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=NC=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=C1OC

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

Molecular Formula C12H14N4O4S
Molecular Weight 310.329
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Cardiac effects of amodiaquine and sulfadoxine-pyrimethamine in malaria-infected African patients.
2001 Dec
Efficacy of mefloquine and sulfadoxine-pyrimethamine for the treatment of uncomplicated Plasmodium falciparum infection in Machinga District, Malawi, 1998.
2001 Dec
The cost-effectiveness of antenatal malaria prevention in sub-Saharan Africa.
2001 Jan-Feb
Short report: differences in dihydrofolate reductase but not dihydropteroate synthase alleles in Plasmodium falciparum isolates from geographically distinct areas in Malaysia.
2001 Jan-Feb
Malaria diagnosis and treatment under the strategy of the integrated management of childhood illness (IMCI): relevance of laboratory support from the rapid immunochromatographic tests of ICT Malaria P.f/P.v and OptiMal.
2001 Jul
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
Cost-effectiveness of sulfadoxine-pyrimethamine for the prevention of malaria-associated low birth weight.
2001 Mar-Apr
History and importance of antimalarial drug resistance.
2001 Nov
Anemia of persistent malarial parasitemia in Nigerian children.
2001 Oct
[Danger of malaria self-treatment. Acute neurologic toxicity of mefloquine and its combination with pyrimethamine-sulfadoxine].
2001 Sep 29
Therapeutic efficacy of sulfadoxine-pyrimethamine, amodiaquine and the sulfadoxine-pyrimethamine-amodiaquine combination against uncomplicated Plasmodium falciparum malaria in young children in Cameroon.
2002
Resistance of Plamodium falciparum to antimalarial drugs in Zaragoza (Antioquia, Colombia), 1998.
2002 Apr
Biofilm bacteria: formation and comparative susceptibility to antibiotics.
2002 Apr
Treatment of imported malaria in an ambulatory setting: prospective study.
2002 Apr 13
High-performance liquid chromatographic assay for the simultaneous determination of sulfadoxine and pyrimethamine from whole blood dried onto filter paper.
2002 Feb 5
[Frequency of persistent or transitory serologic negative values in infants with congenital toxoplasmosis. Experience of the Reims Toxoplasmosis Group (1980-1997)].
2002 Feb 9
Malaria: a rising incidence in the United States.
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
African scientists discuss drug-resistant malaria.
2002 Mar 2
Treatment of uncomplicated malaria in children in Guinea-Bissau with chloroquine, quinine, and sulfadoxine-pyrimethamine.
2002 May-Jun
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
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
Intermittent administration of iron and sulfadoxine-pyrimethamine to control anaemia in Kenyan children: a randomised controlled trial.
2002 Sep 21
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.
Substance Class Chemical
Created
by admin
on Sun Dec 18 19:24:24 UTC 2022
Edited
by admin
on Sun Dec 18 19:24:24 UTC 2022
Record UNII
88463U4SM5
Record Status Validated (UNII)
Record Version
  • Download
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 [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 Sun Dec 18 19:24:25 UTC 2022 , Edited by admin on Sun Dec 18 19:24:25 UTC 2022
NDF-RT N0000008048
Created by admin on Sun Dec 18 19:24:25 UTC 2022 , Edited by admin on Sun Dec 18 19:24:25 UTC 2022
WHO-ESSENTIAL MEDICINES LIST 6.5.3.1 (SUL/PYR)
Created by admin on Sun Dec 18 19:24:25 UTC 2022 , Edited by admin on Sun Dec 18 19:24:25 UTC 2022
WHO-VATC QJ01EW13
Created by admin on Sun Dec 18 19:24:25 UTC 2022 , Edited by admin on Sun Dec 18 19:24:25 UTC 2022
NDF-RT N0000175880
Created by admin on Sun Dec 18 19:24:25 UTC 2022 , Edited by admin on Sun Dec 18 19:24:25 UTC 2022
LIVERTOX NBK548044
Created by admin on Sun Dec 18 19:24:25 UTC 2022 , Edited by admin on Sun Dec 18 19:24:25 UTC 2022
NDF-RT N0000008048
Created by admin on Sun Dec 18 19:24:25 UTC 2022 , Edited by admin on Sun Dec 18 19:24:25 UTC 2022
WHO-VATC QJ01EQ13
Created by admin on Sun Dec 18 19:24:25 UTC 2022 , Edited by admin on Sun Dec 18 19:24:25 UTC 2022
Code System Code Type Description
MERCK INDEX
M10308
Created by admin on Sun Dec 18 19:24:25 UTC 2022 , Edited by admin on Sun Dec 18 19:24:25 UTC 2022
PRIMARY Merck Index
PUBCHEM
17134
Created by admin on Sun Dec 18 19:24:25 UTC 2022 , Edited by admin on Sun Dec 18 19:24:25 UTC 2022
PRIMARY
DRUG BANK
DB01299
Created by admin on Sun Dec 18 19:24:25 UTC 2022 , Edited by admin on Sun Dec 18 19:24:25 UTC 2022
PRIMARY
RS_ITEM_NUM
1626500
Created by admin on Sun Dec 18 19:24:25 UTC 2022 , Edited by admin on Sun Dec 18 19:24:25 UTC 2022
PRIMARY
EVMPD
SUB10700MIG
Created by admin on Sun Dec 18 19:24:25 UTC 2022 , Edited by admin on Sun Dec 18 19:24:25 UTC 2022
PRIMARY
DRUG CENTRAL
2503
Created by admin on Sun Dec 18 19:24:25 UTC 2022 , Edited by admin on Sun Dec 18 19:24:25 UTC 2022
PRIMARY
ECHA (EC/EINECS)
219-504-9
Created by admin on Sun Dec 18 19:24:25 UTC 2022 , Edited by admin on Sun Dec 18 19:24:25 UTC 2022
PRIMARY
MESH
D013413
Created by admin on Sun Dec 18 19:24:25 UTC 2022 , Edited by admin on Sun Dec 18 19:24:25 UTC 2022
PRIMARY
WIKIPEDIA
SULFADOXINE
Created by admin on Sun Dec 18 19:24:25 UTC 2022 , Edited by admin on Sun Dec 18 19:24:25 UTC 2022
PRIMARY
INN
2061
Created by admin on Sun Dec 18 19:24:25 UTC 2022 , Edited by admin on Sun Dec 18 19:24:25 UTC 2022
PRIMARY
EPA CompTox
DTXSID6023608
Created by admin on Sun Dec 18 19:24:25 UTC 2022 , Edited by admin on Sun Dec 18 19:24:25 UTC 2022
PRIMARY
NSC
759319
Created by admin on Sun Dec 18 19:24:25 UTC 2022 , Edited by admin on Sun Dec 18 19:24:25 UTC 2022
PRIMARY
ChEMBL
CHEMBL1539
Created by admin on Sun Dec 18 19:24:25 UTC 2022 , Edited by admin on Sun Dec 18 19:24:25 UTC 2022
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
SULFADOXINE
Created by admin on Sun Dec 18 19:24:25 UTC 2022 , Edited by admin on Sun Dec 18 19:24:25 UTC 2022
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 Sun Dec 18 19:24:25 UTC 2022 , Edited by admin on Sun Dec 18 19:24:25 UTC 2022
PRIMARY
LACTMED
Sulfadoxine and Pyrimethamine
Created by admin on Sun Dec 18 19:24:25 UTC 2022 , Edited by admin on Sun Dec 18 19:24:25 UTC 2022
PRIMARY
NCI_THESAURUS
C47735
Created by admin on Sun Dec 18 19:24:25 UTC 2022 , Edited by admin on Sun Dec 18 19:24:25 UTC 2022
PRIMARY
DAILYMED
88463U4SM5
Created by admin on Sun Dec 18 19:24:25 UTC 2022 , Edited by admin on Sun Dec 18 19:24:25 UTC 2022
PRIMARY
CAS
2447-57-6
Created by admin on Sun Dec 18 19:24:25 UTC 2022 , Edited by admin on Sun Dec 18 19:24:25 UTC 2022
PRIMARY
RXCUI
10173
Created by admin on Sun Dec 18 19:24:25 UTC 2022 , Edited by admin on Sun Dec 18 19:24:25 UTC 2022
PRIMARY RxNorm
FDA UNII
88463U4SM5
Created by admin on Sun Dec 18 19:24:25 UTC 2022 , Edited by admin on Sun Dec 18 19:24:25 UTC 2022
PRIMARY
Related Record Type Details
BINDER->LIGAND
BINDING
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC