(1R,9R,10S,12R,13S,14R,16S,18R)-13-ethyl-8-methyl-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2,4,6-triene-14,18-diol

• ChemBase ID: 1234
• Molecular Formular: C20H26N2O2
• Molecular Mass: 326.43264
• Monoisotopic Mass: 326.19942808
• SMILES: c1ccc2c(c1)[C@@]13[C@@H](N2C)[C@H]2N4[C@@H](C1)C([C@@H](C2)[C@@H]([C@H]4O)CC)[C@H]3O
• Canonical SMILES: CC[C@H]1[C@@H]2C[C@@H]3N([C@@H]1O)[C@@H]1C2[C@@H](O)[C@]2([C@H]3N(C)c3c2cccc3)C1
• InChI: InChI=1S/C20H26N2O2/c1-3-10-11-8-14-17-20(12-6-4-5-7-13(12)21(17)2)9-15(16(11)18(20)23)22(14)19(10)24/h4-7,10-11,14-19,23-24H,3,8-9H2,1-2H3/t10-,11-,14-,15-,16?,17-,18+,19+,20+/m0/s1
• InChIKey: CJDRUOGAGYHKKD-HEFSZTOGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,9R,10S,12R,13S,14R,16S,18R)-13-ethyl-8-methyl-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2,4,6-triene-14,18-diol
• IUPAC Traditional name: ajmaline
• Synonyms: Ajmalin; Ajmaline

Database IDs

• CAS Number: 4360-12-7
• PubChem SID: 160964694
• PubChem CID: 441080

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.280155
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.1535305
• LogD (pH = 7.4): 1.6402448
• Log P: 1.8508078
• Molar Refractivity: 92.5658 cm^3
• Polarizability: 36.288525 Å^3
• Polar Surface Area: 46.94 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.72
• LOG S: -1.9
• Solubility (Water): 4.09e+00 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 1.81 [HANSCH,C ET AL. (1995)]

DETAILS

DrugBank - DB01426

• Drug Groups: approved
• Description: An alkaloid found in the root of Rauwolfia serpentina, among other plant sources. It is a class Ia antiarrhythmic agent that apparently acts by changing the shape and threshold of cardiac action potentials. Ajmaline produces potent sodium channel blocking effects and a very short half-life which makes it a very useful drug for acute intravenous treatments. The drug has been very popular in some countries for the treatment of atrial fibrillation in patients with the Wolff–Parkinson–White syndrome and in well tolerated monomorphic ventricular tachycardias. It has also been used for many years as a drug to challenge the conduction system of the heart in cases of bundle branch block and syncope. In these cases, abnormal prolongation of the HV interval has been taken as a proof for infrahisian conduction defects tributary for permanent pacemaker implantation.
• Indication: For use as an antiarrhythmic agent.
• Pharmacology: Ajmaline is a class 1A antiarrhythmic agent. By interfering with the sodium channels, this drug allows for improvement in abnormal rhythms of the heart
• Affected Organisms: Humans and other mammals
• References: Brugada J, Brugada P, Brugada R: The ajmaline challenge in Brugada syndrome: a useful tool or misleading information? Eur Heart J. 2003 Jun;24(12):1085-6. [Pubmed]
• External Links: Wikipedia

REFERENCES

• Brugada J, Brugada P, Brugada R: The ajmaline challenge in Brugada syndrome: a useful tool or misleading information? Eur Heart J. 2003 Jun;24(12):1085-6. Pubmed