Details
Stereochemistry | ACHIRAL |
Molecular Formula | C13H6Cl6O2 |
Molecular Weight | 406.904 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=C(Cl)C=C(Cl)C(Cl)=C1CC2=C(Cl)C(Cl)=CC(Cl)=C2O
InChI
InChIKey=ACGUYXCXAPNIKK-UHFFFAOYSA-N
InChI=1S/C13H6Cl6O2/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
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 |
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Target ID: CHEMBL3445 Sources: https://www.ncbi.nlm.nih.gov/pubmed/570044 |
59.0 µM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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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 |
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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 |
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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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[The USS (Universal Spine System) in the treatment of thoraco-lumbar spine fractures]. | 2001 |
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[Arthroscopic shoulder stabilization]. | 2001 |
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Surgical management of severe deformity resulting from posterior tibial tendon dysfunction. | 2001 Dec |
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[Efficacy and tolerance of trichlorophene in hymenolepiasis and taeniarinchiasis]. | 2001 Jul-Sep |
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Crescentic proximal metatarsal osteotomy for moderate to severe hallux valgus: a mean 12.2 year follow-up study. | 2001 Oct |
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The effect of acute normovolaemic haemodilution on blood transfusion requirements in abdominal aortic aneurysm repair. | 2001 Oct |
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[Preoperative radiotherapy in rectal cancer: conventional fractionation]. | 2001 Sep-Oct |
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Idiopathic scoliosis. Segmental fusion with transpedicular screws. | 2002 |
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Prognostic significance of nodal disease following preoperative radiation for rectal adenocarcinoma. | 2002 May |
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Preoperative oral arginine and n-3 fatty acid supplementation improves the immunometabolic host response and outcome after colorectal resection for cancer. | 2002 Nov |
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Cardiac grafting of engineered heart tissue in syngenic rats. | 2002 Sep 24 |
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Methicillin-resistant Staphylococcus aureus and infection control for restorative dental treatment in nursing homes. | 2003 |
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Does harvesting the medial third of the patellar tendon cause lateral shift of the patella after ACL reconstruction? | 2003 Aug |
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[Refixation of osteochondral fragments using absorbable implants. First results of a retrospective study]. | 2003 Jun |
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In pursuit of emmetropia: spherical equivalent refraction results with deep lamellar endothelial keratoplasty (DLEK). | 2003 Oct |
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Median nerve function in patients undergoing carpal tunnel release: pre- and post-op nerve conductions. | 2003 Oct-Nov |
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Newborn behavioral and physiological responses to circumcision. | 2003 Sep-Oct |
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[Telangiectatic osteogenic sarcoma]. | 2004 |
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Implantation of Spheramine in advanced Parkinson's disease (PD). | 2004 Jan 1 |
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Repair of atrioventricular valve regurgitation in the modified Fontan operation. | 2004 Jul |
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A study into commanders' understanding of, and attitudes to, stress and stress-related problems. | 2004 Jun |
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Patient satisfaction for carotid endarterectomy performed under local anaesthesia. | 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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Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
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Factors influencing the mean postoperative gradients across stentless porcine valves. | 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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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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[Place and technical aspects of external beam radiation therapy in the treatment of adult soft tissue sarcomas]. | 2006 Feb-Mar |
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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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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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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 |
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Intensity modulated radiation-therapy for preoperative posterior abdominal wall irradiation of retroperitoneal liposarcomas. | 2007 Jan 1 |
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.
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QD08AE01
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IARC | Hexachlorophene | ||
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CFR |
21 CFR 310.531
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WHO-ATC |
D08AE01
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NCI_THESAURUS |
C28394
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WHO-VATC |
QP52AG02
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NDF-RT |
N0000175486
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CFR |
21 CFR 250.250
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Hexachlorophene
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1364
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100000092137
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70-30-4
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200-733-8
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m5986
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D006582
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5293
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SUB08023MIG
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IWW5FV6NK2
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DB00756
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CHEMBL496
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DTXSID6020690
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49115
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C47556
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1305008
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IWW5FV6NK2
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224
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3598
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hexachlorophene
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5693
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)