Bacitracin

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Bacitracin

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Related Glossary Terms:

Triple Antibiotic Ointments (Taos)

Bacitracin (Wikipedia)

Bacitracin
Systematic (IUPAC) name


(4R)-4-[(2S)-2-({2-[(1S)-1-amino-2-methylbutyl]- 4,5-dihydro-1,3-thiazol-5-yl}formamido)-4-methylpentanamido]-4-{[(1S)- 1-{[(3S,6R,9S,12R,15S,18R,21S)- 18-(3-aminopropyl)-12-benzyl-15-(butan-2-yl)-3-(carbamoylmethyl)- 6-(carboxymethyl)-9-(1H-imidazol-5-ylmethyl)-2,5,8,11,14,17,20- heptaoxo-1,4,7,10,13,16,19-heptaazacyclopentacosan-21-yl]carbamoyl}- 2-methylbutyl]carbamoyl}butanoic acid
Clinical data
Trade names	Baciim
AHFS/Drugs.com	monograph
Pregnancy category	AU: D US: C (Risk not ruled out)
Routes of administration	Topical, intramuscular
Legal status
Legal status	AU: S4 (Prescription only) US: OTC for topical administration; Rx-only for injection
Identifiers
CAS Number	1405-87-4^Y
ATC code	D06AX05 (WHO) J01XX10 R02AB04 QA07AA93
PubChem	CID 439542
DrugBank	DB00626^Y
ChemSpider	10481985^Y
UNII	58H6RWO52I^Y
KEGG	D00128^N
ChEMBL	CHEMBL1200558^N
Chemical data
Formula	C₆₆H₁₀₃N₁₇O₁₆S
Molar mass	1422.69 g/mol
SMILES O=C(O)C[C@H]3NC(=O)[C@H](Cc1cncn1)NC(=O)[C@@H](Cc2ccccc2)NC(=O)[C@@H](NC(=O)[C@@H](CCCN)NC(=O)[C@H](CCCCNC(=O)[C@H](CC(N)=O)NC3=O)NC(=O)[C@@H](NC(=O)[C@@H](CCC(=O)O)NC(=O)[C@H](CC(C)C)NC(=O)C4N=C(SC4)\nC(N)C(C)CC)C(C)CC)C(C)CC
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^Y Key:CLKOFPXJLQSYAH-NVOBBBONSA-N^Y
^NY (what is this?) (verify)

Bacitracin is a mixture of related cyclic peptides produced by organisms of the licheniformis group of Bacillus subtilis var Tracy, first isolated in 1945. These peptides disrupt both gram positive and gram negative bacteria by interfering with cell wall and peptidoglycan synthesis.

Bacitracin is primarily used as a topical preparation (as it is can cause kidney damage when used internally).

While the use of any antibiotic can contribute to antibiotic resistance, localized topical applications are less frequently implicated than their systemic counterparts. However, antibiotics such as bacitracin have been shown to act as dermatological irritants and may slow healing.

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