POLIDOCANOL

Synonym: Polidocanol; C12E9, Dodecyl nonaethylene glycol ether, Dodecylnonaglycol, Polidocanol, Polyoxyethylene (9) lauryl ether; trade names: Asclera, Aethoxysklerol and Varithena; Laureth-9; Dodecylnonaoxyethylene glycol monoether

IUPAC/Chemical Name: 3,6,9,12,15,18,21,24,27-nonaoxanonatriacontan-1-ol

3055-99-0
Chemical Formula: C30H62O10
Exact Mass: 582.4343Polidocanol 
CAS Registry Number: 9002-92-0 
CAS Name: a-Dodecyl-w-hydroxypoly(oxy-1,2-ethanediyl) 
Additional Names: polyethylene glycol (9) monododecyl ether; dodecyl alcohol polyoxyethylene ether; hydroxypolyethoxydodecane; laureth 9; polyoxyethylene lauryl ether 
Trademarks: Aethoxysklerol (Kreussler); Aetoxisclerol (Dexo); Atlas G-4829 (ICI); Hetoxol L-9 (Heterene Chem.)Line Formula: C12H25(OCH2CH2)nOH 
Literature References: Contains an average of nine ethylene oxide units and has an average mol wt ~600. Prepd by reaction of ethylene oxide and dodecyl alcohol: Pertsemlides, Soehring, Arzneim.-Forsch.10, 990 (1960). Toxicology: H. S. Zipf et al.,ibid.7, 162 (1957). Review of clinical experience: P. M. Goldman, J. Dermatol. Surg. Oncol.15, 204-209 (1989). 
Properties: Sol in water, ethanol, toluene. Miscible with hot mineral, natural and synthetic oils; with fats and fatty alcohols. LD50 in mice (mg/kg): 1170 orally, 125 i.v. (Zipf). 
Toxicity data: LD50 in mice (mg/kg): 1170 orally, 125 i.v. (Zipf) 
Use: Solvent; nonionic emulsifier; pharmaceutic aid (surfactant); spermaticide. 
Therap-Cat: Anesthetic (topical); antipruritic; sclerosing agent. 
Keywords: Anesthetic (Local); Antipruritic; Sclerosing Agent.

EINECS	221-284-4
CAS No.	3055-99-0	Density	1.007 g/cm3
PSA	103.30000	LogP	4.04900
Solubility		Melting Point	33-36 °C
Formula	C30H62O10	Boiling Point	615.857 °C at 760 mmHg
Molecular Weight	582.43	Flash Point	326.259 °C

Polidocanol is a local anaesthetic and antipruritic component of ointments and bath additives. It relieves itching caused by eczema and dry skin.^[1] It has also been used to treat varicose veins,^[2] hemangiomas, and vascular malformations.^[3] It is formed by the ethoxylation of dodecanol.

Polidocanol is a local anaesthetic and antipruritic component of ointments and bath additives. It relieves itching caused by eczema and dry skin. It is formed by the ethoxylation of dodecanol. The substance is also used as a sclerosant, an irritant injected to treat varicose veins, under the trade names Asclera, Aethoxysklerol and Varithena. Polidocanol causes fibrosis inside varicose veins, occluding the lumen of the vessel, and reducing the appearance of the varicosity. The FDA has approved polidocanol injections for the treatment of small varicose (less than 1 mm in diameter) and reticular veins (1 to 3 mm in diameter). Polidocanol works by damaging the cell lining of blood vessels, causing them to close and eventually be replaced by other types of tissue.

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SYN

 

Yu, Zeqiong; Bo, Shaowei; Wang, Huiyuan; Li, Yu; Yang, Zhigang; Huang, Yongzhuo; Jiang, Zhong-Xing. Application of Monodisperse PEGs in Pharmaceutics: Monodisperse Polidocanols. Molecular Pharmaceutics. Volume 14. Issue 10. Pages 3473-3479. 2017.

SYN 2

Jiang, Zhongxing; Yu, Zeqiong. Process for preparation of monodisperse nona-polyethylene glycol dodecyl alcohol monoether and sulfate. Assignee Wuhan University, Peop. Rep. China. CN 106316802. (2017).

Sclerotherapy

Polidocanol is also used as a sclerosant, an irritant injected to treat varicose veins, under the trade names Asclera, Aethoxysklerol^[4] and Varithena.^[5] Polidocanol causes fibrosis inside varicose veins, occluding the lumen of the vessel, and reducing the appearance of the varicosity.

The FDA has approved polidocanol injections for the treatment of small varicose (less than 1 mm in diameter) and reticular veins (1 to 3 mm in diameter). Polidocanol works by damaging the cell lining of blood vessels, causing them to close and eventually be replaced by other types of tissue.^[6][7] Polidocanol in the form of Varithena injected in the greater saphenous vein can cause the eruption of varicose and spider veins throughout the lower leg. This procedure should be done with caution and with the knowledge that the appearance of the leg may be forever compromised.

Pure polidocanol for pharmaceutical use

On March 30th,2010 the FDA approved Polidocanol under the trade name Asclera. 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 extremities. Varicose veins develop when the small valves inside the veins no longer work properly, allowing the blood to flow backwards and then pool in the vein.
When injected intravenously, Polidocanol works by locally damaging the endothelium of the blood vessel, causing platelets to aggregate at the site of damage and attach to the venous wall. Eventually, a dense network of platelets, cellular debris and fibrin occludes the vessel, which is then replaced with connective fibrous tissue. As one would expect for this type of molecule and also the mechanism of action, there is believed to be no specific molecular target for Polidocanol.
Polidocanol is a large ‘small molecule’ drug (Molecular Weight of 583 g.mol-1), with a mean half-life of 1.5 hr. Polidocanol is administrated intravenously and the strength of the solution and the volume injected depend on the size and extent of the varicose veins. Thus, the recommended dosage is 0.1 to 0.3 mL for each injection (Asclera 0.5% for spider veins and Asclera 1% for reticular veins) into each varicose vein, and a maximum recommended volume per treatment session of 10 mL.
Polidocanol’s chemical structure is 2-[2-[2-[2-[2-[2-[2-[2-[2-(dodecyloxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol. It is a non-ionic detergent, similar to polyethylene glycol (PEG) in structure, consisting of two components, a polar hydrophilic (dodecyl alcohol) and an apolar hydrophobic (polyethylene oxide – the part in brackets in the chemical structure) chain.

References

1. ^ “E45 itch relief cream”. netdoctor.co.uk. Retrieved 2007-07-12.
2. ^ Star P, Connor DE, Parsi K (April 2018). “Novel developments in foam sclerotherapy: Focus on Varithena® (polidocanol endovenous microfoam) in the management of varicose veins”. Phlebology. 33 (3): 150–162. doi:10.1177/0268355516687864. PMID 28166694.
3. ^ Gao Z, Zhang Y, Li W, Shi C (January 2018). “Effectiveness and safety of polidocanol for the treatment of hemangiomas and vascular malformations: A meta-analysis”. Dermatologic Therapy. 31 (1). doi:10.1111/dth.12568. PMID 29082587.
4. ^ Sclerotherapy, Laurence Z Rosenberg, MD, eMedicine.com
5. ^ “Varithena™ (polidocanol injectable foam) For Intravenous Use. Full Prescribing Information” (PDF). Biocompatibles, Inc. Archived from the original (PDF) on 4 August 2016. Retrieved 1 October 2015.
6. ^ Facts and Companies: Varicose Vein Treatment Approved
7. ^ “Asclera Full Prescribing Information in Drug Reference Encyclopedia”. Retrieved 2010-04-11.

Clinical data
Other names	PolydocanolLaureth 9Macrogol lauryl etherLauromacrogolPEG-9 lauryl alcoholPOE-9 lauryl alcoholDodecylpolyethyleneglycoletherHydroxyl polyethoxy dodecaneOxypolyethoxydodecane
AHFS/Drugs.com	International Drug Names
Pregnancy category	Topical: allowed Injection: contraindication in months 1–3 and after week 36
Routes of administration	topical, subcutaneous injection
ATC code	C05BB02 (WHO)
Legal status
Legal status	OTC (topical), ℞ (injection)
Identifiers
showIUPAC name
CAS Number	9002-92-0  3055-99-0
PubChem CID	656641
ChemSpider	570993
UNII	0AWH8BFG9A
KEGG	D01993
ChEMBL	ChEMBL1201751
ECHA InfoCard	100.019.351
Chemical and physical data
Formula	C30H62O10
Molar mass	582.816 g·mol−1
3D model (JSmol)	Interactive image
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////////POLIDOCANOL, Anesthetic ,  Antipruritic, Sclerosing Agent,

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