Omadacycline tosylateProduct ingredient for Omadacycline

Name
Omadacycline tosylate
Drug Entry
Omadacycline

Omadacycline has been used in trials studying the treatment of Bacterial Pneumonia, Bacterial Infections, Community-Acquired Infections, and Skin Structures and Soft Tissue Infections. Omadacycline represents a significant advance over the well-known tetracycline family, and has been shown to be highly effective in animal models at treating increasingly problematic, clinically prevalent infections caused by gram-positive bacteria, such as methicillin-resistant Staphylococcus aureus (MRSA), and by gram-negative, atypical and anaerobic bacteria, including those resistant to currently available classes of antibiotics and known to cause diseases such as pneumonias, urinary tract infections, skin diseases and blood-borne infections in both the hospital and community settings.

Accession Number
DBSALT002607
Structure
Thumb
Synonyms
Amadacyclin tosylate / Omadacycline tosilate
External IDs
PTK 0796 / PTK-0796
UNII
5658Y89YCD
CAS Number
1075240-43-5
Weight
Average: 728.86
Monoisotopic: 728.309114936
Chemical Formula
C36H48N4O10S
InChI Key
SETFNHZTVGTBHC-XGLFQKEBSA-N
InChI
InChI=1S/C29H40N4O7.C7H8O3S/c1-28(2,3)12-31-11-14-10-17(32(4)5)15-8-13-9-16-21(33(6)7)24(36)20(27(30)39)26(38)29(16,40)25(37)18(13)23(35)19(15)22(14)34;1-6-2-4-7(5-3-6)11(8,9)10/h10,13,16,21,31,34,36-37,40H,8-9,11-12H2,1-7H3,(H2,30,39);2-5H,1H3,(H,8,9,10)/t13-,16-,21-,29-;/m0./s1
IUPAC Name
(4S,4aS,5aR,12aS)-4,7-bis(dimethylamino)-9-{[(2,2-dimethylpropyl)amino]methyl}-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide; 4-methylbenzene-1-sulfonic acid
SMILES
CC1=CC=C(C=C1)S(O)(=O)=O.[H][C@@]12CC3=C(C=C(CNCC(C)(C)C)C(O)=C3C(=O)C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@]1([H])C2)N(C)C
External Links
ChemSpider
28528673
ChEMBL
CHEMBL2103854
Predicted Properties
PropertyValueSource
Water Solubility0.213 mg/mLALOGPS
logP0.94ALOGPS
logP-2.2ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)2.87ChemAxon
pKa (Strongest Basic)10.54ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area176.66 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity153.93 m3·mol-1ChemAxon
Polarizability59.61 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon