Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00301)
Name
Gemifloxacin
Synonyms    Click to Show/Hide the Synonyms of This API
Gemifloxacin; 175463-14-6; Gemifloxacin mesilate; Gemifloxacin [INN]; Gemifloxacin mesylate; Gemifioxacin; Gemifloxacin (INN); LB-20304; CHEMBL430; CHEBI:101853; SB-265805; 7-[(4Z)-3-(aminomethyl)-4-methoxyimino-pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid; (E)-7-(3-(aminomethyl)-4-(methoxyimino)pyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid; 7-[3-(aminomethyl)-4-(methoxyimino)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid; Factiv (TN); LB 20304; (Z)-7-(3-(aminomethyl)-4-(methoxyimino)pyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid; SR-05000001958; 7-(3-Aminomethyl-4-methoxyimino-pyrrolidine-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-(1,8)-naphthyridine-3-carboxylic acid; HSDB 8027; 7-(3-(aminomethyl)-4-(methoxyimino)pyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid; BSPBio_002308; SCHEMBL136633; DTXSID3048495; SCHEMBL13414391; BDBM50178917; AKOS015907681; AM84619; DB01155; NCGC00178711-01; NCGC00178711-06; 1,8-Naphthyridine-3-carboxylic acid, 7-(3-(aminomethyl)-4-(methoxyimino)-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-; 204519-64-2; 7-(3-Aminomethyl)-4-methoxyimino-pyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid; SBI-0206906.P001; D08012; AB01563334_01; 463G146; A812090; SR-05000001958-2; BRD-A40787240-066-02-0; BRD-A40787240-066-03-8; (S,Z)-7-(3-(aminomethyl)-4-(methoxyimino)pyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid; 1,4-Dihydro-1-cyclopropyl-4-oxo-6-fluoro-7-[3-(aminomethyl)-4-(methoxyimino)pyrrolidine-1-yl]-1,8-naphthyridine-3-carboxylic acid; 1,4-Dihydro-6-fluoro-1-cyclopropyl-4-oxo-7-[(3E)-4-(aminomethyl)-3-(methoxyimino)pyrrolidine-1-yl]-1,8-naphthyridine-3-carboxylic acid; 1,8-Naphthyridine-3-carboxylic acid, 7-[(4Z)-3-(aminomethyl)-4-(methoxyimino)-1-pyrrolidinyl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-; 7-[(4Z)-3-(aminomethyl)-4-(methoxyimino)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid; 7-[(4Z)-3-(aminomethyl)-4-methoxyimino-1-pyrrolidinyl]-1-cyclopropyl-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid; 7-[(4Z)-3-(aminomethyl)-4-methoxyimino-pyrrolidin-1-yl]-1-cyclopropyl-6-fluoranyl-4-oxidanylidene-1,8-naphthyridine-3-carboxylic acid; 7-{3-Aminomethyl-4-[(Z)-methoxyimino]-pyrrolidin-1-yl}-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid; Gemifloxacin; 7-(3-Aminomethyl)-4-methoxyimino-pyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1, 4-dihydro-[1, 8]naphthyridine-3-carboxylic acid; 210353-56-3
Clinical Status
Approved
Disease Indication Streptococcus bacterial infection ICD-11: 1C41 [1]
PubChem CID
9571107
Formula
C18H20FN5O4
Canonical SMILES
CO/N=C/1\\CN(CC1CN)C2=C(C=C3C(=O)C(=CN(C3=N2)C4CC4)C(=O)O)F
InChI
1S/C18H20FN5O4/c1-28-22-14-8-23(6-9(14)5-20)17-13(19)4-11-15(25)12(18(26)27)7-24(10-2-3-10)16(11)21-17/h4,7,9-10H,2-3,5-6,8,20H2,1H3,(H,26,27)/b22-14+
InChIKey
ZRCVYEYHRGVLOC-HYARGMPZSA-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=9571107"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 389.4 Topological Polar Surface Area 121
XlogP -0.7 Complexity 725
Heavy Atom Count 28 Rotatable Bond Count 5
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 10
Full List of Drug Formulations (DFMs) Containing This API
          Gemifloxacin 320 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
Magnesium stearate; Titanium dioxide; Crospovidone; Polyethylene glycol 4000; Polyethylene glycol 6000; Povidone; Cellulose, microcrystalline; Hypromellose 2910 (15 mpa.s); Hypromellose 2910 (5 mpa.s)
                   Dosage Form Oral Tablet
                   Company Cornerstone Therapeutics; Merus Labs International; Vansen Pharma
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Crospovidone DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Polyethylene glycol 4000 DIG Info Albendazole monooxygenase (Inhibition ratio < 40 %) [4]
Polyethylene glycol 6000 DIG Info Albendazole monooxygenase (Inhibition ratio < 70 %) [4]
References
1 FDA label for approved gemifloxacin from the official website of the U.S. Food and Drug Administration.
2 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
3 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.
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.

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