General Information
Drug ID
DR00688
Drug Name
Gemifloxacin
Synonyms
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-pyrrolidine-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; Factiv (TN); Factive; Factive (TN); Gemifloxacin (INN); Gemifloxacin [INN]; Gemifloxacin mesilate; LB 20304; LB 20304a; LB-20304; SB 265805; SB-265805
Drug Type
Small molecular drug
Indication Bacterial infections [ICD11:1A00-1H0Z] Approved [1]
Therapeutic Class
Antibiotics
Structure
3D MOL 2D MOL
Formula
C18H20FN5O4
Canonical SMILES
CON=C1CN(CC1CN)C2=C(C=C3C(=O)C(=CN(C3=N2)C4CC4)C(=O)O)F
InChI
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
CAS Number
CAS 175463-14-6
Pharmaceutical Properties Molecular Weight 389.4 Topological Polar Surface Area 121
Heavy Atom Count 28 Rotatable Bond Count 5
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 10
XLogP
-0.7
PubChem CID
9571107
PubChem SID
103165376 ,104064190 ,124766444 ,126665045 ,131302500 ,134338130 ,135029930 ,137267488 ,141952322 ,14878468 ,152047100 ,162263733 ,163384560 ,172861476 ,175438039 ,179150073 ,223664023 ,226504227 ,238411063 ,23996711 ,251890177 ,251963973 ,252358754 ,44709303 ,46507905 ,48395332 ,50070532 ,50071315 ,50123382 ,57372939 ,610685 ,79751939 ,85305864 ,85789646 ,91613407 ,96024705
ChEBI ID
CHEBI:101853
TTD Drug ID
D0VR7W
DT(s) Transporting This Drug MRP2 Transporter Info Multidrug resistance-associated protein 2 Substrate [2]
References
1 Gemifloxacin was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 Differential effect of P-gp and MRP2 on cellular translocation of gemifloxacin. Int J Pharm. 2011 Nov 25;420(1):26-33.

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