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Sipatrigine

HCID 60803
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Basic information

CAS
130800-90-7
Standard SMILES
CN1CCN(c2ncc(-c3cc(Cl)cc(Cl)c3Cl)c(N)n2)CC1
InChIKey
PDOCBJADCWMDGL-UHFFFAOYSA-N
Molecular formula
C15H16Cl3N5
Average molar mass
372.7 g/mol
Monoisotopic mass
371.047129

Overview

Sipatrigine is a member of pyrimidines.

Names & identifiers

Preferred name
Sipatrigine
IUPAC
2-(4-methylpiperazin-1-yl)-5-(2,3,5-trichlorophenyl)pyrimidin-4-amine
English name
Sipatrigine
Molecular formula
C15H16Cl3N5
Molecular weight
372.68

Names & synonyms

Sipatrigine130800-90-72-(4-methylpiperazin-1-yl)-5-(2,3,5-trichlorophenyl)pyrimidin-4-amineBW619C89619C89BW-619C89SipatriginaOON9AVW1T3DTXSID201567504-Amino-2-(4-methyl-1-piperazinyl)-5-(2,3,5-trichlorophenyl)pyrimidine619-C-89sipatriginum
Show more names
619 CBW 619C892-(4-methylpiperazin-1-yl)-5-(2,3,5-trichlorophenyl)-pyrimidin-4-amineL-GLUTAMIC ACID, N-[4-[2-(2-AMINO-4,7-DIHYDRO-4- 8 OXO-1H-PYRROLO[2,3-D]PYRIMIDIN-5-YL)ETHYL]BENZOYL]-, DISODIUM SALT, HEPTAHYDRATEL-GLUTAMIC ACID, N-[4-[2-(2-AMINO-4,7-DIHYDRO-4-8 OXO-1H-PYRROLO[2,3-D] PYRIMIDIN-5-YL)ETHYL]BENZOYL]-, DISODIUM SALT, HEPTAHYDRATE
RefChem:931798DTXCID2079241Sipatrigine [INN:BAN]2-(4-Methyl-1-piperazinyl)-5-(2,3,5-trichlorophenyl)-4-pyrimidinamine4-Pyrimidinamine, 2-(4-methyl-1-piperazinyl)-5-(2,3,5-trichlorophenyl)-619CCHEMBL28854619C89;BW 619C89

Database identifiers

CAS
130800-90-7
PubChem CID
60803
DTXSID
DTXSID20156750
ChEMBL
CHEMBL28854
ChEBI
CHEBI:34977
UNII
OON9AVW1T3
Nikkaji
J550.694H

Properties

Computed structural properties

XLogP
3.6
Topological polar surface area
58.3 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
5
Rotatable bonds
2
Heavy atoms
23
Formal charge
0
Complexity
393

Experimental & physicochemical properties

LogP3.39

Physicochemical properties

Boiling point
531.1 · 531.1±60.0 °C(Predicted)
Density
1.419 · 1.419±0.06 g/cm3(Predicted)
storage temp.
2 · 2-8°C
solubility
100 mM · Soluble to 100 mM in DMSO and to 25 mM in ethanol
form
Powder
pka
7.25 · 7.25±0.42(Predicted)
color
White to off-white
FDA UNII
9 AVW1T3 · OON9AVW1T3

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 2 items

Drugs that inhibit the transport of neurotransmitters into axon terminals or into storage vesicles within terminals. For many transmitters, uptake determines the time course of transmitter action so inhibiting uptake prolongs the activity of the transmitter. Blocking uptake may also deplete available transmitter stores. Many clinically important drugs are uptake inhibitors although the indirect reactions of the brain rather than the acute block of uptake itself is often responsible for the therapeutic effects.

Drugs intended to prevent damage to the brain or spinal cord from ischemia, stroke, convulsions, or trauma. Some must be administered before the event, but others may be effective for some time after. They act by a variety of mechanisms, but often directly or indirectly minimize the damage produced by endogenous excitatory amino acids.

Applications

UsesSipatrigine, an analog of lamotrigine (L173250), is a glutamate release inhibitor and a voltage-dependent sodium channel blocker. It also has neuroprotective properties.

Additional notes

DefinitionChEBI: Sipatrigine is a member of pyrimidines.

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