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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
Structure of HEXACHLOROPHENE SODIUM

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

HIDE SMILES / InChI

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

Description
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

Targets

Primary TargetPharmacologyConditionPotency
59.0 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
PRE-OP

Approved Use

INDICATIONS & 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 Date

1978
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
21.15 h
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
Doses

Doses

DosePopulationAdverse events​
3 % 2 times / day multiple, topical
Recommended
Dose: 3 %, 2 times / day
Route: topical
Route: multiple
Dose: 3 %, 2 times / day
Sources:
unhealthy, 18-26
Health Status: unhealthy
Age Group: 18-26
Sex: M+F
Sources:
PubMed

PubMed

TitleDatePubMed
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
Patents

Sample Use Guides

Apply topically to skin as a 3% emulsion.
Route of Administration: Topical
In Vitro Use Guide
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 Mon Mar 31 21:49:36 GMT 2025
Edited
by admin
on Mon Mar 31 21:49:36 GMT 2025
Record UNII
2VQ8FNO9NH
Record Status Validated (UNII)
Record Version
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Name Type Language
ISOBAC
Preferred Name English
HEXACHLOROPHENE SODIUM
Common Name English
J41.461A
Code English
2,2'-METHYLENEBIS(3,4,6-TRICHLOROPHENOL) SODIUM SALT
Common Name English
SODIUM HYDROGEN 2,2'-METHYLENEBIS(3,4,6-TRICHLOROPHENOLATE)
Systematic Name English
MONOSODIUM 2,2'-METHYLENEBIS(3,4,6-TRICHLOROPHENATE)
Systematic Name English
HEXACHLOROPHENE MONOSODIUM SALT
Common Name English
PHENOL, 2,2'-METHYLENEBIS(3,4,6-TRICHLORO-, MONOSODIUM SALT
Systematic Name English
SODIUM 3,4,6-TRICHLORO-2-(2,3,5-TRICHLORO-6-HYDROXYBENZYL)PHENOLATE
Systematic Name English
ISOBAC 20
Brand Name English
SODIUM, ((3,4,6-TRICHLORO-.ALPHA.-(2,3,5-TRICHLORO-6-HYDROXYPHENYL)-O-TOLYL)OXY)-
Systematic Name English
2,4,5-TRICHLORO-6-(2,3,5-TRICHLORO-6-SODIOOXYBENZYL)PHENOL
Systematic Name English
Code System Code Type Description
ECHA (EC/EINECS)
227-245-8
Created by admin on Mon Mar 31 21:49:36 GMT 2025 , Edited by admin on Mon Mar 31 21:49:36 GMT 2025
PRIMARY
EPA CompTox
DTXSID4041313
Created by admin on Mon Mar 31 21:49:36 GMT 2025 , Edited by admin on Mon Mar 31 21:49:36 GMT 2025
PRIMARY
PUBCHEM
23669625
Created by admin on Mon Mar 31 21:49:36 GMT 2025 , Edited by admin on Mon Mar 31 21:49:36 GMT 2025
PRIMARY
FDA UNII
2VQ8FNO9NH
Created by admin on Mon Mar 31 21:49:36 GMT 2025 , Edited by admin on Mon Mar 31 21:49:36 GMT 2025
PRIMARY
CAS
5736-15-2
Created by admin on Mon Mar 31 21:49:36 GMT 2025 , Edited by admin on Mon Mar 31 21:49:36 GMT 2025
PRIMARY
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