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ORGANIC SPECTROSCOPY

Read all about Organic Spectroscopy on ORGANIC SPECTROSCOPY INTERNATIONAL 

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DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO, Born in Mumbai in 1964 and graduated from Mumbai University, Completed his Ph.D from ICT, 1991,Matunga, Mumbai, India, in Organic Chemistry, The thesis topic was Synthesis of Novel Pyrethroid Analogues, Currently he is working with GLENMARK LIFE SCIENCES LTD, Research Centre as Principal Scientist, Process Research (bulk actives) at Mahape, Navi Mumbai, India. Total Industry exp 30 plus yrs, Prior to joining Glenmark, he has worked with major multinationals like Hoechst Marion Roussel, now Sanofi, Searle India Ltd, now RPG lifesciences, etc. He has worked with notable scientists like Dr K Nagarajan, Dr Ralph Stapel, Prof S Seshadri, Dr T.V. Radhakrishnan and Dr B. K. Kulkarni, etc, He did custom synthesis for major multinationals in his career like BASF, Novartis, Sanofi, etc., He has worked in Discovery, Natural products, Bulk drugs, Generics, Intermediates, Fine chemicals, Neutraceuticals, GMP, Scaleups, etc, he is now helping millions, has 9 million plus hits on Google on all Organic chemistry websites. His friends call him Open superstar worlddrugtracker. His New Drug Approvals, Green Chemistry International, All about drugs, Eurekamoments, Organic spectroscopy international, etc in organic chemistry are some most read blogs He has hands on experience in initiation and developing novel routes for drug molecules and implementation them on commercial scale over a 30 PLUS year tenure till date June 2021, Around 35 plus products in his career. He has good knowledge of IPM, GMP, Regulatory aspects, he has several International patents published worldwide . He has good proficiency in Technology transfer, Spectroscopy, Stereochemistry, Synthesis, Polymorphism etc., He suffered a paralytic stroke/ Acute Transverse mylitis in Dec 2007 and is 90 %Paralysed, He is bound to a wheelchair, this seems to have injected feul in him to help chemists all around the world, he is more active than before and is pushing boundaries, He has 9 million plus hits on Google, 2.5 lakh plus connections on all networking sites, 90 Lakh plus views on dozen plus blogs, 233 countries, 7 continents, He makes himself available to all, contact him on +91 9323115463, email amcrasto@gmail.com, Twitter, @amcrasto , He lives and will die for his family, 90% paralysis cannot kill his soul., Notably he has 33 lakh plus views on New Drug Approvals Blog in 233 countries......https://newdrugapprovals.wordpress.com/ , He appreciates the help he gets from one and all, Friends, Family, Glenmark, Readers, Wellwishers, Doctors, Drug authorities, His Contacts, Physiotherapist, etc

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Sotradecol, Sodium tetradecyl sulfate


Sodium 7-ethyl-2-methyl-4-undecanyl sulfate.svg
ChemSpider 2D Image | sodium tetradecyl sulfate | C14H29NaO4S

Sotradecol

Sodium tetradecyl sulfate

cas 139-88-8, Na FORM

free form  300-52-7

  • Molecular FormulaC14H29NaO4S
  • Average mass316.432 Da

139-88-8 [RN], cas 1191-50-0,

4-Undecanol, 7-ethyl-2-methyl-, hydrogen sulfate, sodium salt (1:1)
7-Ethyl-2-methyl-4-undecyl sulfate sodium salt
UNII:Q1SUG5KBD6
натрия тетрадецилсульфат [Russian] [INN]
تتراديسيل سولفات صوديوم [Arabic] [INN]
十四烷硫酸钠 [Chinese] [INN]
CAS Registry Number: 139-88-8 
CAS Name: 7-Ethyl-2-methyl-4-undecanol hydrogen sulfate sodium salt 
Additional Names: 7-ethyl-2-methyl-4-hendecanol sulfate sodium salt; sodium 2-methyl-7-ethyl-4-undecyl sulfate; sodium 7-ethyl-2-methylundecyl-4-sulfate 
Trademarks: Sotradecol (Elkins-Sinn); Tergitol 4; Trombavar; Trombovar 
Molecular Formula: C14H29NaSO4, Molecular Weight: 316.43 
Percent Composition: C 53.14%, H 9.24%, Na 7.27%, S 10.13%, O 20.22% 
Properties: White, waxy solid. Sol in water, alcohol, ether. The pH of a 5% soln is from 6.5 to 9.0. Surface tension (dynes/cm) of aq soln at 25°: 56.5 dynes/cm (0.05% w/w); 52 (0.10%); 47 (0.20%); 40 (0.50%); 35 (1.0%). LD50 orally in rats: 4.95 g/kg, H. F. Smyth, C. P. Carpenter, J. Ind. Hyg. Toxicol.30, 63 (1948). 
Toxicity data: LD50 orally in rats: 4.95 g/kg, H. F. Smyth, C. P. Carpenter, J. Ind. Hyg. Toxicol.30, 63 (1948) 
Use: Wetting agent. 
Therap-Cat: Sclerosing agent., Keywords: Sclerosing Agent.

Synonyms of Sodium Tetradecyl Sulfate [INN]

  • 4-Ethyl-1-isobutyloktylsiran sodny
  • EINECS 205-380-3
  • Natrii tetracylis sulfas
  • Natrii tetradecylis sulfas
  • Natrii tetradecylis sulfas [Latin]
  • Natrii tetradecylsulfas
  • NSC 755887
  • Obliterol
  • Sodium sotradecol
  • Sodium tetradecyl sulfate
  • Sotradecol
  • Tergitol
  • Tergitol 4
  • Tergitol anionic 4
  • Tergitol penetrant 4
  • Tetradecilsulfato sodico
  • Tetradecilsulfato sodico [Spanish]
  • Tetradecyl sulfate de sodium
  • Trombovar
  • UNII-Q1SUG5KBD6
  • Varicol

An anionic surface-active agent used for its wetting properties in industry and used in medicine as an irritant and sclerosing agent for hemorrhoids and varicose veins.

wdt-16

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Sodium tetradecyl sulfate is an anionic surfactant which occurs as a white, waxy solid. The structural formula is as follows:

SOTRADECOL (Sodium Tetradscyl Sulfate) structural formula illustration

C14H28NaS04       7-Ethyl -2-methyl -4-hendecanol sulfate sodium salt       MW 316.44Sotradecol® (sodium tetradecyl sulfate injection) is a sterile nonpyrogenic solution for intravenous use as a sclerosing agent.

1% (10 mg/mL): Each mL contains sodium tetradecyl sulfate 10 mg, benzyl alcohol 0.02 mL and dibasic sodium phosphate, anhydrous 4.0 mg in Water for Injection. pH 7.9; monobasic sodium phosphate and/or sodium hydroxide added, if needed, for pH adjustment.

3% (30 mg/mL): Each mL contains sodium tetradecyl sulfate 30 mg, benzyl alcohol 0.02 mL and dibasic sodium phosphate, anhydrous 9.0 mg in Water for Injection. pH 7.9; monobasic sodium phosphate and/or sodium hydroxide added, if needed, for pH adjustment.

Sodium tetradecyl sulfate (STS) is a commonly used synonym for 7-ethyl-2-methyl-4-undecanyl sulfate sodium salt[1] which is anionicsurfactant that is the active component of the sclerosant drug Sotradecol. It is commonly used in the treatment of varicose and spider veins of the leg, during the procedure of sclerotherapy.[2] Being a detergent, its action is on the lipid molecules in the cells of the vein wall, causing inflammatory destruction of the internal lining of the vein and thrombus formation eventually leading to sclerosis of the vein. It is used in concentrations ranging from 0.1% to 3% for this purpose. It is occasionally used for the treatment of stabilisation of joints that regularly dislocate, particularly in patients with Ehlers-Danlos syndrome.[3] In the UK, Ireland, Italy, Australia, New Zealand and South Africa, it is sold under the trade-name Fibro-Vein in concentrations of 0.2%, 0.5%, 1.0%, and 3%.[4]

Synthesis

It may be prepared by the aldol condensation of methyl isobutyl ketone and 2-ethylhexanal (which is itself formed by the aldol self-concensation of butyraldehyde), followed by sulfonation of the resulting alcohol.

SYN

RSC Advances, 10(22), 12788-12799; 2020

https://pubs.rsc.org/en/content/articlelanding/2020/RA/D0RA00386G

PAT

CN 106278961

CN 106278958

 U.S.S.R., 1051067,

NMR

Compound name:Sodium Tetradecyl Sulfate
Spectrum type:1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)

References

  1. ^ “SOTRADECOL® (Sodium tetradecyl sulfate)” (PDF). Retrieved 29 August 2014.
  2. ^ Jenkinson HA, Wilmas KM, Silapunt S (November 2017). “Sodium Tetradecyl Sulfate: A Review of Clinical Uses”. Dermatologic Surgery43 (11): 1313–1320. doi:10.1097/DSS.0000000000001143PMID 28430735.
  3. ^ Burling F (2019). “Comparison of tetradecyl sulfate versus polidocanol injections for stabilisation of joints that regularly dislocate in an Ehlers-Danlos population”BMJ Open Sport & Exercise Medicine5 (1): e000481. doi:10.1136/bmjsem-2018-000481PMC 6350757PMID 30792884.
  4. ^ Fibro-Vein history and details
Clinical data
Other names7-Ethyl-2-methyl-4-hendecanol sulfate sodium salt
AHFS/Drugs.comConsumer Drug Information
Routes of
administration
Intravenous injection
ATC codeC05BB04 (WHO)
Legal status
Legal statusIn general: ℞ (Prescription only)
Identifiers
showIUPAC name
CAS Number139-88-8 
PubChemCID14492
ChemSpider8440 
UNIIQ1SUG5KBD6
ChEMBLChEMBL1200354 
CompTox Dashboard (EPA)DTXSID3041530 
ECHA InfoCard100.004.892
Chemical and physical data
FormulaC14H29NaO4S
Molar mass316.43 g·mol−1
3D model (JSmol)Interactive image
showSMILES
showInChI
  (what is this?)  (verify)

///////Sodium tetradecyl sulfate, sotradecol, Sclerosing Agent, varicose veins

CCCCCCCCCCCCCCOS(=O)(=O)[O-].[Na+]

wdt-3

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POLIDOCANOL


Polidocanol skeletal.svg
Molecular Structure of 3055-99-0 (3,6,9,12,15,18,21,24,27-Nonaoxanonatriacontan-1-ol)

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.

EINECS221-284-4
CAS No.3055-99-0Density1.007 g/cm3
PSA103.30000LogP4.04900
Solubility Melting Point33-36 °C
FormulaC30H62O10Boiling Point615.857 °C at 760 mmHg
Molecular Weight582.43Flash Point326.259 °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.

wdt-16

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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 AscleraAethoxysklerol[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”. Phlebology33 (3): 150–162. doi:10.1177/0268355516687864PMID 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 Therapy31 (1). doi:10.1111/dth.12568PMID 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 namesPolydocanolLaureth 9Macrogol lauryl etherLauromacrogolPEG-9 lauryl alcoholPOE-9 lauryl alcoholDodecylpolyethyleneglycoletherHydroxyl polyethoxy dodecaneOxypolyethoxydodecane
AHFS/Drugs.comInternational Drug Names
Pregnancy
category
Topical: allowed
Injection: contraindication in months 1–3 and after week 36
Routes of
administration
topical, subcutaneous injection
ATC codeC05BB02 (WHO)
Legal status
Legal statusOTC (topical),  (injection)
Identifiers
showIUPAC name
CAS Number9002-92-0 
3055-99-0
PubChem CID656641
ChemSpider570993 
UNII0AWH8BFG9A
KEGGD01993 
ChEMBLChEMBL1201751 
ECHA InfoCard100.019.351 
Chemical and physical data
FormulaC30H62O10
Molar mass582.816 g·mol−1
3D model (JSmol)Interactive image
showSMILES
showInChI
  (what is this?)  (verify)

////////POLIDOCANOL, Anesthetic ,  Antipruritic, Sclerosing Agent,

CCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO

wdt-2

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