Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C15H18N2O.H2O |
| Molecular Weight | 260.3315 |
| Optical Activity | ( - ) |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.C\C=C1/[C@@H]2CC3=C(C=CC(=O)N3)[C@@]1(N)CC(C)=C2
InChI
InChIKey=JGPPGMFEKUOWLB-NSBUTGITSA-N
InChI=1S/C15H18N2O.H2O/c1-3-11-10-6-9(2)8-15(11,16)12-4-5-14(18)17-13(12)7-10;/h3-6,10H,7-8,16H2,1-2H3,(H,17,18);1H2/b11-3+;/t10-,15+;/m0./s1
| Molecular Formula | H2O |
| Molecular Weight | 18.0153 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C15H18N2O |
| Molecular Weight | 242.3162 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 1 |
| Optical Activity | ( - ) |
DescriptionSources: https://doi.org/10.1016/j.jalz.2009.05.218 | https://adisinsight.springer.com/drugs/800016260http://www.webmd.com/vitamins-supplements/ingredientmono-764-huperzine%20a.aspxCurator's Comment: description was created based on several sources, including:
https://www.braintropic.com/nootropics/huperzine-a/ | https://www.drugs.com/npc/huperzine-a.html | http://medind.nic.in/daa/t11/i1/daat11i1p177.pdf
Sources: https://doi.org/10.1016/j.jalz.2009.05.218 | https://adisinsight.springer.com/drugs/800016260http://www.webmd.com/vitamins-supplements/ingredientmono-764-huperzine%20a.aspx
Curator's Comment: description was created based on several sources, including:
https://www.braintropic.com/nootropics/huperzine-a/ | https://www.drugs.com/npc/huperzine-a.html | http://medind.nic.in/daa/t11/i1/daat11i1p177.pdf
Huperzine A is a plant alkaloid derived from Club moss plant, Huperzine serrata, which is a member or the Lycopodium species. Huperzine-A is in phase III clinical trial in the USA (Alzheimer disease) and is available as a dietary supplement. It selectively and reversibly inhibits acetylcholinesterase. Huperzine A is also a NMDA receptor antagonist, which protects the brain against glutamate induced damage, and it increases nerve growth factor levels. Huperzine A is used for Alzheimer's disease, memory and learning enhancement, and age-related memory impairment. It is also used for treating a muscle disease called myasthenia gravis, for increasing alertness and energy, and for protecting against agents that damage the nerves such as nerve gases. It can cause some side effects including nausea, diarrhea, vomiting, sweating, blurred vision, slurred speech, restlessness, loss of appetite, contraction and twitching of muscle fibers, cramping, increased saliva and urine, inability to control urination, high blood pressure, and slowed heart rate. Various medications used for glaucoma, Alzheimer's disease, and other conditions (Cholinergic drugs) interacts with Huperzine A.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL220 |
64.7 nM [IC50] | ||
Target ID: CHEMBL1907608 |
0.5 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Palliative | Unknown Approved UseUnknown |
|||
| Primary | Huperzine A Approved UseHuperzine A can be used as a memory enhancer. It can also be taken regularly to help protect against age-related declines in memory. |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Effect of huperzine A, a novel acetylcholinesterase inhibitor, on radial maze performance in rats. | 1995 Jun-Jul |
|
| Reversal of scopolamine-induced deficits in radial maze performance by (-)-huperzine A: comparison with E2020 and tacrine. | 1998 May 22 |
|
| Ginkgolide A, B, and huperzine A inhibit nitric oxide-induced neurotoxicity. | 2002 Oct |
|
| Identification of cytochrome P450 1A2 as enzyme involved in the microsomal metabolism of Huperzine A. | 2003 Feb 14 |
|
| Comparative effects of huperzine A, donepezil and rivastigmine on cortical acetylcholine level and acetylcholinesterase activity in rats. | 2004 May 6 |
|
| Neuroprotective effects of huperzine A. A natural cholinesterase inhibitor for the treatment of Alzheimer's disease. | 2005 |
|
| Effects of acetylcholinesterase and butyrylcholinesterase inhibition on breathing in mice adapted or not to reduced acetylcholinesterase. | 2005 Jan |
|
| Effective countermeasure against poisoning by organophosphorus insecticides and nerve agents. | 2006 Aug 29 |
|
| Prolonged effects of poly(lactic-co-glycolic acid) microsphere-containing huperzine A on mouse memory dysfunction induced by scopolamine. | 2007 Mar |
|
| The combination of huperzine A and imidazenil is an effective strategy to prevent diisopropyl fluorophosphate toxicity in mice. | 2008 Sep 16 |
|
| BZYX, a novel acetylcholinesterase inhibitor, significantly improved chemicals-induced learning and memory impairments on rodents and protected PC12 cells from apoptosis induced by hydrogen peroxide. | 2009 Jun 24 |
|
| Coadministration of huperzine A and ligustrazine phosphate effectively reverses scopolamine-induced amnesia in rats. | 2010 Oct |
|
| A combination of [+] and [-]-Huperzine A improves protection against soman toxicity compared to [+]-Huperzine A in guinea pigs. | 2013 Mar 25 |
|
| The role of cholinergic anti-inflammatory pathway in acetic acid-induced colonic inflammation in the rat. | 2013 Sep 5 |
Patents
Sample Use Guides
Patients in the mimopezil arm received 1 mg mimopezil daily orally during the 1-month titration period, 9 mg mimopezil as s.c. implants in the 1-month maintenance I period, and 12 mg mimopezil as s.c. implants in the 4-month maintenance II period.
Route of Administration:
Other
The synthetic racemic mixture (+/-)-huperzine-A was 3 times less potent than (-)-huperzine-A in vitro (IC50s of 3 x 10(-7) M and 10(-7) M, respectively) because the former consisted of a racemic mixture of the compound in which the (+)-huperzine component was considerably less potent (IC50 = 7 x 10(-6) M).
| Substance Class |
Chemical
Created
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| Record UNII |
9F4GM58TAA
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