33:14 GMT 2025
PRIMARY
NSC
759319
Created by admin on Wed Apr 02 08:33:14 GMT 2025 , Edited by admin on Wed Apr 02 08:33:14 GMT 2025
PRIMARY
ChEMBL
CHEMBL1539
Created by admin on Wed Apr 02 08:33:14 GMT 2025 , Edited by admin on Wed Apr 02 08:33:14 GMT 2025
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
SULFADOXINE
Created by admin on Wed Apr 02 08:33:14 GMT 2025 , Edited by admin on Wed Apr 02 08:33:14 GMT 2025
PRIMARY Description: A white or creamy white, crystalline powder; odourless. Solubility: Very slightly soluble in water; slightly soluble in ethanol (~750 g/l) TS and in methanol R; practically insoluble in ether R. Category: Antimalarial drug. Storage: Sulfadoxine should be kept in a well-closed container, protected from light. Definition: Sulfadoxine contains not less than 99.0% and not more than 101.0% of C12H14N4O4S, calculated with reference to the dried substance.
CHEBI
9329
Created by admin on Wed Apr 02 08:33:14 GMT 2025 , Edited by admin on Wed Apr 02 08:33:14 GMT 2025
PRIMARY
LACTMED
Sulfadoxine and Pyrimethamine
Created by admin on Wed Apr 02 08:33:14 GMT 2025 , Edited by admin on Wed Apr 02 08:33:14 GMT 2025
PRIMARY
NCI_THESAURUS
C47735
Created by admin on Wed Apr 02 08:33:14 GMT 2025 , Edited by admin on Wed Apr 02 08:33:14 GMT 2025
PRIMARY
CAS
2447-57-6
Created by admin on Wed Apr 02 08:33:14 GMT 2025 , Edited by admin on Wed Apr 02 08:33:14 GMT 2025
PRIMARY
RXCUI
10173
Created by admin on Wed Apr 02 08:33:14 GMT 2025 , Edited by admin on Wed Apr 02 08:33:14 GMT 2025
PRIMARY RxNorm
FDA UNII
88463U4SM5
Created by admin on Wed Apr 02 08:33:14 GMT 2025 , Edited by admin on Wed Apr 02 08:33:14 GMT 2025
PRIMARY