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2D Structure
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 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

2D Structure

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.