| Identification |
| Chemical Name |
Azithromycin hydrate |
| Accession Number |
HAMDB5 |
| Alternative Names |
CP62993 dihydrate; CP-62993 dihydrate; CP 62993 dihydrate |
| IUPAC Name |
11-[4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-(5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl)oxy-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one;dihydrate |
| Formula |
C38H76N2O14 |
| Canonical SMILES |
CCC1C(C(C(N(CC(CC(C(C(C(C(C(=O)O1)C)OC2CC(C(C(O2)C)O)(C)OC)C)OC3C(C(CC(O3)C)N(C)C)O)(C)O)C)C)C)O)(C)O.O.O |
| Structure |
O1)C)OC2CC(C(C(O2)C)O)(C)OC)C)OC3C(C(CC(O3)C)N(C)C)O)(C)O)C)C)C)O)(C)O.O.O/PNG)
|
| Physicochemical Properties |
| Molecular Weight |
785.020Molecular weight |
| Hbond Donor |
7Number 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 |
15
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) |
3.429
Log of the octanol/water partition coefficient (including implicit hydrogens). [LOGP 1998]
|
| logS |
-3.691
Log of the aqueous solubility (mol/L).
|
| MR |
20.220
Molecular refractivity (including implicit hydrogens).
|
| SlogP |
0.251
Log of the octanol/water partition coefficient. [Crippen 1999]
|
| TPSA |
180.080
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) |
-3.728
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) |
4.973
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 |
| Not Available |
| Biological Behaviors |
| Gene Name |
Not Available |
| Target |
RIG-I like receptors |
| Pathway |
- Autophagy
|
| Biological Description |
Azithromycin hydrate is a macrolide antibiotic useful for the treatment of a number of bacterial infections. |
| Research Area |
Infection |
| Category |
Inhibitor |
| In Vitro |
Azithromycin (2 μM) augments rhinovirus-induced IFNβ expression in primary bronchial epithelial cells from asthmatics, which is associated with over-expression of RIG-I like receptors and repression of viral replication. Knockdown of MDA5, but not knockdown of RIG-I, diminishes azithromycin (2 μM)-enhanced viral-induced IFNβ expression in asthmatic primary bronchial epithelial cells. Azithromycin specifically reduces MMP-9 mRNA and protein levels without affecting NF-κB in endotoxin-challenged monocytic THP-1 cells. |
| In Vivo |
Azithromycin (50 mg/kg) has no effect on bronchoalveolar lavage inflammatory parameters and LDH levels in a mouse model of asthma exacerbation. Azithromycin induces neither general inflammatory parameters nor LDH release in a mouse model of asthma exacerbation, and augments expression of interferon-stimulated genes and the pattern recognition receptor MDA5 but not RIG-I in exacerbating mice. |
| Clinical Trial |
Phase 1 for infection; Phase 4 for Lymphocytic Bronchi(Oli)Tis Post-lung Transplantation |
| External Links |
| CAS Numbers |
117772-70-0 |
| Pubchem |
21946473 |
| HMDB |
Not Available |
| DrugBank |
Not Available |
| References |
- Menzel M, Akbarshahi H, Tufvesson E, Persson C, Bjermer L, Uller L, Azithromycin Augments Rhinovirus-induced Ifnβ Via Cytosolic Mda5 In Experimental Models Of Asthma Exacerbation., Oncotarget.2017 May 9;8(19):31601-31611. Doi: 10.18632/oncotarget.16364. [PMID:28415826 ]
- Vandooren J, Knoops S, Aldinucci Buzzo Jl, Boon L, Martens E, Opdenakker G, Kolaczkowska E, Differential Inhibition Of Activity, Activation And Gene Expression Of Mmp-9 In Thp-1 Cells By Azithromycin And Minocycline Versus Bortezomib: A Comparative Study., Plos One.2017 Apr 3;12(4):e0174853. Doi: 10.1371/journal.pone.0174853. Ecollection 2017. [PMID:28369077 ]
|
