Mibefradil Dihydrochloride

HCID 60662

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Grundinformationen

CAS: 116666-63-8
Standard-SMILES: COCC(=O)O[C@]1(CCN(C)CCCc2nc3ccccc3[nH]2)CCc2cc(F)ccc2[C@@H]1C(C)C.Cl.Cl
InChIKey: MTJLQTFHJIHXIX-GDUXWEAWSA-N
Summenformel: C29H40Cl2FN3O3
Durchschnittliche Molmasse: 568,5 g/mol
Monoisotopische Masse: 567,2430757

Überblick

See also: Mibefradil (has active moiety).

Namen und Bezeichner

Bevorzugter Name: Mibefradil Dihydrochloride
IUPAC: [(1S,2S)-2-[2-[3-(1H-benzimidazol-2-yl)propyl-methylamino]ethyl]-6-fluoro-1-propan-2-yl-3,4-dihydro-1H-naphthalen-2-yl] 2-methoxyacetate;dihydrochloride
Englischer Name: MIBEFRADIL
Summenformel: C29H40Cl2FN3O3
Molmasse: 568.5506032

Namen und Synonyme

Mibefradil dihydrochloride116666-63-8Mibefradil hydrochlorideDTXSID8044204RO 40-5967/001842TUP3PQ8Ro-40-5967/001DTXCID6024204(1S,2S)-(2-((3-(2-Benzimidazolyl)propyl)methylamino)ethyl)-6-fluoro-1,2,3,4-tetrahydro-1-isopropyl-2-naphthyl methoxyacetate, dihydrochlorideAcetic acid, methoxy-, 2-(2-((3-(1H-benzimidazol-2-yl)propyl)methylamino)ethyl)-6-fluoro-1,2,3,4-tetrahydro-1-(1-methylethyl)-2-naphthalenyl ester, dihydrochloride, (1S-cis)-(1S,2S)-[2-[[3-(2-Benzimidazolyl)propyl]methylamino]ethyl]-6-fluoro-1,2,3,4-tetrahydro-1-isopropyl-2-naphthyl methoxyacetate, dihydrochlorideRefChem:158484

Weitere Namen anzeigen

CS-1455MIBEFRADIL(1s-cis)-oridro40-5967/001Mibefradil HClMibefradil diHClRo 40-5967 hydrateMIBEFRADIL USP/EP/BPMibefradil(Ro 40-5967)

848-218-2PosicorMIBEFRADIL 2HCLRo 40-5967MFCD00881804Mibefradil dihydrochloride [USAN]Mibefradil-dihydrochlorideAcetic acid, 2-methoxy-, (1S,2S)-2-[2-[[3-(1H-benzimidazol-2-yl)propyl]methylamino]ethyl]-6-fluoro-1,2,3,4-tetrahydro-1-(1-methylethyl)-2-naphthalenyl ester, hydrochloride (1:2)

Datenbank-Bezeichner

CAS: 116666-63-8
PubChem CID: 60662
DTXSID: DTXSID8044204
ChEMBL: CHEMBL1534525
UNII: 842TUP3PQ8
EC Number: 848-218-2

Eigenschaften

Berechnete Struktureigenschaften

Polarare Oberfläche (TPSA): 67,5 Å²
H-Brücken-Donoren: 3
H-Brücken-Akzeptoren: 6
Frei drehbare Bindungen: 12
Schwere Atome: 38
Formalladung: 0
Komplexität: 709

Physikochemische Eigenschaften

Schmelzpunkt: 128 ℃ · 128℃
storage temp.: 2 · under inert gas (nitrogen or Argon) at 2-8°C
Löslichkeit: 2 O: · H2O: 24 mg/mL, soluble
pka: 4.8 · 4.8; 5.5(at 25℃)
Aggregatzustand: solid
Farbe: white
Wasserlöslichkeit: 2 O: · H2O: soluble >20mg/mLabsolute ethanol: insoluble
Stabilität: Hygroscopic
InChIKey: IZSWBBGKLWFDOC-YKXHUFBBSA-N
SMILES: O.Cl.Cl.COCC(=O)O[C@]3(CCN(C)CCCc1nc2ccccc2[nH]1)CCc4cc(F)ccc4[C@@H]3C(C)C

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Warning

H302 (100%): 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)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Sicherheitsdaten

wgk: 3
RTECS-Nr.: AI8977250
Toxizität: LD50 in mice, rats (mg/kg): 35, 23 i.v.; >800, >800 orally (Clozel)
Speicherklasse: 11 - Combustible Solids
Hazard Classifications: Acute Tox. 4 Oral

Chemie und Industrie

Pharmakologische Informationen

MeSH Pharmacological Classification · 4 Einträge

Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS.

A class of drugs that act by selective inhibition of calcium influx through cellular membranes.

Drugs used to cause dilation of the blood vessels.

Drugs and compounds which inhibit or antagonize the biosynthesis or actions of CYTOCHROME P-450 CYP1A2.

Anwendungen · 2 Einträge

BeschreibungPosicor was launched in Argentina, Azerbaijan, Brazil, the Chile, Czech Republic, Denmark, Germany, Ireland, Kazakhstan, the Netherlands, Norway, Peru, the Philippines, Switzerland, Thailand, Turkmenistan, the UK, the US and Venezuela for use in hypertension. It can be assembled in five steps from 4-(1-benzyloxy-Nmethylformamido) butyric acid with o-phenylenediamine and isobutylchloroformate. Posicor binds to calcium channels in a manner that overlaps the Verapamil, SR-33557 and Diltiazem binding site without effecting the dihydropyridine binding site. Thus it blocks a wide variety of calcium channels with selectivity for T-type followed sequentially by L-type. There is also some calcium agonist activity along with sodium and potassium channel activity. It is chemically distinct from the other calcium antagonists (first member of a new catagory of tetralol calcium antagonists). It has the ability to lower heart rate with no negative inotropic effects and is as effective as Amlodipine and more effective than Diltiazem for the treatment of mild to moderate hypertension. Serious drug interactions are possible because Posicor inhibits both CYP2D6 and CYP3A4.

VerwendenMibefradil has been used as a T-type calcium channel blocker in various cells. It has also been used to reduce apoptosis of retinal ganglion cells (RGC) in EphB2-Fc.