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Canna·wikiPF-03550096

ECS modulator (research)

Unscheduled

PF-03550096

N-[(2S)-1-amino-3,3-dimethyl-1-oxobutan-2-yl]-3-(3-hydroxy-3-methylbutyl)-2-oxobenzimidazole-1-carboxamide

Aliases.PF 03550096 · PF-3550096

A full selective CB2 agonist (human Ki 7.9 nM) active orally against visceral hypersensitivity in the rat.

Updated on

Level of detail

Harm-reduction warning

No characterised human dose: animal / in vitro data only. Effect profile, safety margin and acute toxicity are not documented in human clinical practice. Extremely potent compound: severe effects, seizures and deaths reported in the literature.

Identifiers

Formula
C₁₉H₂₈N₄O₄
Molar mass
376.21 g·mol⁻¹
CAS
910376-39-5
PubChem CID
24857887
Origin
A wholly synthetic compound with no natural occurrence. It was produced within a pharmaceutical research programme and was not commercialised.
InChIKey
GGNIFXBIJCNXCT-CQSZACIVSA-N

In plain terms

PF-03550096 activates the CB2 receptor, found mainly outside the brain, notably in the immune system and the gut. In rats it reduces painful hypersensitivity of the colon. It never became a medicine.

Receptors and activity

  • CB2
    Ki humain = 7,9 ± 1,7 nM ; Ki rat = 47 ± 5,6 nM ; agoniste complet (Kikuchi et coll. 2008)Agonist
  • CB1
    Sélectivité élevée pour le CB2 humain ; pas d'effet central rapportéModulator
  • Agonist
  • Partial agonist
  • Antagonist
  • Modulator
  • Inverse agonist

Hover over a row for the precise value (Ki, EC50…)

Subjective signature

Hover over an axis to read its definition.

  • Calm
    30
  • Clarity
    10
  • Sleep
    15
  • Appetite
    5
  • High
    10

Editorial estimate, not clinical.

Pharmacology

PF-03550096 belongs to a strategy that long appeared the most promising in cannabinoid pharmacology applied to pain: targeting the CB2 receptor rather than CB1. CB2 is weakly expressed in the neurons of the central nervous system and abundantly present on immune cells and in peripheral tissues, so that a selective agonist of that receptor should produce an analgesic and anti-inflammatory effect without intoxication or cognitive disturbance. Kikuchi and colleagues describe in 2008 a compound of that class, built on a benzimidazolone core that sets it apart from the usual cannabinoid chemotypes. The measured affinity is high at the human receptor, on the order of eight nanomolar, and distinctly weaker at the rat receptor, a species difference frequent at CB2 that complicates the extrapolation of animal models. The compound behaves as a full agonist in cellular assay. Given orally to rats, it corrects the lowering of the colonic pain threshold produced by an inflammatory agent, and the demonstration is closed by the use of a selective CB2 antagonist that abolishes the effect without having one of its own. The compound was not developed beyond that stage. The whole class of CB2 agonists met the same fate: despite consistent preclinical pharmacology and a favourable safety profile, no selective CB2 agonist has shown convincing analgesic efficacy in the clinical trials conducted so far.

Key sources.

Origin (research tool)

An entirely chemical route, described here by class only. The molecule is a benzimidazolone carboxamide: the benzimidazol-2-one core carries on one nitrogen a chain bearing a tertiary alcohol, and on the other a carboxamide function linked to an amino acid residue of defined configuration, whose primary amide function terminates the chain. It therefore does not belong to the classical families of CB2 agonists, neither aminoalkylindoles nor bicyclic cannabinoids.

Structural classification

Class
ECS modulator (research)
Origin
A wholly synthetic compound with no natural occurrence. It was produced within a pharmaceutical research programme and was not commercialised.
Status
Unscheduled

References

  1. 1.Kikuchi et coll. 2008 : évaluation pharmacologique du PF-03550096, ligand CB2, in vitro et sur un modèle d'hypersensibilité viscérale chez le ratPMID 18270474

Structured data

InChIKey
GGNIFXBIJCNXCT-CQSZACIVSA-N
SMILES
CC(C)(C)[C@@H](C(=O)N)NC(=O)N1C2=CC=CC=C2N(C1=O)CCC(C)(C)O
Formula
C19H28N4O4
Molar mass
376.21 g·mol⁻¹
CAS
910376-39-5
PubChem CID
24857887
Machine-readable entry (JSON)

LLM ingestion format: a structured superset of the entry (identifiers, binding, versioned legal status). Full corpus.

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