Norcyclizine is a piperazine derivative with antihistamine and antiemetic properties. It is synthesized through a multi-step process involving the reaction of 1-phenyl-2-piperazineethanol with 2-chloro-4-nitrobenzoyl chloride, followed by reduction of the nitro group to an amine. Norcyclizine is effective in treating motion sickness, allergic rhinitis, and urticaria. It exerts its antihistamine effects by competitively blocking histamine receptors, primarily H1 receptors, in the body. Its antiemetic properties are believed to be related to its anticholinergic effects. However, norcyclizine has a relatively short duration of action and can cause drowsiness and other side effects, limiting its widespread use. Its importance lies in its potential therapeutic applications, particularly in managing motion sickness and allergic conditions. Research efforts focus on developing alternative formulations and dosage regimens to improve its efficacy and safety profile. The compound is also studied for its potential in treating other conditions such as anxiety and insomnia.'
norcyclizine: RN given refers to parent cpd; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
| ID Source | ID |
|---|---|
| PubMed CID | 70048 |
| CHEMBL ID | 1490469 |
| SCHEMBL ID | 219432 |
| MeSH ID | M0094412 |
| Synonym |
|---|
| AC-15867 |
| CHEMDIV3_014411 |
| norcyclizine |
| 1-benzhydrylpiperazine |
| nsc-35536 |
| nsc35536 |
| piperazine, 1-(diphenylmethyl)- |
| n-(diphenylmethyl)piperazine |
| normethylcyclizine |
| 1-(diphenylmethyl)piperazine |
| n-benzhydrylpiperazine |
| 841-77-0 |
| benzhydrylpiperazine |
| CBDIVE_013587 |
| CBDIVE_013583 |
| IDI1_030209 |
| OPREA1_339020 |
| diphenylmethylpiperazine |
| brn 0222773 |
| einecs 212-667-7 |
| nsc 35536 |
| 4-benzhydrylpiperazine |
| 1-benzhydryl-piperazine |
| EU-0066577 |
| smr000565014 |
| MLS001202210 |
| 1-(diphenylmethyl)piperazine, >=98.0% (nt) |
| STK400345 |
| HMS1513P01 |
| AKOS000119081 |
| NCGC00245934-01 |
| HMS2868I18 |
| B3760 |
| unii-nu6v5zhd9p |
| nu6v5zhd9p , |
| 5-23-01-00231 (beilstein handbook reference) |
| BP-12848 |
| FT-0633026 |
| GF-0119 |
| AM20050307 |
| AB01730 |
| SCHEMBL219432 |
| CHEMBL1490469 |
| DTXSID80232968 |
| 4-(diphenylmethyl)piperazine |
| benzhydrylpiperazin |
| diphenylmethyl piperazine |
| mono-benzhydrylpiperazine |
| 4-diphenylmethylpiperazine |
| 1-benzhydrylpiperazin |
| diphenylmethylpiperazin |
| n-(diphenylmethyl) -piperazine |
| 4-(diphenylmethyl)-piperazine |
| n-diphenylmethylpiperazine |
| benzhydryl piperazine |
| 1-(diphenylmethyl) piperazine |
| 1-diphenylmethylpiperazine |
| 1-(diphenylmethyl)-piperazine |
| 1-(diphenyl methyl)piperazine |
| 1-benzhydryl piperazine |
| Q-102268 |
| cinnarizine ep impurity a |
| mfcd00038379 |
| F0268-2663 |
| 1-(diphenylmethyl)piperazine; cinnarizine imp. a (ep); cinnarizine impurity a |
| Q5279744 |
| n-(benzhydryl)piperazine |
| benzhydrylpiperazine; 1-benzhydrylpiperazine; 1-(diphenylmethyl)piperazine; 4-(diphenylmethyl)piperazine; 4-benzhydrylpiperazine; n-(diphenylmethyl)piperazine |
| EN300-19049 |
| BRD-K14568538-001-08-9 |
| benzhydrylpiperazine 1-(diphenylmethyl)piperazine |
| cinnarizine impurity a |
| CS-W014092 |
| norcyclizine oxalate (1:2) |
| Z104472428 |
| Excerpt | Reference | Relevance |
|---|---|---|
| " Samples were analyzed to elucidate pharmacokinetic parameters and CYP2D6 genetics." | ( The pharmacokinetics and pharmacogenetics of the antiemetic cyclizine in palliative care patients. Begg, EJ; Chin, PK; Fairhall, M; Jensen, BP; Macleod, SA; Reid, K; Roberts, RL; Vella-Brincat, JW, 2012) | 0.38 |
| Excerpt | Relevance | Reference |
|---|---|---|
| "SC dosing group: The median (interquartile range) cyclizine half-life, volume of distribution, and clearance were 13 (7-48) hours, 23 (12-30)L/kg, and 15 (11-26)mL/min/kg, respectively." | ( The pharmacokinetics and pharmacogenetics of the antiemetic cyclizine in palliative care patients. Begg, EJ; Chin, PK; Fairhall, M; Jensen, BP; Macleod, SA; Reid, K; Roberts, RL; Vella-Brincat, JW, 2012) | 0.38 |
| Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Chain A, Beta-lactamase | Escherichia coli K-12 | Potency | 31.6228 | 0.0447 | 17.8581 | 100.0000 | AID485294 |
| glp-1 receptor, partial | Homo sapiens (human) | Potency | 6.3096 | 0.0184 | 6.8060 | 14.1254 | AID624417 |
| TDP1 protein | Homo sapiens (human) | Potency | 14.9692 | 0.0008 | 11.3822 | 44.6684 | AID686978; AID686979 |
| euchromatic histone-lysine N-methyltransferase 2 | Homo sapiens (human) | Potency | 70.7946 | 0.0355 | 20.9770 | 89.1251 | AID504332 |
| Glycoprotein hormones alpha chain | Homo sapiens (human) | Potency | 4.4668 | 4.4668 | 8.3448 | 10.0000 | AID624291 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Process | via Protein(s) | Taxonomy |
|---|---|---|
| hormone activity | Glycoprotein hormones alpha chain | Homo sapiens (human) |
| protein binding | Glycoprotein hormones alpha chain | Homo sapiens (human) |
| follicle-stimulating hormone activity | Glycoprotein hormones alpha chain | Homo sapiens (human) |
| [Information is prepared from geneontology information from the June-17-2024 release] | ||
| Process | via Protein(s) | Taxonomy |
|---|---|---|
| extracellular region | Glycoprotein hormones alpha chain | Homo sapiens (human) |
| extracellular space | Glycoprotein hormones alpha chain | Homo sapiens (human) |
| Golgi lumen | Glycoprotein hormones alpha chain | Homo sapiens (human) |
| follicle-stimulating hormone complex | Glycoprotein hormones alpha chain | Homo sapiens (human) |
| pituitary gonadotropin complex | Glycoprotein hormones alpha chain | Homo sapiens (human) |
| extracellular space | Glycoprotein hormones alpha chain | Homo sapiens (human) |
| [Information is prepared from geneontology information from the June-17-2024 release] | ||
| 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. |
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2006 | Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5 | Microsphere-based protease assays and screening application for lethal factor and factor Xa. |
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2006 | Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5 | Microsphere-based protease assays and screening application for lethal factor and factor Xa. |
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2006 | Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5 | Microsphere-based protease assays and screening application for lethal factor and factor Xa. |
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID1745845 | Primary qHTS for Inhibitors of ATXN expression | |||
| AID651635 | Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression | |||
| AID504812 | Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign | 2010 | Endocrinology, Jul, Volume: 151, Issue:7 | A small molecule inverse agonist for the human thyroid-stimulating hormone receptor. |
| AID504810 | Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign | 2010 | Endocrinology, Jul, Volume: 151, Issue:7 | A small molecule inverse agonist for the human thyroid-stimulating hormone receptor. |
| AID1794808 | Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL). | 2014 | Journal of biomolecular screening, Jul, Volume: 19, Issue:6 | A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum. |
| AID1794808 | Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL). | |||
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 1 (6.25) | 18.7374 |
| 1990's | 1 (6.25) | 18.2507 |
| 2000's | 4 (25.00) | 29.6817 |
| 2010's | 8 (50.00) | 24.3611 |
| 2020's | 2 (12.50) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
| 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 | 17 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||