DALBAVANCIN B0 HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	5C88H100Cl2N10O28.8ClH
Molecular Weight	9375.147
Optical Activity	UNSPECIFIED
Defined Stereocenters	90 / 90
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of DALBAVANCIN B0 HYDROCHLORIDE

Structure Search

SMILES

Cl.Cl.Cl.Cl.Cl.Cl.Cl.Cl.[H][C@@]1(NC(=O)CCCCCCCCC(C)C)[C@@H](O)[C@H](O)[C@H](O[C@H]1OC2=C3OC4=CC=C(C[C@H]5NC(=O)[C@H](NC)C6=CC(OC7=CC([C@H](NC5=O)C(=O)N[C@@H]8C(C=C2OC9=C(Cl)C=C(C=C9)[C@@H](O)[C@@H]%10NC(=O)[C@H](NC8=O)C%11=CC(=C(O)C=C%11)C%12=C(C=C(O)C=C%12O[C@H]%13O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]%13O)[C@H](NC%10=O)C(=O)NCCCN(C)C)=C3)=C(Cl)C(O)=C7)=C(O)C=C6)C=C4)C(O)=O.[H][C@@]%14(NC(=O)CCCCCCCCC(C)C)[C@@H](O)[C@H](O)[C@H](O[C@H]%14OC%15=C%16OC%17=CC=C(C[C@H]%18NC(=O)[C@H](NC)C%19=CC(OC%20=CC([C@H](NC%18=O)C(=O)N[C@@H]%21C(C=C%15OC%22=C(Cl)C=C(C=C%22)[C@@H](O)[C@@H]%23NC(=O)[C@H](NC%21=O)C%24=CC(=C(O)C=C%24)C%25=C(C=C(O)C=C%25O[C@H]%26O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]%26O)[C@H](NC%23=O)C(=O)NCCCN(C)C)=C%16)=C(Cl)C(O)=C%20)=C(O)C=C%19)C=C%17)C(O)=O.[H][C@@]%27(NC(=O)CCCCCCCCC(C)C)[C@@H](O)[C@H](O)[C@H](O[C@H]%27OC%28=C%29OC%30=CC=C(C[C@H]%31NC(=O)[C@H](NC)C%32=CC(OC%33=CC([C@H](NC%31=O)C(=O)N[C@@H]%34C(C=C%28OC%35=C(Cl)C=C(C=C%35)[C@@H](O)[C@@H]%36NC(=O)[C@H](NC%34=O)C%37=CC(=C(O)C=C%37)C%38=C(C=C(O)C=C%38O[C@H]%39O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]%39O)[C@H](NC%36=O)C(=O)NCCCN(C)C)=C%29)=C(Cl)C(O)=C%33)=C(O)C=C%32)C=C%30)C(O)=O.[H][C@@]%40(NC(=O)CCCCCCCCC(C)C)[C@@H](O)[C@H](O)[C@H](O[C@H]%40OC%41=C%42OC%43=CC=C(C[C@H]%44NC(=O)[C@H](NC)C%45=CC(OC%46=CC([C@H](NC%44=O)C(=O)N[C@@H]%47C(C=C%41OC%48=C(Cl)C=C(C=C%48)[C@@H](O)[C@@H]%49NC(=O)[C@H](NC%47=O)C%50=CC(=C(O)C=C%50)C%51=C(C=C(O)C=C%51O[C@H]%52O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]%52O)[C@H](NC%49=O)C(=O)NCCCN(C)C)=C%42)=C(Cl)C(O)=C%46)=C(O)C=C%45)C=C%43)C(O)=O.[H][C@@]%53(NC(=O)CCCCCCCCC(C)C)[C@@H](O)[C@H](O)[C@H](O[C@H]%53OC%54=C%55OC%56=CC=C(C[C@H]%57NC(=O)[C@H](NC)C%58=CC(OC%59=CC([C@H](NC%57=O)C(=O)N[C@@H]%60C(C=C%54OC%61=C(Cl)C=C(C=C%61)[C@@H](O)[C@@H]%62NC(=O)[C@H](NC%60=O)C%63=CC(=C(O)C=C%63)C%64=C(C=C(O)C=C%64O[C@H]%65O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]%65O)[C@H](NC%62=O)C(=O)NCCCN(C)C)=C%55)=C(Cl)C(O)=C%59)=C(O)C=C%58)C=C%56)C(O)=O

InChI

InChIKey=ALCMRBLIJBFSAZ-XERKAGHASA-N

InChI=1S/5C88H100Cl2N10O28.8ClH/c5*1-38(2)13-10-8-6-7-9-11-14-61(106)94-70-73(109)75(111)78(86(120)121)128-87(70)127-77-58-31-43-32-59(77)124-55-24-19-42(29-50(55)89)71(107)69-85(119)98-67(80(114)92-25-12-26-100(4)5)48-33-44(102)34-57(125-88-76(112)74(110)72(108)60(37-101)126-88)62(48)47-28-40(17-22-52(47)103)65(82(116)99-69)95-83(117)66(43)96-84(118)68-49-35-46(36-54(105)63(49)90)123-56-30-41(18-23-53(56)104)64(91-3)81(115)93-51(79(113)97-68)27-39-15-20-45(122-58)21-16-39;;;;;;;;/h5*15-24,28-36,38,51,60,64-76,78,87-88,91,101-105,107-112H,6-14,25-27,37H2,1-5H3,(H,92,114)(H,93,115)(H,94,106)(H,95,117)(H,96,118)(H,97,113)(H,98,119)(H,99,116)(H,120,121);8*1H/t5*51-,60-,64-,65-,66-,67+,68+,69+,70-,71-,72-,73-,74+,75+,76+,78+,87-,88+;;;;;;;;/m11111......../s1

HIDE SMILES / InChI

Molecular Formula	C88H100Cl2N10O28
Molecular Weight	1816.692
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	18 / 18
E/Z Centers	1
Optical Activity	UNSPECIFIED

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.drugbank.ca/drugs/DB06219 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021883s000lbl.pdf | https://www.dalvance.com/

Dalbavancin is a mixture of five closely related active homologs (A0, A1, B0, B1, and B2); the component B0 is the major component of dalbavancin. The predominant component of dalbavancin is Factor B0, which accounts for >75% of the whole complex. Dalbavancin is a second-generation lipoglycopeptide antibiotic that was designed to improve on the natural glycopeptides currently available, such as vancomycin and teicoplanin. Modifications from these older glycoprotein classes allowed a similar mechanism of action with increased activity and once weekly dosing. Its use is indicated for the treatment of acute bacterial skin and skin structure infections (ABSSSI) caused by the following gram-positive microorganisms: Staphylococcus aureus (including methicillin-susceptible and methicillin-resistant strains), S. pyogenes, S. agalactiae, and S. anginosus group (including S. anginosus, S. intermedius, and S. constellatus). Under the brand name DALVANCE Dalbavancin is indicated for acute bacterial skin and skin structure infections (ABSSSI) caused by designated susceptible strains of Gram-positive microorganisms. The bactericidal action of dalbavancin results primarily from inhibition of cell-wall biosynthesis. Specifically, dalbavancin prevents incorporation of N-acetylmuramic acid (NAM)- and N-acetylglucosamine (NAG)-peptide subunits from being incorporated into the peptidoglycan matrix; which forms the major structural component of Gram-positive cell walls. The large hydrophilic molecule is able to form hydrogen bond interactions with the terminal D-alanyl-D-alanine moieties of the NAM/NAG-peptides, which is normally a five-point interaction. Binding of dalbavancin to the D-Ala-D-Ala prevents the incorporation of the NAM/NAG-peptide subunits into the peptidoglycan matrix. In addition, dalbavancin alters bacterial-cell-membrane permeability and RNA synthesis.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Peptidoglycan 6 Target ID: CHEMBL3041361 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021883s000lbl.pdf	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Acute bacterial skin and skin structure infection 16 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021883s000lbl.pdf https://www.dalvance.com/	Curative		Approved 8429	DALVANCE Approved Use DALVANCE is indicated for acute bacterial skin and skin structure infections (ABSSSI) caused by designated susceptible strains of Gram-positive microorganisms. Launch Date 1.40071679E12

PubMed

Title	Date	PubMed

Patents

Sample Use Guides

In Vivo Use Guide

1. Two-dose regimen: 1000 mg followed one week later by 500 mg (2.1) 2. Dosage adjustment for patients with creatinine clearance less than 30 mL/min and not receiving regularly scheduled hemodialysis: 750 mg followed one week later by 375 mg (2.2) 3. Administer by intravenous infusion over 30 minutes (2.3)

Route of Administration: Intravenous

In Vitro Use Guide

Nearly all (99.8%) multidrug-resistant methicillin-resistant S. aureus isolates were inhibited by dalbavancin at ≤0.12 ug/ml (MIC50/90, 0.06/0.06 ug/ml).

Substance Class	Chemical Created by `admin` on `Sat Dec 16 13:40:02 UTC 2023` Edited by `admin` on `Sat Dec 16 13:40:02 UTC 2023`
Record UNII	D4RU427IQN
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DALBAVANCIN B0 HYDROCHLORIDE

Common Name

English

DALBAVANCIN B0 HYDROCHLORIDE (5:8)

Common Name

English

Code System Code Type Description

FDA UNII

D4RU427IQN

Created by admin on Sat Dec 16 13:40:02 UTC 2023 , Edited by admin on Sat Dec 16 13:40:02 UTC 2023

PRIMARY

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ACTIVE MOIETY