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Showing drug card for Sodium Tetradecyl Sulfate (DB00464)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-04-16 16:47:43
Primary Accession Number DB00464
Secondary Accession Number
  • APRD00575
Name Sodium Tetradecyl Sulfate
Drug Type
  • Approved
  • Small Molecule
Description 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.
Synonyms
  1. Monotetradecylsulfate sodium salt
  2. S.T.D.
  3. STD
  4. Sodium myristyl sulfate
  5. Tetradecyl hydrogen sulphate
  6. Tetradecyl sodium sulfate
  7. Tetradecyl sulfate
  8. Tetradecyl sulfuric Acid
Brand Names
  1. Niaproof-4
  2. Sotradecol
  3. Tergitol-4
  4. Texapon K 14
Brand Mixtures Not Available
Chemical IUPAC Name sodium tetradecyl sulfate
Chemical Formula C14H30O4S
Chemical Structure Structure
CAS Registry Number 1191-50-0
InChI Identifier InChI=1/C14H30O4S/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-18-19(15,16)17/h2-14H2,1H3,(H,15,16,17)/f/h15H
InChI Key URLJMZWTXZTZRR-YAQRNVERCC
KEGG Drug Not Available
KEGG Compound Not Available
PubChem Compound 14492 Link Image
PubChem Substance 14874529 Link Image
ChEBI ID Not Available
PharmGKB ID PA451439 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 00363332 Link Image
RxList Link http://www.rxlist.com/cgi/generic2/sotradecol.htm Link Image
PDRhealth Link Not Available
Wikipedia Link Not Available
FDA Label Not Available
Material Safety Data Sheet (MSDS)
Synthesis Reference Not Available
Average Molecular Weight 294.4510
Monoisotopic Molecular Weight 294.1865
State Solid
Melting Point Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 2.62e-03 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP 2.60 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -5.05 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES CCCCCCCCCCCCCCOS(O)(=O)=O
Canonical SMILES CCCCCCCCCCCCCCOS(O)(=O)=O
Drug Category
  • Sclerosing Agents
  • Surface-Active Agents
ATC Codes
AHFS Codes
  • 24:16.00
Indication For the treatment of small uncomplicated varicose veins of the lower extremities that show simple dilation with competent valves.
Pharmacology Sodium tetradecyl sulfate is an anionic surfactant which occurs as a white, waxy solid. It is used as a sclerosing agent in sclerotherapy. Sclerotherapy is an injection of a sclerosing agent directly through the skin into a lesion and is used primarily for slow-flow vascular anomalies, particularly for venous malformation and lymphatic malformation. Intravenous injection causes intima inflammation and thrombus formation. This usually occludes the injected vein. Subsequent formation of fibrous tissue results in partial or complete vein obliteration that may or may not be permanent.
Mechanism of Action Sodium tetradecyl sulfate is a potent toxin for endothelial cells in that brief exposure to even low concentrations are effective in stripping endothelium over a considerable distance and exposing highly thrombogenic endothelium in the process. Diluted sodium tetradecyl sulfate is also able to induce a hypercoagulable state, possibly by selective inhibition of protein C, and can also promote platelet aggregation.
Absorption Not Available
Toxicity LD50=1250 mg/kg (Orally in rat); LD50=3 ml/kg (Skin in rat)
Protein Binding Not Available
Biotransformation Not Available
Half Life Not Available
Dosage Forms
Form Route
Solution Intravenous
Patient Information Not Available
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions Not Available
Food Interactions Not Available
Pathways Not Available
General References
  1. RxList Link Image
Organisms Affected
  • Humans and other mammals
Targets
  1. Vitamin K-dependent protein C
Drug Target 1 [top]
Target 1 ID 422
Target 1 Name Vitamin K-dependent protein C
Target 1 Synonyms
  1. Anticoagulant protein C
  2. Autoprothrombin IIA
  3. Blood coagulation factor XIV
  4. EC 3.4.21.69
  5. Vitamin K-dependent protein C precursor
Target 1 Gene Name PROC
Target 1 Protein Sequence >Vitamin K-dependent protein C precursor 
MWQLTSLLLFVATWGISGTPAPLDSVFSSSERAHQVLRIRKRANSFLEELRHSSLERECI
EEICDFEEAKEIFQNVDDTLAFWSKHVDGDQCLVLPLEHPCASLCCGHGTCIDGIGSFSC
DCRSGWEGRFCQREVSFLNCSLDNGGCTHYCLEEVGWRRCSCAPGYKLGDDLLQCHPAVK
FPCGRPWKRMEKKRSHLKRDTEDQEDQVDPRLIDGKMTRRGDSPWQVVLLDSKKKLACGA
VLIHPSWVLTAAHCMDESKKLLVRLGEYDLRRWEKWELDLDIKEVFVHPNYSKSTTDNDI
ALLHLAQPATLSQTIVPICLPDSGLAERELNQAGQETLVTGWGYHSSREKEAKRNRTFVL
NFIKIPVVPHNECSEVMSNMVSENMLCAGILGDRQDACEGDSGGPMVASFHGTWFLVGLV
SWGEGCGLLHNYGVYTKVSRYLDWIHGHIRDKEAPQKSWAP
Target 1 Number of Residues 468
Target 1 Molecular Weight 52072
Target 1 Theoretical pI 6.23
Target 1 GO Classification
Function
catalytic activity
hydrolase activity
peptidase activity
endopeptidase activity
serine-type endopeptidase activity
binding
ion binding
cation binding
calcium ion binding
Process
metabolism
macromolecule metabolism
protein metabolism
cellular protein metabolism
proteolysis
physiological process
organismal physiological process
regulation of body fluids
hemostasis
blood coagulation
Component
extracellular region
Target 1 General Function Involved in calcium ion binding
Target 1 Specific Function Protein C is a vitamin K-dependent serine protease that regulates blood coagulation by inactivating factors Va and VIIIa in the presence of calcium ions and phospholipids
Target 1 Pathways Not Available
Target 1 Reactions
  • Degradation of blood coagulation factors Va and VIIIa
Target 1 Pfam Domain Function
Target 1 Signals
  • 1-32
Target 1 Transmembrane Regions
  • None
Target 1 Essentiality Non-Essential
Target 1 GenBank ID Protein 190334 Link Image
Target 1 UniProtKB/Swiss-Prot ID P04070 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name PROC_HUMAN Link Image
Target 1 PDB ID 1AUT Link Image
Target 1 PDB File Show
Target 1 3D Structure
Target 1 Cellular Location
  • Cytoplasmic
Target 1 Gene Sequence >1386 bp 
ATGTGGCAGCTCACAAGCCTCCTGCTGTTCGTGGCCACCTGGGGAATTTCCGGCACACCA
GCTCCTCTTGACTCAGTGTTCTCCAGCAGCGAGCGTGCCCACCAGGTGCTGCGGATCCGC
AAACGTGCCAACTCCTTCCTGGAGGAGCTCCGTCACAGCAGCCTGGAGCGGGAGTGCATA
GAGGAGATCTGTGACTTCGAGGAGGCCAAGGAAATTTTCCAAAATGTGGATGACACACTG
GCCTTCTGGTCCAAGCACGTCGACGGTGACCAGTGCTTGGTCTTGCCCTTGGAGCACCCG
TGCGCCAGCCTGTGCTGCGGGCACGGCACGTGCATCGACGGCATCGGCAGCTTCAGCTGC
GACTGCCGCAGCGGCTGGGAGGGCCGCTTCTGCCAGCGCGAGGTGAGCTTCCTCAATTGC
TCTCTGGACAACGGCGGCTGCACGCATTACTGCCTAGAGGAGGTGGGCTGGCGGCGCTGT
AGCTGTGCGCCTGGCTACAAGCTGGGGGACGACCTCCTGCAGTGTCACCCCGCAGTGAAG
TTCCCTTGTGGGAGGCCCTGGAAGCGGATGGAGAAGAAGCGCAGTCACCTGAAACGAGAC
ACAGAAGACCAAGAAGACCAAGTAGATCCGCGGCTCATTGATGGGAAGATGACCAGGCGG
GGAGACAGCCCCTGGCAGGTGGTCCTGCTGGACTCAAAGAAGAAGCTGGCCTGCGGGGCA
GTGCTCATCCACCCCTCCTGGGTGCTGACAGCGGCCCACTGCATGGATGAGTCCAAGAAG
CTCCTTGTCAGGCTTGGAGAGTATGACCTGCGGCGCTGGGAGAAGTGGGAGCTGGACCTG
GACATCAAGGAGGTCTTCGTCCACCCCAACTACAGCAAGAGCACCACCGACAATGACATC
GCACTGCTGCACCTGGCCCAGCCCGCCACCCTCTCGCAGACCATAGTGCCCATCTGCCTC
CCGGACAGCGGCCTTGCAGAGCGCGAGCTCAATCAGGCCGGCCAGGAGACCCTCGTGACG
GGCTGGGGCTACCACAGCAGCCGAGAGAAGGAGGCCAAGAGAAACCGCACCTTCGTCCTC
AACTTCATCAAGATTCCCGTGGTCCCGCACAATGAGTGCAGCGAGGTCATGAGCAACATG
GTGTCTGAGAACATGCTGTGTGCGGGCATCCTCGGGGACCGGCAGGATGCCTGCGAGGGC
GACAGTGGGGGGCCCATGGTCGCCTCCTTCCACGGCACCTGGTTCCTGGTGGGCCTGGTG
AGCTGGGGTGAGGGCTGTGGGCTCCTTCACAACTACGGCGTTTACACCAAAGTCAGCCGC
TACCTCGACTGGATCCATGGGCACATCAGAGACAAGGAAGCCCCCCAGAAGAGCTGGGCA
CCTTAG
Target 1 GenBank Gene ID
Target 1 GeneCard ID PROC Link Image
Target 1 GenAtlas ID PROC Link Image
Target 1 HGNC ID HGNC:9451 Link Image
Target 1 Chromosome Location 2
Target 1 Locus 2q13-q14
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Gandrille S, Vidaud M, Aiach M, Alhenc-Gelas M, Fischer AM, Gouault-Heilman M, Toulon P, Fiessinger JN, Goossens M: Two novel mutations responsible for hereditary type I protein C deficiency: characterization by denaturing gradient gel electrophoresis. Hum Mutat. 1992;1(6):491-500. [PubMed Link Image]
  2. Bovill EG, Tomczak JA, Grant B, Bhushan F, Pillemer E, Rainville IR, Long GL: Protein CVermont: symptomatic type II protein C deficiency associated with two GLA domain mutations. Blood. 1992 Mar 15;79(6):1456-65. [PubMed Link Image]
  3. Grundy CB, Chisholm M, Kakkar VV, Cooper DN: A novel homozygous missense mutation in the protein C (PROC) gene causing recurrent venous thrombosis. Hum Genet. 1992 Aug;89(6):683-4. [PubMed Link Image]
  4. Grundy CB, Schulman S, Tengborn L, Kakkar VV, Cooper DN: Two different missense mutations at Arg 178 of the protein C (PROC) gene causing recurrent venous thrombosis. Hum Genet. 1992 Aug;89(6):685-6. [PubMed Link Image]
  5. Harris RJ, Ling VT, Spellman MW: O-linked fucose is present in the first epidermal growth factor domain of factor XII but not protein C. J Biol Chem. 1992 Mar 15;267(8):5102-7. [PubMed Link Image]
  6. Yamamoto K, Matsushita T, Sugiura I, Takamatsu J, Iwasaki E, Wada H, Deguchi K, Shirakawa S, Saito H: Homozygous protein C deficiency: identification of a novel missense mutation that causes impaired secretion of the mutant protein C. J Lab Clin Med. 1992 Jun;119(6):682-9. [PubMed Link Image]
  7. Sugahara Y, Miura O, Yuen P, Aoki N: Protein C deficiency Hong Kong 1 and 2: hereditary protein C deficiency caused by two mutant alleles, a 5-nucleotide deletion and a missense mutation. Blood. 1992 Jul 1;80(1):126-33. [PubMed Link Image]
  8. Miletich JP, Broze GJ Jr: Beta protein C is not glycosylated at asparagine 329. The rate of translation may influence the frequency of usage at asparagine-X-cysteine sites. J Biol Chem. 1990 Jul 5;265(19):11397-404. [PubMed Link Image]
  9. Reitsma PH, Poort SR, Allaart CF, Briet E, Bertina RM: The spectrum of genetic defects in a panel of 40 Dutch families with symptomatic protein C deficiency type I: heterogeneity and founder effects. Blood. 1991 Aug 15;78(4):890-4. [PubMed Link Image]
  10. Romeo G, Hassan HJ, Staempfli S, Roncuzzi L, Cianetti L, Leonardi A, Vicente V, Mannucci PM, Bertina R, Peschle C, et al.: Hereditary thrombophilia: identification of nonsense and missense mutations in the protein C gene. Proc Natl Acad Sci U S A. 1987 May;84(9):2829-32. [PubMed Link Image]
  11. 2602169 Grundy C, Chitolie A, Talbot S, Bevan D, Kakkar V, Cooper DN: Protein C London 1: recurrent mutation at Arg 169 (CGG----TGG) in the protein C gene causing thrombosis. Nucleic Acids Res. 1989 Dec 25;17(24):10513.
  12. 2991859 Beckmann RJ, Schmidt RJ, Santerre RF, Plutzky J, Crabtree GR, Long GL: The structure and evolution of a 461 amino acid human protein C precursor and its messenger RNA, based upon the DNA sequence of cloned human liver cDNAs. Nucleic Acids Res. 1985 Jul 25;13(14):5233-47.
  13. 2991887 Foster DC, Yoshitake S, Davie EW: The nucleotide sequence of the gene for human protein C. Proc Natl Acad Sci U S A. 1985 Jul;82(14):4673-7.
  14. 3511471 Plutzky J, Hoskins JA, Long GL, Crabtree GR: Evolution and organization of the human protein C gene. Proc Natl Acad Sci U S A. 1986 Feb;83(3):546-50.
  15. 6589623 Foster D, Davie EW: Characterization of a cDNA coding for human protein C. Proc Natl Acad Sci U S A. 1984 Aug;81(15):4766-70.
  16. 7605880 Millar DS, Bevan D, Chitolie A, Reynaud J, Chisholm M, Kakkar VV, Cooper DN: Three novel mutations in the protein C (PROC) gene causing venous thrombosis. Blood Coagul Fibrinolysis. 1995 Apr;6(2):138-40.
  17. 7792728 Lind B, Schwartz M, Thorsen S: Six different point mutations in seven Danish families with symptomatic protein C deficiency. Thromb Haemost. 1995 Feb;73(2):186-93.
  18. 7841323 Millar DS, Allgrove J, Rodeck C, Kakkar VV, Cooper DN: A homozygous deletion/insertion mutation in the protein C (PROC) gene causing neonatal Purpura fulminans: prenatal diagnosis in an at-risk pregnancy. Blood Coagul Fibrinolysis. 1994 Aug;5(4):647-9.
  19. 7841324 Witt I, Beck S, Seydewitz HH, Tasangil C, Schenck W: A novel homozygous missense mutation (Val 325-->Ala) in the protein C gene causing neonatal purpura fulminans. Blood Coagul Fibrinolysis. 1994 Aug;5(4):651-3.
  20. 7865674 Zheng YZ, Sakata T, Matsusue T, Umeyama H, Kato H, Miyata T: Six missense mutations associated with type I and type II protein C deficiency and implications obtained from molecular modelling. Blood Coagul Fibrinolysis. 1994 Oct;5(5):687-96.
  21. 7878626 Long GL, Tomczak JA, Rainville IR, Dreyfus M, Schramm W, Schwarz HP: Homozygous type I protein C deficiency in two unrelated families exhibiting thrombophilia related to Ala136-->Pro or Arg286-->His mutations. Thromb Haemost. 1994 Oct;72(4):526-33.
  22. 7919373 Gandrille S, Jude B, Alhenc-Gelas M, Emmerich J, Aiach M: First de novo mutations in the protein C gene of two patients with type I deficiency: a missense mutation and a splice site deletion. Blood. 1994 Oct 15;84(8):2566-70.
  23. 7974343 Gaussem P, Gandrille S, Duchemin J, Emmerich J, Alhenc-Gelas M, Aillaud MF, Aiach M: Influence of six mutations of the protein C gene on the Gla domain conformation and calcium affinity. Thromb Haemost. 1994 Jun;71(6):748-54.
  24. 8003977 Fisher CL, Greengard JS, Griffin JH: Models of the serine protease domain of the human antithrombotic plasma factor activated protein C and its zymogen. Protein Sci. 1994 Apr;3(4):588-99.
  25. 8292730 Tsay W, Greengard JS, Montgomery RR, McPherson RA, Fucci JC, Koerper MA, Coughlin J, Griffin JH: Genetic mutations in ten unrelated American patients with symptomatic type 1 protein C deficiency. Blood Coagul Fibrinolysis. 1993 Oct;4(5):791-6.
  26. 8324221 Gandrille S, Alhenc-Gelas M, Gaussem P, Aillaud MF, Dupuy E, Juhan-Vague I, Aiach M: Five novel mutations located in exons III and IX of the protein C gene in patients presenting with defective protein C anticoagulant activity. Blood. 1993 Jul 1;82(1):159-68.
  27. 8398832 Marchetti G, Patracchini P, Gemmati D, Castaman G, Rodeghiero F, Wacey A, Cooper DN, Tuddenham EG, Bernardi F: Symptomatic type II protein C deficiency caused by a missense mutation (Gly 381-->Ser) in the substrate-binding pocket. Br J Haematol. 1993 Jun;84(2):285-9.
  28. 8446940 Reitsma PH, Poort SR, Bernardi F, Gandrille S, Long GL, Sala N, Cooper DN: Protein C deficiency: a database of mutations. For the Protein C & S Subcommittee of the Scientific and Standardization Committee of the International Society on Thrombosis and Haemostasis. Thromb Haemost. 1993 Jan 11;69(1):77-84.
  29. 8477066 Mimuro J, Muramatsu S, Kaneko M, Yoshitake S, Iijima K, Nakamura K, Sakata Y, Matsuda M: An abnormal protein C (protein C Yonago) with an amino acid substitution of Gly for Arg-15 caused by a single base mutation of C to G in codon 57 (CGG-->GGG). Deteriorated calcium-dependent conformation of the gamma-carboxyglutamic acid domain relevant to a thrombotic tendency. Int J Hematol. 1993 Jan;57(1):9-14.
  30. 8499565 Poort SR, Pabinger-Fasching I, Mannhalter C, Reitsma PH, Bertina RM: Twelve novel and two recurrent mutations in 14 Austrian families with hereditary protein C deficiency. Blood Coagul Fibrinolysis. 1993 Apr;4(2):273-80.
  31. 8499568 Millar DS, Grundy CB, Bignell P, Moffat EH, Martin R, Kakkar VV, Cooper DN: A Gla domain mutation (Arg 15-->Trp) in the protein C (PROC) gene causing type 2 protein C deficiency and recurrent venous thrombosis. Blood Coagul Fibrinolysis. 1993 Apr;4(2):345-7.
  32. 8829639 Ireland HA, Boisclair MD, Taylor J, Thompson E, Thein SL, Girolami A, De Caterina M, Scopacasa F, De Stefano V, Leone G, Finazzi G, Cohen H, Lane DA: Two novel (R(-11)C; T394D) and two repeat missense mutations in the protein C gene associated with venous thrombosis in six kindreds. Hum Mutat. 1996;7(2):176-9.
  33. 9003757 Mather T, Oganessyan V, Hof P, Huber R, Foundling S, Esmon C, Bode W: The 2.8 A crystal structure of Gla-domainless activated protein C. EMBO J. 1996 Dec 16;15(24):6822-31.
  34. 9798967 Couture P, Demers C, Morissette J, Delage R, Jomphe M, Couture L, Simard J: Type I protein C deficiency in French Canadians: evidence of a founder effect and association of specific protein C gene mutations with plasma protein C levels. Thromb Haemost. 1998 Oct;80(4):551-6.
Target 1 Drug References
  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed Link Image]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.