Lancovutide
Explore a selection of our essential drug information below, or:
Overview
- DrugBank ID
- DB05029
- Type
- Small Molecule
- Clinical Trials
- Phase 0
- 0
- Phase 1
- 1
- Phase 2
- 1
- Phase 3
- 0
- Phase 4
- 0
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
- Weight
- Average: 2013.3
Monoisotopic: 2011.837910139 - Chemical Formula
- C89H125N23O25S3
- Synonyms
- Duramycin
- Lancovutide
- Leucopeptin
- External IDs
- Antibiotic PA 48009
- Moli 1901
- MOLI-1901
- MOLI1901
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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data2 Completed Treatment Cystic Fibrosis (CF) 1 somestatus stop reason just information to hide 1 Completed Diagnostic Healthy Volunteers (HV) 1 somestatus stop reason just information to hide
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
Property Value Source Water Solubility 0.222 mg/mL ALOGPS logP -2.7 ALOGPS logP -15 Chemaxon logS -4 ALOGPS pKa (Strongest Acidic) 2.85 Chemaxon pKa (Strongest Basic) 10.22 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 28 Chemaxon Hydrogen Donor Count 25 Chemaxon Polar Surface Area 760.09 Å2 Chemaxon Rotatable Bond Count 19 Chemaxon Refractivity 500.3 m3·mol-1 Chemaxon Polarizability 200.68 Å3 Chemaxon Number of Rings 8 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Not Available
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Has primarily calcium-dependent phospholipase and lysophospholipase activities, with a major role in membrane lipid remodeling and biosynthesis of lipid mediators of the inflammatory response (PubMed:10358058, PubMed:14709560, PubMed:16617059, PubMed:17472963, PubMed:18451993, PubMed:27642067, PubMed:7794891, PubMed:8619991, PubMed:8702602, PubMed:9425121). Plays an important role in embryo implantation and parturition through its ability to trigger prostanoid production (By similarity). Preferentially hydrolyzes the ester bond of the fatty acyl group attached at sn-2 position of phospholipids (phospholipase A2 activity) (PubMed:10358058, PubMed:17472963, PubMed:18451993, PubMed:7794891, PubMed:8619991, PubMed:9425121). Selectively hydrolyzes sn-2 arachidonoyl group from membrane phospholipids, providing the precursor for eicosanoid biosynthesis via the cyclooxygenase pathway (PubMed:10358058, PubMed:17472963, PubMed:18451993, PubMed:7794891, PubMed:9425121). In an alternative pathway of eicosanoid biosynthesis, hydrolyzes sn-2 fatty acyl chain of eicosanoid lysophopholipids to release free bioactive eicosanoids (PubMed:27642067). Hydrolyzes the ester bond of the fatty acyl group attached at sn-1 position of phospholipids (phospholipase A1 activity) only if an ether linkage rather than an ester linkage is present at the sn-2 position. This hydrolysis is not stereospecific (PubMed:7794891). Has calcium-independent phospholipase A2 and lysophospholipase activities in the presence of phosphoinositides (PubMed:12672805). Has O-acyltransferase activity. Catalyzes the transfer of fatty acyl chains from phospholipids to a primary hydroxyl group of glycerol (sn-1 or sn-3), potentially contributing to monoacylglycerol synthesis (PubMed:7794891)
- Specific Function
- calcium ion binding
- Gene Name
- PLA2G4A
- Uniprot ID
- P47712
- Uniprot Name
- Cytosolic phospholipase A2
- Molecular Weight
- 85238.2 Da
References
- 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]
- 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]
- 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