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
Pyrimethamine-sulfadoxine resistance in Plasmodium falciparum: what next?
2001 Dec
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
Authentication of artemether, artesunate and dihydroartemisinin antimalarial tablets using a simple colorimetric method.
2001 Dec
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
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
Monitoring antimalarial drug resistance within National Malaria Control Programmes: the EANMAT experience.
2001 Nov
History and importance of antimalarial drug resistance.
2001 Nov
A randomized controlled trial on the efficacy of alternative treatment regimens for uncomplicated falciparum malaria in a multidrug-resistant falciparum area of Bangladesh--narrowing the options for the National Malaria Control Programme?
2001 Nov-Dec
Co-trimoxazole compared with sulfadoxine-pyrimethamine in the treatment of uncomplicated malaria in Kenyan children.
2001 Nov-Dec
Anemia of persistent malarial parasitemia in Nigerian children.
2001 Oct
Prevalence of polymorphisms in the dihydrofolate reductase and dihydropteroate synthetase genes of Plasmodium falciparum isolates from southern Mauritania.
2001 Oct
Chlorproguanil-dapsone for treatment of drug-resistant falciparum malaria in Tanzania.
2001 Oct 13
Gametocytaemia in Senegalese children with uncomplicated falciparum malaria treated with chloroquine, amodiaquine or sulfadoxine + pyrimethamine.
2001 Sep
High-performance liquid chromatographic determination of diazepam in plasma of children with severe malaria.
2001 Sep 25
Assessment of susceptibility of Plasmodium falciparum to chloroquine, quinine, mefloquine, sulfadoxine-pyrimethamine and artemisinin in southern Viet Nam.
2001 Sep-Oct
Therapeutic efficacy of sulfadoxine-pyrimethamine, amodiaquine and the sulfadoxine-pyrimethamine-amodiaquine combination against uncomplicated Plasmodium falciparum malaria in young children in Cameroon.
2002
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
Resistance of Plamodium falciparum to antimalarial drugs in Zaragoza (Antioquia, Colombia), 1998.
2002 Apr
Biofilm bacteria: formation and comparative susceptibility to antibiotics.
2002 Apr
[In vivo sensitivity of Plasmodium falciparum to amino-4-quinolines and sulfadoxine pyrimethamine in Agou (Ivory Coast)].
2002 Apr
Reversion of autoimmune lymphoproliferative syndrome with an antimalarial drug: preliminary results of a clinical cohort study and molecular observations.
2002 Apr
Treatment of imported malaria in an ambulatory setting: prospective study.
2002 Apr 13
Resistance to antimalarials.
2002 Aug
Determinants of treatment response to sulfadoxine-pyrimethamine and subsequent transmission potential in falciparum malaria.
2002 Aug 1
[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
[Frequency of persistent or transitory serologic negative values in infants with congenital toxoplasmosis. Experience of the Reims Toxoplasmosis Group (1980-1997)].
2002 Feb 9
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
The drug sensitivity and transmission dynamics of human malaria on Nias Island, North Sumatra, Indonesia.
2002 Jul
Physico-chemical studies on the charge-transfer complex formed between sulfadoxine and pyrimethamine with chloranilic acid.
2002 Jul 20
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
Clinical efficacy of chloroquine or sulfadoxine-pyrimethamine in children under five from south-western Uganda with uncomplicated falciparum malaria.
2002 Mar-Apr
Effectiveness of twice-weekly pyrimethamine-sulfadoxine as primary prophylaxis of Pneumocystis carinii pneumonia and toxoplasmic encephalitis in patients with advanced HIV infection.
2002 May
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
Intensity of malaria transmission, antimalarial-drug use and resistance in Uganda: what is the relationship between these three factors?
2002 May-Jun
Treatment of uncomplicated malaria in children in Guinea-Bissau with chloroquine, quinine, and sulfadoxine-pyrimethamine.
2002 May-Jun
Transcriptional analysis of genes encoding enzymes of the folate pathway in the human malaria parasite Plasmodium falciparum.
2002 Oct
Simultaneous spectrophotometric determination of sulfadoxine and pyrimethamine in pharmaceutical formulations.
2002 Oct 15
Monitoring the drug-sensitivity of Plasmodium falciparum in coastal towns in Madagascar by use of in vitro chemosensitivity and mutation detection tests.
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 Thu Jul 06 22:21:30 UTC 2023
Edited
by admin
on Thu Jul 06 22:21:30 UTC 2023
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 Thu Jul 06 22:21:31 UTC 2023 , Edited by admin on Thu Jul 06 22:21:31 UTC 2023
NDF-RT N0000008048
Created by admin on Thu Jul 06 22:21:31 UTC 2023 , Edited by admin on Thu Jul 06 22:21:31 UTC 2023
WHO-ESSENTIAL MEDICINES LIST 6.5.3.1 (SUL/PYR)
Created by admin on Thu Jul 06 22:21:31 UTC 2023 , Edited by admin on Thu Jul 06 22:21:31 UTC 2023
WHO-VATC QJ01EW13
Created by admin on Thu Jul 06 22:21:31 UTC 2023 , Edited by admin on Thu Jul 06 22:21:31 UTC 2023
NDF-RT N0000175880
Created by admin on Thu Jul 06 22:21:31 UTC 2023 , Edited by admin on Thu Jul 06 22:21:31 UTC 2023
LIVERTOX NBK548044
Created by admin on Thu Jul 06 22:21:31 UTC 2023 , Edited by admin on Thu Jul 06 22:21:31 UTC 2023
NDF-RT N0000008048
Created by admin on Thu Jul 06 22:21:31 UTC 2023 , Edited by admin on Thu Jul 06 22:21:31 UTC 2023
WHO-VATC QJ01EQ13
Created by admin on Thu Jul 06 22:21:31 UTC 2023 , Edited by admin on Thu Jul 06 22:21:31 UTC 2023
Code System Code Type Description
MERCK INDEX
M10308
Created by admin on Thu Jul 06 22:21:31 UTC 2023 , Edited by admin on Thu Jul 06 22:21:31 UTC 2023
PRIMARY Merck Index
PUBCHEM
17134
Created by admin on Thu Jul 06 22:21:31 UTC 2023 , Edited by admin on Thu Jul 06 22:21:31 UTC 2023
PRIMARY
DRUG BANK
DB01299
Created by admin on Thu Jul 06 22:21:31 UTC 2023 , Edited by admin on Thu Jul 06 22:21:31 UTC 2023
PRIMARY
SMS_ID
100000083266
Created by admin on Thu Jul 06 22:21:31 UTC 2023 , Edited by admin on Thu Jul 06 22:21:31 UTC 2023
PRIMARY
RS_ITEM_NUM
1626500
Created by admin on Thu Jul 06 22:21:31 UTC 2023 , Edited by admin on Thu Jul 06 22:21:31 UTC 2023
PRIMARY
EVMPD
SUB10700MIG
Created by admin on Thu Jul 06 22:21:31 UTC 2023 , Edited by admin on Thu Jul 06 22:21:31 UTC 2023
PRIMARY
DRUG CENTRAL
2503
Created by admin on Thu Jul 06 22:21:31 UTC 2023 , Edited by admin on Thu Jul 06 22:21:31 UTC 2023
PRIMARY
ECHA (EC/EINECS)
219-504-9
Created by admin on Thu Jul 06 22:21:31 UTC 2023 , Edited by admin on Thu Jul 06 22:21:31 UTC 2023
PRIMARY
MESH
D013413
Created by admin on Thu Jul 06 22:21:31 UTC 2023 , Edited by admin on Thu Jul 06 22:21:31 UTC 2023
PRIMARY
WIKIPEDIA
SULFADOXINE
Created by admin on Thu Jul 06 22:21:31 UTC 2023 , Edited by admin on Thu Jul 06 22:21:31 UTC 2023
PRIMARY
INN
2061
Created by admin on Thu Jul 06 22:21:31 UTC 2023 , Edited by admin on Thu Jul 06 22:21:31 UTC 2023
PRIMARY
EPA CompTox
DTXSID6023608
Created by admin on Thu Jul 06 22:21:31 UTC 2023 , Edited by admin on Thu Jul 06 22:21:31 UTC 2023
PRIMARY
NSC
759319
Created by admin on Thu Jul 06 22:21:31 UTC 2023 , Edited by admin on Thu Jul 06 22:21:31 UTC 2023
PRIMARY
ChEMBL
CHEMBL1539
Created by admin on Thu Jul 06 22:21:31 UTC 2023 , Edited by admin on Thu Jul 06 22:21:31 UTC 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
SULFADOXINE
Created by admin on Thu Jul 06 22:21:31 UTC 2023 , Edited by admin on Thu Jul 06 22:21:31 UTC 2023
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 Thu Jul 06 22:21:31 UTC 2023 , Edited by admin on Thu Jul 06 22:21:31 UTC 2023
PRIMARY
LACTMED
Sulfadoxine and Pyrimethamine
Created by admin on Thu Jul 06 22:21:31 UTC 2023 , Edited by admin on Thu Jul 06 22:21:31 UTC 2023
PRIMARY
NCI_THESAURUS
C47735
Created by admin on Thu Jul 06 22:21:31 UTC 2023 , Edited by admin on Thu Jul 06 22:21:31 UTC 2023
PRIMARY
CAS
2447-57-6
Created by admin on Thu Jul 06 22:21:31 UTC 2023 , Edited by admin on Thu Jul 06 22:21:31 UTC 2023
PRIMARY
RXCUI
10173
Created by admin on Thu Jul 06 22:21:31 UTC 2023 , Edited by admin on Thu Jul 06 22:21:31 UTC 2023
PRIMARY RxNorm
FDA UNII
88463U4SM5
Created by admin on Thu Jul 06 22:21:31 UTC 2023 , Edited by admin on Thu Jul 06 22:21:31 UTC 2023
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