Basic information
- CAS
148849-67-6- Standard SMILES
COc1cc2c(cc1OC)CC(=O)N(CCCN(C)C[C@H]1Cc3cc(OC)c(OC)cc31)CC2.Cl- InChIKey
HLUKNZUABFFNQS-ZMBIFBSDSA-N- Molecular formula
- C27H37ClN2O5
- Average molar mass
- 505 g/mol
- Monoisotopic mass
- 504.23909996
Overview
Ivabradine hydrochloride is a hydrochloride obtained by combining ivabradine with one molar equivalent of hydrochloric acid. Used to treat patients with angina who have intolerance to beta blockers and/or heart failure. It has a role as a cardiotonic drug. It contains an ivabradine(1+).
Names & identifiers
- Preferred name
- Ivabradine Hydrochloride
- IUPAC
- 3-[3-[[(7S)-3,4-dimethoxy-7-bicyclo[4.2.0]octa-1,3,5-trienyl]methyl-methylamino]propyl]-7,8-dimethoxy-2,5-dihydro-1H-3-benzazepin-4-one;hydrochloride
- English name
- Ivabradine hydrochloride
- Molecular formula
- C27H37ClN2O5
- Molecular weight
- 505.05
Names & synonyms
Ivabradine hydrochloride148849-67-6Ivabradine HClCoralanIvabrandine hydrochlorideDTXSID2046913AMG 998ivabradine monohydrochlorideUNII-TP19837BZKTP19837BZK2H-3-Benzazepin-2-one, 3-[3-[[[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl]methylamino]propyl]-1,3,4,5-tetrahydro-7,8-dimethoxy-, hydrochloride (1:1)AMG-998
Show more names
ProcoralanIvabradine hydrochloridCS-774S-16257CorlentorS 16257-2C27H37ClN2O5D6-Ivabradine HCl2H-3-Benzazepin-2-on
DTXCID0026913CHEBI:85969(7,8-Dimethoxy 3-(3-(((1S)-(4,5-dimethoxybenzocyclobutan-1-yl)methyl)methylamino)propyl)-1,3,4,5-tetrahydro-2H-benzazepin-2-one hydrochloride2H-3-BENZAZEPIN-2-ONE, 3-(3-((((7S)-3,4-DIMETHOXYBICYCLO(4.2.0)OCTA-1,3,5-TRIEN-7-YL)METHYL)METHYLAMINO)PROPYL)-1,3,4,5-TETRAHYDRO-7,8-DIMETHOXY-, HYDROCHLORIDE (1:1)2H-3-Benzazepin-2-one, 3-(3-((((7S)-3,4-dimethoxybicyclo(4.2.0)octa-1,3,5-trien-7-yl)methyl)methylamino)propyl)-1,3,4,5-tetrahydro-7,8-dimethoxy-, monohydrochloride2H-3-Benzazepin-2-one, 3-(3-(((3,4-dimethoxybicyclo(4.2.0)octa-1,3,5-trien-7-yl)methyl)methylamino)propyl)-1,3,4,5-tetrahydro-7,8-dimethoxy-, monohydrochloride, (S)-3-{3-[{[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}(methyl)amino]propyl}-7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one--hydrogen chloride (1/1)3-(3-((((7S)-3,4-dimethoxybicyclo(4.2.0)octa-1,3,5-trien-7-yl)methyl)(methyl)amino)propyl)-7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one--hydrogen chloride (1/1)
Properties
Computed structural properties
- Topological polar surface area
- 60.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 10
- Heavy atoms
- 35
- Formal charge
- 0
- Complexity
- 663
Experimental & physicochemical properties
Human Drugs
FDA approved drugs -> Active ingredient
EMA approved medicines: Human medicine
EMA approved medicines: Human medicine
EMA approved medicines: Human medicine
EMA approved medicines: Human medicine
FDA approved drugs -> Active ingredient
Physicochemical properties
- Melting point
- 193 · 193-196C
- alpha
- 58921 · 58921 +7.8°; 36521 +27.8° (c = 1% in DMSO)
- storage temp.
- 2 · 2-8°C
- solubility
- 2 O: · H2O: ≥5mg/mL (warmed)
- form
- powder
- color
- white to beige
- optical activity
- 5 to · [α]/D +5 to +9°, c = 1 in DMSO
- Water Solubility
- 2 O: · H2O: ≥5mg/mL (warmed)
- Merck
- 14 · 14,5247
- InChIKey
- HLUKNZUABFFNQS-ZMBIFBSDSA-N
- SMILES
- C([C@H]1CC2=CC(OC)=C(OC)C=C12)N(C)CCCN1CCC2=CC(OC)=C(OC)C=C2CC1=O.Cl |&1:1,r|
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H302 (14.6%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P260, P264, P270, P273, P280, P301+P317, P318, P319, P330, P391, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 48 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (14.6%)
Toxicology
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Ivabradine hydrochloride
vNo-DILI-concern
0
No match
DOI:10.1016/j.drudis.2016.02.015
Safety data
- wgk
- 3
- ridadr
- UN 3077 9 / PGIII
- hs_code
- 2933.79.1500
- risk_code
- 50/53
- Signal word
- Warning
- Symbol(GHS)
- GHS09
- hazard_code
- N
- safety_code
- 60-61
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H400
Chemistry & industry
Applications
DescriptionIn an effort to develop angina agents without the unwanted negative inotropic and hypotensive effects associated with b-adrenergic blockers and calcium channel blockers, a new class of heart-rate reducing compounds that act specifically on the sinoatrial (SA) node has been explored. These bradycardic agents interact directly with the pacemaking cell of the SA node and the hyperpolarization- activated If , the primary pacemaking current. Ivabradine has evolved as a specific inhibitor of If current through its contact with f-channels on the intracellular side of the plasma membrane. As a consequence, ivabradine reduces the speed of diastolic depolarization and decreases heart rate. It has been approved for the treatment of chronic stable angina and provides a viable alternative to patients with a contraindication or intolerance of b-blockers. Evaluation is also underway for the potential treatment of ischemic heart disease. Using a patch-clamp technique on rabbit sinoatrial node cells, inhibition of If current ranged from 6% (0.03 mM) – 80% (10 mM). .
UsesIvabradine hydrochloride has been used as a potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel (HCN)2 blocker in embryoid body (EB) and rat engineered heart tissue (EHT).
UsesIvabradine HCl, a new If inhibitor with IC 50 of 2.9 μM which acts specifically on the pacemaker activity of the sinoatrial node, is a pure heart rate lowering agent
Usesangina therapeutic
UsesSelective bradycardic agent with direct effect on the pacemaker If current of the sinoatrial node. Antianginal
Upstream & downstream products
Upstream raw materials
Related reactions
7 records
Compound notes
Loading…