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
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)
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 |
---|---|---|---|---|
Curative | SULTRIN Approved UseSULTRIN (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 Date1945 |
Cmax
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 |
T1/2
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 |
single, ocular |
SULFACETAMIDE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
82% |
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: |
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) Sources: 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) |
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 Health Status: unhealthy Condition: Conjunctivitis Sources: |
Other AEs: Stevens-Johnson syndrome, Toxic epidermal necrolysis... Other AEs: Stevens-Johnson syndrome (grade 3-4, rare) Sources: 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) |
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: |
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 Health Status: unhealthy Condition: Conjunctivitis Sources: |
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 Health Status: unhealthy Condition: Conjunctivitis Sources: |
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 Health Status: unhealthy Condition: Conjunctivitis Sources: |
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 Health Status: unhealthy Condition: Conjunctivitis Sources: |
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 Health Status: unhealthy Condition: Conjunctivitis Sources: |
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 Health Status: unhealthy Condition: Conjunctivitis Sources: |
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 Health Status: unhealthy Condition: Conjunctivitis Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical 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
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sample Use Guides
In Vivo Use Guide
Sources: http://www.drugs.com/mtm/triple-sulfa-vaginal.html
Unknown
Route of Administration:
Other
In Vitro Use Guide
Sources: http://jcmb.halic.edu.tr/pdf/10-1/6.pdf
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
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C28394
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C29739
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)