| Identification |
| Chemical Name |
Amiodarone |
| Accession Number |
HAMDB414 |
| Alternative Names |
Not Available |
| IUPAC Name |
(2-butyl-1-benzofuran-3-yl)-[4-[2-(diethylamino)ethoxy]-3,5-diiodophenyl]methanone |
| Formula |
C25H29I2NO3 |
| Canonical SMILES |
CCCCC1=C(C2=CC=CC=C2O1)C(=O)C3=CC(=C(C(=C3)I)OCCN(CC)CC)I |
| Structure |
C(=O)C3=CC(=C(C(=C3)I)OCCN(CC)CC)I/PNG)
|
| Physicochemical Properties |
| Molecular Weight |
645.310Molecular weight |
| Hbond Donor |
0Number of hydrogen bond acceptor atoms
(not counting acidic atoms but counting atoms that are both hydrogen bond donors and acceptors such as -OH).
|
| Hbond Acceptor |
3
Number of hydrogen bond donor atoms (not counting basic atoms but counting atoms that are both hydrogen bond donors and acceptors such as -OH).
|
| logP (o/w) |
8.188
Log of the octanol/water partition coefficient (including implicit hydrogens). [LOGP 1998]
|
| logS |
-9.034
Log of the aqueous solubility (mol/L).
|
| MR |
14.566
Molecular refractivity (including implicit hydrogens).
|
| SlogP |
6.936
Log of the octanol/water partition coefficient. [Crippen 1999]
|
| TPSA |
42.680
Polar surface area (Å2) calculated using group contributions to approximate the polar surface area from connection table information only. The parameterization is that of Ertl et al. [Ertl 2000].
|
| logD (PH=7) |
6.331
The octanol/water distribution coefficient at pH 7.
|
| pKa (PH=7) |
14.000
The pKa of the reaction that removes a proton from the ensemble of states with a hydrogen count equal to the input structure.
|
| pKb (PH=7) |
4.999
The pKb of the reaction that adds a proton from the ensemble of states with a hydrogen count equal to the input structure.
|
| Lipinski druglike |
0
One if and only if lip_violation < 2 otherwise zero.
|
| Solubility |
10 mM in DMSO |
| Role in Autophagy |
|
4 related item(s)
1. amiodarone |
| Chemical Name |
amiodarone |
| Relationship with Autophagy |
increased activity of amiodarone affects formation of autophagosomes
|
| Mutation Evidence
|
wild type |
| Biomarker Application
|
not applicable |
| Species Evidence
|
Uncategorized |
| Drug Target Evidence
|
not applicable |
| Expression Evidence
|
not applicable |
| Causal or Correlated
|
causal |
| Findings |
1 |
References
- Renna M, Jimenez-sanchez M, Sarkar S, Rubinsztein Dc, Chemical Inducers Of Autophagy That Enhance The Clearance Of Mutant Proteins In Neurodegenerative Diseases., J Biol Chem.2010 Apr 9;285(15):11061-7. Doi: 10.1074/jbc.r109.072181. [PMID:20147746 ]
2. amiodarone |
| Chemical Name |
amiodarone |
| Relationship with Autophagy |
increased activity of amiodarone increases autophagy of brain cancer cell lines
|
| Mutation Evidence
|
wild type |
| Biomarker Application
|
not applicable |
| Species Evidence
|
Human |
| Drug Target Evidence
|
not applicable |
| Expression Evidence
|
not applicable |
| Causal or Correlated
|
causal |
| Findings |
1 |
References
- Zhang L, Yu J, Pan H, Hu P, Hao Y, Cai W, Zhu H, Yu Ad, Xie X, Ma D, Yuan J, Small Molecule Regulators Of Autophagy Identified By An Image-based High-throughput Screen., Proc Natl Acad Sci U S A.2007 Nov 27;104(48):19023-8. [PMID:18024584 ]
3. amiodarone |
| Chemical Name |
amiodarone |
| Relationship with Autophagy |
increased activity of amiodarone increases autophagy
|
| Mutation Evidence
|
wild type |
| Biomarker Application
|
not applicable |
| Species Evidence
|
Rat |
| Drug Target Evidence
|
not applicable |
| Expression Evidence
|
not applicable |
| Causal or Correlated
|
causal |
| Findings |
1 |
References
- Renna M, Jimenez-sanchez M, Sarkar S, Rubinsztein Dc, Chemical Inducers Of Autophagy That Enhance The Clearance Of Mutant Proteins In Neurodegenerative Diseases., J Biol Chem.2010 Apr 9;285(15):11061-7. Doi: 10.1074/jbc.r109.072181. [PMID:20147746 ]
4. amiodarone |
| Chemical Name |
amiodarone |
| Relationship with Autophagy |
increased activity of amiodarone increases autophagy of cells
|
| Mutation Evidence
|
wild type |
| Biomarker Application
|
not applicable |
| Species Evidence
|
Uncategorized |
| Drug Target Evidence
|
not applicable |
| Expression Evidence
|
not applicable |
| Causal or Correlated
|
causal |
| Findings |
3 |
References
- Renna M, Jimenez-sanchez M, Sarkar S, Rubinsztein Dc, Chemical Inducers Of Autophagy That Enhance The Clearance Of Mutant Proteins In Neurodegenerative Diseases., J Biol Chem.2010 Apr 9;285(15):11061-7. Doi: 10.1074/jbc.r109.072181. [PMID:20147746 ]
|
| Biological Behaviors |
| Gene Name |
Not Available |
| Target |
Autophagy; Potassium Channel |
| Pathway |
- Autophagy
- Membrane Transporter/Ion Channel
|
| Biological Description |
Amiodarone is an antiarrhythmic drug for inhibition of ATP-sensitive potassium channel with IC50 of 19.1 μM. Target: Potassium Channel Amiodarone shows beta blocker-like and potassium channel blocker-like actions on the SA and AV nodes, increases the refr |
| Research Area |
Cardiovascular Disease |
| Category |
Activator |
| In Vitro |
Not Available |
| In Vivo |
Not Available |
| Clinical Trial |
Phase 1; Phase 2; Phase 3; Phase 4 |
| External Links |
| CAS Numbers |
1951-25-3 |
| Pubchem |
2157 |
| HMDB |
HMDB15250 |
| DrugBank |
DB01118 |
| References |
- Singh Bn, Vaughan Williams Em, The Effect Of Amiodarone, A New Anti-anginal Drug, On Cardiac Muscle., Br J Pharmacol.1970 Aug;39(4):657-67. [PMID:5485142 ]
- Rosenbaum Mb, Chiale Pa, Halpern Ms, Nau Gj, Przybylski J, Levi Rj, Lázzari Jo, Elizari Mv, Clinical Efficacy Of Amiodarone As An Antiarrhythmic Agent., Am J Cardiol.1976 Dec;38(7):934-44. [PMID:793369 ]
|
