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=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	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 8,297		0.14 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Plasmodium falciparum malaria 63	Curative		Approved 8,429	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...

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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
Genome comparison of progressively drug resistant Plasmodium falciparum lines derived from drug sensitive clone.	2001 Apr	11313656
Authentication of artemether, artesunate and dihydroartemisinin antimalarial tablets using a simple colorimetric method.	2001 Dec	11737833
The comparative efficacy of chloroquine and sulfadoxine-pyrimethamine for the treatment of uncomplicated falciparum malaria in Kampala, Uganda.	2001 Jan-Feb	11280066
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
Folic acid antagonists during pregnancy and risk of birth defects.	2001 Mar 22	11263427

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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.

Substance Class	Chemical
Record UNII	88463U4SM5
Record Status	`Validated (UNII)`
Record Version

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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

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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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Related Record

Type

Details


					6D53G0FD0Z

PLASMA PROTEIN FRACTION (HUMAN)

BINDER->LIGAND

Interaction Type:

BINDING

Amount:

90 % (average)

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Related Record

Type

Details


					88463U4SM5

SULFADOXINE

ACTIVE MOIETY

Amount:

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Name	Property Type	Amount	Referenced Substance	Defining	Parameters	References
Biological Half-life	PHARMACOKINETIC	200 hours (average)

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