U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of HEXACHLOROPHENE

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

HIDE SMILES / InChI

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
n = 9
Health Status: unhealthy
Condition: acne vulgaris
Age Group: 18-26
Sex: M+F
Population Size: 9
Sources:
PubMed

PubMed

TitleDatePubMed
A comparison of spongiosis induced in the brain by hexachlorophene, cuprizone and triethyl tin in the Sprague-Dawley rat.
1991 Nov
[The USS (Universal Spine System) in the treatment of thoraco-lumbar spine fractures].
2001
[Arthroscopic shoulder stabilization].
2001
Surgical management of severe deformity resulting from posterior tibial tendon dysfunction.
2001 Dec
[Efficacy and tolerance of trichlorophene in hymenolepiasis and taeniarinchiasis].
2001 Jul-Sep
Crescentic proximal metatarsal osteotomy for moderate to severe hallux valgus: a mean 12.2 year follow-up study.
2001 Oct
The effect of acute normovolaemic haemodilution on blood transfusion requirements in abdominal aortic aneurysm repair.
2001 Oct
[Preoperative radiotherapy in rectal cancer: conventional fractionation].
2001 Sep-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
Cardiac grafting of engineered heart tissue in syngenic rats.
2002 Sep 24
Methicillin-resistant Staphylococcus aureus and infection control for restorative dental treatment in nursing homes.
2003
Does harvesting the medial third of the patellar tendon cause lateral shift of the patella after ACL reconstruction?
2003 Aug
[Refixation of osteochondral fragments using absorbable implants. First results of a retrospective study].
2003 Jun
In pursuit of emmetropia: spherical equivalent refraction results with deep lamellar endothelial keratoplasty (DLEK).
2003 Oct
Median nerve function in patients undergoing carpal tunnel release: pre- and post-op nerve conductions.
2003 Oct-Nov
Newborn behavioral and physiological responses to circumcision.
2003 Sep-Oct
[Telangiectatic osteogenic sarcoma].
2004
Implantation of Spheramine in advanced Parkinson's disease (PD).
2004 Jan 1
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
Diode laser, vitrectomy and intravitreal triamcinolone. A comparative study for the treatment of diffuse non tractional diabetic macular edema.
2004 Mar-Jun
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
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
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Factors influencing the mean postoperative gradients across stentless porcine valves.
2005 Mar
Transanal local wide excision for rectal adenocarcinoma.
2005 Mar-Apr
Apical derotation in the treatment of idiopathic scoliosis.
2005 Oct
Characterization and inhibition of SARS-coronavirus main protease.
2006
Technical considerations in replantation of total scalp avulsions.
2006
[Diagnosis and treatment of acquired laryngotracheal stenosis. I. Diagnosis and pre-op evaluation].
2006 Apr
[Place and technical aspects of external beam radiation therapy in the treatment of adult soft tissue sarcomas].
2006 Feb-Mar
Partial regeneration of the human hip via autologous bone marrow nucleated cell transfer: A case study.
2006 Jul
Comparison of serum calcium change following thyroid and nonthyroid neck surgery.
2006 Jun
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
Continuity of care experience of residents in an academic vascular department: are trainees learning complete surgical care?
2006 May
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
A segmental radiological study of the spine and rib--cage in children with progressive infantile idiopathic scoliosis.
2006 Oct 18
Intraoperative assessment of mitral regurgitation: role of phenylephrine challenge.
2006 Sep
Intensity modulated radiation-therapy for preoperative posterior abdominal wall irradiation of retroperitoneal liposarcomas.
2007 Jan 1
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.
Name Type Language
HEXACHLOROPHENE
HSDB   INCI   INN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
INN   INCI  
Official Name English
HEXACHLOROPHENE [MI]
Common Name English
SCRUBTEAM SURGICAL SPONGEBRUSH
Brand Name English
TURGEX
Brand Name English
HEXACHLOROPHENE [USP-RS]
Common Name English
hexachlorophene [INN]
Common Name English
GAMOPHEN
Brand Name English
GERMA-MEDICA
Brand Name English
HEXACHLOROPHENE [HSDB]
Common Name English
HEXACHLOROPHENE [MART.]
Common Name English
E-Z SCRUB
Brand Name English
PRE-OP
Brand Name English
Hexachlorophene [WHO-DD]
Common Name English
HEXACHLOROPHENE [ORANGE BOOK]
Common Name English
HEXACHLOROPHANE
Common Name English
SOY-DOME
Brand Name English
PHISOHEX
Brand Name English
DIAL
Brand Name English
SEPTISOL
Brand Name English
HEXACHLOROPHENE [VANDF]
Common Name English
NSC-49115
Code English
HEXACHLOROPHENE [IARC]
Common Name English
HEXACHLOROPHENE [USP MONOGRAPH]
Common Name English
HEXACHLOROPHENE [INCI]
Common Name English
HEXASCRUB
Brand Name English
PHENOL, 2,2'-METHYLENEBIS(3,4,6-TRICHLORO-
Systematic Name English
2,2'-METHYLENEBIS(3,4,6-TRICHLOROPHENOL)
Systematic Name English
PHISO-SCRUB
Brand Name English
SEPTI-SOFT
Brand Name English
HEXA-GERM
Brand Name English
Classification Tree Code System Code
WHO-VATC QD08AE01
Created by admin on Sat Dec 16 16:55:59 GMT 2023 , Edited by admin on Sat Dec 16 16:55:59 GMT 2023
IARC Hexachlorophene
CFR 21 CFR 310.531
Created by admin on Sat Dec 16 16:55:59 GMT 2023 , Edited by admin on Sat Dec 16 16:55:59 GMT 2023
WHO-ATC D08AE01
Created by admin on Sat Dec 16 16:55:59 GMT 2023 , Edited by admin on Sat Dec 16 16:55:59 GMT 2023
NCI_THESAURUS C28394
Created by admin on Sat Dec 16 16:55:59 GMT 2023 , Edited by admin on Sat Dec 16 16:55:59 GMT 2023
WHO-VATC QP52AG02
Created by admin on Sat Dec 16 16:55:59 GMT 2023 , Edited by admin on Sat Dec 16 16:55:59 GMT 2023
NDF-RT N0000175486
Created by admin on Sat Dec 16 16:55:59 GMT 2023 , Edited by admin on Sat Dec 16 16:55:59 GMT 2023
CFR 21 CFR 250.250
Created by admin on Sat Dec 16 16:55:59 GMT 2023 , Edited by admin on Sat Dec 16 16:55:59 GMT 2023
Code System Code Type Description
INN
2033
Created by admin on Sat Dec 16 16:55:59 GMT 2023 , Edited by admin on Sat Dec 16 16:55:59 GMT 2023
PRIMARY
WIKIPEDIA
Hexachlorophene
Created by admin on Sat Dec 16 16:55:59 GMT 2023 , Edited by admin on Sat Dec 16 16:55:59 GMT 2023
PRIMARY
DRUG CENTRAL
1364
Created by admin on Sat Dec 16 16:55:59 GMT 2023 , Edited by admin on Sat Dec 16 16:55:59 GMT 2023
PRIMARY
SMS_ID
100000092137
Created by admin on Sat Dec 16 16:55:59 GMT 2023 , Edited by admin on Sat Dec 16 16:55:59 GMT 2023
PRIMARY
CAS
70-30-4
Created by admin on Sat Dec 16 16:55:59 GMT 2023 , Edited by admin on Sat Dec 16 16:55:59 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-733-8
Created by admin on Sat Dec 16 16:55:59 GMT 2023 , Edited by admin on Sat Dec 16 16:55:59 GMT 2023
PRIMARY
MERCK INDEX
m5986
Created by admin on Sat Dec 16 16:55:59 GMT 2023 , Edited by admin on Sat Dec 16 16:55:59 GMT 2023
PRIMARY Merck Index
MESH
D006582
Created by admin on Sat Dec 16 16:55:59 GMT 2023 , Edited by admin on Sat Dec 16 16:55:59 GMT 2023
PRIMARY
RXCUI
5293
Created by admin on Sat Dec 16 16:55:59 GMT 2023 , Edited by admin on Sat Dec 16 16:55:59 GMT 2023
PRIMARY RxNorm
EVMPD
SUB08023MIG
Created by admin on Sat Dec 16 16:55:59 GMT 2023 , Edited by admin on Sat Dec 16 16:55:59 GMT 2023
PRIMARY
DAILYMED
IWW5FV6NK2
Created by admin on Sat Dec 16 16:55:59 GMT 2023 , Edited by admin on Sat Dec 16 16:55:59 GMT 2023
PRIMARY
DRUG BANK
DB00756
Created by admin on Sat Dec 16 16:55:59 GMT 2023 , Edited by admin on Sat Dec 16 16:55:59 GMT 2023
PRIMARY
ChEMBL
CHEMBL496
Created by admin on Sat Dec 16 16:55:59 GMT 2023 , Edited by admin on Sat Dec 16 16:55:59 GMT 2023
PRIMARY
EPA CompTox
DTXSID6020690
Created by admin on Sat Dec 16 16:55:59 GMT 2023 , Edited by admin on Sat Dec 16 16:55:59 GMT 2023
PRIMARY
NSC
49115
Created by admin on Sat Dec 16 16:55:59 GMT 2023 , Edited by admin on Sat Dec 16 16:55:59 GMT 2023
PRIMARY
NCI_THESAURUS
C47556
Created by admin on Sat Dec 16 16:55:59 GMT 2023 , Edited by admin on Sat Dec 16 16:55:59 GMT 2023
PRIMARY
RS_ITEM_NUM
1305008
Created by admin on Sat Dec 16 16:55:59 GMT 2023 , Edited by admin on Sat Dec 16 16:55:59 GMT 2023
PRIMARY
FDA UNII
IWW5FV6NK2
Created by admin on Sat Dec 16 16:55:59 GMT 2023 , Edited by admin on Sat Dec 16 16:55:59 GMT 2023
PRIMARY
HSDB
224
Created by admin on Sat Dec 16 16:55:59 GMT 2023 , Edited by admin on Sat Dec 16 16:55:59 GMT 2023
PRIMARY
PUBCHEM
3598
Created by admin on Sat Dec 16 16:55:59 GMT 2023 , Edited by admin on Sat Dec 16 16:55:59 GMT 2023
PRIMARY
ALANWOOD
hexachlorophene
Created by admin on Sat Dec 16 16:55:59 GMT 2023 , Edited by admin on Sat Dec 16 16:55:59 GMT 2023
PRIMARY
CHEBI
5693
Created by admin on Sat Dec 16 16:55:59 GMT 2023 , Edited by admin on Sat Dec 16 16:55:59 GMT 2023
PRIMARY