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5,5'-Dimethyl-2,2'-bipyridyl

HCID 15664
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Grundinformationen

CAS
1762-34-1
Standard-SMILES
Cc1ccc(-c2ccc(C)cn2)nc1
InChIKey
PTRATZCAGVBFIQ-UHFFFAOYSA-N
Summenformel
C12H12N2
Durchschnittliche Molmasse
184,24 g/mol
Monoisotopische Masse
184,10004839

Überblick

Abametapir is a member of bipyridines.

Namen und Bezeichner

Bevorzugter Name
5,5'-Dimethyl-2,2'-bipyridyl
IUPAC
5-methyl-2-(5-methyl-2-pyridinyl)pyridine
Englischer Name
5,5'-Dimethyl-2,2'-dipyridyl
Summenformel
C12H12N2
Molmasse
184.24

Namen und Synonyme

5,5'-Dimethyl-2,2'-bipyridylDMBP cpdRefChem:58442629-235-2Abametapir1762-34-15,5'-Dimethyl-2,2'-bipyridine5,5'-Dimethyl-2,2'-dipyridyl6,6'-Bi-3-picolineXeglyze2,2'-BIPYRIDINE, 5,5'-DIMETHYL-5-methyl-2-(5-methylpyridin-2-yl)pyridine
Weitere Namen anzeigen
5,5’-dimethyl-2’-bipyridineabametapiDimethylbipyridyl
HA-44HA445,5-Dimethyl-2,2-bipyridine6,6'-Di-3-picolylMFCD01740554BRN 01231836,6'-Di-3-picoline6UO390AMFB

Datenbank-Bezeichner

CAS
1762-34-1
PubChem CID
15664
DTXSID
DTXSID00170095
ChEMBL
CHEMBL2205807
ChEBI
CHEBI:192617
UNII
6UO390AMFB
EC Number
629-235-2
Nikkaji
J23.945C

Eigenschaften

Berechnete Struktureigenschaften

XLogP
2,2
Polarare Oberfläche (TPSA)
25,8 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
1
Schwere Atome
14
Formalladung
0
Komplexität
161

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15
Human Drugs · 2 Einträge

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Physikochemische Eigenschaften

Schmelzpunkt
114 · 114-117 °C(lit.)
Siedepunkt
140 ℃/3mm · 140℃/3mm
Dichte
1.06 · 1.060±0.06 g/cm3(Predicted)
storage temp.
Inert atmosphere,Room Temperature
Löslichkeit
15 mg/mL,DMSO: · DMF: 15mg/mL,DMSO: 10mg/mL,Ethanol: 15mg/mL,Ethanol:PBS (pH 7.2) (1:4): 0.2mg/mL
Aggregatzustand
powder to crystal
pka
4.78 · 4.78±0.32(Predicted)
Farbe
White to Yellow to Orange
InChI
InChI=1S/C12H12N2/c1-9-3-5-11(13-7-9)12-6-4-10(2)8-14-12/h3-8H,1-2H3
InChIKey

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 4 Einträge

Warning

H302 (88.9%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 45 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 4 (88.9%)

Sicherheitsdaten

wgk
3
hs_code
29333990
RTECS-Nr.
DW1766000
risk_code
36/37/38-22
Toxizität
mouse,LD50,intraperitoneal,225mg/kg (225mg/kg),Toxicon. Vol. 23, Pg. 815, 1985.
hazard_code
Xi,Xn
safety_code
26-36
Speicherklasse
11 - Combustible Solids
Hazard Classifications
Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3

Chemie und Industrie

Pharmakologische Informationen

ATC CodeP - Antiparasitic products, insecticides and repellents
Protein Binding · 1 Eintrag

Both abametapir and abametapir carboxyl are high protein-bound in plasma, although the specific proteins to which they bind are unclear. Following topical administration, abametapir is 91.3-92.3% protein-bound and abametapir carboxyl is 96.0-97.5% protein-bound.

Pharmacodynamics · 1 Eintrag

Abametavir has been shown to inhibit all stages of embryo development in both head and body lice by interfering with enzymes critical to this process. It is relatively unique amongst lice treatments in that it requires only a single application, whereas many current therapies require two applications, due to its exceptional potency and unique mechanism. Its predominant metabolite, abametapir carboxyl, has a prolonged residence time in the body, with an estimated half-life of 71 ± 40 hours or longer in adults - as this metabolite has been shown to inhibit cytochrome P450 enzymes _in vitro_, the use of substrates of CYP3A4, CYP2B6, or CYP1A2 should be avoided for two weeks following the administration of abametapir. Abametapir lotion is formulated with [benzyl alcohol], which has been associated with significant toxicity following unintentional systemic exposure, particularly in neonates and low birth weight infants. Benzyl alcohol-containing formulations should not be administered to patients <6 months of age, and should be administered to pediatric patients cautiously and under direct supervision of an adult to mitigate the risk of unintentional oral ingestion.

Mechanism of Action · 1 Eintrag

There are several metalloproteinases (enzymes requiring metal co-factors to function) involved in the process of louse egg hatching and survival. _In vitro_ studies have demonstrated that metal-chelating agents can inhibit the activity of these proteins, and may therefore be valuable pediculicidal agents. Abametapir is a metalloproteinase inhibitor that targets louse metalloproteinases which are critical to their development and hatching.

Biological Half-LifeThe elimination half-lives of abametapir and its metabolites have not been well-characterized, but the estimated half-life of abametapir carboxyl is 71 ± 40 hours (or longer) in adults.

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HRID 1297993als KatalysatorHigh-throughput exploration of 50,688 Pd-, Ni- and Cu-catalysed C–N coupling reactions
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HRID 1297994als KatalysatorHigh-throughput exploration of 50,688 Pd-, Ni- and Cu-catalysed C–N coupling reactions
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HRID 1297995als KatalysatorHigh-throughput exploration of 50,688 Pd-, Ni- and Cu-catalysed C–N coupling reactions
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HRID 1297996als KatalysatorHigh-throughput exploration of 50,688 Pd-, Ni- and Cu-catalysed C–N coupling reactions
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HRID 1297997als KatalysatorHigh-throughput exploration of 50,688 Pd-, Ni- and Cu-catalysed C–N coupling reactions
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HRID 1297998als KatalysatorHigh-throughput exploration of 50,688 Pd-, Ni- and Cu-catalysed C–N coupling reactions
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PTRATZCAGVBFIQ-UHFFFAOYSA-N
SMILES
C1(C2=NC=C(C)C=C2)=NC=C(C)C=C1
CAS Datenbank
1762 · 1762-34-1(CAS DataBase Reference)
Metabolism/Metabolites · 1 Eintrag

The biotransformation of abametapir is extensive and primarily mediated by CYP1A2. It is metabolized first to abametapir hydroxyl and then further to abametapir carboxyl - the latter is cleared slowly from the plasma, resulting in higher systemic concentrations than that of the parent drug. _In vitro_ studies suggest that abametapir carboxyl may act as an inhibitor of CYP3A4, CYP2B6, and CYP1A2, particularly at the relatively high and prolonged concentrations observed following topical administration of abametapir.

Absorption, Distribution and Excretion · 4 Einträge

In a pharmacokinetic trial with both adult and pediatric patients, the Cmax and AUC0-8h in the adult group were 41 ng/mL and 121 ng.h/mL and the Cmax and AUC0-8h in the pediatric group were 73 ng/mL and 264 ng.h/mL. In general, systemic exposure to abametapir appears to decrease with increasing age. The median Tmax of abemetapir is 0.57 - 1.54 hours. Following topical administration, benzyl alcohol was found in detectable quantities in the serum of 7 out of 39 pediatric patients. The Cmax of benzyl alcohol in these subjects ranged from 0.52 to 3.57 μg/mL. The predominant circulating metabolite of abemetapir (abemtapir carboxylate) is eliminated slowly from the circulation and is therefore found at higher serum concentrations than its parent drug - based on data collected for 72 hours post-administration, the ratios of serum Cmax and AUC0-72h between abametapir and abametapir carboxylate were approximately 30 and 250, respectively.

The clearance and excretion of abametapir has not been examined in patients.

Data regarding the volume of distribution of abametapir are not available.

The clearance and excretion of abametapir has not been examined in patients.

Anwendungen · 1 Eintrag

Verwenden5,5'-Dimethyl-2,2'-bipyridine is widely used as an intermediate in organic synthesis and pharmaceuticals. It is also used as a raw material in the synthesis of dyestuffs and agrochemicals. It is used as a precursor for the preparation of 5-methyl-5'vinyl-2,2'-bipyridine.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

2-Bromo-5-methylpyridineBis(2-methoxyethyl)etherNickel(II) acetate tetrahydrateDichlormethanNatrium-2-methylpropan-2-olatTriphenylphosphinMagnesiumsulfat5,6'-Dimethyl-[2,2']bipyridinyl6,6'-Dimethyl-2,2'-bipyridin5-Methyl-2-(tributylstannyl)pyridine, 96%5-Methyl-2-pyridylamin2-Brom-6-methylpyridin2-Chloro-5-methylpyridine

Nachgelagerte Produkte

BIPY531, 2,2'-([2,2'-Bipyridine]-5,5'-diyl)diacetonitrile5,5'-diMethoxycarbonyl-2,2'-bipyridine

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