Preferred name
ARCAINE
Synonyms
ARCAINE SULFATE ()
Arcaine (sulfate) ()
1-(4-Guanidinobutyl)Guanidine ()
P&D ID
PD049089
CAS
36587-93-6
14923-17-2
544-05-8
Tags
available
drug candidate
Drug indication
Discovery agent
Structure
SMILES
NC(N)=NCCCCN=C(N)N
InChI
InChI=1S/C6H16N6/c7-5(8)11-3-1-2-4-12-6(9)10/h1-4H2,(H4,7,8,11)(H4,9,10,12)
InChIkey
HGMDNMBBCKDWTQ-UHFFFAOYSA-N
MOL
ARCAINE
RDKit 2D
12 11 0 0 0 0 0 0 0 0999 V2000
-3.8971 0.7500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-2.5981 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.5981 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-1.2990 0.7500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.2990 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.5981 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.8971 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.1962 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
6.4952 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
7.7942 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
6.4952 2.2500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
1 2 1 0
2 3 1 0
2 4 2 3
4 5 1 0
5 6 1 0
6 7 1 0
7 8 1 0
8 9 1 0
9 10 2 3
10 11 1 0
10 12 1 0
M END
> <ID>
PD049089
> <Name>
ARCAINE
(extracted from source data)
DESCRIPTION
Arcaine is a natural product isolated from the bivalve mollusc Arca noae.
(GtoPdb)
DESCRIPTION
Potent competitive antagonist of the polyamine site on the NMDA glutmate receptor
(LOPAC library)
DESCRIPTION
Arcaine sulfate is the sulfate salt of arcaine, which is a potent, competitive and novel antagonist of the polyamine site on the NMDA receptor.
(BOC Sciences Bioactive Compounds)
5
5.2
ALOX15 Polyunsaturated fatty acid lipoxygenase ALOX15
BIOCHEM 4.3x
BIOCHEM 4.3x
10
1
4.88
CHRM1 Muscarinic acetylcholine receptor M1
2
1
4.57
GRIN1,GRIN2A... Glutamate NMDA receptor
0
3
4.4
CYP3A4 Cytochrome P450 3A4
7
1
ASIC3 Acid-sensing ion channel 3 activator
1
0
20
Aflatoxin activation and detoxification
CYP3A4
Aspirin ADME
CYP3A4
Atorvastatin ADME
CYP3A4
Biosynthesis of DHA-derived SPMs
ALOX15
Biosynthesis of DPAn-3-derived protectins and resolvins
ALOX15
Biosynthesis of DPAn-6 SPMs
ALOX15
Biosynthesis of E-series 18(R)-resolvins
ALOX15
Biosynthesis of E-series 18(S)-resolvins
ALOX15
Biosynthesis of maresin-like SPMs
CYP3A4
Biosynthesis of protectins
ALOX15
G alpha (q) signalling events
CHRM1
Interleukin-4 and Interleukin-13 signaling
ALOX15
Muscarinic acetylcholine receptors
CHRM1
Phase I - Functionalization of compounds
CYP3A4
Prednisone ADME
CYP3A4
Stimuli-sensing channels
ASIC3
Synthesis of 12-eicosatetraenoic acid derivatives
ALOX15
Synthesis of 15-eicosatetraenoic acid derivatives
ALOX15
Synthesis of Leukotrienes (LT) and Eoxins (EX)
ALOX15
Xenobiotics
CYP3A4
6
Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity (dataset)
2015
Pentamidine analogs as inhibitors of [(3)H]MK-801 and [(3)H]ifenprodil binding to rat brain NMDA receptors.
Berger ML, Maciejewska D et al. Bioorg. Med. Chem.
2015
Differential influence of 7 cations on 16 non-competitive NMDA receptor blockers.
Berger ML, Rebernik P. Bioorg. Med. Chem. Lett.
1998
Aromatic analogs of arcaine inhibit MK-801 binding to the NMDA receptor.
Sharma TA, Carr AJ et al. Bioorg. Med. Chem. Lett.
PUBCHEM_BIOASSAY: qHTS Assay for Inhibitors and Activators of N370S glucocerebrosidase as a Potential Chaperone Treatment of Gaucher Disease: Purified N370S Glucocerebrosidase. (Class of assay: confirmatory) [Related pubchem assays: 2101 ]
AID 2597
13
BOC Sciences Bioactive Compounds
Cayman Chemical Bioactives
Concise Guide to Pharmacology 2017/18
Concise Guide to Pharmacology 2019/20
Concise Guide to Pharmacology 2021/22
Concise Guide to Pharmacology 2023/24
DrugMAP
DrugMatrix
Guide to Pharmacology
Ki Database
LOPAC library
MedChem Express Bioactive Compound Library
ReFrame library
6
BOC Sciences Bioactive Compounds
Cayman Chemical Bioactives
LOPAC library
MedChem Express Bioactive Compound Library
42
(calculated by RDKit )
Molecular Weight
172.14
Hydrogen Bond Acceptors
2
Hydrogen Bond Donors
4
Rotatable Bonds
5
Ring Count
0
Aromatic Ring Count
0
cLogP
-1.69
TPSA
128.8
Fraction CSP3
0.67
Chiral centers
0.0
Largest ring
0.0
QED
0.22
0
No structural alerts detected
(extracted from source data)
Selectivity
NMDA-Polyamine
Pathway
Membrane Transporter/Ion Channel
Neuronal Signaling
Target
iGluR
