BACITRACIN B3

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C65H101N17O16S
Molecular Weight	1408.667
Optical Activity	UNSPECIFIED
Defined Stereocenters	14 / 14
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]1(CCCN)NC(=O)[C@H](CCCCNC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](CC(O)=O)NC(=O)[C@H](CC2=CNC=N2)NC(=O)[C@@H](CC3=CC=CC=C3)NC(=O)[C@@]([H])(NC1=O)[C@@H](C)CC)NC(=O)[C@@H](NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H]4CSC(=N4)[C@@H](N)[C@@H](C)CC)C(C)C

InChI

InChIKey=KPXXOQKPVWZIEU-QTFUODODSA-N

InChI=1S/C65H101N17O16S/c1-9-35(7)51(68)65-80-47(31-99-65)62(96)75-42(25-33(3)4)58(92)73-41(21-22-49(84)85)57(91)81-52(34(5)6)63(97)74-39-19-14-15-24-70-54(88)45(28-48(67)83)77-61(95)46(29-50(86)87)78-60(94)44(27-38-30-69-32-71-38)76-59(93)43(26-37-17-12-11-13-18-37)79-64(98)53(36(8)10-2)82-56(90)40(20-16-23-66)72-55(39)89/h11-13,17-18,30,32-36,39-47,51-53H,9-10,14-16,19-29,31,66,68H2,1-8H3,(H2,67,83)(H,69,71)(H,70,88)(H,72,89)(H,73,92)(H,74,97)(H,75,96)(H,76,93)(H,77,95)(H,78,94)(H,79,98)(H,81,91)(H,82,90)(H,84,85)(H,86,87)/t35-,36-,39-,40+,41+,42-,43+,44-,45-,46+,47-,51-,52-,53-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C65H101N17O16S
Molecular Weight	1408.667
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	14 / 14
E/Z Centers	4
Optical Activity	UNSPECIFIED

Description
Sources: https://link.springer.com/article/10.1365/s10337-009-1100-5
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/28493314 | https://www.ncbi.nlm.nih.gov/pubmed/26362361 | https://www.ncbi.nlm.nih.gov/pubmed/21481187

Bacitracin B3 is one of major components of bacitracin, a mixture of related cyclic polypeptides produced by organisms of the licheniformis group of Bacillus subtilis var Tracy. Bacitracin exerts pronounced antibacterial action in vitro against a variety of gram-positive and a few gram-negative organisms. However, among systemic diseases, only staphylococcal infections qualify for consideration of bacitracin therapy. Bacitracin A, B1, B2 and B3, short bacitracins A and B represent about 96% of the total microbiological activity in pharmaceutical formulations

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Protein disulfide-isomerase A6 1 Target ID: CHEMBL2146308 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21481187	Inhibitor 8297		1050.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial eye infections 5 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2004/50417slr011_neosporin_lbl.pdf	Curative		Approved 8429	NEOSPORIN Approved Use NEOSPORIN Ophthalmic Ointment is indicated for the topical treatment of superficial infections of the external eye and its adnexa caused by susceptible bacteria. Such infections encompass conjunctivitis, keratitis and keratoconjunctivitis, blepharitis and blepharoconjunctivitis. Launch Date -4.73472E10
Corticosteroid-responsive dematoses with secondary infection 1 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2003/50168slr078_cotisporin_lbl.pdf	Primary		Approved 8429	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed

Patents

Sample Use Guides

In Vivo Use Guide

400 units, topically

Route of Administration: Topical

In Vitro Use Guide

As a polypeptide, toxic, and difficult to use chemical, bacitracin doesn't work well orally, however is very effective topically. Insulin (1 mgЖmL)1) was incubated in 100 mm potassium phosphate and 1 mm EDTA (pH 7.4), in the presence of 10 mkg/mL PDI and varying amounts of bacitracin analog (Bacitracin B) at room temperature. The reaction was initiated after 10 min by the addition of 0.1 mm dithiothreitol, and the increase in turbidity was monitored at 562 nm on an Elx808 Ultra Microplate Reader (Bio-Tex Instruments, Winooski, VT, USA) over 100 min. Dose–response curves were generated, with expression of PDI activity as absorbance at 100 min as a percentage of the absorbance of the control reaction containing no inhibitor, after subtraction of the absorbance of the uncatalyzed reaction containing no PDI.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:45:28 UTC 2023` Edited by `admin` on `Fri Dec 15 15:45:28 UTC 2023`
Record UNII	1RE2J07DT4
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BACITRACIN B3

Common Name

English

BACITRACIN B2 (SIEGEL)

Common Name

English

L-ASPARAGINE, N-(((4R)-2-((1S,2S)-1-AMINO-2-METHYLBUTYL)-4,5-DIHYDRO-4-THIAZOLYL)CARBONYL)-L-LEUCYL-D-.ALPHA.-GLUTAMYL-L-VALYL-L-LYSYL-D-ORNITHYL-L-ISOLEUCYL-D-PHENYLALANYL-L-HISTIDYL-D-.ALPHA.-ASPARTYL-, (10->4)-LACTAM

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C295