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

SMILES

COC1=C(OC)C(NS(=O)(=O)C2=CC=C(N)C=C2)=NC=N1

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)

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Description

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	Inhibitor 8,504		0.14 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Plasmodium falciparum malaria 63	Curative		Approved 8,583	FANSIDAR

C_max

Value	Dose	Co-administered	Analyte	Population
71.7 μg/mL	500 mg single, oral	PYRIMETHAMINE	SULFADOXINE plasma	Homo sapiens
165.15 mg/L	1500 mg single, oral	PYRIMETHAMINE	SULFADOXINE plasma	Homo sapiens
60 mg/L	500 mg single, oral	PYRIMETHAMINE	SULFADOXINE plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
12394 μg × h/mL	500 mg single, oral	PYRIMETHAMINE	SULFADOXINE plasma	Homo sapiens
21761.02 mg × h/L	1500 mg single, oral	PYRIMETHAMINE	SULFADOXINE plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
155.8 h	500 mg single, oral	PYRIMETHAMINE	SULFADOXINE plasma	Homo sapiens
200 h	500 mg single, oral	PYRIMETHAMINE	SULFADOXINE plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
10%	500 mg single, oral	PYRIMETHAMINE	SULFADOXINE plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
500 mg 3 times / day single, oral Recommended	unhealthy, adult	Disc. AE: Stevens-Johnson syndrome...
500 mg 3 times / day single, oral Recommended	unhealthy, adult	Disc. AE: Toxic epidermal necrolysis, Stevens-Johnson syndrome...

Showing 1 to 2 of 2 entries

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AEs

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AE	Significance	Dose	Population
Stevens-Johnson syndrome	Disc. AE	500 mg 3 times / day single, oral Recommended	unhealthy, adult
Toxic epidermal necrolysis	Disc. AE	500 mg 3 times / day single, oral Recommended	unhealthy, adult
Stevens-Johnson syndrome	grade 5 Disc. AE	500 mg 3 times / day single, oral Recommended	unhealthy, adult
Toxic epidermal necrolysis	grade 5 Disc. AE	500 mg 3 times / day single, oral Recommended	unhealthy, adult

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Sourcing

Sourcing

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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
eMolecules	511843	https://www.emolecules.com/cgi-bin/more?vid=511843
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

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PubMed

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Title	Date	PubMed
Chloroquine or amodiaquine combined with sulfadoxine-pyrimethamine for treating uncomplicated malaria.	2001	11687077
Authentication of artemether, artesunate and dihydroartemisinin antimalarial tablets using a simple colorimetric method.	2001 Dec	11737833
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
Evaluation of a new sulfadoxine sensitivity assay in vitro for field isolates of Plasmodium falciparum.	2001 Jan-Feb	11280067
Therapeutic efficacy of sulfadoxine-pyrimethamine in uncomplicated Plasmodium falciparum malaria 3 years after introduction in Mpumalanga.	2001 Nov	11847920

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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.

Show entries

Name

Type

Language

J21.373J

Preferred Name

English

SULFADOXINE

Official Name

English

RO 4-4393

Code

English

FANSIDAR COMPONENT SULFADOXINE

Common Name

English

SULFADOXINE [WHO-IP]

Common Name

English

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Classification Tree

Code System

Code

Sulfones

NDF-RT

N0000008048

Sulfones

NDF-RT

N0000008048

Antimalarial medicines

WHO-ESSENTIAL MEDICINES LIST

6.5.3.1 (SUL/PYR)

Combinations of sulfonamides and trimethoprim, incl. derivatives

WHO-VATC

QJ01EW13

Established Pharmacologic Class

NDF-RT

N0000175880

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Code System

Code

Type

Description

MERCK INDEX

m10308

PRIMARY

Merck Index

PUBCHEM

17134

PRIMARY

DRUG BANK

DB01299

PRIMARY

SMS_ID

100000083266

PRIMARY

RS_ITEM_NUM

1626500

PRIMARY

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ACTIVE MOIETY


					88463U4SM5

SULFADOXINE

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound