Polidocanol

Identification

Name
Polidocanol
Accession Number
DB06811
Type
Small Molecule
Groups
Approved
Description

Polidocanol is a sclerosing agent indicated to treat uncomplicated spider veins (varicose veins ≤1 mm in diameter) and uncomplicated reticular veins (varicose veins 1 to 3 mm in diameter) in the lower extremity. It is marketed under the brand names Asclera and Varithena. The formula for Polidocanol has the structural formula C12H25(OCH2CH2)nOH, a mean extent of polymerization (n) of approximately 9 and a mean molecular weight of approximately 600.

Structure
Thumb
Synonyms
  • Aethoxy-sklerol
  • Laureth 9
  • Laureth-9
  • Macrogol 9 lauryl ether
  • Nonaethylene glycol monododecyl ether
  • Nonaethylene glycol monolauryl ether
  • PEG-9 lauryl ether
  • Polydocanol
  • Polyethylene glycol 450 lauryl ether
  • Polyoxyl 9 lauryl ether
External IDs
3055-99-0
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AscleraInjection, solution0.00500 g/1mLIntravenousMerz North America, Inc.2010-06-01Not applicableUs
AscleraInjection, solution0.01000 g/1mLIntravenousMerz North America, Inc.2010-06-01Not applicableUs
VarithenaKit1.3 mgIntravenousProvensis Ltd2016-11-30Not applicableCanada
VarithenaKit180 mg/1mLBiocompatibles, Inc.2013-11-25Not applicableUs
VarithenaKit180 mg/1mLBiocompatibles, Inc.2014-07-10Not applicableUs
Varithena TMKit180 mg/1mLBiocompatibles, Inc.2014-07-10Not applicableUs
International/Other Brands
Aethoxysklerol
Categories
UNII
0AWH8BFG9A
CAS number
9002-92-0
Weight
Average: 582.8073
Monoisotopic: 582.434298204
Chemical Formula
C30H62O10
InChI Key
ONJQDTZCDSESIW-UHFFFAOYSA-N
InChI
InChI=1S/C30H62O10/c1-2-3-4-5-6-7-8-9-10-11-13-32-15-17-34-19-21-36-23-25-38-27-29-40-30-28-39-26-24-37-22-20-35-18-16-33-14-12-31/h31H,2-30H2,1H3
IUPAC Name
3,6,9,12,15,18,21,24,27-nonaoxanonatriacontan-1-ol
SMILES
CCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO

Pharmacology

Indication

Polidocanol is a sclerosing agent indicated to treat uncomplicated spider veins and uncomplicated reticular veins in the lower extremity.

Associated Conditions
Pharmacodynamics

Polidocanol has a concentration and volume dependent damaging effect on the blood vessel endothelium.

Mechanism of action

When administered, polidocanol locally damages blood vessel endothelium. Following the endothelial damage, platelets aggregate at the site and attach to the venous wall eventually resulting in a dense network of platelets, cellular debris, and fibrin that occludes the vessel. Eventually the vessel is replaced by connective fibrous tissue.

Absorption

When given intravenously, the maximum blood concentrations were reached in 15 mins.

Volume of distribution

When given intravenously, the volume of distribution was 35-82L.

Protein binding

Plasma protein binding was not measured.

Metabolism

Metabolism was not measured.

Route of elimination

Route of elimination was not indicated.

Half life

The half-life is approximately 1.5 h.

Clearance

Sytemic clearance was 0.2-0.4 L/min.

Toxicity

Most adverse reactions are related to the intravenous administration such as local irritation, pain, and hematoma. Extravasation can also be an issue.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
Abicipar PegolThe therapeutic efficacy of Abicipar Pegol can be decreased when used in combination with Polidocanol.
Antihemophilic Factor (Recombinant), PEGylatedThe therapeutic efficacy of Antihemophilic Factor (Recombinant), PEGylated can be decreased when used in combination with Polidocanol.
Cepeginterferon alfa-2BThe therapeutic efficacy of Cepeginterferon alfa-2B can be decreased when used in combination with Polidocanol.
Certolizumab pegolThe therapeutic efficacy of Certolizumab pegol can be decreased when used in combination with Polidocanol.
Damoctocog alfa pegolThe therapeutic efficacy of Damoctocog alfa pegol can be decreased when used in combination with Polidocanol.
Egaptivon pegolThe therapeutic efficacy of Polidocanol can be decreased when used in combination with Egaptivon pegol.
ElapegademaseThe therapeutic efficacy of Elapegademase can be decreased when used in combination with Polidocanol.
Eptacog alfa pegol (activated)The therapeutic efficacy of Eptacog alfa pegol (activated) can be decreased when used in combination with Polidocanol.
GlycoPEG-GCSFThe therapeutic efficacy of Polidocanol can be decreased when used in combination with GlycoPEG-GCSF.
Heptaethylene Glycol, Peg330The therapeutic efficacy of Polidocanol can be decreased when used in combination with Heptaethylene Glycol, Peg330.
Food Interactions
No interactions found.

References

General References
  1. Peterson JD, Goldman MP, Weiss RA, Duffy DM, Fabi SG, Weiss MA, Guiha I: Treatment of reticular and telangiectatic leg veins: double-blind, prospective comparative trial of polidocanol and hypertonic saline. Dermatol Surg. 2012 Aug;38(8):1322-30. doi: 10.1111/j.1524-4725.2012.02422.x. Epub 2012 May 23. [PubMed:22620717]
  2. Weiss RA, Voigts R, Howell DJ: Absence of concentration congruity in six compounded polidocanol samples obtained for leg sclerotherapy. Dermatol Surg. 2011 Jun;37(6):812-5. doi: 10.1111/j.1524-4725.2011.01906..x. [PubMed:21605244]
  3. Link [Link]
External Links
KEGG Drug
D01993
KEGG Compound
C13493
PubChem Compound
656641
PubChem Substance
175427093
ChemSpider
570993
ChEBI
46859
ChEMBL
CHEMBL1231723
HET
CE9
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Polidocanol
ATC Codes
C05BB02 — Polidocanol
AHFS Codes
  • 24:16.00 — Sclerosing Agents
PDB Entries
3dm8 / 5k9d
FDA label
Download (86.7 KB)
MSDS
Download (567 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2Unknown StatusTreatmentEpicondylitis / Tendinopathy1
3CompletedTreatmentAsthma Bronchial1
3CompletedTreatmentBronchial Asthma1
4CompletedTreatmentTelangiectasias / Varicosities of the great saphenous vein1
4CompletedTreatmentVaricosities of the great saphenous vein2
4Not Yet RecruitingTreatmentCystic tumour of the ganglia1
4WithdrawnTreatmentReflux / Ulcer, Leg / Varicose Ulcers / Varicose Veins Leg / Varicosities of the great saphenous vein / Venous Leg Ulcer (VLU) / Venous Reflux / Venous Ulcers1
Not AvailableRecruitingNot AvailableVenous Leg Ulcer (VLU)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
Injection, solutionIntravenous0.00500 g/1mL
Injection, solutionIntravenous0.01000 g/1mL
Kit180 mg/1mL
KitIntravenous1.3 mg
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US7814943No2010-10-192027-11-19Us
US7842282No2010-11-302020-05-26Us
US7604185No2009-10-202020-05-26Us
US7357336No2008-04-152020-05-26Us
US7025290No2006-04-112020-05-26Us
US6572873No2003-06-032020-05-26Us
US7731986No2010-06-082024-11-17Us
USRE40640No2009-02-172016-10-14Us
US8734833No2014-05-272020-05-26Us
US8122917No2012-02-282024-09-09Us
US6942165No2005-09-132020-05-26Us
US8323677No2012-12-042020-05-26Us
US6846412No2005-01-252022-07-19Us
US7842283No2010-11-302020-05-26Us
US9480652No2016-11-012032-05-12Us

Properties

State
Liquid
Experimental Properties
PropertyValueSource
melting point (°C)33-36 °CNot Available
boiling point (°C)615.857 °C at 760 mmHgNot Available
water solubilitymiscible http://ec.europa.eu/health/ph_risk/committees/04_sccp/docs/sccp_o_113.pdf
logP3.94# http://www.chemicalize.org/structure/#!mol=polidocanol
Predicted Properties
PropertyValueSource
Water Solubility0.000403 mg/mLALOGPS
logP3.15ALOGPS
logP3.94ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)15.12ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area103.3 Å2ChemAxon
Rotatable Bond Count37ChemAxon
Refractivity158.33 m3·mol-1ChemAxon
Polarizability74.49 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Download (10.2 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as polyethylene glycols. These are oligomers or polymers of ethylene oxide, with the general formula (C2H4O)n (with n>=3).
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Ethers
Direct Parent
Polyethylene glycols
Alternative Parents
Primary alcohols / Hydrocarbon derivatives
Substituents
Polyethylene glycol / Hydrocarbon derivative / Primary alcohol / Alcohol / Aliphatic acyclic compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
hydroxypolyether (CHEBI:46859)

Drug created on September 14, 2010 10:21 / Updated on November 18, 2018 04:53