NAV

LGD-1550

Identification

Generic Name
LGD-1550
DrugBank Accession Number
DB05785
Background

LGD-1550 is an orally-active synthetic aromatic retinoic acid agent with potential antineoplastic and chemopreventive activities.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 340.507
Monoisotopic: 340.24023027
Chemical Formula
C23H32O2
Synonyms
Not Available
External IDs
  • ALRT-1550
  • LGD-1550
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Pharmacology

Indication

Investigated for use/treatment in cancer/tumors (unspecified).

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Pharmacodynamics

Not Available

Mechanism of action

LGD 1550 selectively binds to all three retinoic acid receptors (RAR-alpha, RAR-beta, and RAR-gamma), resulting in alterations in the expression of genes responsible for cell differentiation and proliferation. This agent also acts as an inhibitor of activator protein 1 (AP-1), a protein that mediates trophic responses and malignant transformation.

TargetActionsOrganism
URetinoic acid receptor alphaNot AvailableHumans
URetinoic acid receptor betaNot AvailableHumans
URetinoic acid receptor gammaNot AvailableHumans
UTranscription factor AP-1Not AvailableHumans
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
H62AOA2IYF
CAS number
178600-20-9
InChI Key
JMPZTWDLOGTBPM-OUQSKUGOSA-N
InChI
InChI=1S/C23H32O2/c1-16(12-21(24)25)10-9-11-17(2)18-13-19(22(3,4)5)15-20(14-18)23(6,7)8/h9-15H,1-8H3,(H,24,25)/b10-9+,16-12+,17-11+
IUPAC Name
(2E,4E,6E)-7-(3,5-di-tert-butylphenyl)-3-methylocta-2,4,6-trienoic acid
SMILES
C\C(\C=C\C=C(/C)C1=CC(=CC(=C1)C(C)(C)C)C(C)(C)C)=C/C(O)=O

References

General References
  1. Miller AB, Nettesheim P, Stewart BW: An International Evaluation of the Cancer-Preventive Potential of Nine Retinoids. Asian Pac J Cancer Prev. 2000;1(3):195-202. [Article]
PubChem Substance
347910230
ChemSpider
4450017
BindingDB
50052033
ChEMBL
CHEMBL89241
PDBe Ligand
ARL
PDB Entries
1nq7

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility0.000304 mg/mLALOGPS
logP7.54ALOGPS
logP6.82Chemaxon
logS-6ALOGPS
pKa (Strongest Acidic)4.57Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area37.3 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity109.59 m3·mol-1Chemaxon
Polarizability41.93 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
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/MSsplash10-05fu-3029000000-32710d05d29a8fdd3382
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0090000000-acc5e782b31480a89635
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-052v-0191000000-74714fc849664b0254c6
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004j-0090000000-e07f9c193e19e6572eb3
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0090000000-ce697d82937f95449a46
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ab9-3960000000-f339ce81f0fa6e0c77a3
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-209.63597
predicted
DeepCCS 1.0 (2019)
[M+H]+211.53136
predicted
DeepCCS 1.0 (2019)
[M+Na]+217.30994
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Retinoic acid receptor alpha
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expressi...
Gene Name
RARA
Uniprot ID
P10276
Uniprot Name
Retinoic acid receptor alpha
Molecular Weight
50770.805 Da
Details2. Retinoic acid receptor beta
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expressi...
Gene Name
RARB
Uniprot ID
P10826
Uniprot Name
Retinoic acid receptor beta
Molecular Weight
50488.63 Da
Details3. Retinoic acid receptor gamma
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expressi...
Gene Name
RARG
Uniprot ID
P13631
Uniprot Name
Retinoic acid receptor gamma
Molecular Weight
50341.405 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Details4. Transcription factor AP-1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transcriptional activator activity, rna polymerase ii transcription factor binding
Specific Function
Transcription factor that recognizes and binds to the enhancer heptamer motif 5'-TGA[CG]TCA-3'. Promotes activity of NR5A1 when phosphorylated by HIPK3 leading to increased steroidogenic gene expre...
Gene Name
JUN
Uniprot ID
P05412
Uniprot Name
Transcription factor AP-1
Molecular Weight
35675.32 Da

Drug created at November 18, 2007 18:27 / Updated at March 26, 2021 03:54