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 |
DescriptionCurator'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
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
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 |
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 |
|---|---|---|
| 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. | 2007-02-14 |
|
| Arthroscopic collagen meniscus implant results at 6 to 8 years follow up. | 2007-02 |
|
| Intensity modulated radiation-therapy for preoperative posterior abdominal wall irradiation of retroperitoneal liposarcomas. | 2007-01-01 |
|
| Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006-11 |
|
| A segmental radiological study of the spine and rib--cage in children with progressive infantile idiopathic scoliosis. | 2006-10-18 |
|
| Intraoperative assessment of mitral regurgitation: role of phenylephrine challenge. | 2006-09 |
|
| Hexachlorophene inhibits Wnt/beta-catenin pathway by promoting Siah-mediated beta-catenin degradation. | 2006-09 |
|
| Multicenter experience with the Monarc transobturator sling system to treat stress urinary incontinence. | 2006-09 |
|
| [Classification-based surgical approach in surgical management of thoracolumbar fractures of the spine]. | 2006-07 |
|
| Partial regeneration of the human hip via autologous bone marrow nucleated cell transfer: A case study. | 2006-07 |
|
| The effect of Gonioscopy on keratometry and corneal surface topography. | 2006-06-17 |
|
| Changes in aortic root function after valve replacement in patients with aortic stenosis. | 2006-06-07 |
|
| Comparison of serum calcium change following thyroid and nonthyroid neck surgery. | 2006-06 |
|
| A study exploring the role of intercostal nerve damage in chronic pain after thoracic surgery. | 2006-06 |
|
| Residual mobility of instrumented and non-fused segments in thoracolumbar spine fractures. | 2006-06 |
|
| Benefits of active motion for joint position sense. | 2006-06 |
|
| Continuity of care experience of residents in an academic vascular department: are trainees learning complete surgical care? | 2006-05 |
|
| Surgical resection of hepatic metastases from colorectal cancer: a systematic review of published studies. | 2006-04-10 |
|
| [Diagnosis and treatment of acquired laryngotracheal stenosis. I. Diagnosis and pre-op evaluation]. | 2006-04 |
|
| Orogastric tube complications in laparoscopic Roux-en-Y gastric bypass. | 2006-04 |
|
| Do variations in the theatre team have an impact on the incidence of complications? | 2006-03-16 |
|
| Altered plasma matrix metalloproteinase-9/tissue inhibitor of matrix [corrected] metalloproteinase-1 concentration during the early postoperative period in patients with colorectal cancer. | 2006-03 |
|
| A prospective randomized study comparing a cervical carbon fiber cage to the Smith-Robinson technique with allograft and plating: up to 24 months follow-up. | 2006-02 |
|
| Characterization and inhibition of SARS-coronavirus main protease. | 2006 |
|
| Technical considerations in replantation of total scalp avulsions. | 2006 |
|
| Real-time CT fluoroscopy (CTF)-guided vertebroplasty in osteoporotic spine fractures. | 2005-10-31 |
|
| [Place and technical aspects of external beam radiation therapy in the treatment of adult soft tissue sarcomas]. | 2005-10-28 |
|
| Mannan-binding lectin and procalcitonin measurement for prediction of postoperative infection. | 2005-10-05 |
|
| Apical derotation in the treatment of idiopathic scoliosis. | 2005-10 |
|
| A new practical technique to reduce allogeneic blood exposure and hospital costs while preserving clotting factors after cardiopulmonary bypass: the Hemobag. | 2005-10 |
|
| [Orthotopic bladder substitution in the treatment of interstitial cystitis]. | 2005-09 |
|
| Methodology and measurement properties of health-related quality of life instruments: a prospective study of patients undergoing breast reduction surgery. | 2005-07-22 |
|
| The combination of intravitreal triamcinolone and phacoemulsification surgery in patients with diabeticfoveal oedema and cataract. | 2005-06-22 |
|
| Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005-06 |
|
| MOS short form 36 and Oswestry Disability Index outcomes in lumbar fusion: a multicenter experience. | 2005-04-13 |
|
| Transanal local wide excision for rectal adenocarcinoma. | 2005-04-09 |
|
| Patterns of care survey (PCS) in lung cancer: how well does current U.S. practice with chemotherapy in the non-metastatic setting follow the literature? | 2005-04 |
|
| Factors influencing the mean postoperative gradients across stentless porcine valves. | 2005-03 |
|
| Universal protocol cuts hip surgery fatalities. | 2005-03 |
|
| Diode laser, vitrectomy and intravitreal triamcinolone. A comparative study for the treatment of diffuse non tractional diabetic macular edema. | 2005-01-22 |
|
| Prospective study on cardiopulmonary bypass prime reduction and its effect on intraoperative blood product and hemoconcentrator use. | 2005-01 |
|
| Magnetic resonance criteria for future trials of cardiac resynchronization therapy. | 2005 |
|
| Gender comparison of knee strength recovery following ACL reconstruction with contralateral patellar tendon graft. | 2005 |
|
| The problem of post-breast cancer lymphedema: impact and measurement issues. | 2005 |
|
| [Cysteamine attenuates suppression of peripheral IL-2 and lymphocytic proliferation induced by ruminal and duodenal operations in goats]. | 2004-12 |
|
| Refractive index change in bovine and human corneal stroma before and after lasik: a study of untreated and re-treated corneas implicating stromal hydration. | 2004-10 |
|
| A study into commanders' understanding of, and attitudes to, stress and stress-related problems. | 2004-06 |
|
| [Telangiectatic osteogenic sarcoma]. | 2004 |
|
| Idiopathic scoliosis. Segmental fusion with transpedicular screws. | 2002 |
|
| A comparison of spongiosis induced in the brain by hexachlorophene, cuprizone and triethyl tin in the Sprague-Dawley rat. | 1991-11 |
Sample Use Guides
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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admin on Mon Mar 31 21:49:36 GMT 2025 , Edited by admin on Mon Mar 31 21:49:36 GMT 2025
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