Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C25H38O3 |
Molecular Weight | 386.5674 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12CC(CO)=CC[C@]1([H])C(C)(C)OC3=C2C(O)=CC(=C3)C(C)(C)CCCCCC
InChI
InChIKey=SSQJFGMEZBFMNV-PMACEKPBSA-N
InChI=1S/C25H38O3/c1-6-7-8-9-12-24(2,3)18-14-21(27)23-19-13-17(16-26)10-11-20(19)25(4,5)28-22(23)15-18/h10,14-15,19-20,26-27H,6-9,11-13,16H2,1-5H3/t19-,20-/m0/s1
Dexanabinol is the synthetic cannabinoid. It is inactive as a cannabimimetic, but exhibits pharmacological properties characteristic of an N-methyl-D-aspartate (NMDA)-receptor antagonist. It blocks NMDA-receptors stereospecifically by interacting with a site close to, but distinct from, that of uncompetitive NMDA-receptor antagonists and from the recognition sites of glutamate, glycine, and polyamines. This agent also scavenges peroxy radicals and protects neurons from the damages of reactive oxygen species. Furthermore, dexanabinol inhibits the activity of nuclear factor kappa B (NF-kB), thereby preventing the expression of NF-kB target genes, such as tumor necrosis factor alpha, cytokines and inducible nitric oxide synthase. Dexanabinol is a potent cerebroprotective agent, with a therapeutic window of about 4 h. Dexanabinol is safe, but is not efficacious in the treatment of traumatic brain injury. It was introduced into clinical trials for breast cancer and advanced solid tumors.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2094124 |
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Target ID: WP408 Sources: DOI: 10.1002/1098-2299(200007/08)50:3/4<211::AID-DDR3>3.0.CO;2-G |
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Target ID: CHEMBL2094258 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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4226 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/33615223 |
24 mg/kg 1 times / week multiple, intravenous dose: 24 mg/kg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
DEXANABINOL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
7018 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/33615223 |
28 mg/kg 1 times / week multiple, intravenous dose: 28 mg/kg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
DEXANABINOL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
813 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/33615223 |
8 mg/kg 1 times / week multiple, intravenous dose: 8 mg/kg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
DEXANABINOL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
20139 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/33615223 |
36 mg/kg 1 times / week multiple, intravenous dose: 36 mg/kg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
DEXANABINOL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
204 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/33615223 |
2 mg/kg 1 times / week multiple, intravenous dose: 2 mg/kg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
DEXANABINOL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
2885 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/33615223 |
16 mg/kg 1 times / week multiple, intravenous dose: 16 mg/kg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
DEXANABINOL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
387 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/33615223 |
4 mg/kg 1 times / week multiple, intravenous dose: 4 mg/kg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
DEXANABINOL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
10800 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/33615223 |
24 mg/kg 1 times / week multiple, intravenous dose: 24 mg/kg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
DEXANABINOL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
15400 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/33615223 |
28 mg/kg 1 times / week multiple, intravenous dose: 28 mg/kg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
DEXANABINOL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
1890 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/33615223 |
8 mg/kg 1 times / week multiple, intravenous dose: 8 mg/kg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
DEXANABINOL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
38300 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/33615223 |
36 mg/kg 1 times / week multiple, intravenous dose: 36 mg/kg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
DEXANABINOL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
475 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/33615223 |
2 mg/kg 1 times / week multiple, intravenous dose: 2 mg/kg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
DEXANABINOL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
5750 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/33615223 |
16 mg/kg 1 times / week multiple, intravenous dose: 16 mg/kg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
DEXANABINOL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
881 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/33615223 |
4 mg/kg 1 times / week multiple, intravenous dose: 4 mg/kg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
DEXANABINOL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/33615223 |
24 mg/kg 1 times / week multiple, intravenous dose: 24 mg/kg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
DEXANABINOL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
1.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/33615223 |
28 mg/kg 1 times / week multiple, intravenous dose: 28 mg/kg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
DEXANABINOL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
2.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/33615223 |
8 mg/kg 1 times / week multiple, intravenous dose: 8 mg/kg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
DEXANABINOL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/33615223 |
36 mg/kg 1 times / week multiple, intravenous dose: 36 mg/kg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
DEXANABINOL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
2.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/33615223 |
2 mg/kg 1 times / week multiple, intravenous dose: 2 mg/kg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
DEXANABINOL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
1.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/33615223 |
16 mg/kg 1 times / week multiple, intravenous dose: 16 mg/kg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
DEXANABINOL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
1.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/33615223 |
4 mg/kg 1 times / week multiple, intravenous dose: 4 mg/kg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
DEXANABINOL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
PubMed
Title | Date | PubMed |
---|---|---|
Cardiovascular effects of (-)-11-OH-delta 8-tetrahydrocannabinol-dimethylheptyl in rats. | 1996 Aug |
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Cannabinoid-induced hypotension and bradycardia in rats mediated by CB1-like cannabinoid receptors. | 1997 Jun |
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Cannabinoid-induced mesenteric vasodilation through an endothelial site distinct from CB1 or CB2 receptors. | 1999 Nov 23 |
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The cannabinoid dexanabinol is an inhibitor of the nuclear factor-kappa B (NF-kappa B). | 2004 Sep |
|
Cannabinoid receptor 1 is a potential drug target for treatment of translocation-positive rhabdomyosarcoma. | 2009 Jul |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16361021
Single injection of 150 mg dexanabinol, given within 6 h of injury
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9424014
Dexanabinol inhibited the binding of the radioactive dopamine D1 receptor antagonist only at a very high concentration: 50 uM Dexanabinol inhibited 29.7 % of the specific binding of [3H]SCH-23390 to the forebrain membranes, while 100 uM inhibited 52.7%.
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FDA ORPHAN DRUG |
179803
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NCI_THESAURUS |
C274
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m4216
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112924-45-5
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C99381
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SUB33615
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DEXANABINOL
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DB06444
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ACTIVE MOIETY