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Details

Stereochemistry ABSOLUTE
Molecular Formula C88H100Cl2N10O28
Molecular Weight 1816.6951
Optical Activity UNSPECIFIED
Defined Stereocenters 18 / 18
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DALBAVANCIN B0

SMILES

CC(C)CCCCCCCCC(=N[C@]1([H])[C@]([H])([C@@]([H])([C@@]([H])(C(=O)O)O[C@@]1([H])Oc2c3cc4cc2Oc5ccc(cc5Cl)[C@]([H])([C@@]6([H])C(=N[C@@]([H])(c7cc(cc(c7-c8cc(ccc8O)[C@]([H])(C(=N6)O)N=C([C@]4([H])N=C([C@]9([H])c%10cc(cc(c%10Cl)O)Oc%11cc(ccc%11O)[C@]([H])(C(=N[C@]([H])(Cc%12ccc(cc%12)O3)C(=N9)O)O)NC)O)O)O[C@]%13([H])[C@]([H])([C@]([H])([C@@]([H])([C@@]([H])(CO)O%13)O)O)O)O)C(=NCCCN(C)C)O)O)O)O)O)O

InChI

InChIKey=KGPGQDLTDHGEGT-SZUNQUCBSA-N
InChI=1S/C88H100Cl2N10O28/c1-38(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/h15-24,28-36,38,51,60,64-76,78,87-88,91,101-105,107-112H,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)/t51-,60-,64-,65-,66-,67+,68+,69+,70-,71-,72-,73-,74+,75+,76+,78+,87-,88+/m1/s1

HIDE SMILES / InChI

Molecular Formula C88H100Cl2N10O28
Molecular Weight 1816.6951
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 18 / 18
E/Z Centers 0
Optical Activity UNSPECIFIED

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

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

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
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

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

Sample Use Guides

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
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 Jun 26 09:45:32 UTC 2021
Edited
by admin
on Sat Jun 26 09:45:32 UTC 2021
Record UNII
B0U42518WL
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DALBAVANCIN B0
Common Name English
RISTOMYCIN A AGLYCONE, 5,31-DICHLORO-38-DE(METHOXYCARBONYL)-7-DEMETHYL-19-DEOXY-56-O-(2-DEOXY-2-((10-METHYL-1-OXOUNDECYL)AMINO)-.BETA.-D-GLUCOPYRANURONOSYL)-38-(((3-(DIMETHYLAMINO)PROPYL)AMINO)CARBONYL)-42-O-.ALPHA.-D-MANNOPYRANOSYL-N15-METHYL-
Systematic Name English
Code System Code Type Description
DRUG BANK
DB06219
Created by admin on Sat Jun 26 09:45:32 UTC 2021 , Edited by admin on Sat Jun 26 09:45:32 UTC 2021
PRIMARY
CAS
171500-79-1
Created by admin on Sat Jun 26 09:45:32 UTC 2021 , Edited by admin on Sat Jun 26 09:45:32 UTC 2021
PRIMARY
PUBCHEM
16134627
Created by admin on Sat Jun 26 09:45:32 UTC 2021 , Edited by admin on Sat Jun 26 09:45:32 UTC 2021
PRIMARY
FDA UNII
B0U42518WL
Created by admin on Sat Jun 26 09:45:32 UTC 2021 , Edited by admin on Sat Jun 26 09:45:32 UTC 2021
PRIMARY
Related Record Type Details
ACTIVE MOIETY