Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C13H4Cl6O2.2Na |
| Molecular Weight | 450.867 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].[Na+].[O-]C1=C(Cl)C=C(Cl)C(Cl)=C1CC2=C(Cl)C(Cl)=CC(Cl)=C2[O-]
InChI
InChIKey=UQWJZQUQIILWBP-UHFFFAOYSA-L
InChI=1S/C13H6Cl6O2.2Na/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;2*+1/p-2
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 |
|---|---|---|
| A comparison of spongiosis induced in the brain by hexachlorophene, cuprizone and triethyl tin in the Sprague-Dawley rat. | 1991 Nov |
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| Idiopathic scoliosis. Segmental fusion with transpedicular screws. | 2002 |
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| [Telangiectatic osteogenic sarcoma]. | 2004 |
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| [Cysteamine attenuates suppression of peripheral IL-2 and lymphocytic proliferation induced by ruminal and duodenal operations in goats]. | 2004 Dec |
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| A study into commanders' understanding of, and attitudes to, stress and stress-related problems. | 2004 Jun |
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| Diode laser, vitrectomy and intravitreal triamcinolone. A comparative study for the treatment of diffuse non tractional diabetic macular edema. | 2004 Mar-Jun |
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| 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 |
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| Magnetic resonance criteria for future trials of cardiac resynchronization therapy. | 2005 |
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| Gender comparison of knee strength recovery following ACL reconstruction with contralateral patellar tendon graft. | 2005 |
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| The problem of post-breast cancer lymphedema: impact and measurement issues. | 2005 |
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| 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 Apr |
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| Prospective study on cardiopulmonary bypass prime reduction and its effect on intraoperative blood product and hemoconcentrator use. | 2005 Jan |
|
| Methodology and measurement properties of health-related quality of life instruments: a prospective study of patients undergoing breast reduction surgery. | 2005 Jul 22 |
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| Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
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| The combination of intravitreal triamcinolone and phacoemulsification surgery in patients with diabeticfoveal oedema and cataract. | 2005 Jun 22 |
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| Factors influencing the mean postoperative gradients across stentless porcine valves. | 2005 Mar |
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| Universal protocol cuts hip surgery fatalities. | 2005 Mar |
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| Transanal local wide excision for rectal adenocarcinoma. | 2005 Mar-Apr |
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| Apical derotation in the treatment of idiopathic scoliosis. | 2005 Oct |
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| A new practical technique to reduce allogeneic blood exposure and hospital costs while preserving clotting factors after cardiopulmonary bypass: the Hemobag. | 2005 Oct |
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| Real-time CT fluoroscopy (CTF)-guided vertebroplasty in osteoporotic spine fractures. | 2005 Oct 31 |
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| Mannan-binding lectin and procalcitonin measurement for prediction of postoperative infection. | 2005 Oct 5 |
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| [Orthotopic bladder substitution in the treatment of interstitial cystitis]. | 2005 Sep |
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| Characterization and inhibition of SARS-coronavirus main protease. | 2006 |
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| Technical considerations in replantation of total scalp avulsions. | 2006 |
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| [Diagnosis and treatment of acquired laryngotracheal stenosis. I. Diagnosis and pre-op evaluation]. | 2006 Apr |
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| Orogastric tube complications in laparoscopic Roux-en-Y gastric bypass. | 2006 Apr |
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| Surgical resection of hepatic metastases from colorectal cancer: a systematic review of published studies. | 2006 Apr 10 |
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| 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 Feb |
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| [Place and technical aspects of external beam radiation therapy in the treatment of adult soft tissue sarcomas]. | 2006 Feb-Mar |
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| MOS short form 36 and Oswestry Disability Index outcomes in lumbar fusion: a multicenter experience. | 2006 Jan-Feb |
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| [Classification-based surgical approach in surgical management of thoracolumbar fractures of the spine]. | 2006 Jul |
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| Partial regeneration of the human hip via autologous bone marrow nucleated cell transfer: A case study. | 2006 Jul |
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| Comparison of serum calcium change following thyroid and nonthyroid neck surgery. | 2006 Jun |
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| A study exploring the role of intercostal nerve damage in chronic pain after thoracic surgery. | 2006 Jun |
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| Residual mobility of instrumented and non-fused segments in thoracolumbar spine fractures. | 2006 Jun |
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| Benefits of active motion for joint position sense. | 2006 Jun |
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| The effect of Gonioscopy on keratometry and corneal surface topography. | 2006 Jun 17 |
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| Changes in aortic root function after valve replacement in patients with aortic stenosis. | 2006 Jun 7 |
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| 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 |
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| Do variations in the theatre team have an impact on the incidence of complications? | 2006 Mar 16 |
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| Continuity of care experience of residents in an academic vascular department: are trainees learning complete surgical care? | 2006 May |
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| Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006 Nov |
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| A segmental radiological study of the spine and rib--cage in children with progressive infantile idiopathic scoliosis. | 2006 Oct 18 |
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| Intraoperative assessment of mitral regurgitation: role of phenylephrine challenge. | 2006 Sep |
|
| Hexachlorophene inhibits Wnt/beta-catenin pathway by promoting Siah-mediated beta-catenin degradation. | 2006 Sep |
|
| Multicenter experience with the Monarc transobturator sling system to treat stress urinary incontinence. | 2006 Sep |
|
| Arthroscopic collagen meniscus implant results at 6 to 8 years follow up. | 2007 Feb |
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| 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 |
|
| Intensity modulated radiation-therapy for preoperative posterior abdominal wall irradiation of retroperitoneal liposarcomas. | 2007 Jan 1 |
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.
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EPA PESTICIDE CODE |
44903
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2D18IOW6VR
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76734
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3247-34-5
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DTXSID9041312
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221-824-9
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ACTIVE MOIETY
SUBSTANCE RECORD
