ECS modulator (research)
Prescription medicineÉpidiolexCannabidiol (Epidiolex)
2-[(1R,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol
Aliases.Epidiolex · Epidyolex · GWP42003-P · CBD purifié pharmaceutique · Cannabidiol oral solution
Purified pharmaceutical-grade cannabidiol, authorised for rare epilepsies.
Updated on
Level of detail
Identifiers
- Formula
- C₂₁H₃₀O₂
- Molar mass
- 314.50 g·mol⁻¹
- CAS
- 13956-29-1
- PubChem CID
- 644019
- First described
- Le cannabidiol a été isolé dès 1940 et sa structure élucidée en 1963. Sa version pharmaceutique, l'Épidiolex (code de développement GWP42003-P), a été mise au point par GW Pharmaceuticals et autorisée par la FDA américaine en 2018 puis par l'Agence européenne des médicaments (EMA) en septembre 2019 sous le nom Epidyolex.
- Origin
- A medicine of plant origin: an oral solution of highly purified cannabidiol, extracted from selected Cannabis sativa plants.
- InChIKey
- QHMBSVQNZZTUGM-ZWKOTPCHSA-N
In plain terms
Epidiolex is a medicine based on purified cannabidiol, prescribed for certain rare childhood epilepsies. It is not a wellness product and it does not make you high.
Receptors and activity
- CB1modulateur allostérique négatif, faible affinité orthostériqueModulator
- CB2Modulator
- 5-HT1AAgonist
- 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.
- Calm55
- Clarity30
- Sleep45
- Appetite20
- High20
Editorial estimate, not clinical.
Pharmacology
Epidiolex (Epidyolex in Europe) is an oral solution of highly purified cannabidiol, authorised by the EMA since 2019 in combination with clobazam for the seizures of Dravet syndrome and Lennox-Gastaut syndrome. Cannabidiol barely activates the CB1/CB2 receptors: it acts above all as a negative allosteric modulator of CB1 and through non-cannabinoid targets (5-HT1A, TRPV1, GPR55), which explains its non-psychotropic profile. What is at issue here is the medicinal form, distinct from wellness oils, reserved for supervised clinical use.
Key sources.
Origin (research tool)
Route of production: in the plant, cannabidiol derives from cannabidiolic acid (CBDA), itself arising from cannabigerolic acid (CBGA) through the action of CBDA synthase, and then decarboxylated. For Epidiolex, this cannabidiol is extracted from Cannabis sativa flowers grown under controlled conditions, then purified to a very high degree and formulated as an oral oily solution at a standardised concentration.
Legal framework
France
In France, Epidiolex is a prescription-only medicine, available under its European marketing authorisation (and previously through early access/ATU). Cannabidiol as a molecule is not classified as a narcotic, but this medicinal product falls strictly within the pharmaceutical circuit and requires a specialist prescription.
European Union
Epidyolex holds a centralised marketing authorisation granted by the EMA since September 2019, in combination with clobazam, for the seizures associated with Dravet syndrome and Lennox-Gastaut syndrome (an indication subsequently extended to tuberous sclerosis complex).
Sources: EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA. Our method.
Structural classification
- Class
- ECS modulator (research)
- Origin
- A medicine of plant origin: an oral solution of highly purified cannabidiol, extracted from selected Cannabis sativa plants.
- Status
- Prescription medicine
Cannabinoïde de type résorcinol (dérivé du 5-pentyl-benzène-1,3-diol), à cycle terpénique ouvert, contrairement au noyau tricyclique benzo[c]chromène des THC.
Pharmacokinetics
Administré par voie orale, le cannabidiol est fortement soumis à l'effet de premier passage hépatique ; sa biodisponibilité augmente nettement lorsqu'il est pris avec un repas riche en graisses. Il est très lipophile et se distribue largement dans les tissus.
Metabolism
Le cannabidiol est métabolisé au foie par les cytochromes CYP2C19 et CYP3A4, avec formation notamment du 7-hydroxy-cannabidiol actif. Il peut modifier les concentrations de médicaments associés, d'où sa co-prescription encadrée avec le clobazam.
References
- 1.EMA : Epidyolex (EPAR, autorisation de mise sur le marché)
- 2.CURE Epilepsy : Oral Cannabidiol Epidyolex Approved in Europe for Dravet and Lennox-Gastaut Syndromes
- 3.PubChem CID 644019 : Cannabidiol (identité, formule, InChIKey)
- 4.PMC5569602 : Cannabidiol safety and pharmacology review (cibles TRPV1, 5-HT1A)
Structured data
- InChIKey
- QHMBSVQNZZTUGM-ZWKOTPCHSA-N
- SMILES
- CCCCCC1=CC(=C(C(=C1)O)[C@@H]2C=C(CC[C@H]2C(=C)C)C)O
- Formula
- C21H30O2
- Molar mass
- 314.50 g·mol⁻¹
- CAS
- 13956-29-1
- PubChem CID
- 644019
LLM ingestion format: a structured superset of the entry (identifiers, binding, versioned legal status). Full corpus.