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Canna·wikiRosonabant

ECS modulator (research)

Unscheduled

Rosonabant

3-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-N-piperidin-1-yl-3,4-dihydropyrazole-5-carboxamide

Aliases.E-6776 · E 6776

A CB1 antagonist from Esteve against obesity, halted along with its whole class after the withdrawal of rimonabant.

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
C₂₁H₂₁Cl₃N₄O
Molar mass
450.08 g·mol⁻¹
CAS
861151-12-4
PubChem CID
11316914
Origin
A wholly synthetic compound with no natural occurrence. It was produced within a pharmaceutical development programme that did not succeed.
InChIKey
WMMMJGKFKKBRQR-UHFFFAOYSA-N

In plain terms

Rosonabant was an experimental appetite suppressant from the Esteve laboratory, built on the same principle as rimonabant. Its development was stopped when that whole family of medicines was abandoned over psychiatric risk.

Receptors and activity

  • CB1
    Antagoniste et agoniste inverse de la série des pyrazolines ; valeurs non publiées dans les sources retenuesAntagonist
  • CB2
    Aucune action documentée sur le CB2Modulator
  • 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
    10
  • Clarity
    15
  • Sleep
    10
  • Appetite
    5
  • High
    5

Editorial estimate, not clinical.

Pharmacology

Rosonabant is a characteristic example of a molecule carried away by the failure of an entire class rather than by a flaw of its own. Developed by the Spanish laboratory Esteve under the code E-6776, this pyrazoline derivative belongs to the same chemical family as rimonabant, the first CB1 receptor antagonist authorised in Europe in 2006 as a treatment for obesity. Janero and Makriyannis mention it in 2009 in their review of the class among the follow-on compounds actually carried into the clinic, alongside taranabant, otenabant, surinabant, SLV-319, AVE-1625 and V-24343. That list is the roll of a complete generation interrupted at the same moment. Rimonabant was withdrawn from the European market in 2008 after adverse psychiatric effects were established, notably anxiety, depression and suicidal ideation, and the authorities took the view that this risk stemmed from the mechanism itself, that is from the blockade of CB1 receptors in the central nervous system, rather than from a peculiarity of one molecule. Competing developments therefore ceased. Rosonabant was never the subject of a detailed pharmacological characterisation in the accessible literature, which makes this entry deliberately sober: what is established concerns its class and its programme, not a set of published measurements. The field subsequently reoriented towards two routes intended to avoid that risk, antagonists restricted to the periphery and genuinely neutral antagonists.

Key sources.

Origin (research tool)

An entirely chemical route, described here by class only. The molecule belongs to the pyrazoline antagonists: a pyrazoline ring, the partially reduced form of the pyrazole, bears a dichlorophenyl on the nitrogen, an adjacent chlorophenyl and a piperidine carboxamide. This is the same structural grammar as that of rimonabant, apart from the reduction of the central ring.

Structural classification

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

References

  1. 1.Janero et Makriyannis 2009 : antagonistes des récepteurs cannabinoïdes, opportunités pharmacologiques, expérience clinique et pronostic translationnelPMID 19249987

Structured data

InChIKey
WMMMJGKFKKBRQR-UHFFFAOYSA-N
SMILES
C1CCN(CC1)NC(=O)C2=NN(C(C2)C3=CC=C(C=C3)Cl)C4=C(C=C(C=C4)Cl)Cl
Formula
C21H21Cl3N4O
Molar mass
450.08 g·mol⁻¹
CAS
861151-12-4
PubChem CID
11316914
Machine-readable entry (JSON)

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

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