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

Details

Stereochemistry ACHIRAL
Molecular Formula C12H14N4O4S
Molecular Weight 310.3305
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SULFADOXINE

SMILES

COc1c(ncnc1OC)NS(=O)(=O)c2ccc(cc2)N

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

3.73075214E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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
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
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
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
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
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
Co-administed with::
pyrimethamine
Sources:
unhealthy, adult
Health Status: unhealthy
Condition: malaria
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:
500 mg 3 times / day single, oral
Recommended
Dose: 500 mg, 3 times / day
Route: oral
Route: single
Dose: 500 mg, 3 times / day
Co-administed with::
pyrimethamine(25 mg/3 times/day)
Sources:
unhealthy, adult
Health Status: unhealthy
Condition: malaria
Age Group: adult
Sex: unknown
Sources:
Disc. AE: Stevens-Johnson syndrome...
AEs leading to
discontinuation/dose reduction:
Stevens-Johnson syndrome
Sources:
AEs

AEs

AESignificanceDosePopulation
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
Co-administed with::
pyrimethamine
Sources:
unhealthy, adult
Health Status: unhealthy
Condition: malaria
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
Co-administed with::
pyrimethamine
Sources:
unhealthy, adult
Health Status: unhealthy
Condition: malaria
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
Co-administed with::
pyrimethamine
Sources:
unhealthy, adult
Health Status: unhealthy
Condition: malaria
Age Group: adult
Sex: unknown
Sources:
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
Co-administed with::
pyrimethamine(25 mg/3 times/day)
Sources:
unhealthy, adult
Health Status: unhealthy
Condition: malaria
Age Group: adult
Sex: unknown
Sources:
PubMed

PubMed

TitleDatePubMed
Chloroquine or amodiaquine combined with sulfadoxine-pyrimethamine for treating uncomplicated malaria.
2001
Atovaquone and proguani hydrochloride compared with chloroquine or pyrimethamine/sulfodaxine for treatment of acute Plasmodium falciparum malaria in Peru.
2001 Apr
Artesunate reduces but does not prevent posttreatment transmission of Plasmodium falciparum to Anopheles gambiae.
2001 Apr 15
Changing the first line drug for malaria treatment--cost-effectiveness analysis with highly uncertain inter-temporal trade-offs.
2001 Dec
Perception of chloroquine efficacy and alternative treatments for uncomplicated malaria in children in a holoendemic area of Tanzania: implications for the change of treatment policy.
2001 Dec
Parasitaemia and gametocytaemia after treatment with chloroquine, pyrimethamine/sulfadoxine, and pyrimethamine/sulfadoxine combined with artesunate in young Gambians with uncomplicated malaria.
2001 Feb
[Resistance of Plasmodium falciparum to 3 antimalarials in Turbo (Antioquia, Colombia), 1998].
2001 Jan
Twice-weekly pyrimethamine-sulfadoxine effectively prevents Pneumocystis carinii pneumonia relapse and toxoplasmic encephalitis in patients with AIDS.
2001 Jan
Neonatal screening for congenital toxoplasmosis in a cohort of 165 women infected during pregnancy and influence of in utero treatment on the results of neonatal tests.
2001 Jan
Short report: differences in dihydrofolate reductase but not dihydropteroate synthase alleles in Plasmodium falciparum isolates from geographically distinct areas in Malaysia.
2001 Jan-Feb
Effectiveness of short-course quinine and single-dose sulfadoxine-pyrimethamine in the treatment of Plasmodium falciparum malaria in Mpumalanga Province, South Africa.
2001 Jul
The safety of the combination artesunate and pyrimethamine-sulfadoxine given during pregnancy.
2001 Jul-Aug
Sulfa-drug resistance in Plasmodium falciparum.
2001 Jun
Therapeutic efficacy of sulphadoxine/pyrimethamine and susceptibility in vitro of P. falciparum isolates to sulphadoxine-pyremethamine and other antimalarial drugs in Malawian children.
2001 Jun
Determination of sulfadoxine in human blood plasma using packed-column supercritical fluid chromatography.
2001 Jun 5
Folic acid antagonists during pregnancy and risk of birth defects.
2001 Mar 22
Molecular analysis of DHFR and DHPS genes in P. falciparum clinical isolates from the Haut--Ogooué region in Gabon.
2001 Mar 30
Rationale and prospects of combination therapy as a strategy for delaying antimalarial drug resistance.
2001 Mar-Jun
Therapeutic efficacy of sulfadoxine-pyrimethamine in uncomplicated Plasmodium falciparum malaria 3 years after introduction in Mpumalanga.
2001 Nov
Failure of sulphadoxine-pyrimethamine in treating Plasmodium falciparum malaria in KwaZulu-Natal.
2001 Nov
Monitoring antimalarial drug resistance within National Malaria Control Programmes: the EANMAT experience.
2001 Nov
Anemia of persistent malarial parasitemia in Nigerian children.
2001 Oct
Malaria control in Tanzania.
2001 Sep 1
High-performance liquid chromatographic determination of diazepam in plasma of children with severe malaria.
2001 Sep 25
[Danger of malaria self-treatment. Acute neurologic toxicity of mefloquine and its combination with pyrimethamine-sulfadoxine].
2001 Sep 29
Plasmodium falciparum dihydrofolate reductase Val-16 and Thr-108 mutation associated with in vivo resistance to antifolate drug: a case study.
2001 Sep-Dec
Therapeutic efficacy of chloroquine and sulfadoxine/pyrimethamine against Plasmodium falciparum infection in Somalia.
2002
Resistance of Plamodium falciparum to antimalarial drugs in Zaragoza (Antioquia, Colombia), 1998.
2002 Apr
Reversion of autoimmune lymphoproliferative syndrome with an antimalarial drug: preliminary results of a clinical cohort study and molecular observations.
2002 Apr
Resistance to antimalarials.
2002 Aug
[Congenital toxoplasmosis: prevention in the pregnant woman and management of the neonate].
2002 Feb
Molecular markers for failure of sulfadoxine-pyrimethamine and chlorproguanil-dapsone treatment of Plasmodium falciparum malaria.
2002 Feb 1
High-performance liquid chromatographic assay for the simultaneous determination of sulfadoxine and pyrimethamine from whole blood dried onto filter paper.
2002 Feb 5
Do mutations in Plasmodium falciparum dihydropteroate synthase and dihydrofolate reductase confer resistance to sulfadoxine-pyrimethamine in Iran?
2002 Jan-Feb
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
Pyrimethamine-sulfadoxine resistance in Plasmodium falciparum must be delayed in Africa.
2002 Jul
The safety and efficacy of sulfadoxine-pyrimethamine, amodiaquine, and their combination in the treatment of uncomplicated Plasmodium falciparum malaria.
2002 Jul
Molecular epidemiology of malaria in Cameroon. X. Evaluation of PFMDR1 mutations as genetic markers for resistance to amino alcohols and artemisinin derivatives.
2002 Jun
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
Intermittent malaria treatment as a component of the EPI (Expanded Programme on Immunization) schedule in Africa.
2002 Mar 15
African scientists discuss drug-resistant malaria.
2002 Mar 2
Effectiveness of twice-weekly pyrimethamine-sulfadoxine as primary prophylaxis of Pneumocystis carinii pneumonia and toxoplasmic encephalitis in patients with advanced HIV infection.
2002 May
Treatment of uncomplicated malaria in children in Guinea-Bissau with chloroquine, quinine, and sulfadoxine-pyrimethamine.
2002 May-Jun
Origin and dissemination of Plasmodium falciparum drug-resistance mutations in South America.
2002 Oct 1
Monitoring the drug-sensitivity of Plasmodium falciparum in coastal towns in Madagascar by use of in vitro chemosensitivity and mutation detection tests.
2002 Sep
A possible novel mechanism of opportunistic infection in systemic lupus erythematosus, based on a case of toxoplasmic encephalopathy.
2002 Sep
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
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
J21.373J
Code English
SULFADOXINE [WHO-IP]
Common Name English
RO-44393
Code English
SULPHADOXINE
Common Name English
SULFADOXINE COMPONENT OF FANSIDAR
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 [WHO-DD]
Common Name English
SULFADOXINE [USP-RS]
Common Name English
SULFADOXINE [INN]
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 Fri Jun 25 21:01:08 UTC 2021 , Edited by admin on Fri Jun 25 21:01:08 UTC 2021
NDF-RT N0000008048
Created by admin on Fri Jun 25 21:01:08 UTC 2021 , Edited by admin on Fri Jun 25 21:01:08 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 6.5.3.1 (SUL/PYR)
Created by admin on Fri Jun 25 21:01:08 UTC 2021 , Edited by admin on Fri Jun 25 21:01:08 UTC 2021
WHO-VATC QJ01EW13
Created by admin on Fri Jun 25 21:01:08 UTC 2021 , Edited by admin on Fri Jun 25 21:01:08 UTC 2021
NDF-RT N0000175880
Created by admin on Fri Jun 25 21:01:08 UTC 2021 , Edited by admin on Fri Jun 25 21:01:08 UTC 2021
LIVERTOX 907
Created by admin on Fri Jun 25 21:01:08 UTC 2021 , Edited by admin on Fri Jun 25 21:01:08 UTC 2021
NDF-RT N0000008048
Created by admin on Fri Jun 25 21:01:08 UTC 2021 , Edited by admin on Fri Jun 25 21:01:08 UTC 2021
WHO-VATC QJ01EQ13
Created by admin on Fri Jun 25 21:01:08 UTC 2021 , Edited by admin on Fri Jun 25 21:01:08 UTC 2021
Code System Code Type Description
MERCK INDEX
M10308
Created by admin on Fri Jun 25 21:01:08 UTC 2021 , Edited by admin on Fri Jun 25 21:01:08 UTC 2021
PRIMARY Merck Index
PUBCHEM
17134
Created by admin on Fri Jun 25 21:01:08 UTC 2021 , Edited by admin on Fri Jun 25 21:01:08 UTC 2021
PRIMARY
DRUG BANK
DB01299
Created by admin on Fri Jun 25 21:01:08 UTC 2021 , Edited by admin on Fri Jun 25 21:01:08 UTC 2021
PRIMARY
EVMPD
SUB10700MIG
Created by admin on Fri Jun 25 21:01:08 UTC 2021 , Edited by admin on Fri Jun 25 21:01:08 UTC 2021
PRIMARY
DRUG CENTRAL
2503
Created by admin on Fri Jun 25 21:01:08 UTC 2021 , Edited by admin on Fri Jun 25 21:01:08 UTC 2021
PRIMARY
ECHA (EC/EINECS)
219-504-9
Created by admin on Fri Jun 25 21:01:08 UTC 2021 , Edited by admin on Fri Jun 25 21:01:08 UTC 2021
PRIMARY
MESH
D013413
Created by admin on Fri Jun 25 21:01:08 UTC 2021 , Edited by admin on Fri Jun 25 21:01:08 UTC 2021
PRIMARY
WIKIPEDIA
SULFADOXINE
Created by admin on Fri Jun 25 21:01:08 UTC 2021 , Edited by admin on Fri Jun 25 21:01:08 UTC 2021
PRIMARY
INN
2061
Created by admin on Fri Jun 25 21:01:08 UTC 2021 , Edited by admin on Fri Jun 25 21:01:08 UTC 2021
PRIMARY
USP_CATALOG
1626500
Created by admin on Fri Jun 25 21:01:08 UTC 2021 , Edited by admin on Fri Jun 25 21:01:08 UTC 2021
PRIMARY USP-RS
EPA CompTox
2447-57-6
Created by admin on Fri Jun 25 21:01:08 UTC 2021 , Edited by admin on Fri Jun 25 21:01:08 UTC 2021
PRIMARY
ChEMBL
CHEMBL1539
Created by admin on Fri Jun 25 21:01:08 UTC 2021 , Edited by admin on Fri Jun 25 21:01:08 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
SULFADOXINE
Created by admin on Fri Jun 25 21:01:08 UTC 2021 , Edited by admin on Fri Jun 25 21:01:08 UTC 2021
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.
LACTMED
Sulfadoxine and Pyrimethamine
Created by admin on Fri Jun 25 21:01:08 UTC 2021 , Edited by admin on Fri Jun 25 21:01:08 UTC 2021
PRIMARY
NCI_THESAURUS
C47735
Created by admin on Fri Jun 25 21:01:08 UTC 2021 , Edited by admin on Fri Jun 25 21:01:08 UTC 2021
PRIMARY
CAS
2447-57-6
Created by admin on Fri Jun 25 21:01:08 UTC 2021 , Edited by admin on Fri Jun 25 21:01:08 UTC 2021
PRIMARY
RXCUI
10173
Created by admin on Fri Jun 25 21:01:08 UTC 2021 , Edited by admin on Fri Jun 25 21:01:08 UTC 2021
PRIMARY RxNorm
FDA UNII
88463U4SM5
Created by admin on Fri Jun 25 21:01:08 UTC 2021 , Edited by admin on Fri Jun 25 21:01:08 UTC 2021
PRIMARY