General
Preferred name
TRICLOCARBAN
Synonyms
Trichlorcarban ()
3,4,4¡ä-Trichlorocarbanilide ()
3,4,4??-Trichlorocarbanilide ()
Cutisan ()
Procutene ()
Solubacter ()
3,4,4??Trichlorocarbanilide ()
3,4,4′-Trichlorocarbanilide ()
GELUNGEL ()
NSC-72005 ()
TCC ()
3,4,4'-trichlorocarbanilide ()
P&D ID
PD014559
CAS
101-20-2
Tags
available
drug
Approved by
FDA
Drug Status
approved
Max Phase
4.0
Drug indication
Disinfectant
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
ROE The metabolism of (14)C-TCC (3,4,4'-trichlorocarbanilide) has been investigated in humans following oral exposure to 2.2 mumol/kg. Fecal elimination (70% of dose) was complete at the 120 hour point after administration and the urinary excretion (27% of dose) was complete after 80 hours post-administration [L2685].; ; Urinary glucuronides appear to be valuable biomarkers of triclocarban exposure [A32932].
ABSORPTION A human exposure study in a small group of subjects demonstrated that a portion of the TCC present in bar soaps is absorbed through the skin and is excreted in urine as N-glucuronides [A32932].; ; Because they are produced and used in large quantities in various products, they are absorbed into the human body of the general population [L2679].; ; The absorption of triclocarban during a human pharmacokinetic study was estimated at 0.6% of the 70 + or - 15 mg of triclocarban in the soap used. The triclocarban-N-glucuronide urine concentration varied considerably among the study subjects, and continuous daily use of the soap led to steady-state levels of excretion [L2685].;
METABOLISM Blood levels after parenteral injection are low and comparison of the radioactivity and chemical determinations suggest rapid metabolism of the Triclocarban [L2685].; ; Human metabolism of TCC involves direct glucuronidation to form N- and N'- glucuronides as well as ring hydroxylation to 2'-hydroxy-TCC and 6-hydroxy-TCC, which are further metabolized to sulfate and glucuronide conjugates. In human subjects given a single oral dose of TCC, 27% of the dose was excreted in the urine within 80 hours. About 70% of the administered dose was excreted in the feces within 5 days [L2685].; ; The major urinary metabolites were N-glucuronides (average levels, 30 ng/mL) and a major plasma metabolite was the sulfate conjugate of 2'-OH-TCC (levels ranged from 0-20 ng/mL [L2685].; ; The maximum plasma level occurred 2.8 hr after dosing and was 3.7 nmol-equivalents of TCC per g of plasma (approximately 1.2 ppm). Biotransformation of TCC was rapid but did not appear to involve splitting of the basic TCC structure. The major plasma metabolites were N- and N'-glucuronides of TCC which were eliminated with half-life approximately 2 hr to the urine and 2'-hydroxy-TCC sulfate and 6-hydroxy-TCC sulfate (the o-hydroxy-TCC sulfates) which were removed with half life approximately 20 hr (presumably into the bile) [L2685].
TOXICITY Ld50 of 2100 mg/kg in mice [L2674].; ; There has been concern voiced over the endocrine effect of triclocarban ande, in particular, on estrogen [A32947], [A32948],[A32949],[L2684].; ; One study determined that triclocarban by itself stimulates _AroB_ (brain aromatase) gene expression only slightly, but TCC strongly enhances the overexpression of AroB that is induced by exogenous estrogen. TCC has the potential to elevate levels of aromatase enzymes and, thereby, levels of endogenous estrogens in the developing brain [L2685]. The effects of triclocarban on the endocrine system are presently not fully elucidated.
PHARMACODYNAMICS The antimicrobial mechanism underlying the bacteriostatic and bactericidal effects of triclocarban is believed to be an unspecific adsorption to cell membranes and interruption of their function. As a result, the growth of gram-positive as well as gram-negative bacteria is inhibited [L2682].;
Cell lines
1
Organisms
1
Compound Sets
14
ChEMBL Approved Drugs
CHEMBL1076347
ChEMBL Drugs
CHEMBL1076347
Drug Repurposing Hub
DrugBank
DB11155
DrugBank Approved Drugs
DB11155
DrugCentral
3630
DrugCentral Approved Drugs
3630
EU-OPENSCREEN Bioactive Compound Library
EOS100112
MedChem Express Bioactive Compound Library
HY-B1805
NPC Screening Collection
ReFrame library
Selleckchem Bioactive Compound Library
triclocarban
TargetMol Bioactive Compound Library
T4504
ZINC Tool Compounds
ZINC000000121480
External IDs
34
Properties
(calculated by RDKit )
Molecular Weight
313.98
Hydrogen Bond Acceptors
1
Hydrogen Bond Donors
2
Rotatable Bonds
2
Ring Count
2
Aromatic Ring Count
2
cLogP
5.29
TPSA
41.13
Fraction CSP3
0.0
Chiral centers
0.0
Largest ring
6.0
QED
0.78
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Pathway
Microbiology&virology
Anti-infection
Target
Bacterial
MOA
Antibacterial
other antibiotic
Indication
first-aid antiseptic
Source data