SULFABENZAMIDE SODIUM

US Previously Marketed

First approved in 1945

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H11N2O3S.Na
Molecular Weight	298.293
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].NC1=CC=C(C=C1)S(=O)(=O)[N-]C(=O)C2=CC=CC=C2

InChI

InChIKey=PUTNOWNJUKOGEY-UHFFFAOYSA-M

InChI=1S/C13H12N2O3S.Na/c14-11-6-8-12(9-7-11)19(17,18)15-13(16)10-4-2-1-3-5-10;/h1-9H,14H2,(H,15,16);/q;+1/p-1

HIDE SMILES / InChI

Description
Sources: http://www.rxlist.com/sultrin-drug/indications-dosage.htm

Sulfabenzamide is an antibacterial/antimicrobial. Often used in conjunction with sulfathiazole and sulfacetamide (trade name - Sultrin) as a topical, intravaginal antibacterial preparation against Haemophilus (Gardnerella) vaginalis bacteria. The mode of action of SULTRIN is not completely known. Indirect effects, such as lowering the vaginal pH, may be equally important mechanisms.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Vaginitis caused by Gardnerella vaginalis 2 Sources: http://www.rxlist.com/sultrin-drug/indications-dosage.htm	Curative		Approved 8583	SULTRIN Approved Use SULTRIN (sulfathiazole, sulfacetamide and sulfabenzamide) Cream is indicated for the treatment of vaginitis caused by Haemophilus (Gardnerella) vaginalis bacteria. The diagnosis of a Haemophilus (Gardnerella) vaginalis vaginitis should be firmly established before initiation of treatment with SULTRIN (sulfathiazole, sulfacetamide and sulfabenzamide) Launch Date 1945

C_max

Value	Dose	Co-administered	Analyte	Population
99.2 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6663474/	750 mg single, oral dose: 750 mg route of administration: Oral experiment type: SINGLE co-administered:		SULFACETAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
1803 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6663474/	750 mg single, oral dose: 750 mg route of administration: Oral experiment type: SINGLE co-administered:		SULFACETAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
10.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6663474/	750 mg single, oral dose: 750 mg route of administration: Oral experiment type: SINGLE co-administered:		SULFACETAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
13 h REVIEW https://www.sciencedirect.com/science/article/pii/S0099542808606103	single, ocular		SULFACETAMIDE plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
82% REVIEW https://www.sciencedirect.com/science/article/pii/S0099542808606103	single, ocular		SULFACETAMIDE plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
10 % 2 times / day multiple, topical Recommended Dose: 10 %, 2 times / day Route: topical Route: multiple Dose: 10 %, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019931s019lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019931s019lbl.pdf	Other AEs: Stevens-Johnson syndrome, Toxic epidermal necrolysis... Other AEs: Stevens-Johnson syndrome (grade 3-4, rare) Toxic epidermal necrolysis (grade 3-4, rare) Hepatic necrosis (grade 3-4, rare) Agranulocytosis (grade 3-4, rare) Aplastic anemia (grade 3-4, rare) Blood dyscrasia (grade 3-4, rare) Hypersensitivity reaction (grade 3-4, rare) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019931s019lbl.pdf
2 drop 1 times / 3 hours multiple, topical Recommended Dose: 2 drop, 1 times / 3 hours Route: topical Route: multiple Dose: 2 drop, 1 times / 3 hours Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=5e0415cd-5803-44b2-be24-af823c48c6d0&type=display	unhealthy Health Status: unhealthy Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=5e0415cd-5803-44b2-be24-af823c48c6d0&type=display	Other AEs: Stevens-Johnson syndrome, Toxic epidermal necrolysis... Other AEs: Stevens-Johnson syndrome (grade 3-4, rare) Toxic epidermal necrolysis (grade 3-4, rare) Hepatic necrosis (grade 3-4, rare) Agranulocytosis (grade 3-4, rare) Aplastic anemia (grade 3-4, rare) Blood dyscrasia (grade 3-4, rare) Hypersensitivity reaction (grade 3-4, rare) Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=5e0415cd-5803-44b2-be24-af823c48c6d0&type=display

AEs

AE	Significance	Dose	Population
Agranulocytosis	grade 3-4, rare	10 % 2 times / day multiple, topical Recommended Dose: 10 %, 2 times / day Route: topical Route: multiple Dose: 10 %, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019931s019lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019931s019lbl.pdf
Aplastic anemia	grade 3-4, rare	10 % 2 times / day multiple, topical Recommended Dose: 10 %, 2 times / day Route: topical Route: multiple Dose: 10 %, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019931s019lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019931s019lbl.pdf
Blood dyscrasia	grade 3-4, rare	10 % 2 times / day multiple, topical Recommended Dose: 10 %, 2 times / day Route: topical Route: multiple Dose: 10 %, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019931s019lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019931s019lbl.pdf
Hepatic necrosis	grade 3-4, rare	10 % 2 times / day multiple, topical Recommended Dose: 10 %, 2 times / day Route: topical Route: multiple Dose: 10 %, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019931s019lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019931s019lbl.pdf
Hypersensitivity reaction	grade 3-4, rare	10 % 2 times / day multiple, topical Recommended Dose: 10 %, 2 times / day Route: topical Route: multiple Dose: 10 %, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019931s019lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019931s019lbl.pdf
Stevens-Johnson syndrome	grade 3-4, rare	10 % 2 times / day multiple, topical Recommended Dose: 10 %, 2 times / day Route: topical Route: multiple Dose: 10 %, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019931s019lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019931s019lbl.pdf
Toxic epidermal necrolysis	grade 3-4, rare	10 % 2 times / day multiple, topical Recommended Dose: 10 %, 2 times / day Route: topical Route: multiple Dose: 10 %, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019931s019lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019931s019lbl.pdf
Agranulocytosis	grade 3-4, rare	2 drop 1 times / 3 hours multiple, topical Recommended Dose: 2 drop, 1 times / 3 hours Route: topical Route: multiple Dose: 2 drop, 1 times / 3 hours Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=5e0415cd-5803-44b2-be24-af823c48c6d0&type=display	unhealthy Health Status: unhealthy Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=5e0415cd-5803-44b2-be24-af823c48c6d0&type=display
Aplastic anemia	grade 3-4, rare	2 drop 1 times / 3 hours multiple, topical Recommended Dose: 2 drop, 1 times / 3 hours Route: topical Route: multiple Dose: 2 drop, 1 times / 3 hours Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=5e0415cd-5803-44b2-be24-af823c48c6d0&type=display	unhealthy Health Status: unhealthy Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=5e0415cd-5803-44b2-be24-af823c48c6d0&type=display
Blood dyscrasia	grade 3-4, rare	2 drop 1 times / 3 hours multiple, topical Recommended Dose: 2 drop, 1 times / 3 hours Route: topical Route: multiple Dose: 2 drop, 1 times / 3 hours Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=5e0415cd-5803-44b2-be24-af823c48c6d0&type=display	unhealthy Health Status: unhealthy Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=5e0415cd-5803-44b2-be24-af823c48c6d0&type=display
Hepatic necrosis	grade 3-4, rare	2 drop 1 times / 3 hours multiple, topical Recommended Dose: 2 drop, 1 times / 3 hours Route: topical Route: multiple Dose: 2 drop, 1 times / 3 hours Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=5e0415cd-5803-44b2-be24-af823c48c6d0&type=display	unhealthy Health Status: unhealthy Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=5e0415cd-5803-44b2-be24-af823c48c6d0&type=display
Hypersensitivity reaction	grade 3-4, rare	2 drop 1 times / 3 hours multiple, topical Recommended Dose: 2 drop, 1 times / 3 hours Route: topical Route: multiple Dose: 2 drop, 1 times / 3 hours Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=5e0415cd-5803-44b2-be24-af823c48c6d0&type=display	unhealthy Health Status: unhealthy Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=5e0415cd-5803-44b2-be24-af823c48c6d0&type=display
Stevens-Johnson syndrome	grade 3-4, rare	2 drop 1 times / 3 hours multiple, topical Recommended Dose: 2 drop, 1 times / 3 hours Route: topical Route: multiple Dose: 2 drop, 1 times / 3 hours Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=5e0415cd-5803-44b2-be24-af823c48c6d0&type=display	unhealthy Health Status: unhealthy Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=5e0415cd-5803-44b2-be24-af823c48c6d0&type=display
Toxic epidermal necrolysis	grade 3-4, rare	2 drop 1 times / 3 hours multiple, topical Recommended Dose: 2 drop, 1 times / 3 hours Route: topical Route: multiple Dose: 2 drop, 1 times / 3 hours Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=5e0415cd-5803-44b2-be24-af823c48c6d0&type=display	unhealthy Health Status: unhealthy Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=5e0415cd-5803-44b2-be24-af823c48c6d0&type=display

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2A6 879 CYP2C19 2057 CYP2E1 1060 OATP1B1 1079 OATP1B3 961

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyNDMifX0%3D	no [IC50 >10 uM]
CYP2A6 911	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyNDMifX0%3D	no [IC50 >10 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyNDMifX0%3D	no [IC50 >10 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyODkiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTI0MyJ9fQ%3D%3D	no [IC50 >10 uM]
CYP2E1 1146	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyNDMifX0%3D	no [IC50 >10 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTI0MyJ9fQ%3D%3D	no [IC50 >10 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://pubs.acs.org/doi/abs/10.1021/bi961950t	no [IC50 >500 uM]
OATP1B1 1095	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNjk3NjY4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyNDMifX0%3D	yes [Inhibition 10 uM]
OATP1B3 970	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTIxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyNDMifX0%3D	yes [Inhibition 10 uM]

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTI0MyJ9fQ%3D%3D

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:94677	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:94677
ChemicalBook	CB7321423	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7321423
eMolecules	511801	https://www.emolecules.com/cgi-bin/more?vid=511801
MolPort	MolPort-003-666-285	https://www.molport.com/shop/molecule-link/MolPort-003-666-285
ZINC	ZINC000005421253	http://zinc15.docking.org/substances/ZINC000005421253

PubMed

Title	Date	PubMed
Analytical method for simultaneous determination of pesticide and veterinary drug residues in milk by CE-MS.	2009-05	19384986
A systematic study on hydrogen bond interactions in sulfabenzamide: DFT calculations of the N-14, O-17, and H-2 NQR parameters.	2009-02	19028005
Pressurized liquid extraction combined with capillary electrophoresis-mass spectrometry as an improved methodology for the determination of sulfonamide residues in meat.	2007-08-03	17433345
Determination of pKa values by capillary zone electrophoresis with a dynamic coating procedure.	2005-11	16342805
Multiresidue determination of sulfonamides in a variety of biological matrices by supported liquid membrane with high pressure liquid chromatography-electrospray mass spectrometry detection.	2004-09-08	18969572
Inhibition of recombinant Pneumocystis carinii dihydropteroate synthetase by sulfa drugs.	1995-08	7486915
Interaction of Pneumocystis carinii dihydropteroate synthase with sulfonamides and diaminodiphenyl sulfone (dapsone).	1994-02	8106784
Interaction of sulfonamide and sulfone compounds with Toxoplasma gondii dihydropteroate synthase.	1990-02	2298911

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Other

In Vitro Use Guide

The MTT assay was used to evaluate the viability of Epithelial tumor cell line, T-47D incubated with different concentrations of sulfabenzamide (0.0-20 mM). The 50% growth inhibition (LC50) concentration for sulfabenzamide after 48 h, were calculated as 10.8 mM. Cells incubated with sulfabenzamide exhibited negligible levels of apoptosis, necrosis and cell cycle arrest when compared to untreated cells. Despite negligible detection of DNA fragmentation, a considerable increase in caspase-3 activity was observed in cells incubated with sulfabenzamide. line incubated with different concentrations of sulfabenzamide (0.0-20 mM) after 24, 48 and 72 h

Name

Type

Language

BENZAMIDE, N-((4-AMINOPHENYL)SULFONYL)-, MONOSODIUM SALT

Preferred Name

English

SULFABENZAMIDE SODIUM

Common Name

English

SODIUM SULFABENZAMIDE

Common Name

English

BENZAMIDE, N-((4-AMINOPHENYL)SULFONYL)-, SODIUM SALT (1:1)

Common Name

English

Code System Code Type Description

FDA UNII

ZY48TOH8CR