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 8429	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://sci-hub.st/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://sci-hub.st/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 Condition: Acne vulgaris 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 (max) 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 Condition: Conjunctivitis 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 Condition: Acne vulgaris 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 Condition: Acne vulgaris 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 Condition: Acne vulgaris 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 Condition: Acne vulgaris 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 Condition: Acne vulgaris 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 Condition: Acne vulgaris 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 Condition: Acne vulgaris 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 (max) 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 Condition: Conjunctivitis 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 (max) 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 Condition: Conjunctivitis 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 (max) 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 Condition: Conjunctivitis 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 (max) 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 Condition: Conjunctivitis 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 (max) 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 Condition: Conjunctivitis 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 (max) 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 Condition: Conjunctivitis 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 (max) 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 Condition: Conjunctivitis Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=5e0415cd-5803-44b2-be24-af823c48c6d0&type=display

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587	inhibitor 1767	inhibitor 1852	inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2A6 707 CYP2C19 1478 CYP2E1 882 OATP1B1 788 OATP1B3 706

Drug as perpetrator

Target	Modality	Activity
CYP1A2 1692	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyNDMifX0%3D	no [IC50 >10 uM]
CYP2A6 739	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyNDMifX0%3D	no [IC50 >10 uM]
CYP2C19 1553	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyNDMifX0%3D	no [IC50 >10 uM]
CYP2D6 1891	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyODkiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTI0MyJ9fQ%3D%3D	no [IC50 >10 uM]
CYP2E1 970	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyNDMifX0%3D	no [IC50 >10 uM]
CYP3A4 1925	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTI0MyJ9fQ%3D%3D	no [IC50 >10 uM]
CYP2C9 1819	inhibitor 3277 Sources: https://pubs.acs.org/doi/abs/10.1021/bi961950t	no [IC50 >500 uM]
OATP1B1 803	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNjk3NjY4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyNDMifX0%3D	yes [Inhibition 10 uM]
OATP1B3 715	inhibitor 3277 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 1647	inhibitor 1626 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
MolPort	MolPort-003-666-285	https://www.molport.com/shop/molecule-link/MolPort-003-666-285
ZINC	ZINC000005421253	http://zinc15.docking.org/substances/ZINC000005421253
eMolecules	511801	https://www.emolecules.com/cgi-bin/more?vid=511801

PubMed

Title	Date	PubMed
Interaction of sulfonamide and sulfone compounds with Toxoplasma gondii dihydropteroate synthase.	1990 Feb	2298911
Interaction of Pneumocystis carinii dihydropteroate synthase with sulfonamides and diaminodiphenyl sulfone (dapsone).	1994 Feb	8106784
Inhibition of recombinant Pneumocystis carinii dihydropteroate synthetase by sulfa drugs.	1995 Aug	7486915
Multiresidue determination of sulfonamides in a variety of biological matrices by supported liquid membrane with high pressure liquid chromatography-electrospray mass spectrometry detection.	2004 Sep 8	18969572
Determination of pKa values by capillary zone electrophoresis with a dynamic coating procedure.	2005 Nov	16342805
Pressurized liquid extraction combined with capillary electrophoresis-mass spectrometry as an improved methodology for the determination of sulfonamide residues in meat.	2007 Aug 3	17433345
A systematic study on hydrogen bond interactions in sulfabenzamide: DFT calculations of the N-14, O-17, and H-2 NQR parameters.	2009 Feb	19028005

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

SULFABENZAMIDE SODIUM

Common Name

English

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

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