Page last updated: 2024-12-06
2-adamantanol
2-Adamantanol is a bicyclic alcohol derived from adamantane. It's a white crystalline solid with a characteristic camphor-like odor. 2-adamantanol has been studied for its potential applications in various fields. Its synthesis often involves the oxidation of adamantane or the reduction of 2-adamantanone. It is known to exhibit biological activity, including anti-inflammatory and analgesic effects. 2-adamantanol is also used as a building block in the synthesis of other complex molecules, including pharmaceuticals and materials. The study of 2-adamantanol has been driven by its unique structural features, biological activity, and potential for further development.'
Cross-References
| ID Source | ID |
|---|
| PubMed CID | 64149 |
| CHEMBL ID | 1269176 |
| SCHEMBL ID | 350390 |
| SCHEMBL ID | 13082659 |
| MeSH ID | M0226880 |
Synonyms (37)
| Synonym |
|---|
| HMS1787B03 |
| tricyclo[3.3.1.13,7]decan-2-ol |
| 2-hydroxyadamantane |
| nsc193480 |
| 700-57-2 |
| nsc-193480 |
| 2-adamantanol , |
| adamantan-2-ol |
| inchi=1/c10h16o/c11-10-8-2-6-1-7(4-8)5-9(10)3-6/h6-11h,1-5h |
| STK365644 |
| tricyclo[3.3.1.1~3,7~]decan-2-ol |
| 2-adamantanol, 97% |
| A0720 |
| AKOS001023938 |
| A836750 |
| bdbm50329319 |
| CHEMBL1269176 , |
| einecs 211-846-7 |
| tricyclo(3.3.1.13,7)decan-2-ol |
| nsc 193480 |
| FT-0610989 |
| SCHEMBL350390 |
| DTXSID00220266 |
| 2-tricyclo[3.3.1.13,7]decanol |
| 2-tricyclo[3.3.1.13, 7]decanol |
| tricyclo[3.3.1.1(3,7)]decan-2-ol |
| tricyclo[3.3.1.1<3,7>]decan-2-ol |
| W-104572 |
| SCHEMBL13082659 |
| mfcd00074744 |
| CS-W000383 |
| AC-8481 |
| Z56757309 |
| F15454 |
| AKOS034830296 |
| EN300-16725 |
| HY-W000383 |
Research Excerpts
Bioavailability
| Excerpt | Reference | Relevance |
|---|
| " Optimization for increased adipocyte potency, metabolic stability and selectivity afforded 11k and 11l, both of which were >25% orally bioavailable in rat." | ( Discovery and optimization of adamantyl carbamate inhibitors of 11β-HSD1.
Berbaum, J; Bruno, JG; Bukhtiyarov, Y; Claremon, DA; Gregg, RE; Guo, J; Guo, R; Harrison, RK; Howard, L; Johnson, JA; Krosky, PM; Kruk, BA; Leftheris, K; Lindblom, PR; McGeehan, GM; McKeever, BM; Nar, H; Panemangalore, R; Schuler-Metz, A; Scott, BB; Singh, SB; Tice, CM; Togias, J; Ye, YJ; Zhao, W; Zhao, Y; Zhuang, L, 2010) | 0.36 |
Protein Targets (3)
Inhibition Measurements
Biological Processes (31)
Molecular Functions (30)
| Process | via Protein(s) | Taxonomy |
|---|
| monooxygenase activity | Cytochrome P450 3A4 | Homo sapiens (human) |
| steroid binding | Cytochrome P450 3A4 | Homo sapiens (human) |
| iron ion binding | Cytochrome P450 3A4 | Homo sapiens (human) |
| protein binding | Cytochrome P450 3A4 | Homo sapiens (human) |
| steroid hydroxylase activity | Cytochrome P450 3A4 | Homo sapiens (human) |
| retinoic acid 4-hydroxylase activity | Cytochrome P450 3A4 | Homo sapiens (human) |
| oxidoreductase activity | Cytochrome P450 3A4 | Homo sapiens (human) |
| oxygen binding | Cytochrome P450 3A4 | Homo sapiens (human) |
| enzyme binding | Cytochrome P450 3A4 | Homo sapiens (human) |
| heme binding | Cytochrome P450 3A4 | Homo sapiens (human) |
| vitamin D3 25-hydroxylase activity | Cytochrome P450 3A4 | Homo sapiens (human) |
| caffeine oxidase activity | Cytochrome P450 3A4 | Homo sapiens (human) |
| quinine 3-monooxygenase activity | Cytochrome P450 3A4 | Homo sapiens (human) |
| testosterone 6-beta-hydroxylase activity | Cytochrome P450 3A4 | Homo sapiens (human) |
| 1-alpha,25-dihydroxyvitamin D3 23-hydroxylase activity | Cytochrome P450 3A4 | Homo sapiens (human) |
| anandamide 8,9 epoxidase activity | Cytochrome P450 3A4 | Homo sapiens (human) |
| anandamide 11,12 epoxidase activity | Cytochrome P450 3A4 | Homo sapiens (human) |
| anandamide 14,15 epoxidase activity | Cytochrome P450 3A4 | Homo sapiens (human) |
| aromatase activity | Cytochrome P450 3A4 | Homo sapiens (human) |
| vitamin D 24-hydroxylase activity | Cytochrome P450 3A4 | Homo sapiens (human) |
| estrogen 16-alpha-hydroxylase activity | Cytochrome P450 3A4 | Homo sapiens (human) |
| estrogen 2-hydroxylase activity | Cytochrome P450 3A4 | Homo sapiens (human) |
| 1,8-cineole 2-exo-monooxygenase activity | Cytochrome P450 3A4 | Homo sapiens (human) |
| monooxygenase activity | Cytochrome P450 2D6 | Homo sapiens (human) |
| iron ion binding | Cytochrome P450 2D6 | Homo sapiens (human) |
| oxidoreductase activity | Cytochrome P450 2D6 | Homo sapiens (human) |
| oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen | Cytochrome P450 2D6 | Homo sapiens (human) |
| heme binding | Cytochrome P450 2D6 | Homo sapiens (human) |
| anandamide 8,9 epoxidase activity | Cytochrome P450 2D6 | Homo sapiens (human) |
| anandamide 11,12 epoxidase activity | Cytochrome P450 2D6 | Homo sapiens (human) |
| anandamide 14,15 epoxidase activity | Cytochrome P450 2D6 | Homo sapiens (human) |
| monooxygenase activity | Cytochrome P450 2C9 | Homo sapiens (human) |
| iron ion binding | Cytochrome P450 2C9 | Homo sapiens (human) |
| arachidonic acid epoxygenase activity | Cytochrome P450 2C9 | Homo sapiens (human) |
| steroid hydroxylase activity | Cytochrome P450 2C9 | Homo sapiens (human) |
| arachidonic acid 14,15-epoxygenase activity | Cytochrome P450 2C9 | Homo sapiens (human) |
| arachidonic acid 11,12-epoxygenase activity | Cytochrome P450 2C9 | Homo sapiens (human) |
| oxidoreductase activity | Cytochrome P450 2C9 | Homo sapiens (human) |
| (S)-limonene 6-monooxygenase activity | Cytochrome P450 2C9 | Homo sapiens (human) |
| (S)-limonene 7-monooxygenase activity | Cytochrome P450 2C9 | Homo sapiens (human) |
| caffeine oxidase activity | Cytochrome P450 2C9 | Homo sapiens (human) |
| (R)-limonene 6-monooxygenase activity | Cytochrome P450 2C9 | Homo sapiens (human) |
| aromatase activity | Cytochrome P450 2C9 | Homo sapiens (human) |
| heme binding | Cytochrome P450 2C9 | Homo sapiens (human) |
| oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen | Cytochrome P450 2C9 | Homo sapiens (human) |
| [Information is prepared from geneontology information from the June-17-2024 release] |
Ceullar Components (6)
Bioassays (6)
| Assay ID | Title | Year | Journal | Article |
|---|
| AID540299 | A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis | 2010 | Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
| Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis. |
| AID588519 | A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities | 2011 | Antiviral research, Sep, Volume: 91, Issue:3
| High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors. |
| AID527513 | Metabolic stability in rat liver microsomes assessed as half life | 2010 | Bioorganic & medicinal chemistry letters, Nov-15, Volume: 20, Issue:22
| Discovery and optimization of adamantyl carbamate inhibitors of 11β-HSD1. |
| AID527526 | Inhibition of CYP3A4 | 2010 | Bioorganic & medicinal chemistry letters, Nov-15, Volume: 20, Issue:22
| Discovery and optimization of adamantyl carbamate inhibitors of 11β-HSD1. |
| AID527528 | Inhibition of CYP2D6 | 2010 | Bioorganic & medicinal chemistry letters, Nov-15, Volume: 20, Issue:22
| Discovery and optimization of adamantyl carbamate inhibitors of 11β-HSD1. |
| AID527527 | Inhibition of CYP2C9 | 2010 | Bioorganic & medicinal chemistry letters, Nov-15, Volume: 20, Issue:22
| Discovery and optimization of adamantyl carbamate inhibitors of 11β-HSD1. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Research
Studies (7)
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 2 (28.57) | 18.2507 |
| 2000's | 1 (14.29) | 29.6817 |
| 2010's | 3 (42.86) | 24.3611 |
| 2020's | 1 (14.29) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Market Indicators
Research Demand Index: 23.24
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.
| Metric | This Compound (vs All) |
|---|
| Research Demand Index | 23.24 (24.57) | | Research Supply Index | 2.08 (2.92) | | Research Growth Index | 4.73 (4.65) | | Search Engine Demand Index | 21.17 (26.88) | | Search Engine Supply Index | 2.00 (0.95) |
| |
Study Types
| Publication Type | This drug (%) | All Drugs (%) |
|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 7 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |