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    Erythromycin Stearate

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

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    2D Structure
    Also known as: 643-22-1, Abboticine, Bristamycin, Erypar, Dowmycin e, Wyamycin s
    Molecular Formula
    C55H103NO15
    Molecular Weight
    1018.4  g/mol
    InChI Key
    YAVZHCFFUATPRK-YZPBMOCRSA-N
    FDA UNII
    LXW024X05M
    Erythromycin Stearate is the stearate salt form of erythromycin, a broad-spectrum, topical macrolide antibiotic with antibacterial activity. Erythromycin stearate diffuses through the bacterial cell membrane and reversibly binds to the 50S subunit of the bacterial ribosome. This prevents bacterial protein synthesis. Erythromycin stearate may be bacteriostatic or bactericidal in action, depending on the concentration of the drug at the site of infection and the susceptibility of the organism involved.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione;octadecanoic acid
    2.1.2 InChI
    InChI=1S/C37H67NO13.C18H36O2/c1-14-25-37(10,45)30(41)20(4)27(39)18(2)16-35(8,44)32(51-34-28(40)24(38(11)12)15-19(3)47-34)21(5)29(22(6)33(43)49-25)50-26-17-36(9,46-13)31(42)23(7)48-26;1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h18-26,28-32,34,40-42,44-45H,14-17H2,1-13H3;2-17H2,1H3,(H,19,20)/t18-,19-,20+,21+,22-,23+,24+,25-,26+,28-,29+,30-,31+,32-,34+,35-,36-,37-;/m1./s1
    2.1.3 InChI Key
    YAVZHCFFUATPRK-YZPBMOCRSA-N
    2.1.4 Canonical SMILES
    CCCCCCCCCCCCCCCCCC(=O)O.CCC1C(C(C(C(=O)C(CC(C(C(C(C(C(=O)O1)C)OC2CC(C(C(O2)C)O)(C)OC)C)OC3C(C(CC(O3)C)N(C)C)O)(C)O)C)C)O)(C)O
    2.1.5 Isomeric SMILES
    CCCCCCCCCCCCCCCCCC(=O)O.CC[C@@H]1[C@@]([C@@H]([C@H](C(=O)[C@@H](C[C@@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]2C[C@@]([C@H]([C@@H](O2)C)O)(C)OC)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)O)C)C)O)(C)O
    2.2 Other Identifiers
    2.2.1 UNII
    LXW024X05M
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Gallimycin

    2.3.2 Depositor-Supplied Synonyms

    1. 643-22-1

    2. Abboticine

    3. Bristamycin

    4. Erypar

    5. Dowmycin E

    6. Wyamycin S

    7. Pfizer-e

    8. Erythrocin Stearate

    9. Gallimycin

    10. Sk-erythromycin

    11. Erythromycin Octadecanoate (salt)

    12. Nsc-756747

    13. Nci-c55674

    14. Lxw024x05m

    15. Eratrex

    16. Meberyt

    17. Qidmycin

    18. Ethril

    19. Ethril 250

    20. Ethril 500

    21. Erythromycin Stearate (salt)

    22. Erythromycin, Stearate (salt)

    23. Erythromycin Steraric Acid Salt

    24. Ccris 1504

    25. Oe 7

    26. Hsdb 4178

    27. Einecs 211-396-1

    28. Unii-lxw024x05m

    29. Stearic Acid, Compd. With Erythromycin (1:1)

    30. Bristamycin (tn)

    31. Octadecanoic Acid, Compd. With Erythromycin (1:1)

    32. Erythromycini Stearas

    33. Erythromycin Stearate [usp:ban:jan]

    34. Chembl1200510

    35. Chebi:34742

    36. Hms501d19

    37. Erythromycin Stearate [mi]

    38. Erythromycin Stearate/ >550ug/mg

    39. Hms3264b08

    40. Pharmakon1600-01500281

    41. Erythromycin Stearate (jp17/usp)

    42. Erythromycin Stearate [jan]

    43. Erythromycin Stearate [hsdb]

    44. Ccg-39117

    45. Erythromycin Stearate [vandf]

    46. Mfcd00084690

    47. Nsc756747

    48. Erythromycin Stearate [mart.]

    49. Erythromycin Stearate [usp-rs]

    50. Erythromycin Stearate [who-dd]

    51. Erythromycin Stearate [who-ip]

    52. Nsc 756747

    53. Ncgc00180891-01

    54. Erythromycin Stearate [orange Book]

    55. Sbi-0207065.p001

    56. Erythromycin Stearate [usp Impurity]

    57. Hy-108875

    58. Cs-0031206

    59. Erythromycin Stearate [usp Monograph]

    60. Erythromycini Stearas [who-ip Latin]

    61. D02184

    62. Erythromycin Stearate For Impurity S Identification

    63. Sr-01000872741

    64. Sr-01000872741-1

    65. W-104851

    66. Q27283244

    67. Erythromycin Stearate, Antibiotic For Culture Media Use Only

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 1018.4 g/mol
    Molecular Formula C55H103NO15
    Hydrogen Bond Donor Count6
    Hydrogen Bond Acceptor Count16
    Rotatable Bond Count23
    Exact Mass1017.73277158 g/mol
    Monoisotopic Mass1017.73277158 g/mol
    Topological Polar Surface Area231 Ų
    Heavy Atom Count71
    Formal Charge0
    Complexity1380
    Isotope Atom Count0
    Defined Atom Stereocenter Count18
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameErythrocin stearate
    Drug LabelERYTHROCIN STEARATE Filmtab tablets (erythromycin stearate tablets, USP) are an antibacterial product containing the stearate salt of erythromycin in a unique film coating.Erythromycin is produced by a strain of Saccharopolyspora erythraea (formerly...
    Active IngredientErythromycin stearate
    Dosage FormTablet
    RouteOral
    Strengtheq 250mg base
    Market StatusPrescription
    CompanyArbor Pharms

    2 of 2  
    Drug NameErythrocin stearate
    Drug LabelERYTHROCIN STEARATE Filmtab tablets (erythromycin stearate tablets, USP) are an antibacterial product containing the stearate salt of erythromycin in a unique film coating.Erythromycin is produced by a strain of Saccharopolyspora erythraea (formerly...
    Active IngredientErythromycin stearate
    Dosage FormTablet
    RouteOral
    Strengtheq 250mg base
    Market StatusPrescription
    CompanyArbor Pharms

    4.2 Therapeutic Uses

    ITS ACTIONS & USES ARE IDENTICAL TO THOSE OF ERYTHROMYCIN.

    Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1124

    ERYTHROMYCIN MAY BE USEFUL FOR DISSEMINATED GONOCOCCAL DISEASE IN PREGNANT PT WHO IS ALLERGIC TO PENICILLIN... 13 PT...TREATED WITH 500 MG OF ERYTHROMYCIN... STEARATE, GIVEN ORALLY EVERY 6 HR FOR 5 DAYS, SHOWED RAPID CLINICAL & BACTERIOLOGICAL RESPONSES.

    Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 1225

    ANTIBACTERIAL AGENT

    MEDICATION (VET): ANTIBACTERIAL AGENT

    4.3 Drug Warning

    ...ERYTHROMYCIN & ITS DERIV SELDOM CAUSE SERIOUS ADVERSE REACTIONS.

    American Medical Association, AMA Department of Drugs. AMA Drug Evaluations. 4th ed. Chicago: American Medical Association, 1980., p. 1258

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Anti-Bacterial Agents

    Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

    Gastrointestinal Agents

    Drugs used for their effects on the gastrointestinal system, as to control gastric acidity, regulate gastrointestinal motility and water flow, and improve digestion. (See all compounds classified as Gastrointestinal Agents.)

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Macrolide Antimicrobial [EPC]; Macrolide [EPC]; Macrolides [CS]; Decreased Sebaceous Gland Activity [PE]
    5.3 Absorption, Distribution and Excretion

    PEAK CONCN IN PLASMA...0.3-0.5 UG/ML 4 HR AFTER ORAL ADMIN OF 250 MG OF BASE & ARE 0.3-1.9 UG/ML AFTER...500-MG TABLET. VARIOUS ESTERS OF ERYTHROMYCIN HAVE BEEN PREPARED TO...IMPROVE STABILITY & FACILITATE ABSORPTION. ...CONCN OF ERYTHROMYCIN IN PLASMA ARE LITTLE DIFFERENT IF STEARATE IS GIVEN ORALLY.

    Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 1223

    ...DIFFUSES READILY INTO INTRACELLULAR FLUIDS, & ANTIBACTERIAL ACTIVITY... ACHIEVED AT...ALL SITES EXCEPT BRAIN & CSF. ...ONE OF FEW ANTIBIOTICS THAT PENETRATES INTO PROSTATIC FLUID, CONCN ARE APPROX 40% OF...PLASMA. EXTENT OF BINDING...TO PLASMA PROTEINS VARIES...PROBABLY EXCEEDS 70% IN ALL.../FORMS OF DRUG/. /ERYTHROMYCIN/

    Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 1223

    ERYTHROMYCIN BASE IS ADEQUATELY ABSORBED FROM UPPER PART OF SMALL INTESTINE; IT IS INACTIVATED BY GASTRIC JUICE... FOOD IN STOMACH DELAYS ITS ULTIMATE ABSORPTION. /ERYTHROMYCIN/

    Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 1223

    ERYTHROMYCIN TRAVERSES PLACENTAL BARRIER; & CONCN OF DRUG IN FETAL PLASMA ARE ABOUT 5-20% OF THOSE IN MATERNAL CIRCULATION. /ERYTHROMYCIN/

    Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 1223

    For more Absorption, Distribution and Excretion (Complete) data for ERYTHROMYCIN STEARATE (11 total), please visit the HSDB record page.

    5.4 Metabolism/Metabolites

    IT IS HYDROLYZED IN SMALL INTESTINE & IN TISSUES TO YIELD ERYTHROMYCIN.

    Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1124

    5.5 Mechanism of Action

    ...INHIBIT PROTEIN SYNTH BY BINDING TO 50 S RIBOSOMAL SUBUNITS OF SENSITIVE MICROORGANISMS. ... ASSOC BETWEEN ERYTHROMYCIN & RIBOSOME IS REVERSIBLE BUT TAKES PLACE ONLY WHEN 50 S SUBUNIT IS FREE FROM TRNA MOLECULES BEARING NASCENT PEPTIDE CHAINS. PRODN...OF HIGHLY POLYMERIZED HOMOPEPTIDES IS SUPPRESSED. /ERYTHROMYCIN/

    Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 1223

    THE NONIONIZED FORM OF THE DRUG IS CONSIDERABLY MORE PERMEABLE TO CELLS, & THIS PROBABLY EXPLAINS INCREASED ANTIMICROBIAL ACTIVITY THAT IS OBSERVED AT ALKALINE PH. /ERYTHROMYCIN/

    Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 1223