SULFADOXINE

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 Search

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

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18557slr015_fansidar_lbl.pdf | John E. Bennett, 'Mandell, Douglas, and Bennett's Principles and Practice of Infectious Diseases' (2014), p. 507, Retrieved from | https://books.google.es/books?id=73pYBAAAQBAJ&dq

Sulfadoxine is an antimalarial agent which, together with pyrimethamine, composes an FDA-approved drug, Fansidar. Sulfadoxine acts by inhibiting dihydropteroate synthase; it crosses the blood-brain barrier and achieves 30% to 60% of the plasma concentration.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Dihydropteroate synthetase 10 Target ID: CHEMBL2013 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18557slr015_fansidar_lbl.pdf	Inhibitor 8146		0.14 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Plasmodium falciparum malaria 62 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18557slr015_fansidar_lbl.pdf	Curative		Approved 8307	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

C_max

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	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	PYRIMETHAMINE	SULFADOXINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
60 mg/L DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18557slr015_fansidar_lbl.pdf	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: PYRIMETHAMINE	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	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	PYRIMETHAMINE	SULFADOXINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

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	PYRIMETHAMINE	SULFADOXINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
200 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18557slr015_fansidar_lbl.pdf	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: PYRIMETHAMINE	PYRIMETHAMINE	SULFADOXINE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
10% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18557slr015_fansidar_lbl.pdf	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: PYRIMETHAMINE	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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18557slr015_fansidar_lbl.pdf	unhealthy, adult Health Status: unhealthy Condition: malaria Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18557slr015_fansidar_lbl.pdf	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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18557slr015_fansidar_lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18557slr015_fansidar_lbl.pdf	unhealthy, adult Health Status: unhealthy Condition: malaria Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18557slr015_fansidar_lbl.pdf	Disc. AE: Stevens-Johnson syndrome... AEs leading to discontinuation/dose reduction: Stevens-Johnson syndrome Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18557slr015_fansidar_lbl.pdf

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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18557slr015_fansidar_lbl.pdf	unhealthy, adult Health Status: unhealthy Condition: malaria Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18557slr015_fansidar_lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18557slr015_fansidar_lbl.pdf	unhealthy, adult Health Status: unhealthy Condition: malaria Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18557slr015_fansidar_lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18557slr015_fansidar_lbl.pdf	unhealthy, adult Health Status: unhealthy Condition: malaria Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18557slr015_fansidar_lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18557slr015_fansidar_lbl.pdf	unhealthy, adult Health Status: unhealthy Condition: malaria Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/18557slr015_fansidar_lbl.pdf

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:9329	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9329
ChemicalBook	CB8171942	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB8171942
MolPort	MolPort-003-850-341	https://www.molport.com/shop/molecule-link/MolPort-003-850-341
Selleck Chemicals	Sulfadoxine(Sulphadoxine)	http://www.selleckchem.com/products/Sulfadoxine(Sulphadoxine).html
ZINC	ZINC000000002094	http://zinc15.docking.org/substances/ZINC000000002094
eMolecules	511843	https://www.emolecules.com/cgi-bin/more?vid=511843

PubMed

Title	Date	PubMed
Cardiac effects of amodiaquine and sulfadoxine-pyrimethamine in malaria-infected African patients.	2001 Dec	11791962
Efficacy of mefloquine and sulfadoxine-pyrimethamine for the treatment of uncomplicated Plasmodium falciparum infection in Machinga District, Malawi, 1998.	2001 Dec	11791956
The cost-effectiveness of antenatal malaria prevention in sub-Saharan Africa.	2001 Jan-Feb	11425177
Short report: differences in dihydrofolate reductase but not dihydropteroate synthase alleles in Plasmodium falciparum isolates from geographically distinct areas in Malaysia.	2001 Jan-Feb	11425158
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	11487366
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	11422956
Cost-effectiveness of sulfadoxine-pyrimethamine for the prevention of malaria-associated low birth weight.	2001 Mar-Apr	11442215
History and importance of antimalarial drug resistance.	2001 Nov	11703837
Anemia of persistent malarial parasitemia in Nigerian children.	2001 Oct	11695725
[Danger of malaria self-treatment. Acute neurologic toxicity of mefloquine and its combination with pyrimethamine-sulfadoxine].	2001 Sep 29	11675924
Therapeutic efficacy of sulfadoxine-pyrimethamine, amodiaquine and the sulfadoxine-pyrimethamine-amodiaquine combination against uncomplicated Plasmodium falciparum malaria in young children in Cameroon.	2002	12163917
Resistance of Plamodium falciparum to antimalarial drugs in Zaragoza (Antioquia, Colombia), 1998.	2002 Apr	12048572
Biofilm bacteria: formation and comparative susceptibility to antibiotics.	2002 Apr	11989739
Treatment of imported malaria in an ambulatory setting: prospective study.	2002 Apr 13	11950734
High-performance liquid chromatographic assay for the simultaneous determination of sulfadoxine and pyrimethamine from whole blood dried onto filter paper.	2002 Feb 5	11863287
[Frequency of persistent or transitory serologic negative values in infants with congenital toxoplasmosis. Experience of the Reims Toxoplasmosis Group (1980-1997)].	2002 Feb 9	11878142
Malaria: a rising incidence in the United States.	2002 Jul	12217468
Molecular epidemiology of malaria in Cameroon. X. Evaluation of PFMDR1 mutations as genetic markers for resistance to amino alcohols and artemisinin derivatives.	2002 Jun	12224572
African scientists discuss drug-resistant malaria.	2002 Mar 2	11888598
Treatment of uncomplicated malaria in children in Guinea-Bissau with chloroquine, quinine, and sulfadoxine-pyrimethamine.	2002 May-Jun	12174785
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	12390597
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	12408659
Intermittent administration of iron and sulfadoxine-pyrimethamine to control anaemia in Kenyan children: a randomised controlled trial.	2002 Sep 21	12354473

Patents

Sample Use Guides

In Vivo Use Guide

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

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

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