Basic information
- 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- Molecular formula
- C29H40Cl2FN3O3
- Average molar mass
- 568.5 g/mol
- Monoisotopic mass
- 567.2430757
Overview
See also: Mibefradil (has active moiety).
Names & identifiers
- Preferred 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
- English name
- MIBEFRADIL
- Molecular formula
- C29H40Cl2FN3O3
- Molecular weight
- 568.5506032
Names & synonyms
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
Show more names
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)
Properties
Computed structural properties
- Topological polar surface area
- 67.5 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 12
- Heavy atoms
- 38
- Formal charge
- 0
- Complexity
- 709
Physicochemical properties
- Melting point
- 128 ℃ · 128℃
- storage temp.
- 2 · under inert gas (nitrogen or Argon) at 2-8°C
- solubility
- 2 O: · H2O: 24 mg/mL, soluble
- pka
- 4.8 · 4.8; 5.5(at 25℃)
- form
- solid
- color
- white
- Water Solubility
- 2 O: · H2O: soluble >20mg/mLabsolute ethanol: insoluble
- Stability
- 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
- FDA UNII
- 842 TUP3PQ8 · 842TUP3PQ8
- ATC code
- 8 CX01 · C08CX01
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302
Safety & regulation
GHS classification
GHS Classification
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.
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- rtecs
- AI8977250
- Toxicity
- LD50 in mice, rats (mg/kg): 35, 23 i.v.; >800, >800 orally (Clozel)
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P280-P305+P351+P338
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
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.
Applications
DescriptionPosicor 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.
UsesVasodilator.
UsesMibefradil 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.
Upstream & downstream products
Related reactions
3 records
Compound notes
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