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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

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

Description

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

CNS Non-penetrant
1014
Curator's Comment: Dalbavancin was widely distributed into tissues, but did not cross the blood brain barrier.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
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

2014
PubMed

PubMed

TitleDatePubMed
Activity of dalbavancin tested against Gram-positive clinical isolates causing skin and skin-structure infections in paediatric patients from US hospitals (2014-2015).
2017 Dec
Subinhibitory Dalbavancin Attenuates Exotoxin Production from Methicillin-Sensitive and Methicillin-Resistant Staphylococcus aureus In Vitro.
2017 Nov
Once-Daily Treatments for Methicillin-Susceptible Staphylococcus aureus Bacteremia: Are They Good Enough?
2017 Sep 23
Emergence of dalbavancin non-susceptible, vancomycin-intermediate Staphylococcus aureus (VISA) after treatment of MRSA central line-associated bloodstream infection with a dalbavancin- and vancomycin-containing regimen.
2018 Apr
Patents

Patents

US6900175
4
US7119061
4

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).
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 GMT 2023 , Edited by admin on Sat Dec 16 13:40:02 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of DALBAVANCIN B0
NIH
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