This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

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Name
Labradimil
Accession Number
DB06549
Type
Small Molecule
Groups
Investigational
Description
Not Available
Structure
Thumb
Synonyms
  • Labradimil
External IDs
RMP-7
International/Other Brands
Cereport
Categories
UNII
2MK663C346
CAS number
159768-75-9
Weight
Average: 1098.29
Monoisotopic: 1097.544034089
Chemical Formula
C49H75N15O12S
InChI Key
IDXCXSCCZNCXCL-XMADEQCMSA-N
InChI
InChI=1S/C49H75N15O12S/c1-76-31-14-12-28(13-15-31)21-29(24-57-34(47(74)75)9-3-17-56-49(53)54)59-43(70)37-10-4-18-62(37)45(72)36(27-65)61-41(68)35(23-32-7-6-20-77-32)60-40(67)25-58-42(69)39-22-30(66)26-64(39)46(73)38-11-5-19-63(38)44(71)33(50)8-2-16-55-48(51)52/h6-7,12-15,20,29-30,33-39,57,65-66H,2-5,8-11,16-19,21-27,50H2,1H3,(H,58,69)(H,59,70)(H,60,67)(H,61,68)(H,74,75)(H4,51,52,55)(H4,53,54,56)/t29-,30+,33-,34-,35-,36-,37-,38-,39-/m0/s1
IUPAC Name
(2S)-2-{[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-(2-{[(2S,4R)-1-[(2S)-1-[(2S)-2-amino-5-[(diaminomethylidene)amino]pentanoyl]pyrrolidine-2-carbonyl]-4-hydroxypyrrolidin-2-yl]formamido}acetamido)-3-(thiophen-2-yl)propanamido]-3-hydroxypropanoyl]pyrrolidin-2-yl]formamido}-3-(4-methoxyphenyl)propyl]amino}-5-[(diaminomethylidene)amino]pentanoic acid
SMILES
COC1=CC=C(C[C@@H](CN[C@@H](CCCN=C(N)N)C(O)=O)NC(=O)[C@@H]2CCCN2C(=O)[C@H](CO)NC(=O)[C@H](CC2=CC=CS2)NC(=O)CNC(=O)[C@@H]2C[C@@H](O)CN2C(=O)[C@@H]2CCCN2C(=O)[C@@H](N)CCCN=C(N)N)C=C1

Pharmacology

Indication

Investigated for use/treatment in brain cancer and pediatric indications.

Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UB2 bradykinin receptor
agonist
Humans
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
Toxicity
Not Available
Affected organisms
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

References

General References
Not Available
External Links
ChemSpider
5293490
ChEMBL
CHEMBL2105864

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentBrain and Central Nervous System Tumors1
1CompletedTreatmentGliomas / Medulloblastomas / Neoplasms, Brain1

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 Solubility0.0428 mg/mLALOGPS
logP-2.5ALOGPS
logP-7.2ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)1.65ChemAxon
pKa (Strongest Basic)11.48ChemAxon
Physiological Charge3ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area431.17 Å2ChemAxon
Rotatable Bond Count29ChemAxon
Refractivity279.12 m3·mol-1ChemAxon
Polarizability113.82 Å3ChemAxon
Number of Rings5ChemAxon
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/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Oligopeptides
Alternative Parents
N-acyl-alpha amino acids and derivatives / Proline and derivatives / Alpha amino acid amides / Amphetamines and derivatives / L-alpha-amino acids / Anisoles / Methoxybenzenes / N-acylpyrrolidines / Phenoxy compounds / Pyrrolidinecarboxamides
show 21 more
Substituents
Alpha-oligopeptide / N-acyl-alpha amino acid or derivatives / Proline or derivatives / Alpha-amino acid amide / Amphetamine or derivatives / Alpha-amino acid or derivatives / L-alpha-amino acid / N-substituted-alpha-amino acid / Alpha-amino acid / Phenoxy compound
show 45 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Type 1 angiotensin receptor binding
Specific Function
Receptor for bradykinin. It is associated with G proteins that activate a phosphatidylinositol-calcium second messenger system.
Gene Name
BDKRB2
Uniprot ID
P30411
Uniprot Name
B2 bradykinin receptor
Molecular Weight
44460.15 Da
References
  1. Emerich DF, Snodgrass P, Dean RL, Lafreniere D, Agostino M, Wiens T, Xiong H, Hasler B, Marsh J, Pink M, Kim BS, Bartus RT: Bradykinin modulation of tumor vasculature: I. Activation of B2 receptors increases delivery of chemotherapeutic agents into solid peripheral tumors, enhancing their efficacy. J Pharmacol Exp Ther. 2001 Feb;296(2):623-31. [PubMed:11160651]
  2. Emerich DF, Dean RL, Snodgrass P, Lafreniere D, Agostino M, Wiens T, Xiong H, Hasler B, Marsh J, Pink M, Kim BS, Perdomo B, Bartus RT: Bradykinin modulation of tumor vasculature: II. activation of nitric oxide and phospholipase A2/prostaglandin signaling pathways synergistically modifies vascular physiology and morphology to enhance delivery of chemotherapeutic agents to tumors. J Pharmacol Exp Ther. 2001 Feb;296(2):632-41. [PubMed:11160652]
  3. Emerich DF, Dean RL, Osborn C, Bartus RT: The development of the bradykinin agonist labradimil as a means to increase the permeability of the blood-brain barrier: from concept to clinical evaluation. Clin Pharmacokinet. 2001;40(2):105-23. doi: 10.2165/00003088-200140020-00003. [PubMed:11286321]

Drug created on March 19, 2008 10:36 / Updated on November 02, 2019 01:58