Details of the Drug

General Information of Drug (ID: DMMAWLU)

Drug Name
Huperzine A
Synonyms
Fordine; ( inverted exclamation markA)-Huperazine A; ( inverted exclamation markA)-Huperzine A; C15H18N2O; 5,9-Methanocycloocta(b)pyridin-2(1H)-one, 5-amino-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-; rac-huperzine A; NCGC00159362-02; SCHEMBL679315; SCHEMBL1047469; CHEMBL394259; CHEBI:91724; MolPort-003-941-680
Indication
Disease Entry ICD 11 Status REF
Alzheimer disease 8A20 Approved [1], [2]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 242.32
Topological Polar Surface Area (xlogp) 0
Rotatable Bond Count (rotbonds) 0
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 2
Chemical Identifiers
Formula
C15H18N2O
IUPAC Name
(1R,9R,13E)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.02,7]trideca-2(7),3,10-trien-5-one
Canonical SMILES
C/C=C/1\\[C@@H]2CC3=C([C@]1(CC(=C2)C)N)C=CC(=O)N3
InChI
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
InChIKey
ZRJBHWIHUMBLCN-YQEJDHNASA-N
Cross-matching ID
PubChem CID
854026
ChEBI ID
CHEBI:78330
CAS Number
102518-79-6
DrugBank ID
DB04864
TTD ID
D06XWB

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Acetylcholinesterase (AChE) TT1RS9F ACES_HUMAN Inhibitor [3]
N-methyl-D-aspartate receptor (NMDAR) TT9IK2Z NOUNIPROTAC Antagonist [4]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Alzheimer disease
ICD Disease Classification 8A20
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Acetylcholinesterase (AChE) DTT ACHE 6.39E-02 -1.07 -1.15
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800000687)
3 Huperzine A attenuates cognitive deficits and brain injury in neonatal rats after hypoxia-ischemia. Brain Res. 2002 Sep 13;949(1-2):162-70.
4 Progress report on new antiepileptic drugs: a summary of the Ninth Eilat Conference (EILAT IX). Epilepsy Res. 2009 Jan;83(1):1-43.
5 Evidence that the clinical effects of cholinesterase inhibitors are related to potency and targeting of action. Int J Clin Pract Suppl. 2002 Jun;(127):6-19.
6 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Target id: 2465).
7 Acetylcholinesterase activity in Corbicula fluminea Mull., as a biomarker of organophosphate pesticide pollution in Pinacanauan River, Philippines. Environ Monit Assess. 2010 Jun;165(1-4):331-40.
8 [From symptomatic to disease modifying therapy Recent developments in the pharmacotherapy of Alzheimer's disease]. Fortschr Neurol Psychiatr. 2009 Jun;77(6):326-33.
9 Screening of acetylcholinesterase inhibitors by CE after enzymatic reaction at capillary inlet. J Sep Sci. 2009 May;32(10):1748-56.
10 Alpha6-containing nicotinic acetylcholine receptors dominate the nicotine control of dopamine neurotransmission in nucleus accumbens. Neuropsychopharmacology. 2008 Aug;33(9):2158-66.
11 The effects of topical ocular application of 0.25% demecarium bromide on serum acetylcholinesterase levels in normal dogs. Vet Ophthalmol. 2003 Mar;6(1):23-5.
12 Rational design of alkylene-linked bis-pyridiniumaldoximes as improved acetylcholinesterase reactivators. Chem Biol. 2003 Jun;10(6):491-502.
13 Neuromuscular blockade, reversal agent use, and operating room time: retrospective analysis of US inpatient surgeries. Curr Med Res Opin. 2009 Apr;25(4):943-50.
14 Altered expression of genes involved in GABAergic transmission and neuromodulation of granule cell activity in the cerebellum of schizophrenia pati... Am J Psychiatry. 2008 Dec;165(12):1594-603.
15 How many modes of action should an antibiotic have Curr Opin Pharmacol. 2008 Oct;8(5):564-73.
16 Amphetamine inhibits the N-methyl-D-aspartate receptor-mediated responses by directly interacting with the receptor/channel complex. J Pharmacol Exp Ther. 2002 Mar;300(3):1008-16.
17 Ketamine modulates theta and gamma oscillations. J Cogn Neurosci. 2010 Jul;22(7):1452-64.
18 Molecular determinants of the anticonvulsant felbamate binding site in the N-methyl-D-aspartate receptor. J Med Chem. 2008 Mar 27;51(6):1534-45.
19 The NMDA receptor antagonist memantine as a symptomatological and neuroprotective treatment for Alzheimer's disease: preclinical evidence. Int J Geriatr Psychiatry. 2003 Sep;18(Suppl 1):S23-32.
20 Neuroprotective agents for the treatment of acute ischemic stroke. Curr Neurol Neurosci Rep. 2003 Jan;3(1):9-20.
21 Magnesium sulfate diminishes the effects of amide local anesthetics in rat sciatic-nerve block. Reg Anesth Pain Med. 2007 Jul-Aug;32(4):288-95.
22 Emerging drugs for acute ischemic stroke. Expert Opin Emerg Drugs. 2009 Mar;14(1):33-42.
23 Involvement of voltage-gated sodium channels blockade in the analgesic effects of orphenadrine. Pain. 2009 Apr;142(3):225-35.