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Synthetic

S-777469

Selective CB2 agonist from Shionogi, studied against pruritus then abandoned in clinical development.

Unscheduled
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.

C₂₃H₂₇FN₂O₄

CAS 885496-53-7

Family
Synthetic CB receptor agonistResearch ligand or medicine
Molar mass
414.50 g/mol

Updated on

In plain terms

S-777469 is a laboratory molecule developed by a Japanese pharmaceutical company. It has nothing to do with hemp: it was made to bind to only one of the body's two cannabinoid receptors, the one found mainly in immune cells and in the skin. Studied for the itch of eczema, it was never marketed.

Receptors and activity

Target network

CB2AgonistKi = 186 nM · humanradioligand binding; pKi 6.73 (±0.04)
  • Activates
  • Binds or modulates

The lower the cited value, the closer the target sits to S-777469: one ring per factor of 100. A target with no measured value stays on the edge.

Where these targets live

Where each target has been found in humans, according to the cited studies. The map shows the target, not an effect of S-777469.

Brain, side view
Body, front view
Blood

CB2CB2 found in 5 regions of the body

  1. SpleendenseHighly abundant in the spleen1
  2. Immune cellspresentMainly B cells and natural killer cells1
  3. SkinpresentKeratinocytes, mast cells and nerve fibres2
  4. GutpresentImmune cells of the colonic mucosa3
  5. BonepresentPresent on osteoclasts4

Map sources

  1. Galiègue S et al. Expression of central and peripheral cannabinoid receptors in human immune tissues and leukocyte subpopulations. Eur J Biochem, 1995 (new tab)
  2. Ständer S et al. Distribution of cannabinoid receptor 1 (CB1) and 2 (CB2) on sensory nerve fibers and adnexal structures in human skin. J Dermatol Sci, 2005 (new tab)
  3. Wright K et al. Differential expression of cannabinoid receptors in the human colon: cannabinoids promote epithelial wound healing. Gastroenterology, 2005 (new tab)
  4. Rossi F et al. The endovanilloid/endocannabinoid system in human osteoclasts: possible involvement in bone formation and resorption. Bone, 2009 (new tab)

Cited values

  1. CB2AgonistKi = 186 nM · human46 out of 100

    Sharma et al., Int J Mol Sci 2023 (table 1) (new tab) · radioligand binding; pKi 6.73 (±0.04)

  2. CB1Binding (function not established)no measured value cited
Bar length follows the measured value (Ki, Kd, EC50 or IC50), on one scale shared by every entry, from 100 µM to 0.1 nM. A target with no cited value has no bar.

Pharmacology

S-777469 belongs to the chemical family of 3-carbamoyl-2-pyridones and shares no structure with plant cannabinoids. Its interest lies in its selectivity: it activates the CB2 receptor, with a pKi of 6.73 at the human receptor against about 4.80 for CB1, a preference of about 80-fold (Sharma et al. 2023). In mice, oral administration reduced scratching induced by compound 48/80 by 55% and 61% at 1 and 10 mg/kg (Odan et al. 2012); the effect is abolished by the CB2 antagonist SR144528 and extends to scratching induced by histamine, substance P (mice) or serotonin (rats); the molecule also inhibits histamine-induced peripheral nerve firing (Haruna et al. 2015). In mouse models of dermatitis, it reduced ear swelling, epidermal thickness and the infiltration of mast cells and eosinophils (Haruna et al. 2017). In humans, the molecule is rapidly absorbed by mouth and extensively metabolised (Sekiguchi et al. 2015). Two Shionogi clinical trials (NCT00697710, NCT00703573) were registered, including a placebo-controlled phase 2 trial in atopic dermatitis in 209 participants, with no result posted. No therapeutic benefit is established in humans.

Key sources.

History

Source
An entirely synthetic substance, produced by industrial medicinal chemistry. It exists in no plant, does not form in hemp and is not produced by the human body. Its purpose is pharmacological: to serve as a selective probe of the CB2 receptor and, originally, as an orally active antipruritic drug candidate. It has never been marketed or authorised as a medicine.

Origin

Laboratory synthesis

No known biological route: the molecule is entirely synthetic and has no natural precursor. Its 3-carbamoyl-2-pyridone skeleton belongs to pharmaceutical synthetic chemistry and lies outside the cannabigerol pathway that gives rise to the hemp cannabinoids.

Classification

Family, origin and source verification

Family

Synthetic CB receptor agonist › Research ligand or medicine

Class

pyridone-3-carboxamide

Verification

Classification, sources and binding values checked on 20 October 2026; text read against its sources and Wikipedia.

Wikipedia (English)

S-777,469 (new tab)

Article paired by the molecule's structure (InChIKey), revision read on 19 October 2026. Read as a second opinion, never cited as a source.

References

  1. Odan M et al., Bioorg Med Chem Lett 2012: discovery of S-777469 (new tab)PMID 22444677
  2. Haruna T et al., Pharmacology 2015: inhibition of scratching in rodents through inhibition of itch signal transmission (new tab)PMID 25721168
  3. Haruna T et al., Pharmacology 2017: effect on skin inflammation in mice (new tab)PMID 28214870
  4. Sharma R et al., Int J Mol Sci 2023: CB2 agonists with reduced lipophilicity (binding data for UOSS77 / S-777469) (new tab)PMID 37047385
  5. Sekiguchi K et al., Xenobiotica 2014: non-clinical metabolism, pharmacokinetics and excretion (new tab)PMID 23763649
  6. Sekiguchi K et al., Xenobiotica 2015: metabolism and pharmacokinetics of [14C]-S-777469 in healthy volunteers (new tab)PMID 25180977
  7. Sekiguchi K et al., Xenobiotica 2016: inhibition and stimulation of microsomal metabolism by long-chain fatty acids and albumin (new tab)PMID 26677906
  8. Takai N et al., Mass Spectrom (Tokyo) 2014: quantification of drugs in tissue sections by imaging mass spectrometry (new tab)PMID 24738041
  9. ClinicalTrials.gov NCT00703573: phase 2 of S-777469 in atopic dermatitis (Shionogi, 05/2008 to 12/2009, 209 participants, no results posted) (new tab)
  10. ClinicalTrials.gov NCT00697710: phase Ib/IIa of S-777469 (Shionogi, 07/2007 to 09/2008, 37 participants, no results posted) (new tab)

Identifiers

Names

IUPAC name
1-[[6-ethyl-1-[(4-fluorophenyl)methyl]-5-methyl-2-oxopyridine-3-carbonyl]amino]cyclohexane-1-carboxylic acid
Other names
S-777,469 · UOSS77

Identifiers

Formula
C₂₃H₂₇FN₂O₄
CAS
885496-53-7
PubChem CID
57331749(new tab)
InChIKey
JIYXOJFSPOFZPY-UHFFFAOYSA-N
SMILES
CCC1=C(C=C(C(=O)N1CC2=CC=C(C=C2)F)C(=O)NC3(CCCCC3)C(=O)O)C

Machine-readable entry (JSON)

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