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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H18N2O
Molecular Weight 242.3162
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of HUPERZINE A

SMILES

C\C=C1/[C@@H]2CC3=C(C=CC(=O)N3)[C@@]1(N)CC(C)=C2

InChI

InChIKey=ZRJBHWIHUMBLCN-YQEJDHNASA-N
InChI=1S/C15H18N2O/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)/b11-3+/t10-,15+/m0/s1

HIDE SMILES / InChI

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 UNSPECIFIED

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
64.7 nM [IC50]
0.5 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Comparative effects of huperzine A, donepezil and rivastigmine on cortical acetylcholine level and acetylcholinesterase activity in rats.
2004 May 6
Effects of acetylcholinesterase and butyrylcholinesterase inhibition on breathing in mice adapted or not to reduced acetylcholinesterase.
2005 Jan
Protection of red blood cell acetylcholinesterase by oral huperzine A against ex vivo soman exposure: next generation prophylaxis and sequestering of acetylcholinesterase over butyrylcholinesterase.
2008 Sep 25
Patents

Patents

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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
by admin
on Fri Dec 15 16:28:04 UTC 2023
Edited
by admin
on Fri Dec 15 16:28:04 UTC 2023
Record UNII
0111871I23
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
HUPERZINE A
MI   VANDF   WHO-DD  
Common Name English
L-HUPERZINE A
Common Name English
(-)-HUPERZINE A
Common Name English
HUPERZINE A [VANDF]
Common Name English
HUPERZINE A [MI]
Common Name English
Huperzine a [WHO-DD]
Common Name English
SELAGINE
Common Name English
(-)-SELAGINE
Common Name English
(5R,9R,11E)-5-AMINO-11-ETHYLIDENE-5,6,9,10-TETRAHYDRO-7-METHYL-5,9-METHANOCYCLOOCTA(B)PYRIDIN-2(1H)-ONE
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 744420
Created by admin on Fri Dec 15 16:28:04 UTC 2023 , Edited by admin on Fri Dec 15 16:28:04 UTC 2023
DSLD 708 (Number of products:164)
Created by admin on Fri Dec 15 16:28:04 UTC 2023 , Edited by admin on Fri Dec 15 16:28:04 UTC 2023
NCI_THESAURUS C66880
Created by admin on Fri Dec 15 16:28:04 UTC 2023 , Edited by admin on Fri Dec 15 16:28:04 UTC 2023
DSLD 3336 (Number of products:266)
Created by admin on Fri Dec 15 16:28:04 UTC 2023 , Edited by admin on Fri Dec 15 16:28:04 UTC 2023
FDA ORPHAN DRUG 559916
Created by admin on Fri Dec 15 16:28:04 UTC 2023 , Edited by admin on Fri Dec 15 16:28:04 UTC 2023
FDA ORPHAN DRUG 885322
Created by admin on Fri Dec 15 16:28:04 UTC 2023 , Edited by admin on Fri Dec 15 16:28:04 UTC 2023
Code System Code Type Description
CHEBI
178022
Created by admin on Fri Dec 15 16:28:04 UTC 2023 , Edited by admin on Fri Dec 15 16:28:04 UTC 2023
PRIMARY
WIKIPEDIA
HUPERZINE A
Created by admin on Fri Dec 15 16:28:04 UTC 2023 , Edited by admin on Fri Dec 15 16:28:04 UTC 2023
PRIMARY
DRUG BANK
DB04864
Created by admin on Fri Dec 15 16:28:04 UTC 2023 , Edited by admin on Fri Dec 15 16:28:04 UTC 2023
PRIMARY
EVMPD
SUB127430
Created by admin on Fri Dec 15 16:28:04 UTC 2023 , Edited by admin on Fri Dec 15 16:28:04 UTC 2023
PRIMARY
CAS
102518-79-6
Created by admin on Fri Dec 15 16:28:04 UTC 2023 , Edited by admin on Fri Dec 15 16:28:04 UTC 2023
PRIMARY
SMS_ID
100000153436
Created by admin on Fri Dec 15 16:28:04 UTC 2023 , Edited by admin on Fri Dec 15 16:28:04 UTC 2023
PRIMARY
MERCK INDEX
m6064
Created by admin on Fri Dec 15 16:28:04 UTC 2023 , Edited by admin on Fri Dec 15 16:28:04 UTC 2023
PRIMARY Merck Index
PUBCHEM
854026
Created by admin on Fri Dec 15 16:28:04 UTC 2023 , Edited by admin on Fri Dec 15 16:28:04 UTC 2023
PRIMARY
EPA CompTox
DTXSID8046038
Created by admin on Fri Dec 15 16:28:04 UTC 2023 , Edited by admin on Fri Dec 15 16:28:04 UTC 2023
PRIMARY
RXCUI
2267703
Created by admin on Fri Dec 15 16:28:04 UTC 2023 , Edited by admin on Fri Dec 15 16:28:04 UTC 2023
PRIMARY
FDA UNII
0111871I23
Created by admin on Fri Dec 15 16:28:04 UTC 2023 , Edited by admin on Fri Dec 15 16:28:04 UTC 2023
PRIMARY
DAILYMED
0111871I23
Created by admin on Fri Dec 15 16:28:04 UTC 2023 , Edited by admin on Fri Dec 15 16:28:04 UTC 2023
PRIMARY
EVMPD
SUB33678
Created by admin on Fri Dec 15 16:28:04 UTC 2023 , Edited by admin on Fri Dec 15 16:28:04 UTC 2023
ALTERNATIVE
NCI_THESAURUS
C97271
Created by admin on Fri Dec 15 16:28:04 UTC 2023 , Edited by admin on Fri Dec 15 16:28:04 UTC 2023
PRIMARY
MESH
C050426
Created by admin on Fri Dec 15 16:28:04 UTC 2023 , Edited by admin on Fri Dec 15 16:28:04 UTC 2023
PRIMARY
CHEBI
78330
Created by admin on Fri Dec 15 16:28:04 UTC 2023 , Edited by admin on Fri Dec 15 16:28:04 UTC 2023
PRIMARY
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SOLVATE->ANHYDROUS
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
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PRODRUG -> METABOLITE ACTIVE
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ACTIVE MOIETY