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Substance Name: Bacitracin [USP:INN:BAN:JAN]
RN: 1405-87-4
UNII: 58H6RWO52I
InChIKey: CLKOFPXJLQSYAH-ABRJDSQDSA-N

Notes

  • A complex of cyclic peptide antibiotics produced by the Tracy-I strain of Bacillus subtilis. The commercial preparation is a mixture of at least nine bacitracins with bacitracin A as the major constituent. It is used topically to treat open infections such as infected eczema and infected dermal ulcers. (From Goodman and Gilman, The Pharmacological Basis of Therapeutics, 8th ed, p1140)
  • TSCA Definition 2018: A complex combination of polypeptides produced by the metabolic processes of Bacillus subtilis and licheniformis.

Molecular Formula

  • Unspecified

Molecular Weight

  • 1422.7087
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Anti-Infective Agents, Local
  • Antibacterial
  • Drug / Therapeutic Agent
  • Mutation Data

Names and Synonyms

Name of Substance

  • Bacitracin
  • Bacitracin [USP:INN:BAN:JAN]

MeSH Heading

  • Bacitracin

Synonyms

  • AI3-50147-X
  • Ak-Tracin
  • Altracin
  • Ayfivin
  • Baci-Jel
  • Baci-RX
  • Baciguent
  • Baciim
  • Baciliquin
  • Bacitek ointment
  • Bacitracin
  • Bacitracin-Neomycin-Polymyxin Ointment
  • Bacitracina
  • Bacitracina [Spanish]
  • Bacitracine
  • Bacitracine [French]
  • Bacitracinum
  • Bacitracinum [Latin]
  • Bactine Triple Antibiotic
  • Campho-Phenique Triple Plus Pain Reliever
  • EINECS 215-786-2
  • Fortracin
  • HSDB 6418
  • Mycitracin Plus Pain Reliever
  • Mycitracin Triple Antibiotic First Aid Ointment Maximum Strength
  • Parentracin
  • Penitracin
  • Septa
  • Spectrocin Plus
  • Topitracin
  • Topitrasin
  • UNII-58H6RWO52I
  • USAF CB-7
  • Zutracin

Systematic Name

  • Bacitracin

Superlist Name

  • Bacitracin

Mixture Name

  • Mycitracin

Registry Numbers

CAS Registry Number

  • 1405-87-4

FDA UNII

  • 58H6RWO52I

Other Registry Numbers

  • 12640-37-8
  • 1405-75-0
  • 60454-67-3

Related Registry Number

  • 1405-89-6 (zinc complex)

System Generated Number

  • 0001405874

Structure Descriptors

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

InChIKey

CLKOFPXJLQSYAH-ABRJDSQDSA-N

Smiles

CC[C@H](C)[C@H](N)C1=N[C@@H](CS1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CCC(=O)O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@H]2CCCCNC(=O)[C@H](CC(=O)N)NC(=O)[C@@H](CC(=O)O)NC(=O)[C@H](Cc3c[nH]cn3)NC(=O)[C@@H](Cc4ccccc4)NC(=O)[C@@H](NC(=O)[C@@H](CCCN)NC2=O)[C@@H](C)CC

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 oral 2gm/kg (2000mg/kg)   Antibiotics and Chemotherapy Vol. 4, Pg. 304, 1954.
mouse LD50 intraperitoneal 300mg/kg (300mg/kg)   National Technical Information Service. Vol. AD277-689,
mouse LD50 intravenous 360mg/kg (360mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Proceedings of the Society for Experimental Biology and Medicine. Vol. 64, Pg. 503, 1947.
mouse LD50 oral > 3750mg/kg (3750mg/kg)   Antimicrobial Agents Annual. Vol. -, Pg. 595, 1960.
mouse LD50 subcutaneous 1300mg/kg (1300mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Proceedings of the Society for Experimental Biology and Medicine. Vol. 64, Pg. 503, 1947.
quail LD50 oral > 316mg/kg (316mg/kg)   Ecotoxicology and Environmental Safety. Vol. 6, Pg. 149, 1982.
rat LD50 intraperitoneal 190mg/kg (190mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Proceedings of the Society for Experimental Biology and Medicine. Vol. 64, Pg. 503, 1947.