Cas no 85175-67-3 (Zatebradine)

Zatebradine is a selective bradycardic agent that acts as an inhibitor of the pacemaker current (If) in the sinoatrial node, thereby reducing heart rate without significantly affecting myocardial contractility or blood pressure. Its mechanism of action involves blocking hyperpolarization-activated cyclic nucleotide-gated (HCN) channels, which are critical for cardiac rhythm regulation. Zatebradine is primarily investigated for its potential therapeutic applications in conditions requiring heart rate control, such as ischemic heart disease and heart failure. The compound demonstrates high specificity for If channels, minimizing off-target effects. Its pharmacokinetic profile includes moderate bioavailability and a predictable dose-response relationship, making it a candidate for further clinical evaluation in cardiovascular therapeutics.
Zatebradine structure
Zatebradine structure
Product Name:Zatebradine
CAS No:85175-67-3
MF:C26H36N2O5
MW:456.574447631836
CID:726681
PubChem ID:65637
Update Time:2025-10-17

Zatebradine Chemical and Physical Properties

Names and Identifiers

    • 2H-3-Benzazepin-2-one,3-[3-[[2-(3,4-dimethoxyphenyl)ethyl]methylamino]propyl]-1,3,4,5-tetrahydro-7,8-dimethoxy-
    • 3-[3-[2-(3,4-dimethoxyphenyl)ethyl-methylamino]propyl]-7,8-dimethoxy-2,5-dihydro-1H-3-benzazepin-4-one
    • UL-FS49
    • ZATEBRADINE
    • [14C]-Zatebradine
    • 3-[3-[(3,4-Dimethoxy phenethyl)methylamino]-propyl]-1,3,4,5-tetrahydro-7,8-dimethoxy-2H-3-benzazepin-2-one
    • 7,8-dimethoxy-3-<3-<<2-(3,4-dimethoxyphenyl)ethyl>-methylamino>propyl>-1,3,4,5-tetrahydro-2H-benzazepin-2-one
    • UL-FS-49
    • Zatebradina
    • Zatebradina [INN-Spanish]
    • Zatebradine [INN]
    • Zatebradinum
    • Zatebradinum [INN-Latin]
    • 3-[3-[[2-(3,4-Dimethoxyphenyl)ethyl]methylamino]propyl]-1,3,4,5-tetrahydro-7,8-dimethoxy-2H-3-benzazepin-2-one (ACI)
    • 1,3,4,5-tetrahydro-7,8-dimethoxy-3-(3-((2-(3,4-dimethoxyphenyl)ethyl)methylimino)propyl)-2H-3-benzazepin-2-one hydrochloride
    • HY-13422A
    • MFCD00867014
    • Zatebradina (INN-Spanish)
    • 3-(3-((3,4-Dimethoxyphenethyl)methylamino)propyl)-1,3,4,5-tetrahydro-7,8-dimethoxy-2H-3-benzazepin-2-one
    • KEDQCFRVSHYKLR-UHFFFAOYSA-N
    • 125846-52-8
    • TV27RY5876
    • 3-(3-((3,4-Dimethoxyphenethyl)(methyl)amino)propyl)-7,8-dimethoxy-4,5-dihydro-1H-benzo[d]azepin-2(3H)-one
    • CHEBI:93613
    • AKOS030213235
    • 3-(3-{[2-(3,4-Dimethoxy-phenyl)-ethyl]-methyl-amino}-propyl)-7,8-dimethoxy-1,3,4,5-tetrahydro-benzo[d]azepin-2-one
    • BRD-K92446736-003-01-4
    • Q27089283
    • ZATEBRADINE [MI]
    • CS-3620
    • 3-(3-(2-(3,4-dimethoxyphenyl)ethyl-methylamino)propyl)-7,8-dimethoxy-2,5-dihydro-1H-3-benzazepin-4-one
    • SCHEMBL295751
    • CHEMBL69679
    • Zatebradinum (INN-Latin)
    • F85097
    • 1-[7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-on-3-yl]-3-[N-methyl-N-(2-{3,4-dimethoxy-phenyl}ethyl)-amino]-propane
    • UL-FS 49
    • DTXSID1048413
    • BRD-K92446736-003-03-0
    • Zatabradine
    • BRD-K92446736-003-02-2
    • BCP16190
    • BDBM50326988
    • DTXCID9028386
    • 85175-67-3
    • UNII-TV27RY5876
    • 1-[7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-on-3-yl]-3-[N-methyl-N-(2-{3,4-dimethoxy-phenyl}-ethyl)-amino]-propane
    • GTPL2358
    • MS-28329
    • BRD-K92446736-001-01-8
    • UL-FS-49 (free base);UL-FS-49CL (free base)
    • UL-FS-49 free base
    • UL-FS-49CL free base
    • Zatebradine
    • Inchi： 1S/C26H36N2O5/c1-27(13-9-19-7-8-22(30-2)23(15-19)31-3)11-6-12-28-14-10-20-16-24(32-4)25(33-5)17-21(20)18-26(28)29/h7-8,15-17H,6,9-14,18H2,1-5H3
    • InChI Key： KEDQCFRVSHYKLR-UHFFFAOYSA-N
    • SMILES： O=C1CC2C(=CC(=C(C=2)OC)OC)CCN1CCCN(CCC1C=C(OC)C(OC)=CC=1)C

Computed Properties

  • Exact Mass: 456.26200
  • Monoisotopic Mass: 456.26242225g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 7
  • Heavy Atom Count: 33
  • Rotatable Bond Count: 11
  • Complexity: 591
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • Tautomer Count: 2
  • XLogP3: 3.6
  • Topological Polar Surface Area: 60.5?2

Experimental Properties

  • PSA: 60.47000
  • LogP: 3.15070

Zatebradine Security Information

  • Storage Condition：Pure form -20°C 3 years ? 4°C 2 years In solvent -80°C 6 months ? -20°C 1 month

Zatebradine Pricemore >>

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Zatebradine Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Potassium tert-butoxide Solvents: Dimethyl sulfoxide ;  2 h, 50 °C
Reference
Silver nitrate-promoted ring enlargement of 1-tribromomethyl-1,2-dihydro- and 1-tribromomethyl-1,2,3,4-tetrahydro-isoquinoline derivatives: application to the synthesis of the anti-anginal zatebradine
Pauvert, Mickael; Collet, Sylvain; Guingant, Andre, Tetrahedron Letters, 2003, 44(22), 4203-4206

Production Method 2

Reaction Conditions
Reference
Benzazepine derivatives
, Federal Republic of Germany, , ,

Zatebradine Raw materials

Zatebradine Preparation Products

Zatebradine Related Literature

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