SULFAGUANIDINE

US Previously Marketed

First approved in 1941

Details

Stereochemistry	ACHIRAL
Molecular Formula	C7H10N4O2S
Molecular Weight	214.245
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC(=N)NS(=O)(=O)C1=CC=C(N)C=C1

InChI

InChIKey=BRBKOPJOKNSWSG-UHFFFAOYSA-N

InChI=1S/C7H10N4O2S/c8-5-1-3-6(4-2-5)14(12,13)11-7(9)10/h1-4H,8H2,(H4,9,10,11)

HIDE SMILES / InChI

Description
Sources: http://jama.jamanetwork.com/article.aspx?articleid=257101
Curator's Comment: description was created based on several sources, including http://jama.jamanetwork.com/article.aspx?articleid=254816 https://www.mpbio.com/product.php?pid=02102984&country=195

Sulfaguanidine is used to treat the gastrointestinal infections particularly bacillary dysentery. Sulfaguanidine is a sulfonamide antibiotic that blocks the synthesis of dihydrofolic acid by inhibiting the enzyme dihydropteroate synthase in bacteria. Sulfonamides are active against Gram positive bacteria and Gram negative bacteria.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
bacterial dihydropteroate synthase 1 Target ID: bacterial dihydropteroate synthase Sources: https://www.mpbio.com/product.php?pid=02102984&country=195	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacillary dysentery 3 Sources: http://jama.jamanetwork.com/article.aspx?articleid=254816	Curative		Phase III 656	Unknown Approved Use Unknown
Infectious (bacterial) diarrhea 1 Sources: https://www.onmeda.fr/medicament/enteropathyl-93171802.html http://www.siphat.rns.tn/produits/fr/detail.php?id_produit=1422337899	Curative		Approved 8429	ENTEROPATHYL Approved Use Acute or chronic diarrhea caused by sulfaguanidine-sensitive organisms.

C_max

Value	Dose	Co-administered	Analyte	Population
0.41 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3820055/	2.5 mg/kg single, oral dose: 2.5 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		SULFAGUANIDINE plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
1.04 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3820055/	2.5 mg/kg single, oral dose: 2.5 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		SULFAGUANIDINE plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3820055/	2.5 mg/kg single, oral dose: 2.5 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		SULFAGUANIDINE plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
4 g 6 times / day multiple, oral Dose: 4 g, 6 times / day Route: oral Route: multiple Dose: 4 g, 6 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20248057/	unhealthy, 32 n = 1 Health Status: unhealthy Condition: diarrhea Age Group: 32 Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/20248057/	Other AEs: Anuria... Other AEs: Anuria Sources: https://pubmed.ncbi.nlm.nih.gov/20248057/
0.05 g/kg 6 times / day multiple, oral Dose: 0.05 g/kg, 6 times / day Route: oral Route: multiple Dose: 0.05 g/kg, 6 times / day Sources: https://jamanetwork.com/journals/jama/article-abstract/257467	unhealthy, 45 n = 1 Health Status: unhealthy Condition: diarrhea Age Group: 45 Sex: F Population Size: 1 Sources: https://jamanetwork.com/journals/jama/article-abstract/257467	Disc. AE: Headache, Nausea... AEs leading to discontinuation/dose reduction: Headache Nausea Sources: https://jamanetwork.com/journals/jama/article-abstract/257467

AEs

AE	Significance	Dose	Population
Anuria		4 g 6 times / day multiple, oral Dose: 4 g, 6 times / day Route: oral Route: multiple Dose: 4 g, 6 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20248057/	unhealthy, 32 n = 1 Health Status: unhealthy Condition: diarrhea Age Group: 32 Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/20248057/
Headache	Disc. AE	0.05 g/kg 6 times / day multiple, oral Dose: 0.05 g/kg, 6 times / day Route: oral Route: multiple Dose: 0.05 g/kg, 6 times / day Sources: https://jamanetwork.com/journals/jama/article-abstract/257467	unhealthy, 45 n = 1 Health Status: unhealthy Condition: diarrhea Age Group: 45 Sex: F Population Size: 1 Sources: https://jamanetwork.com/journals/jama/article-abstract/257467
Nausea	Disc. AE	0.05 g/kg 6 times / day multiple, oral Dose: 0.05 g/kg, 6 times / day Route: oral Route: multiple Dose: 0.05 g/kg, 6 times / day Sources: https://jamanetwork.com/journals/jama/article-abstract/257467	unhealthy, 45 n = 1 Health Status: unhealthy Condition: diarrhea Age Group: 45 Sex: F Population Size: 1 Sources: https://jamanetwork.com/journals/jama/article-abstract/257467

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:94621	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:94621
ChemicalBook	CB7152799	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7152799
MolPort	MolPort-000-900-613	https://www.molport.com/shop/molecule-link/MolPort-000-900-613
MolPort	MolPort-002-939-432	https://www.molport.com/shop/molecule-link/MolPort-002-939-432
Selleck Chemicals	sulfaguanidine	http://www.selleckchem.com/products/sulfaguanidine.html
ZINC	ZINC000003873927	http://zinc15.docking.org/substances/ZINC000003873927
eMolecules	474314	https://www.emolecules.com/cgi-bin/more?vid=474314

PubMed

Title	Date	PubMed
In vitro model to assess effect of antimicrobial agents on Encephalitozoon cuniculi.	1994 Oct	7840584
Inhibition of recombinant Pneumocystis carinii dihydropteroate synthetase by sulfa drugs.	1995 Aug	7486915
Monodrug efficacies of sulfonamides in prophylaxis for Pneumocystis carinii pneumonia.	1996 Apr	8849260
Efficacy of 101 antimicrobials and other agents on the development of Cryptosporidium parvum in vitro.	1996 Dec	9039272

Patents

Sample Use Guides

In Vivo Use Guide

0.08 mg/kg per day; 7-14 days (daily dose: 2-3 mg)

Route of Administration: Oral

In Vitro Use Guide

Sulfaguanidine at dose of 2500 ppm proved to be most toxic against A. corymbifera causing 56.39 percent inhibition in the mycelial growth, while the same dose could not be found much effective against other test fungi.

Name

Type

Language

SULFAGUANIDINE

Official Name

English

SULFAGUANIDINE [EP IMPURITY]

Common Name

English

SULFAGUANIDINE [EP MONOGRAPH]

Common Name

English

Sulfaguanidine [WHO-DD]

Common Name

English

sulfaguanidine [INN]

Common Name

English

SULFAGUANIDINE [MART.]

Common Name

English

NSC-14041

Code

English

SULFADIAZINE IMPURITY C [EP IMPURITY]

Common Name

English

SULFADIMIDINE IMPURITY C [EP IMPURITY]

Common Name

English

SULFAGUANIDINE [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29739