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
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)
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 |
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2013 |
0.14 µM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | FANSIDAR Approved UseFansidar is indicated for the treatment of acute, uncomplicated P. falciparum malaria for those patients in whom chloroquine resistance is suspected. Launch Date3.73075214E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
SULFADOXINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
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 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
SULFADOXINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
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 |
SULFADOXINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
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 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
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 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 Sources: Stevens-Johnson syndrome (grade 5) Toxic epidermal necrolysis (grade 5) |
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
AE | Significance | Dose | Population |
---|---|---|---|
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
Title | Date | PubMed |
---|---|---|
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 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12499187
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
Edited
Thu Jul 06 22:21:30 UTC 2023
by
admin
on
Thu Jul 06 22:21:30 UTC 2023
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Record UNII |
88463U4SM5
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000008048
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NDF-RT |
N0000008048
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WHO-ESSENTIAL MEDICINES LIST |
6.5.3.1 (SUL/PYR)
Created by
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WHO-VATC |
QJ01EW13
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NDF-RT |
N0000175880
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LIVERTOX |
NBK548044
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NDF-RT |
N0000008048
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WHO-VATC |
QJ01EQ13
Created by
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M10308
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PRIMARY | Merck Index | ||
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17134
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DB01299
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100000083266
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1626500
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SUB10700MIG
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2503
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219-504-9
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D013413
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SULFADOXINE
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2061
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DTXSID6023608
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759319
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CHEMBL1539
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SULFADOXINE
Created by
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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. | ||
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9329
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Sulfadoxine and Pyrimethamine
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C47735
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2447-57-6
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10173
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88463U4SM5
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BINDING
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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