Identification

Generic Name
Pam2csk4
DrugBank Accession Number
DB16474
Background

Not Available

Type
Small Molecule
Groups
Investigational
Structure
Weight
Average: 1271.84
Monoisotopic: 1270.927740711
Chemical Formula
C65H126N10O12S
Synonyms
  • Pam2
  • Pam2CSK4
  • Pam2CSK4 acetate
External IDs
  • CBLB 601

Pharmacology

Indication

Not Available

Reduce drug development failure rates
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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

Pam2 is a synthetic lipopeptide which acts as an agonist at TLR2 and TLR6. Actions at these receptors suggest that Pam2 has potential antiviral properties.

TargetActionsOrganism
UToll-like receptor 6
agonist
Humans
UToll-like receptor 2
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

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
L33ZW7BO91
CAS number
574741-81-4
InChI Key
LJUIOEFZFQRWJG-KKIBDXJDSA-N
InChI
InChI=1S/C65H126N10O12S/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-41-58(77)86-48-51(87-59(78)42-28-26-24-22-20-18-16-14-12-10-8-6-4-2)49-88-50-52(70)60(79)75-57(47-76)64(83)73-54(38-30-34-44-67)62(81)71-53(37-29-33-43-66)61(80)72-55(39-31-35-45-68)63(82)74-56(65(84)85)40-32-36-46-69/h51-57,76H,3-50,66-70H2,1-2H3,(H,71,81)(H,72,80)(H,73,83)(H,74,82)(H,75,79)(H,84,85)/t51?,52-,53-,54-,55-,56-,57-/m0/s1
IUPAC Name
(2S)-6-amino-2-[(2S)-6-amino-2-[(2S)-6-amino-2-[(2S)-6-amino-2-[(2S)-2-[(2R)-2-amino-3-{[2,3-bis(hexadecanoyloxy)propyl]sulfanyl}propanamido]-3-hydroxypropanamido]hexanamido]hexanamido]hexanamido]hexanoic acid
SMILES
CCCCCCCCCCCCCCCC(=O)OCC(CSC[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(O)=O)OC(=O)CCCCCCCCCCCCCCC

References

General References
  1. Leiva-Juarez MM, Kirkpatrick CT, Gilbert BE, Scott B, Tuvim MJ, Dickey BF, Evans SE, Markesich D: Combined aerosolized Toll-like receptor ligands are an effective therapeutic agent against influenza pneumonia when co-administered with oseltamivir. Eur J Pharmacol. 2018 Jan 5;818:191-197. doi: 10.1016/j.ejphar.2017.10.035. Epub 2017 Oct 21. [Article]
  2. Drake MG, Evans SE, Dickey BF, Fryer AD, Jacoby DB: Toll-like receptor-2/6 and Toll-like receptor-9 agonists suppress viral replication but not airway hyperreactivity in guinea pigs. Am J Respir Cell Mol Biol. 2013 Jun;48(6):790-6. doi: 10.1165/rcmb.2012-0498OC. [Article]
  3. External Link [Link]
ChemSpider
8164606
ChEBI
46889

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

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

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00145 mg/mLALOGPS
logP1.46ALOGPS
logP5.11ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)3.59ChemAxon
pKa (Strongest Basic)10.78ChemAxon
Physiological Charge4ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area385.73 Å2ChemAxon
Rotatable Bond Count65ChemAxon
Refractivity349.79 m3·mol-1ChemAxon
Polarizability151.16 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Participates in the innate immune response to Gram-positive bacteria and fungi. Specifically recognizes diacylated and, to a lesser extent, triacylated lipopeptides (PubMed:20037584). In response to diacylated lipopeptides, forms the activation cluster TLR2:TLR6:CD14:CD36, this cluster triggers signaling from the cell surface and subsequently is targeted to the Golgi in a lipid-raft dependent pathway (PubMed:16880211). Acts via MYD88 and TRAF6, leading to NF-kappa-B activation, cytokine secretion and the inflammatory response. Recognizes mycoplasmal macrophage-activating lipopeptide-2kD (MALP-2), soluble tuberculosis factor (STF), phenol-soluble modulin (PSM) and B.burgdorferi outer surface protein A lipoprotein (OspA-L) cooperatively with TLR2 (PubMed:11441107). In complex with TLR4, promotes sterile inflammation in monocytes/macrophages in response to oxidized low-density lipoprotein (oxLDL) or amyloid-beta 42. In this context, the initial signal is provided by oxLDL- or amyloid-beta 42-binding to CD36. This event induces the formation of a heterodimer of TLR4 and TLR6, which is rapidly internalized and triggers inflammatory response, leading to the NF-kappa-B-dependent production of CXCL1, CXCL2 and CCL9 cytokines, via MYD88 signaling pathway, and CCL5 cytokine, via TICAM1 signaling pathway, as well as IL1B secretion (PubMed:11441107, PubMed:20037584).
Specific Function
Amyloid-beta binding
Gene Name
TLR6
Uniprot ID
Q9Y2C9
Uniprot Name
Toll-like receptor 6
Molecular Weight
91878.845 Da
References
  1. Goldblatt DL, Flores JR, Valverde Ha G, Jaramillo AM, Tkachman S, Kirkpatrick CT, Wali S, Hernandez B, Ost DE, Scott BL, Chen J, Evans SE, Tuvim MJ, Dickey BF: Inducible epithelial resistance against acute Sendai virus infection prevents chronic asthma-like lung disease in mice. Br J Pharmacol. 2020 May;177(10):2256-2273. doi: 10.1111/bph.14977. Epub 2020 Feb 12. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Triacyl lipopeptide binding
Specific Function
Cooperates with LY96 to mediate the innate immune response to bacterial lipoproteins and other microbial cell wall components. Cooperates with TLR1 or TLR6 to mediate the innate immune response to ...
Gene Name
TLR2
Uniprot ID
O60603
Uniprot Name
Toll-like receptor 2
Molecular Weight
89836.575 Da
References
  1. Goldblatt DL, Flores JR, Valverde Ha G, Jaramillo AM, Tkachman S, Kirkpatrick CT, Wali S, Hernandez B, Ost DE, Scott BL, Chen J, Evans SE, Tuvim MJ, Dickey BF: Inducible epithelial resistance against acute Sendai virus infection prevents chronic asthma-like lung disease in mice. Br J Pharmacol. 2020 May;177(10):2256-2273. doi: 10.1111/bph.14977. Epub 2020 Feb 12. [Article]

Drug created at January 21, 2021 01:43 / Updated at May 03, 2022 17:51