U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C13H12N2O3S
Molecular Weight 276.311
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SULFABENZAMIDE

SMILES

NC1=CC=C(C=C1)S(=O)(=O)NC(=O)C2=CC=CC=C2

InChI

InChIKey=PBCZLFBEBARBBI-UHFFFAOYSA-N
InChI=1S/C13H12N2O3S/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)

HIDE SMILES / InChI

Molecular Formula C13H12N2O3S
Molecular Weight 276.311
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
99.2 μg/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
1803 μg × h/mL
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
10.3 h
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
single, ocular
SULFACETAMIDE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
82%
single, ocular
SULFACETAMIDE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
10 % 2 times / day multiple, topical
Recommended
Dose: 10 %, 2 times / day
Route: topical
Route: multiple
Dose: 10 %, 2 times / day
Sources:
unhealthy
Health Status: unhealthy
Condition: Acne vulgaris
Sources:
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:
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:
unhealthy
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:
AEs

AEs

AESignificanceDosePopulation
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:
unhealthy
Health Status: unhealthy
Condition: Acne vulgaris
Sources:
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:
unhealthy
Health Status: unhealthy
Condition: Acne vulgaris
Sources:
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:
unhealthy
Health Status: unhealthy
Condition: Acne vulgaris
Sources:
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:
unhealthy
Health Status: unhealthy
Condition: Acne vulgaris
Sources:
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:
unhealthy
Health Status: unhealthy
Condition: Acne vulgaris
Sources:
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:
unhealthy
Health Status: unhealthy
Condition: Acne vulgaris
Sources:
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:
unhealthy
Health Status: unhealthy
Condition: Acne vulgaris
Sources:
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
Overview

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer






Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >500 uM]
yes [Inhibition 10 uM]
yes [Inhibition 10 uM]
Tox targets
PubMed

PubMed

TitleDatePubMed
Interaction of sulfonamide and sulfone compounds with Toxoplasma gondii dihydropteroate synthase.
1990 Feb
Interaction of Pneumocystis carinii dihydropteroate synthase with sulfonamides and diaminodiphenyl sulfone (dapsone).
1994 Feb
Inhibition of recombinant Pneumocystis carinii dihydropteroate synthetase by sulfa drugs.
1995 Aug
Pressurized liquid extraction combined with capillary electrophoresis-mass spectrometry as an improved methodology for the determination of sulfonamide residues in meat.
2007 Aug 3
A systematic study on hydrogen bond interactions in sulfabenzamide: DFT calculations of the N-14, O-17, and H-2 NQR parameters.
2009 Feb
Analytical method for simultaneous determination of pesticide and veterinary drug residues in milk by CE-MS.
2009 May
Patents

Patents

Sample Use Guides

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
Substance Class Chemical
Created
by admin
on Sat Dec 16 16:42:39 GMT 2023
Edited
by admin
on Sat Dec 16 16:42:39 GMT 2023
Record UNII
G58F8OPL4I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SULFABENZAMIDE
INN   MART.   MI   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
GYNE-SULF COMPONENT SULFABENZAMIDE
Common Name English
SULFABENZAMIDE [USP-RS]
Common Name English
SULFABENZAMIDE [MI]
Common Name English
NSC-74587
Code English
SULFABENZAMIDE [USAN]
Common Name English
sulfabenzamide [INN]
Common Name English
TRYSUL COMPONENT SULFABENZAMIDE
Common Name English
VAGILIA COMPONENT SULFABENZAMIDE
Common Name English
Sulfabenzamide [WHO-DD]
Common Name English
SULFABENZAMIDE COMPONENT OF SULTRIN
Common Name English
TRIPLE SULFA (SULFABENZAMIDE)
Common Name English
SULFABENZAMIDE COMPONENT OF GYNE-SULF
Common Name English
SULFABENZAMIDE [MART.]
Common Name English
N-Sulfanilylbenzamide
Systematic Name English
SULTRIN COMPONENT SULFABENZAMIDE
Common Name English
SULFABENZAMIDE [USP IMPURITY]
Common Name English
SULFABENZAMIDE [VANDF]
Common Name English
SULFABENZAMIDE COMPONENT OF TRYSUL
Common Name English
SULFABENZAMIDE [ORANGE BOOK]
Common Name English
BENZAMIDE, N-((4-AMINOPHENYL)SULFONYL)-
Systematic Name English
BENZOYL SULFANILAMIDE
Systematic Name English
SULFABENZAMIDE COMPONENT OF VAGILIA
Common Name English
TRIPLE SULFA (SULFABENZAMIDE) [ORANGE BOOK]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C28394
Created by admin on Sat Dec 16 16:42:40 GMT 2023 , Edited by admin on Sat Dec 16 16:42:40 GMT 2023
NCI_THESAURUS C29739
Created by admin on Sat Dec 16 16:42:40 GMT 2023 , Edited by admin on Sat Dec 16 16:42:40 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C87216
Created by admin on Sat Dec 16 16:42:40 GMT 2023 , Edited by admin on Sat Dec 16 16:42:40 GMT 2023
PRIMARY
RXCUI
37320
Created by admin on Sat Dec 16 16:42:40 GMT 2023 , Edited by admin on Sat Dec 16 16:42:40 GMT 2023
PRIMARY RxNorm
MERCK INDEX
m10299
Created by admin on Sat Dec 16 16:42:40 GMT 2023 , Edited by admin on Sat Dec 16 16:42:40 GMT 2023
PRIMARY Merck Index
ChEMBL
CHEMBL1243
Created by admin on Sat Dec 16 16:42:40 GMT 2023 , Edited by admin on Sat Dec 16 16:42:40 GMT 2023
PRIMARY
DRUG CENTRAL
3558
Created by admin on Sat Dec 16 16:42:40 GMT 2023 , Edited by admin on Sat Dec 16 16:42:40 GMT 2023
PRIMARY
SMS_ID
100000083240
Created by admin on Sat Dec 16 16:42:40 GMT 2023 , Edited by admin on Sat Dec 16 16:42:40 GMT 2023
PRIMARY
DRUG BANK
DB09355
Created by admin on Sat Dec 16 16:42:40 GMT 2023 , Edited by admin on Sat Dec 16 16:42:40 GMT 2023
PRIMARY
MESH
C034094
Created by admin on Sat Dec 16 16:42:40 GMT 2023 , Edited by admin on Sat Dec 16 16:42:40 GMT 2023
PRIMARY
CHEBI
94677
Created by admin on Sat Dec 16 16:42:40 GMT 2023 , Edited by admin on Sat Dec 16 16:42:40 GMT 2023
PRIMARY
NSC
74587
Created by admin on Sat Dec 16 16:42:40 GMT 2023 , Edited by admin on Sat Dec 16 16:42:40 GMT 2023
PRIMARY
INN
3177
Created by admin on Sat Dec 16 16:42:40 GMT 2023 , Edited by admin on Sat Dec 16 16:42:40 GMT 2023
PRIMARY
ECHA (EC/EINECS)
204-859-4
Created by admin on Sat Dec 16 16:42:40 GMT 2023 , Edited by admin on Sat Dec 16 16:42:40 GMT 2023
PRIMARY
CAS
127-71-9
Created by admin on Sat Dec 16 16:42:40 GMT 2023 , Edited by admin on Sat Dec 16 16:42:40 GMT 2023
PRIMARY
FDA UNII
G58F8OPL4I
Created by admin on Sat Dec 16 16:42:40 GMT 2023 , Edited by admin on Sat Dec 16 16:42:40 GMT 2023
PRIMARY
RS_ITEM_NUM
1623706
Created by admin on Sat Dec 16 16:42:40 GMT 2023 , Edited by admin on Sat Dec 16 16:42:40 GMT 2023
PRIMARY
EPA CompTox
DTXSID7045287
Created by admin on Sat Dec 16 16:42:40 GMT 2023 , Edited by admin on Sat Dec 16 16:42:40 GMT 2023
PRIMARY
EVMPD
SUB10684MIG
Created by admin on Sat Dec 16 16:42:40 GMT 2023 , Edited by admin on Sat Dec 16 16:42:40 GMT 2023
PRIMARY
PUBCHEM
5319
Created by admin on Sat Dec 16 16:42:40 GMT 2023 , Edited by admin on Sat Dec 16 16:42:40 GMT 2023
PRIMARY
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