NAV

Lancovutide

Identification

Generic Name
Lancovutide
DrugBank Accession Number
DB05029
Background

Lancovutide, a peptide antibiotic, is in clinical development for the treatment of cystic fibrosis. Lancovutide is a 19-amino-acid tetracyclic peptide produced by Streptoverticillium cinnamoneus and is closely related to cinnamycin (Ro09-0198). It belongs to the lantibiotics. Lantibiotics are bacteriocins that are characterized by the presence of a high proportion of unusual amino acids.

Type
Small Molecule
Groups
Investigational
Structure
Similar Structures
Weight
Average: 2013.3
Monoisotopic: 2011.837910139
Chemical Formula
C89H125N23O25S3
Synonyms
  • Duramycin
  • Lancovutide
  • Leucopeptin
External IDs
  • Antibiotic PA 48009
  • Moli 1901
  • MOLI-1901
  • MOLI1901
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Pharmacology

Indication

Investigated for use/treatment in cystic fibrosis and eye disorders/infections.

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Pharmacodynamics

Not Available

Mechanism of action

Duramycin becomes deposited in cellular membranes where it binds to phosphatidylethanolamine. It may thereby change biophysical membrane properties and perturb ion channel function. Duramycin stimulates secretion of electrically charged atoms (ions) of chloride from epithelial cells in the lungs. Increased chloride secretion is accompanied by obligatory increase in water secretion from same cells. This may prevent the thickening of lung secretions and prevent further mucus build up and its progressive contribution to lung tissue damage.

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
BPR0F3X56H
CAS number
1391-36-2
InChI Key
SFWLDKQAUHFCBS-AOEYGKNYSA-N
InChI
InChI=1S/C89H125N23O25S3/c1-44(2)67-85(131)107-60-42-138-41-59-80(126)106-61-43-140-46(4)69(87(133)103-56(76(122)108-67)35-49-23-12-7-13-24-49)109-77(123)55(34-48-21-10-6-11-22-48)102-83(129)62-27-18-32-112(62)66(116)39-96-73(119)54(33-47-19-8-5-9-20-47)101-79(125)58(104-81(61)127)37-94-31-17-15-26-53(88(134)135)100-86(132)68(110-78(124)57(36-64(93)114)97-65(115)38-95-84(130)70(111-82(60)128)71(117)89(136)137)45(3)139-40-50(91)72(118)98-51(25-14-16-30-90)74(120)99-52(75(121)105-59)28-29-63(92)113/h5-13,19-24,44-46,50-62,67-71,94,117H,14-18,25-43,90-91H2,1-4H3,(H2,92,113)(H2,93,114)(H,95,130)(H,96,119)(H,97,115)(H,98,118)(H,99,120)(H,100,132)(H,101,125)(H,102,129)(H,103,133)(H,104,127)(H,105,121)(H,106,126)(H,107,131)(H,108,122)(H,109,123)(H,110,124)(H,111,128)(H,134,135)(H,136,137)/t45-,46-,50-,51-,52-,53-,54-,55-,56-,57-,58-,59+,60-,61-,62-,67-,68+,69+,70-,71+/m0/s1
IUPAC Name
(1S,4S,13S,16S,19S,22S,25S,28R,31S,37S,40S,41S,44R,47S,50S,53S,56R,65S,70S)-44-amino-47-(4-aminobutyl)-4,16,22-tribenzyl-50-(2-carbamoylethyl)-37-(carbamoylmethyl)-31-[(R)-carboxy(hydroxy)methyl]-41,70-dimethyl-2,5,8,14,17,20,23,26,29,32,35,38,45,48,51,54,57,67-octadecaoxo-25-(propan-2-yl)-42,69,72-trithia-3,6,9,15,18,21,24,27,30,33,36,39,46,49,52,55,58,60,66-nonadecaazapentacyclo[38.18.9.3^{19,56}.3^{28,53}.0^{9,13}]triheptacontane-65-carboxylic acid
SMILES
CC(C)[C@@H]1NC(=O)[C@H](CC2=CC=CC=C2)NC(=O)[C@@H]2NC(=O)[C@H](CC3=CC=CC=C3)NC(=O)[C@@H]3CCCN3C(=O)CNC(=O)[C@H](CC3=CC=CC=C3)NC(=O)[C@@H]3CNCCCC[C@H](NC(=O)[C@@H]4NC(=O)[C@H](CC(N)=O)NC(=O)CNC(=O)[C@@H](NC(=O)[C@H](CSC[C@@H](NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](N)CS[C@H]4C)C(=O)N[C@@H](CS[C@H]2C)C(=O)N3)NC1=O)[C@@H](O)C(O)=O)C(O)=O

References

General References
Not Available
PubChem Substance
347909900
ChemSpider
81367925

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentCystic Fibrosis (CF)1
1CompletedDiagnosticHealthy Volunteers (HV)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.222 mg/mLALOGPS
logP-2.7ALOGPS
logP-15Chemaxon
logS-4ALOGPS
pKa (Strongest Acidic)2.85Chemaxon
pKa (Strongest Basic)10.22Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count28Chemaxon
Hydrogen Donor Count25Chemaxon
Polar Surface Area760.09 Å2Chemaxon
Rotatable Bond Count19Chemaxon
Refractivity500.3 m3·mol-1Chemaxon
Polarizability200.68 Å3Chemaxon
Number of Rings8Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03dl-9000000005-17b3d134335f030c9c84
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-1000000009-a495f7e9aa5e115ef15d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fxw-0000000009-7cd0bc7e0e5ce105f087
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0000000009-96635cb32c409a3a223b
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9000000003-a43045947216720b84e3
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-000l-8000000089-087b44ea34a607ba65cd
Chromatographic Properties
Collision Cross Sections (CCS)
Not Available

Enzymes

Details1. Cytosolic phospholipase A2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Phospholipase a2 activity
Specific Function
Selectively hydrolyzes arachidonyl phospholipids in the sn-2 position releasing arachidonic acid. Together with its lysophospholipid activity, it is implicated in the initiation of the inflammatory...
Gene Name
PLA2G4A
Uniprot ID
P47712
Uniprot Name
Cytosolic phospholipase A2
Molecular Weight
85238.2 Da
References
  1. Tanaka K, Itazaki H, Yoshida T: Cinatrins, a novel family of phospholipase A2 inhibitors. II. Biological activities. J Antibiot (Tokyo). 1992 Jan;45(1):50-5. [Article]
  2. Marki F, Hanni E, Fredenhagen A, van Oostrum J: Mode of action of the lanthionine-containing peptide antibiotics duramycin, duramycin B and C, and cinnamycin as indirect inhibitors of phospholipase A2. Biochem Pharmacol. 1991 Oct 24;42(10):2027-35. [Article]
  3. Hechard Y, Sahl HG: Mode of action of modified and unmodified bacteriocins from Gram-positive bacteria. Biochimie. 2002 May-Jun;84(5-6):545-57. [Article]

Drug created at October 21, 2007 22:23 / Updated at March 26, 2021 03:54