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Chemistry

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Also known as: 3055-99-0, Nonaethylene glycol monododecyl ether, 3,6,9,12,15,18,21,24,27-nonaoxanonatriacontan-1-ol, 9043-30-5, Laureth-9, Polyoxyethylene (9) lauryl ether
Molecular Formula
C30H62O10
Molecular Weight
582.8  g/mol
InChI Key
ONJQDTZCDSESIW-UHFFFAOYSA-N

Dodecylnonaglycol
Polidocanol is an alkyl polyglycol ether of lauryl alcohol with sclerosing and potential antineoplastic activities. Upon intralesional administration, polidocanol induces endothelial cell injury by disrupting calcium signaling and nitric oxide pathways. Following endothelial damage, platelets aggregate at the site of injury and attach to the venous wall, resulting in a dense network of platelets, cellular debris, and fibrin that occludes the vessel. Inducing endothelial cell damage within melanoma metastases may incite an antitumor response in untreated bystander lesions and inhibit the growth of in transit metastases and other cutaneous lesions.
1 2D Structure

Dodecylnonaglycol

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-[2-[2-[2-[2-[2-[2-[2-(2-dodecoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol
2.1.2 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
2.1.3 InChI Key
ONJQDTZCDSESIW-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO
2.2 Synonyms
2.2.1 Depositor-Supplied Synonyms

1. 3055-99-0

2. Nonaethylene Glycol Monododecyl Ether

3. 3,6,9,12,15,18,21,24,27-nonaoxanonatriacontan-1-ol

4. 9043-30-5

5. Laureth-9

6. Polyoxyethylene (9) Lauryl Ether

7. Polyethylene Glycol Monoisotridecyl Ether

8. Dodecyl Alcohol, Ethoxylated

9. Nonaoxyethylene Monododecyl Ether

10. Nonaethylene Glycol Monolauryl Ether

11. Polyoxyl 9 Lauryl Ether

12. 2-[2-[2-[2-[2-[2-[2-[2-(2-dodecoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol

13. Chebi:46859

14. Ncgc00166290-02

15. Dodecyl Nona Ethylene Glycol Ether

16. Genapol X-080

17. Dodecylnonaglycol

18. Dsstox_cid_19721

19. Dsstox_rid_79436

20. Dsstox_gsid_39721

21. Asclera

22. Cas-3055-99-0

23. C12e9

24. Polydocanol

25. Aethoxy-sklerol

26. Polidocanol [inn:dcf:jan]

27. Einecs 221-284-4

28. Mfcd00043375

29. Poele

30. Varithena

31. Peg-9 Lauryl Ether

32. Macrogol 9 Lauryl Ether

33. Polydocanol; Thesit

34. Polyoxyethylen-9-laurylether

35. Aeo-9

36. Schembl25580

37. Chembl1231723

38. Dtxsid5039721

39. Polyoxyethylene Isotridecyl Ether

40. Amy22525

41. Zinc8214662

42. Tox21_112394

43. C12-e9

44. Polyethylene Glycol 450 Lauryl Ether

45. Akos028108701

46. Dodecylnonaoxyethylene Glycol Monoether

47. Tox21_112394_1

48. Db06811

49. Ncgc00166290-01

50. Ncgc00166290-03

51. Bs-51745

52. Hy-108294

53. Cs-0028163

54. N1204

55. F20806

56. Sr-01000944476

57. J-018016

58. Poly(oxy-1,2-ethanediyl),a-isotridecyl-w-hydroxy-

59. Sr-01000944476-1

60. Nonaethylene Glycol Monododecyl Ether, Nonionic Surfactant

61. Polyethylene Glycol Monododecyl Ether (average Polymer, N = 9)

62. Nonaethylene Glycol Monododecyl Ether [for Biochemical Research]

63. Polyethylene Glycol Monododecyl Ether (average Polymer, N = 9; Nonaethylene Glycol Monododecyl Ether)

2.3 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 582.8 g/mol
Molecular Formula C30H62O10
XLogP33.9
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count10
Rotatable Bond Count37
Exact Mass582.43429817 g/mol
Monoisotopic Mass582.43429817 g/mol
Topological Polar Surface Area103 Ų
Heavy Atom Count40
Formal Charge0
Complexity431
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

A randomized, open, multicenter study comparing the safety and efficacy of single or repeated endoscopic injection of Beriplast, a fibrin glue, with those of single endoscopic injection of 1% polidocanol (Aethoxysklerol) for the prevention of GI hemorrhage was conducted in 850 patients (ages 21-94 yr) with bleeding gastroduodenal ulcers. Recurrent bleeding rates among patients in whom the rates could be assessed were 58 of 254 in the polidocanol group, 51 of 266 in the fibrin glue single group, and 41 of 270 in the fibrin glue repeated group. The difference between fibrin glue repeated treatment and polidocanol was significant. Treatment failed, making other therapy necessary, in 34 of 261 in the polidocanol group, 34 of 274 in the fibrin glue single group, and 21 of 274 in the fibrin glue repeated group. The 30 day mortality rates were low in all groups. The safety profiles of the 3 treatments were similar.

Rutgeerts P et al; Lancet 350: 692-696 (1997)


Sclerosing Solutions; Tissue Adhesives; Detergents

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


IN VARIOUS CONCN THESIT AND A MIXT OF SIMILAR ALKYL ETHOXYLATES KNOWN BY THE CODE NAME SCH 600 HAVE BEEN USED IN MAN AND ANIMALS FOR CORNEAL ANESTHESIA, FOR MUCOSAL ANESTHESIA PRECEDING ENDOSCOPY, FOR RELIEF FROM ITCHING (APPLIED LOCALLY TO THE ANUS, RECTUM, VAGINA, SKIN LESIONS, ETC), FOR NERVE BLOCKS (BY INFILTRATION), FOR SPERMICIDAL ACTIVITY (WHEN INSTILLED IN THE VAGINA), FOR RELIEF OF PAIN FROM PEPTIC ULCER (WHEN INGESTED).

Gosselin, R.E., H.C. Hodge, R.P. Smith, and M.N. Gleason. Clinical Toxicology of Commercial Products. 4th ed. Baltimore: Williams and Wilkins, 1976., p. II-180


MEDICATION (VET): PERFUSION OF ISOLATED GUINEA PIG HEARTS WITH POLIDOCANOL @ 20, 40, OR 100 UG DOSE-DEPENDENTLY DECR HEART RATE & CONTRACTILE STRENGTH & INCR ATRIAL REFRACTORY PERIOD. IN RATS, POLIDOCANOL INFUSION @ 10, 20, 30, AND 40 MG/KG DECR BLOOD PRESSURE & HEART RATE. DURING INFUSION, PQ INTERVAL OF THE ECG WAS ALSO PROLONGED. THESE CHANGES WERE DISCUSSED IN TERMS OF ITS USE FOR SCLEROTHERAPY OF PATIENTS WITH ESOPHAGEAL VARICES.

THIES E ET AL; CARDIAC EFFECTS OF POLIDOCANOL, A SCLEROTHERAPEUTIC DRUG- EXPERIMENTAL EVALUATIONS; CHIR FORUM EXP KLIN FORSCH 313 (1982)


For more Therapeutic Uses (Complete) data for DODECYL ALCOHOL, ETHOXYLATED (6 total), please visit the HSDB record page.


4.2 Minimum/Potential Fatal Human Dose

3. 3= MODERATELY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 0.5-5 G/KG, BETWEEN 1 OZ AND 1 PT (OR 1 LB) FOR 70 KG PERSON (150 LB).

Gosselin, R.E., H.C. Hodge, R.P. Smith, and M.N. Gleason. Clinical Toxicology of Commercial Products. 4th ed. Baltimore: Williams and Wilkins, 1976., p. II-180


4.3 Drug Indication

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


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

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


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Sclerosing Agent [EPC]; Vascular Sclerosing Activity [PE]; Sclerosing Activity [MoA]
5.3 ATC Code

C05BB02

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


C - Cardiovascular system

C05 - Vasoprotectives

C05B - Antivaricose therapy

C05BB - Sclerosing agents for local injection

C05BB02 - Polidocanol


5.4 Absorption, Distribution and Excretion

Absorption

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


Route of Elimination

Route of elimination was not indicated.


Volume of Distribution

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


Clearance

Sytemic clearance was 0.2-0.4 L/min.


5.5 Metabolism/Metabolites

Metabolism was not measured.


5.6 Biological Half-Life

The half-life is approximately 1.5 h.


5.7 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.


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