Onternabez

{{short description|Cannabidiol-derivative drug}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| class = CB₂ receptor agonist

| verifiedrevid = 426291380

| IUPAC_name = [(1S,2S,5S)-2-[2,6-Dimethoxy-4-(2-methyloctan-2-yl)phenyl]-7,7-dimethyl-4-bicyclo[3.1.1]hept-3-enyl]methanol

| image = Onternabez.svg

| image_class = skin-invert-image

| caption =

| width =

| tradename =

| pregnancy_AU =

| pregnancy_category =

| legal_AU =

| legal_CA = Schedule II

| legal_UK = Class B

| legal_US = Unscheduled

| legal_US_comment =

| legal_status = Florida: Schedule I

| routes_of_administration =

| bioavailability =

| protein_bound =

| metabolism = Liver

| elimination_half-life =

| excretion = Kidneys

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 256934-39-1

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 8I5L034D55

| ATC_prefix = None

| ATC_suffix =

| PubChem = 11553430

| ChEBI = 146244

| synonyms = HU-308, HU308, PPP-003, ARDS-003

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| KEGG = D12305

| ChemSpiderID = 8020425

| C = 27

| H = 42

| O = 3

| smiles = CCCCCCC(C)(C)C1=CC(=C(C(=C1)OC)[C@H]2C=C([C@@H]3C[C@H]2C3(C)C)CO)OC

| StdInChI = 1S/C27H42O3/c1-8-9-10-11-12-26(2,3)19-14-23(29-6)25(24(15-19)30-7)20-13-18(17-28)21-16-22(20)27(21,4)5/h13-15,20-22,28H,8-12,16-17H2,1-7H3/t20-,21-,22+/m0/s1

| StdInChIKey = CFMRIVODIXTERW-FDFHNCONSA-N

}}

Onternabez (also known as HU-308, HU308, PPP-003, and ARDS-003) is a synthetic cannabinoid that acts as a potent cannabinoid agonist. It is highly selective for the cannabinoid-2 receptor (CB₂ receptor) subtype, with a selectivity more than 5,000 times greater for the CB₂ receptor than the CB₁ receptor.{{cite journal| vauthors = Mechoulam R, Lander N, Breuer A, Zahalka J |date=1990-04-11|title=Synthesis of the individual, pharmacologically distinct enantiomers of a tetrahydrocannabinol derivative|journal=Tetrahedron Asymmetry|volume=1|issue=5|language=en|pages=315–318|doi=10.1016/S0957-4166(00)86322-3|pmid=|pmc=|issn=|doi-access=free}}{{cite journal | vauthors = Hanus L, Breuer A, Tchilibon S, Shiloah S, Goldenberg D, Horowitz M, Pertwee RG, Ross RA, Mechoulam R, Fride E | display-authors = 6 | title = HU-308: a specific agonist for CB(2), a peripheral cannabinoid receptor | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 96 | issue = 25 | pages = 14228–14233 | date = December 1999 | pmid = 10588688 | pmc = 24419 | doi = 10.1073/pnas.96.25.14228 | doi-access = free | bibcode = 1999PNAS...9614228H }}{{cite web |title=Properties of HU-308 ~ Formula C27H42O3 |url=http://pqr.pitt.edu/mol/CFMRIVODIXTERW-BHIFYINESA-N |website=Pitt Quantum Repository |publisher=University of Pittsburgh Department of Chemistry}} The synthesis and characterization of onternabez took place in the laboratory of Raphael Mechoulam at the Hebrew University of Jerusalem (the HU in HU-308) in the late 1990s. The pinene dimethoxy-DMH-CBD derivative onternabez was identified as a potent peripheral CB₂-selective agonist in in vitro and animal studies in 1990 and 1999.