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    Pyroxylin

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    2D Structure
    Also known as: 9004-70-0, Piroxilina, Pyroxyline, Pyroxylinum, Pyroxylin, Gun cotton
    Molecular Formula
    C18H21N11O38
    Molecular Weight
    999.4  g/mol
    InChI Key
    FJWGYAHXMCUOOM-QHOUIDNNSA-N
    A nitrocellulose solution in ether and alcohol. Collodion has a wide range of uses in industry including applications in the manufacture of photographic film, in fibers, in lacquers, and in engraving and lithography. In medicine it is used as a drug solvent and a wound sealant.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [(2S,3R,4S,5R,6R)-2-[(2R,3R,4S,5R,6S)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2R,3R,4S,5R,6S)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate
    2.1.2 InChI
    InChI=1S/C18H21N11O38/c30-19(31)52-1-4-7(58-17-14(65-27(46)47)12(63-25(42)43)9(60-22(36)37)6(56-17)3-54-21(34)35)10(61-23(38)39)13(64-26(44)45)16(55-4)59-8-5(2-53-20(32)33)57-18(67-29(50)51)15(66-28(48)49)11(8)62-24(40)41/h4-18H,1-3H2/t4-,5-,6-,7-,8-,9-,10+,11+,12+,13-,14-,15-,16+,17+,18+/m1/s1
    2.1.3 InChI Key
    FJWGYAHXMCUOOM-QHOUIDNNSA-N
    2.1.4 Canonical SMILES
    C(C1C(C(C(C(O1)OC2C(OC(C(C2O[N+](=O)[O-])O[N+](=O)[O-])O[N+](=O)[O-])CO[N+](=O)[O-])O[N+](=O)[O-])O[N+](=O)[O-])OC3C(C(C(C(O3)CO[N+](=O)[O-])O[N+](=O)[O-])O[N+](=O)[O-])O[N+](=O)[O-])O[N+](=O)[O-]
    2.1.5 Isomeric SMILES
    C([C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@@H]2[C@H](O[C@H]([C@@H]([C@H]2O[N+](=O)[O-])O[N+](=O)[O-])O[N+](=O)[O-])CO[N+](=O)[O-])O[N+](=O)[O-])O[N+](=O)[O-])O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO[N+](=O)[O-])O[N+](=O)[O-])O[N+](=O)[O-])O[N+](=O)[O-])O[N+](=O)[O-]
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. Celloidin

    2. Cellulose Nitrate

    3. Collodion

    4. Collodion Cotton

    5. Cotton, Collodion

    6. Nitrate, Cellulose

    7. Pyroxylin

    2.2.2 Depositor-Supplied Synonyms

    1. 9004-70-0

    2. Piroxilina

    3. Pyroxyline

    4. Pyroxylinum

    5. Pyroxylin

    6. Gun Cotton

    7. Cellulose Nitrate

    8. Cellulose Tetranitrate

    9. Chebi:53325

    10. [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] Nitrate

    2.3 Create Date
    2009-11-19
    3 Chemical and Physical Properties
    Molecular Weight 999.4 g/mol
    Molecular Formula C18H21N11O38
    XLogP33.1
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count38
    Rotatable Bond Count18
    Exact Mass999.0048952 g/mol
    Monoisotopic Mass999.0048952 g/mol
    Topological Polar Surface Area652 Ų
    Heavy Atom Count67
    Formal Charge0
    Complexity1820
    Isotope Atom Count0
    Defined Atom Stereocenter Count15
    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

    In medicine it is used as a drug solvent and a wound sealant.

    National Library of Medicine's Medical Subject Headings online file (MeSH, 2010)

    CHIEFLY TO SEAL SMALL WOUNDS OR FOR PREPN OF MEDICATED COLLODIONS. ... /FLEXIBLE COLLODION/ APPLIED EXTERNALLY TO CUTS & SMALL BURNS AS PROTECTIVE. ITS APPLICATION IS ACCOMPANIED BY CONSIDERABLE PAIN, BUT IT IS EFFECTIVE AS ANTISEPTIC & FOR EXCLUDING AIR FROM OPEN WOUNDS.

    Osol, A. (ed.). Remington's Pharmaceutical Sciences. 16th ed. Easton, Pennsylvania: Mack Publishing Co., 1980., p. 717

    MEDICATION (VET): SKIN PROTECTANT

    O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 417

    VEHICLE FOR PROLONGED-CONTACT APPLICATION OF MEDICINALS

    American Hospital Formulary Service. Volumes I and II. Washington, DC: American Society of Hospital Pharmacists, to 1984., p. 84:24

    Corn removers.

    Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 15th Edition. John Wiley & Sons, Inc. New York, NY 2007., p. 321

    4.2 Drug Warning

    A case of an unusual caustic ingestion involving Compound W, an over the counter wart remover is presented. Chemical burns of the tongue, pharynx and larynx developed. The active ingredient in this preparation: salicylic acid in a flexible collodion vehicle produces caustic injury through a keratolytic action, which may be enhanced by the presence of collodion.

    PMID:3778605 Sacchetti A, Ramoska E; Am J Emerg Med 4 (6): 554-5 (1986)

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Explosive Agents

    Substances that are energetically unstable and can produce a sudden expansion of the material, called an explosion, which is accompanied by heat, pressure and noise. Other things which have been described as explosive that are not included here are explosive action of laser heating, human performance, sudden epidemiological outbreaks, or fast cell growth. (See all compounds classified as Explosive Agents.)

    Tissue Adhesives

    Substances used to cause adherence of tissue to tissue or tissue to non-tissue surfaces, as for prostheses. (See all compounds classified as Tissue Adhesives.)