Bacitracin

Bacitracin

Clinical data
Trade names	Baciim
AHFS/Drugs.com	Monograph
Pregnancy category	AU: D US: C (Risk not ruled out)
Routes of administration	Topical, intramuscular
ATC code	D06AX05 (WHO) J01XX10 (WHO) R02AB04 (WHO) QA07AA93 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) US: OTC for topical administration; Rx-only for injection
Identifiers
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
CAS Number	1405-87-4 Y
PubChem (CID)	439542
DrugBank	DB00626 Y
ChemSpider	10481985 Y
UNII	58H6RWO52I Y
KEGG	D00128 N
ChEMBL	CHEMBL1200558 N
ECHA InfoCard	100.014.351
Chemical and physical data
Formula	C66H103N17O16S
Molar mass	1422.69 g/mol
3D model (Jmol)	Interactive image
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?)

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 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.

Bacitracin is used in human medicine as a polypeptide antibiotic and is "approved by the U.S. Food and Drug Administration (FDA) for use in chickens and turkeys," though use in animals contributes to antibiotic resistance.

As bacitracin zinc salt, in combination with other topical antibiotics (usually polymyxin B and neomycin) as an ointment ("triple antibiotic ointment," with a common brand name Neosporin), it is used for topical treatment of a variety of localized skin and eye infections, as well as for the prevention of wound infections. A non-ointment form of ophthalmic solution is also available for eye infections.

Although allergic cross reaction with sulfa drugs has been occasionally reported, bacitracin-containing topical preparations remain a possible alternative to silver sulfadiazine (Silvadene) for burn patients with a sulfa allergy.