Details
Stereochemistry | ACHIRAL |
Molecular Formula | C13H5Cl6O2.Na |
Molecular Weight | 428.885 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].OC1=C(Cl)C=C(Cl)C(Cl)=C1CC2=C(Cl)C(Cl)=CC(Cl)=C2[O-]
InChI
InChIKey=JNAQOQQXXBMQKT-UHFFFAOYSA-M
InChI=1S/C13H6Cl6O2.Na/c14-6-2-8(16)12(20)4(10(6)18)1-5-11(19)7(15)3-9(17)13(5)21;/h2-3,20-21H,1H2;/q;+1/p-1
Molecular Formula | Na |
Molecular Weight | 22.98976928 |
Charge | 1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C13H5Cl6O2 |
Molecular Weight | 405.896 |
Charge | -1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: https://www.drugs.com/monograph/hexachlorophene.htmlCurator's Comment: description was created based on several sources, including
https://www.drugs.com/pro/phisohex.html | https://www.ncbi.nlm.nih.gov/pubmed/570044 | https://www.ncbi.nlm.nih.gov/pubmed/19734050 | https://www.ncbi.nlm.nih.gov/pubmed/5001202
Sources: https://www.drugs.com/monograph/hexachlorophene.html
Curator's Comment: description was created based on several sources, including
https://www.drugs.com/pro/phisohex.html | https://www.ncbi.nlm.nih.gov/pubmed/570044 | https://www.ncbi.nlm.nih.gov/pubmed/19734050 | https://www.ncbi.nlm.nih.gov/pubmed/5001202
Hexachlorophene, also known as Nabac, is an organochlorine compound that was once widely used as a disinfectant. The compound occurs as a white odorless solid, although commercial samples can be off-white and possess a slightly phenolic odor. It is insoluble in water but dissolves in acetone, ethanol, diethyl ether, and chloroform. Exact mechanism(s) of action unknown, but at low concentrations appears to interrupt bacterial electron transport and inhibit membrane-bound enzymes. Higher concentrations rupture bacterial membranes. It induces leakage, causes protoplast lysis, and inhibits respiration. In medicine, hexachlorophene is a useful as a topical anti-infective, anti-bacterial agent, often used in soaps and toothpaste. It is also used in agriculture as a soil fungicide, plant bactericide, and acaricide.
CNS Activity
Sources: https://www.drugs.com/pro/phisohex.html#Warn
Curator's Comment: Rapid absorption of hexachlorophene may occur with resultant toxic blood levels when preparations containing hexachlorophene are applied to skin lesions such as ichthyosis congenita, the dermatitis of Letterer-Siwe's syndrome, or other generalized dermatological conditions. Application to burns has also produced neurotoxicity and death.
Serum concentrations of ≥1 mcg/mL in animals associated with CNS toxicity.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL3445 Sources: https://www.ncbi.nlm.nih.gov/pubmed/570044 |
59.0 µM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | PRE-OP Approved UseINDICATIONS & USAGE pHisoHex is indicated for use as a surgical scrub and a bacteriostatic skin cleanser. It may also be used to control an outbreak of gram-positive infection where other infection control procedures have been unsuccessful. Use only as long as necessary for infection control (see PRECAUTIONS: Information for Patients). Launch Date1978 |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
21.15 h DRUG LABEL https://pubmed.ncbi.nlm.nih.gov/894425/ |
3 % unknown, topical dose: 3 % route of administration: Topical experiment type: UNKNOWN co-administered: |
HEXACHLOROPHENE blood | Homo sapiens population: UNKNOWN age: NEWBORN sex: UNKNOWN food status: UNKNOWN |
PubMed
Title | Date | PubMed |
---|---|---|
Non-N-methyl-D-aspartate (NMDA) receptor antagonist 1,2,3, 4-tetrahydro-6-nitro-2,3-dioxo-benzo(f)quinoxaline-7-sulphonamide (NBQX) decreases functional disorders in cytotoxic brain oedema. | 2000 Jan |
|
[Arthroscopic shoulder stabilization]. | 2001 |
|
The effect of acute normovolaemic haemodilution on blood transfusion requirements in abdominal aortic aneurysm repair. | 2001 Oct |
|
Idiopathic scoliosis. Segmental fusion with transpedicular screws. | 2002 |
|
Prognostic significance of nodal disease following preoperative radiation for rectal adenocarcinoma. | 2002 May |
|
Preoperative oral arginine and n-3 fatty acid supplementation improves the immunometabolic host response and outcome after colorectal resection for cancer. | 2002 Nov |
|
Nailing down pre-op clearance exams. | 2002 Oct 11 |
|
In myasthenia gravis, clinical and immunological improvement post-thymectomy segregate with results of in vitro antibody secretion by immunocytes. | 2002 Oct 15 |
|
What preoperative assessment is necessary for insulinomas? Calculating the degree of waste: analysis of 29 cases. | 2002 Sep-Oct |
|
Surgical placement of two implants in the anterior edentulous mandible--how much time does it take? | 2003 Apr |
|
Preoperative radiotherapy for adult head and neck soft tissue sarcoma: assessment of wound complication rates and cancer outcome in a prospective series. | 2003 Jul |
|
[The study of peri-operative chemotherapy in stage I-IIIa NSCLC]. | 2003 Jun 10 |
|
Median nerve function in patients undergoing carpal tunnel release: pre- and post-op nerve conductions. | 2003 Oct-Nov |
|
[Multimodal intraoperative electrophysiological monitoring during cerebellopontine angle tumor surgery. Benefit or loss?]. | 2003 Sep-Oct |
|
[Telangiectatic osteogenic sarcoma]. | 2004 |
|
[Cysteamine attenuates suppression of peripheral IL-2 and lymphocytic proliferation induced by ruminal and duodenal operations in goats]. | 2004 Dec |
|
Effectiveness of topical chlorhexidine powder as an alternative to hexachlorophane for the control of Staphylococcus aureus in neonates. | 2004 Feb |
|
Implantation of Spheramine in advanced Parkinson's disease (PD). | 2004 Jan 1 |
|
[Efficacy of the Russian anthelmintic agent trichlorophen]. | 2004 Jan-Mar |
|
Repair of atrioventricular valve regurgitation in the modified Fontan operation. | 2004 Jul |
|
A study into commanders' understanding of, and attitudes to, stress and stress-related problems. | 2004 Jun |
|
Patient satisfaction for carotid endarterectomy performed under local anaesthesia. | 2004 Jun |
|
Effects of subthalamic nucleus stimulation on parkinsonian dysarthria and speech intelligibility. | 2004 Mar |
|
Diode laser, vitrectomy and intravitreal triamcinolone. A comparative study for the treatment of diffuse non tractional diabetic macular edema. | 2004 Mar-Jun |
|
Anti-estrogenic activity of fifty chemicals evaluated by in vitro assays. | 2004 May 7 |
|
Refractive index change in bovine and human corneal stroma before and after lasik: a study of untreated and re-treated corneas implicating stromal hydration. | 2004 Oct |
|
Gender comparison of knee strength recovery following ACL reconstruction with contralateral patellar tendon graft. | 2005 |
|
Prospective study on cardiopulmonary bypass prime reduction and its effect on intraoperative blood product and hemoconcentrator use. | 2005 Jan |
|
Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
Factors influencing the mean postoperative gradients across stentless porcine valves. | 2005 Mar |
|
Apical derotation in the treatment of idiopathic scoliosis. | 2005 Oct |
|
Real-time CT fluoroscopy (CTF)-guided vertebroplasty in osteoporotic spine fractures. | 2005 Oct 31 |
|
Mannan-binding lectin and procalcitonin measurement for prediction of postoperative infection. | 2005 Oct 5 |
|
[Diagnosis and treatment of acquired laryngotracheal stenosis. I. Diagnosis and pre-op evaluation]. | 2006 Apr |
|
MOS short form 36 and Oswestry Disability Index outcomes in lumbar fusion: a multicenter experience. | 2006 Jan-Feb |
|
Comparison of serum calcium change following thyroid and nonthyroid neck surgery. | 2006 Jun |
|
Residual mobility of instrumented and non-fused segments in thoracolumbar spine fractures. | 2006 Jun |
|
The effect of Gonioscopy on keratometry and corneal surface topography. | 2006 Jun 17 |
|
Altered plasma matrix metalloproteinase-9/tissue inhibitor of matrix [corrected] metalloproteinase-1 concentration during the early postoperative period in patients with colorectal cancer. | 2006 Mar |
|
Do variations in the theatre team have an impact on the incidence of complications? | 2006 Mar 16 |
|
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006 Nov |
|
Arthroscopic collagen meniscus implant results at 6 to 8 years follow up. | 2007 Feb |
|
Clinical presentation is the main predictor of in-hospital death for patients with acute type A aortic dissection admitted for surgical treatment: a 25 years experience. | 2007 Feb 14 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/monograph/hexachlorophene.html
Apply topically to skin as a 3% emulsion.
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/5001202
Cells of the asporogenous KM strain of B. megaterium were grown in aerated batch culture. Cells was treated by Hexachlorophene (ethanol solution, up to 400 mkg/ml) for 30 min. Protoplast lysis was proportional to Hexachlorophene concentration up to about 50 mg of cell dry weight per mg.
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 21:49:36 GMT 2025
by
admin
on
Mon Mar 31 21:49:36 GMT 2025
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Record UNII |
2VQ8FNO9NH
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Record Status |
Validated (UNII)
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Record Version |
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227-245-8
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DTXSID4041313
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23669625
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2VQ8FNO9NH
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5736-15-2
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