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Baciguent

HCID 65281
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
1405-87-4
Standard SMILES
CCC(C)C(N)C1=NC(C(=O)NC(CC(C)C)C(=O)NC(CCC(=O)O)C(=O)NC(C(=O)NC2CCCCNC(=O)C(CC(N)=O)NC(=O)C(CC(=O)O)NC(=O)C(Cc3cnc[nH]3)NC(=O)C(Cc3ccccc3)NC(=O)C(C(C)CC)NC(=O)C(CCCN)NC2=O)C(C)CC)CS1
InChIKey
CLKOFPXJLQSYAH-UHFFFAOYSA-N
Molecular formula
C66H103N17O16S
Average molar mass
1,422.7 g/mol
Monoisotopic mass
1,421.74894144

Overview

bacitracin a has been reported in Bacillus licheniformis with data available.

Names & identifiers

Preferred name
Baciguent
IUPAC
4-[[2-[[2-(1-amino-2-methylbutyl)-4,5-dihydro-1,3-thiazole-4-carbonyl]amino]-4-methylpentanoyl]amino]-5-[[1-[[3-(2-amino-2-oxoethyl)-18-(3-aminopropyl)-12-benzyl-15-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
English name
Bacitracin
Molecular formula
C66H102N17O16S
Molecular weight
1421.68538

Names & synonyms

BaciguentRefChem:9166454-((2-((2-(1-amino-2-methylbutyl)-4,5-dihydro-1,3-thiazole-4-carbonyl)amino)-4-methylpentanoyl)amino)-5-((1-((3-(2-amino-2-oxoethyl)-18-(3-aminopropyl)-12-benzyl-15-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 acidBacitracin A22601-59-8NSC-45737BACITRACIN_majorC66H103N17O16SSCHEMBL12652843Pharmakon1600-01500134XAA60159NSC755905
Show more names
septaZiba-RXBacitracin iMpurityayfivinAgfivinbaci-jelusafcb-7BACIDRIN
s4146AB30570Bacitracin F,5-dihydro-4-thiazolyl]carbonyl]-L-leucine]-4-[[2-[[2-(1-amino-2-methyl-butyl)-4,5-dihydrothiazole-4-carbonyl]amino]-4-methyl-pentanoyl]amino]-5-[[1-[[3-(2-amino-2-oxo-ethyl)-18-(3-aminopropyl)-12-benzyl-6-(carboxymethyl)-9-(1H-imidazol-5-ylmethyl)-2,5,8,11,14,17,20-heptaoxo-15-sec-butyl-1,4,7,10,13,16,19-heptazacyclopentacos-21-yl]carbamoyl]-2-methyl-butyl]amino]-5-oxo-pentanoic acid

Properties

Computed structural properties

XLogP
-4.1
Topological polar surface area
556 Ų
Hydrogen bond donors
17
Hydrogen bond acceptors
21
Rotatable bonds
31
Heavy atoms
100
Formal charge
0
Complexity
2,850

Experimental & physicochemical properties

Human DrugsBreast Feeding; Lactation; Milk, Human; Anti-Infective Agents, Local; Antibacterial Agents

Physicochemical properties

Melting point
221 · 221-225°C
Density
1.0166 · 1.0166 (rough estimate)
refractive index
1.67 · 1.6700 (estimate)
storage temp.
2 · Keep in dark place,Inert atmosphere,2-8°C
solubility
2 O: · H2O: 50 mg/mL, clear to very slightly hazy, deep yellow
form
Powder
color
white to faintly beige
Odor
odorless or acetic odor
Water Solubility
soluble
Merck
13 · 13,936
InChIKey
QSNOBVJFKSQBBD-UHFFFAOYSA-N
LogP
-0.05 · -0.050 (est)
FDA 21 CFR

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS ClassificationNot Classified

Hazard information

Hazard Classes and CategoriesNot Classified

Toxicology

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Safety data

F
21
wgk
2
tsca
TSCA listed
rtecs
CP0175000
hs_code
29419090
Toxicity
LD50 oral in guinea pig: 2gm/kg
risk_code
20/21/22
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xn
safety_code
22-24/25-45-36
Storage Class
11 - Combustible Solids
Hazard statements
H317
Precautionary statements
P260-P271-P272-P280g-P302+P352-P304+P340-P312-P363-P403+P233-P501c
Hazardous Substances Data
1405-87-4(Hazardous Substances Data)

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 2 items

Substances used on humans and other animals that destroy harmful microorganisms or inhibit their activity. They are distinguished from DISINFECTANTS, which are used on inanimate objects.

Substances that inhibit the growth or reproduction of BACTERIA.

Applications · 5 items

DescriptionBacitracin is a mixture of similar peptides produced by fermentation of the bacterium Bacillus subtil is. The A-type component predominates. Its mode of action is to inhibit both peptidoglycan biosynthesis at a late stage (probably at the dephosphorylation of the phospholipid carrier step) and disruptions of plasma membrane function.

Usesantibiotic agent effective against gram-positive organisms and spirochetes; in products for topieal treatment, ear medications and ophthalmie drugs

UsesPolypeptide antibacterial.

UsesBacitracin is a peptide antibiotic effective against gram-postive bacteria. Bacitracin is an inhibitor of peptidoglycan synthesis. Bacitracin disrupts bacterial cell wall synthesis by inhibiting depho sphorylation of lipid pyrophosphate. Bacitracin also strongly inhibits proline endopeptidase from human muscle.

General DescriptionThe organism from which Johnson et al. produced bacitracinin 1945 is a strain of B. subtilis. The organism hadbeen isolated from debrided tissue from a compound fracturein 7-year-old Margaret Tracy, hence the name “bacitracin.”Bacitracin is now produced from the licheniformisgroup (B. subtilis). Like tyrothricin, the first useful antibioticobtained from bacterial cultures, bacitracin is a complex mixture of polypeptides. So far, at least 10 polypeptideshave been isolated by countercurrent distribution techniques:A, A1, B, C, D, E, F1, F2, F3, and G. The commercialproduct known as bacitracin is a mixture of principallyA, with smaller amounts of B, D, E, and F1–3.The official product is a white to pale buff powder that isodorless or nearly so. The activity of bacitracin is measured in units per milligram.The potency per milligram is not less than40 units/mg except for material prepared for parenteral use,which has a potency of not less than 50 units/mg. It is a bactericidalantibiotic that is active against a wide variety ofGram-positive organisms, very few Gram-negative organisms,and some others. It is believed to exert its bactericidaleffect through inhibition of mucopeptide cell wall synthesis.Its action is enhanced by zinc. Although bacitracin hasfound its widest use in topical preparations for local infections,it is quite effective in several systemic and local infectionswhen administered parenterally. It is not absorbedfrom the GI tract; accordingly, oral administration is withouteffect, except for the treatment of amebic infectionswithin the alimentary canal.

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes

Database identifiers

CAS
1405-87-4、22601-59-8
PubChem CID
65281
ChEMBL
CHEMBL1790520
EC Number
245-115-9
556.7 · 556.70
EWG's Food Scores
1 · 1
FDA UNII
58 H6RWO52I · 58H6RWO52I
NCI Drug Dictionary
bacitracin
ATC code
6 AX05,J01XX10,R02AB04 · D06AX05,J01XX10,R02AB04
EPA Substance Registry System
Bacitracin (1405-87-4)
UNSPSC Code
12352200 · 12352200
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
317 · H317
Precautionary statements
260 · P260-P271-P272-P280g-P302+P352-P304+P340-P312-P363-P403+P233-P501c
Hazard Codes
Xn
Risk Statements
20 · 20/21/22
Safety Statements
22 · 22-24/25-45-36
WGK Germany
2 · 2
RTECS
175000 · CP0175000
F
21 · 21
TSCA
TSCA listed
HS Code
29419090 · 29419090
Storage Class
11 · 11 - Combustible Solids
Hazardous Substances Data
1405 · 1405-87-4(Hazardous Substances Data)
Toxicity
50 oral · LD50 oral in guinea pig: 2gm/kg

Upstream & downstream products

Upstream raw materials

Calcium carbonateSOYBEAN MEALZinc oxideSucroseBBK8 AMIKACIN SULFATEAMBERLITE(R) IRA-400 (CL)CornSteepLiquirMolassesBacillus subtilisDye-based qPCR Kit

Downstream products

Polymyxin B, N-sulfomethyl deriv., sodium salt

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
Baoji Guokang Healthchem co.,ltd+8615604608665 15604608665 · [email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
山东八方化工科技有限公司0535-15589503653 15589503653 · [email protected]
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北京绿百草科技发展有限公司010-61136123 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
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艾科试剂4008-755-333 18080918076 · [email protected]
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南京杜莱生物技术有限公司025-84699383-8003;025-846993838003-8003 18013301590 · [email protected]
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上海将来实业股份有限公司021-61552785 · [email protected]
HBCChem, Inc.+1-510-219-6317 · [email protected]
成都零六生物科技有限公司400-1166-196 13458535857 · [email protected]
雷丁试剂0510-85629785 18013409632 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
杭州杰恒化工有限公司0571-87396432 · [email protected]
江苏艾康生物医药研发有限公司025-66028182 17714375163 · [email protected]
南京百鑫德诺生物科技有限公司025-58849295 · [email protected]
上海孚一生物科技有限公司+86 (21) 61124340
凯试(上海)科技有限公司021-50135380 · [email protected]
湖北巨胜科技有限公司027-59599241 18871490274 · [email protected]
池州凯隆进出口贸易有限公司[email protected]
桦特昇生物科技(武汉)有限公司027-59207879 1972026995 18140587686 · [email protected]
天津阿尔塔科技有限公司022-6537-8550 15522853686 · [email protected]
TargetMol中国(陶术生物)021-021-33632979 15002134094 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
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九鼎化学(上海)科技有限公司4009209199 · [email protected]
Henan Alfa Chemical Co., Ltd+8618339805032 · [email protected]
湖南汇百益新材料有限公司400-0909710 13319523173 · [email protected]
西安天广源生物科技有限公司+86-029-86333380 +86-18829239519 · [email protected]
BOC Sciences16314854226 · [email protected]
北京华威锐科化工科技有限公司89508211 18501085097 · [email protected]
华北制药华胜有限公司[email protected]
Target molecule Corp.857-239-0968 · [email protected]
山东西亚化学有限公司4009903999 13395398332 · [email protected]

Additional notes

DefinitionA complex of cyclic peptide antibiotic of known chemical structure isolated from the Tracy-I strain of Bacillus subtilis.