Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D01299)
Name
Omadacycline
Synonyms    Click to Show/Hide the Synonyms of This API
Omadacycline; Amadacycline; nuzyra; PTK-0796; UNII-090IP5RV8F; 389139-89-3; 090IP5RV8F; PTK 0796; 389139-89-3 (free base); (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; Amadacycline methanesulfonate; (4S,4aS,5aR,12aR)-4,7-bis(dimethylamino)-9-[(2,2-dimethylpropylamino)methyl]-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide; Omadacycline [USAN:INN]; (4S,4aS,5aR,12aS)-4,7-bis(dimethylamino)-9-[(2,2-dimethylpropylamino)methyl]-3,10,12,12a-tetrahydroxy-1,11-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide; 2-Naphthacenecarboxamide, 4,7-bis(dimethylamino)-9-[[(2,2-dimethylpropyl)amino]methyl]-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-, (4S,4aS,5aR,12aS)-; Omadacycline (USAN); SCHEMBL1525961; 9-neopentylaminomethylminocycline; CHEMBL1689772; SCHEMBL17150976; SCHEMBL20952297; GTPL10839; PTK-796; PTK0796; BCP12946; EX-A4252; ZINC4836283; compound 6 [PMID: 21302930]; CS-1338; DB12455; MK-2764; BAY 73-6944; BAY-73-6944; BAY-73-7388; NCGC00378946-03; HY-14865; PTK 0796, BAY 73-6944; D09647; W-5819; Q15426992; 2-Naphthacenecarboxamide, 4,7-bis(dimethylamino)-9-(((2,2- dimethylpropyl)amino)methyl)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a- tetrahydroxy-1,11-dioxo-, (4S,4aS,5aR,12aS)-
Clinical Status
Approved
PubChem CID
54697325
Formula
C29H40N4O7
Canonical SMILES
CC(C)(C)CNCC1=CC(=C2C[C@H]3C[C@H]4[C@@H](C(=O)C(=C([C@]4(C(=O)C3=C(C2=C1O)O)O)O)C(=O)N)N(C)C)N(C)C
InChI
1S/C29H40N4O7/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/h10,13,16,21,31,34-35,38,40H,8-9,11-12H2,1-7H3,(H2,30,39)/t13-,16-,21-,29-/m0/s1
InChIKey
VJYKVCURWJGLPG-IQZGDKDPSA-N
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=54697325"></iframe>
3D MOL is unavailable 2D MOL
Physicochemical Properties Molecular Weight 556.6 Topological Polar Surface Area 177
XlogP 3 Complexity 1140
Heavy Atom Count 40 Rotatable Bond Count 7
Hydrogen Bond Donor Count 6 Hydrogen Bond Acceptor Count 10
Full List of Drug Formulations (DFMs) Containing This API
          Omadacycline 150 mg tablet Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Colloidal Silicon Dioxide; Crospovidone; Glycerol Monocaprylocaprate; Iron Oxide Yellow; Lactose Monohydrate; Microcrystalline Cellulose; Polyvinyl Alcohol; Sodium Bisulfite; Sodium Lauryl Sulfate; Sodium Stearyl Fumarate; Talc; Titanium Dioxide
                   Dosage Form Tablet
                   Company Paratek Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [1]
Sodium stearyl fumarate DIG Info Leukemia K562 cells (IC50 = 20.2 ug.mL-1) [2]
Polyvinyl alcohol DIG Info Debrisoquine 4-hydroxylase (EC50 = 354.8 uM) [3]
Sodium sulhydrate DIG Info Albendazole monooxygenase (Inhibition ratio < 90 %) [4]
Crospovidone DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
          Omadacycline 100 mg For Injection Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Sucrose; Hydrochloric Acid; Sodium Hydroxide
                   Dosage Form For Injection
                   Company Paratek Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Hydrochloric acid DIG Info Carbonic anhydrase V (Ki = 156 nM) [6]
References
1 Bacterial metabolism rescues the inhibition of intestinal drug absorption by food and drug additives. Proc Natl Acad Sci U S A. 2020 Jul 7;117(27):16009-16018.
2 Synthesis and evaluation of (-)-Massoialactone and analogues as potential anticancer and anti-inflammatory agents. Eur J Med Chem. 2014 Apr 9; 76:291-300.
3 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
4 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.
5 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.
6 Carbonic anhydrase inhibitors. Inhibition of the newly isolated murine isozyme XIII with anions. Bioorg Med Chem Lett. 2004 Nov 1; 14(21):5435-9.

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