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    Chemistry

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    Also known as: Bacitracin a2a, Baciguent, Fortracin, Bacitracinum, Parentracin, Penitracin
    Molecular Formula
    C66H103N17O16S
    Molecular Weight
    1422.7  g/mol
    InChI Key
    CLKOFPXJLQSYAH-ABRJDSQDSA-N
    FDA UNII
    DDA3RRX0P7
    Bacitracin Zinc
    Bacitracin is a combination of at least 9 bacitracins. 60-80% of commercially prepared bacitracin is bacitracin A. The bacillus that produces bacitracin was first isolated from a knee scrape in 1945 from the knee wound of a child named Margaret Tracy. Bacitracin was granted FDA approval on 29 July 1948.
    1 2D Structure

    Bacitracin Zinc

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (4R)-4-[[(2S)-2-[[(4R)-2-[(1S,2S)-1-amino-2-methylbutyl]-4,5-dihydro-1,3-thiazole-4-carbonyl]amino]-4-methylpentanoyl]amino]-5-[[(2S,3S)-1-[[(3S,6R,9S,12R,15S,18R,21S)-3-(2-amino-2-oxoethyl)-18-(3-aminopropyl)-12-benzyl-15-[(2S)-butan-2-yl]-6-(carboxymethyl)-9-(1H-imidazol-5-ylmethyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptazacyclopentacos-21-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-5-oxopentanoic acid
    2.1.2 InChI
    InChI=1S/C66H103N17O16S/c1-9-35(6)52(69)66-81-48(32-100-66)63(97)76-43(26-34(4)5)59(93)74-42(22-23-50(85)86)58(92)83-53(36(7)10-2)64(98)75-40-20-15-16-25-71-55(89)46(29-49(68)84)78-62(96)47(30-51(87)88)79-61(95)45(28-39-31-70-33-72-39)77-60(94)44(27-38-18-13-12-14-19-38)80-65(99)54(37(8)11-3)82-57(91)41(21-17-24-67)73-56(40)90/h12-14,18-19,31,33-37,40-48,52-54H,9-11,15-17,20-30,32,67,69H2,1-8H3,(H2,68,84)(H,70,72)(H,71,89)(H,73,90)(H,74,93)(H,75,98)(H,76,97)(H,77,94)(H,78,96)(H,79,95)(H,80,99)(H,82,91)(H,83,92)(H,85,86)(H,87,88)/t35-,36-,37-,40-,41+,42+,43-,44+,45-,46-,47+,48-,52-,53-,54-/m0/s1
    2.1.3 InChI Key
    CLKOFPXJLQSYAH-ABRJDSQDSA-N
    2.1.4 Canonical SMILES
    CCC(C)C1C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCCCCC(C(=O)NC(C(=O)N1)CCCN)NC(=O)C(C(C)CC)NC(=O)C(CCC(=O)O)NC(=O)C(CC(C)C)NC(=O)C2CSC(=N2)C(C(C)CC)N)CC(=O)N)CC(=O)O)CC3=CN=CN3)CC4=CC=CC=C4
    2.1.5 Isomeric SMILES
    CC[C@H](C)[C@H]1C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)NCCCC[C@@H](C(=O)N[C@@H](C(=O)N1)CCCN)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@@H](CCC(=O)O)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H]2CSC(=N2)[C@H]([C@@H](C)CC)N)CC(=O)N)CC(=O)O)CC3=CN=CN3)CC4=CC=CC=C4
    2.2 Other Identifiers
    2.2.1 UNII
    DDA3RRX0P7
    2.3 Synonyms
    2.3.1 Depositor-Supplied Synonyms

    1. Bacitracin A2a

    2. Baciguent

    3. Fortracin

    4. Bacitracinum

    5. Parentracin

    6. Penitracin

    7. Topitracin

    8. Zutracin

    9. Baciim

    10. Baci-rx

    11. Solu-tracin 50

    12. 22601-59-8

    13. Chebi:35862

    14. Dda3rrx0p7

    15. Altracin

    16. Bacitracin A1

    17. E700

    18. Bacitracin F, 1-(n-((2-(1-amino-2-methylbutyl)-4,5-dihydro-4-thiazolyl)carbonyl)-l-leucine)-

    19. Ayfivin

    20. Unii-dda3rrx0p7

    21. Baciliquin

    22. Bacilliquin

    23. Bacitracina

    24. Bacitracine

    25. Mycitracin

    26. Topitrasin

    27. Tropitracin

    28. Septa

    29. Spectrocin Plus

    30. Bacitek Ointment

    31. Nsc-45737

    32. Bacitracin Powder

    33. Ak-tracin

    34. Baci-jel

    35. Bacitracin Complex

    36. Nsc-755905

    37. Baciferm 50

    38. Bacitracin, Sterile

    39. Einecs 245-115-9

    40. Nsc 45737

    41. Bacitracine [french]

    42. Bacitracinum [latin]

    43. Albac 50

    44. Bacitracina [spanish]

    45. Bactine Triple Antibiotic

    46. Bacitracin(non-injectable)

    47. Usaf Cb-7

    48. Unii-58h6rwo52i

    49. Mycitracin Plus Pain Reliever

    50. 58h6rwo52i

    51. Chembl1200558

    52. Schembl20385900

    53. Hsdb 6418

    54. Bacitracin [usp:inn:ban:jan]

    55. Einecs 215-786-2

    56. Bdbm50458054

    57. Bacitracin-neomycin-polymyxin Ointment

    58. Db00626

    59. Nsc 755905

    60. Ai3-50147-x

    61. Campho-phenique Triple Plus Pain Reliever

    62. Q424319

    63. Mycitracin Triple Antibiotic First Aid Ointment Maximum Strength

    64. 85800-09-5

    65. L-asparagine, N-(((4r)-2-((1s,2s)-1-amino-2-methylbutyl)-4,5-dihydro-4-thiazolyl)carbonyl)-l-leucyl-d-.alpha.-glutamyl-l-isoleucyl-l-lysyl-d-ornithyl-l-isoleucyl-d-phenylalanyl-l-histidyl-d-.alpha.-aspartyl-, (10->4)-lactam

    66. N-({(4r)-2-[(1s,2s)-1-amino-2-methylbutyl]-4,5-dihydro-1,3-thiazol-4-yl}carbonyl)-l-leucyl-d-alpha-glutamyl-n-[(3s,6r,9s,12r,15s,18r,21s)-3-(2-amino-2-oxoethyl)-18-(3-aminopropyl)-12-benzyl-15-[(2s)-butan-2-yl]-6-(carboxymethyl)-9-(1h-imidazol-4-ylmethyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptaazacyclopentacosan-21-yl]-l-isoleucinamide

    2.4 Create Date
    2006-10-26
    3 Chemical and Physical Properties
    Molecular Weight 1422.7 g/mol
    Molecular Formula C66H103N17O16S
    XLogP3-4.1
    Hydrogen Bond Donor Count17
    Hydrogen Bond Acceptor Count21
    Rotatable Bond Count31
    Exact Mass1421.74894144 g/mol
    Monoisotopic Mass1421.74894144 g/mol
    Topological Polar Surface Area556 Ų
    Heavy Atom Count100
    Formal Charge0
    Complexity2850
    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 Drug Information
    1 of 2  
    Drug NameBaciim
    Drug LabelBacitracin for Injection, USP is a sterile antibiotic for intramuscular administration. Bacitracin is derived from cultures of Bacillus subtilis (Tracey). It is a white to pale buff, hygroscopic powder, odorless or having a slight odor. It is freely...
    Active IngredientBacitracin
    Dosage FormInjectable
    RouteInjection
    Strength50,000 units/vial
    Market StatusPrescription
    CompanyX Gen Pharms

    2 of 2  
    Drug NameBaciim
    Drug LabelBacitracin for Injection, USP is a sterile antibiotic for intramuscular administration. Bacitracin is derived from cultures of Bacillus subtilis (Tracey). It is a white to pale buff, hygroscopic powder, odorless or having a slight odor. It is freely...
    Active IngredientBacitracin
    Dosage FormInjectable
    RouteInjection
    Strength50,000 units/vial
    Market StatusPrescription
    CompanyX Gen Pharms

    4.2 Drug Indication

    Bacitracin is indicated in topical formulations for acute and chronic localized skin infections. Occasionally, it is also used intramuscularly for infantile streptococcal pneumonia and empyema. Bacitracin is also formulated as an ointment with neomycin and polymyxin B for over the counter use. A bacitracin ointment formulated with neomycin and polymyxin B along with hydrocortisone is indicated for the treatment of corticosteroid responsive dermatoses with secondary infection.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Bacitracin is a mixture of polypeptides that prevent the formation of the bacterial cell wall and oxidatively cleave DNA. It has a short duration of action as it must be given every 3 to 4 hours topically. Bacitracin is nephrotoxic when given intramuscularly and may lead to renal failure.

    5.2 Absorption, Distribution and Excretion

    Absorption

    Topical, ophthalmic, and oral formulations of bacitracin are poorly absorbed systemically. Intramuscular bacitracin is readily and completely absorbed.

    Route of Elimination

    Bacitracin is mainly excreted renally with 87% of and intramuscular dose being recovered in the urine after 6 hours.

    Volume of Distribution

    Data regarding the volume of distribution of bacitracin in humans is not readily available.

    Clearance

    Data regarding the clearance of bacitracin in humans has not been well studied. A study of 9 subjects in 1947 shows a renal clearance of 105-283mL/min with an average renal clearance of 159mL/min.

    5.3 Metabolism/Metabolites

    Data regarding the metabolism of bacitracin in humans is not readily available. Because bacitracin is a protein it is expected to be metabolized into smaller polypeptides and amino acids. However, the structure of bacitracin may afford it some protection from the action of proteases.

    5.4 Biological Half-Life

    Data regarding the half life of bacitracin in humans is not readily available.

    5.5 Mechanism of Action

    Bacitracin binds to a divalent metal ion such as Mn(II), Co(II), Ni(II), Cu(II), or Zn(II). These complexes bind C55-isoprenyl pyrophosphate, preventing the hydrolysis of a lipid dolichol pyrophosphate, which finally inhibits cell wall synthesis. Bacitracin metal complexes also bind and oxidatively cleave DNA.

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    16-Jan-2021
    28-Oct-2024
    KGS
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    DOSAGE - OINTMENT;TOPICAL - 400 UNITS/GM;1%;E...DOSAGE - OINTMENT;TOPICAL - 400 UNITS/GM;1%;EQ 3.5MG BASE/GM;5,000 UNITS/GM **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 50168

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    DOSAGE - OINTMENT;OPHTHALMIC - EQ 400 UNITS/G...DOSAGE - OINTMENT;OPHTHALMIC - EQ 400 UNITS/GM;EQ 3.5MG BASE/GM;EQ 10,000 UNITS/GM

    USFDA APPLICATION NUMBER - 50417

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