Garenoxacin: Difference between revisions

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			{{Short description\|Chemical compound}}
	{{Drugbox		{{Drugbox
			\| Verifiedfields = changed
⚫	\| verifiedrevid = ~~443450244~~
			\| Watchedfields = changed
⚫	\| IUPAC_name = 1-~~cyclopropyl~~-8-(difluoromethoxy)-7--4-oxo-1,4-dihydroquinoline-3-carboxylic acid
		⚫	\| verifiedrevid = 443977394
		⚫	\| IUPAC_name = 1-Cyclopropyl-8-(difluoromethoxy)-7--4-oxo-1,4-dihydroquinoline-3-carboxylic acid
	\| image = Garenoxacin.svg		\| image = Garenoxacin.svg

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	\| metabolism =		\| metabolism =
	\| elimination_half-life =		\| elimination_half-life =
	\| excretion =		\| excretion =

	<!--Identifiers-->		<!--Identifiers-->
			\| CAS_number_Ref = {{cascite\|changed\|??}}
	\| CAS_number = ~~91421~~-42-0		\| CAS_number = 194804-75-6
	\| ATC_prefix = J01		\| ATC_prefix = J01
	\| ATC_suffix = MA19		\| ATC_suffix = MA19
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	\| KEGG_Ref = {{keggcite\|correct\|kegg}}		\| KEGG_Ref = {{keggcite\|correct\|kegg}}
	\| KEGG = D04031		\| KEGG = D04031
			\| ChEBI_Ref = {{ebicite\|changed\|EBI}}
			\| ChEBI = 131716
			\| ChemSpiderID_Ref = {{chemspidercite\|changed\|chemspider}}
			\| ChemSpiderID = 110579
			\| smiles = FC(F)Oc1c(ccc2c1N(/C=C(\C2=O)C(=O)O)C3CC3)c4ccc5c(c4)CN5C
			\| StdInChI_Ref = {{stdinchicite\|changed\|chemspider}}
			\| StdInChI = 1S/C23H20F2N2O4/c1-11-15-5-2-12(8-13(15)9-26-11)16-6-7-17-19(21(16)31-23(24)25)27(14-3-4-14)10-18(20(17)28)22(29)30/h2,5-8,10-11,14,23,26H,3-4,9H2,1H3,(H,29,30)/t11-/m1/s1
			\| StdInChIKey_Ref = {{stdinchicite\|changed\|chemspider}}
			\| StdInChIKey = NJDRXTDGYFKORP-LLVKDONJSA-N

	<!--Chemical data-->		<!--Chemical data-->
	\| C=23 \| H=20 \| F=2 \| N=2 \| O=4		\| C=23 \| H=20 \| F=2 \| N=2 \| O=4
	\| molecular_weight = 426.412 ]/]
	}}		}}

	'''Garenoxacin''' (]) is a quinolone antibiotic for the treatment of ~~gram~~-positive and ~~gram~~-negative bacterial infections.		'''Garenoxacin''' (]) is a ] ] for the treatment of ] and ] bacterial infections.<ref name="pmid18790608">{{cite journal \| vauthors = Takagi H, Tanaka K, Tsuda H, Kobayashi H \| title = Clinical studies of garenoxacin \| journal = International Journal of Antimicrobial Agents \| volume = 32 \| issue = 6 \| pages = 468–74 \| date = December 2008 \| pmid = 18790608 \| doi = 10.1016/j.ijantimicag.2008.06.032 \| doi-access = free }}</ref>

	It was discovered by Toyama Chemical Co., Ltd. of Tokyo, Japan, and is currently being marketed in ] under the tradename Geninax. ] holds worldwide rights for garenoxacin, except for Japan, ], and ].		Garenoxacin was discovered by Toyama Chemical Co., Ltd. of Tokyo, Japan, and is currently being marketed in ] under the tradename Geninax. ] holds worldwide rights for garenoxacin, except for Japan, ], and ].{{cn\|date=January 2023}}

	On February 13, 2006, Schering-Plough announced that the ] ] ~~has~~ accepted the New Drug Application (NDA) for garenoxacin, and ~~has~~ been granted a 10-month review.<ref>{{cite web \|url=~~http~~://www.drugs.com/nda/garenoxacin_060213.html \|title=Drugs.com, Schering-Plough Reports Garenoxacin NDA Accepted for FDA Review \|~~accessdate~~=2008-03-25 ~~\|format= \|work=~~ }}</ref>		On February 13, 2006, ] announced that the ] ] had accepted the New Drug Application (NDA) for garenoxacin, and had been granted a 10-month review.<ref>{{cite web \|url=https://www.drugs.com/nda/garenoxacin_060213.html \|title=Drugs.com, Schering-Plough Reports Garenoxacin NDA Accepted for FDA Review \|access-date=2008-03-25 }}</ref> As of 2015, however, it has not been approved in the US.{{cn\|date=January 2023}}

	Schering-Plough later withdrew its application to the United States Food and Drug Administration, FDA, (August 20, 2006) for approval of the antibiotic Garenoxacin.<ref>http://www.fiercebiotech.com/story/schering-plough-pulls-its-garenoxacin-app/2006-08-21</ref>		Schering-Plough later withdrew its application to the United States Food and Drug Administration, FDA, (August 20, 2006) for approval of the antibiotic Garenoxacin.<ref>{{Cite web \| url=http://www.fiercebiotech.com/story/schering-plough-pulls-its-garenoxacin-app/2006-08-21 \| title=Schering-Plough pulls its garenoxacin app\| date=20 August 2006}}</ref>

			The ] (EMA) had also been formally notified by Schering-Plough Europe (July 25, 2007) of its decision to withdraw the application for a centralized marketing authorization for garenoxacin as well.<ref>{{Cite web \|url=http://www.medicalnewstoday.com/articles/78052.php \|title=Schering-Plough Europe Withdraws Its Marketing Authorisation Application For Garenoxacin Mesylate \|access-date=2009-05-30 \|archive-date=2007-08-08 \|archive-url=https://web.archive.org/web/20070808183432/http://www.medicalnewstoday.com/articles/78052.php \|url-status=dead \| publisher = MediLexicon International Ltd \| date = 28 July 2007 }}</ref><ref>{{cite web \| title=Garenoxacin mesylate: Withdrawn application \| website=] (EMA) \| date=17 September 2018 \| url= https://www.ema.europa.eu/en/medicines/human/withdrawn-applications/garenoxacin-mesylate \| access-date=13 July 2020}}</ref><ref>{{cite press release \| title=Schering-Plough Europe withdraws its marketing authorisation applicationfor Garenoxacin mesylate \| website=] (EMA) \| url=https://www.ema.europa.eu/en/news/schering-plough-europe-withdraws-its-marketing-authorisation-applicationfor-garenoxacin-mesylate \| access-date=13 July 2020}}</ref> Based on the CHMP review of the data regarding safety and efficacy (risk/benefit), the CHMP considered the application for garenoxacin to be unapprovable.<ref>{{cite web \| title = Withdrawal Assessment report for Garenoxacin Mesylate (garenoxacin) \| url = https://www.ema.europa.eu/en/documents/withdrawal-report/withdrawal-assessment-report-garenoxacin-mesylate_en.pdf \| publisher = European Medicines Agency \| date = 18 October 2007 }}</ref>
	The European Medicines Agency (EMEA) had also been formally notified by Schering-Plough Europe (July 28 2007) of its decision to withdraw the application for a centralized marketing authorization for Garenoxacin as well.
	<ref>http://www.medicalnewstoday.com/articles/78052.php</ref><ref>http://www.emea.europa.eu/humandocs/PDFs/EPAR/garenoxacinmesylate/34117407en.pdf</ref><ref>http://www.emea.europa.eu/humandocs/PDFs/EPAR/garenoxacinmesylate/H-747-WAR.pdf</ref>

	Based on the CHMP review of the data regarding safety and efficacy, (risk/benefit) the CHMP considered the application for Garenoxacin to be unapprovable. <ref> http://www.emea.europa.eu/humandocs/PDFs/EPAR/garenoxacinmesylate/H-747-WAR.pdf</ref>

	==See also==
	*]
	*]

	==References==		==References==
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Latest revision as of 15:22, 9 December 2024

Chemical compound Pharmaceutical compound

Garenoxacin
Clinical data

Routes of administration	Oral
ATC code	J01MA19 (WHO)
Identifiers
IUPAC name 1-Cyclopropyl-8-(difluoromethoxy)-7--4-oxo-1,4-dihydroquinoline-3-carboxylic acid
CAS Number	194804-75-6
PubChem CID	124093
ChemSpider	110579
UNII	V72H9867WB
KEGG	D04031
ChEBI	CHEBI:131716
CompTox Dashboard (EPA)	DTXSID30173135
Chemical and physical data
Formula	C₂₃H₂₀F₂N₂O₄
Molar mass	426.420 g·mol
3D model (JSmol)	Interactive image
SMILES FC(F)Oc1c(ccc2c1N(/C=C(\C2=O)C(=O)O)C3CC3)c4ccc5c(c4)CN5C
InChI InChI=1S/C23H20F2N2O4/c1-11-15-5-2-12(8-13(15)9-26-11)16-6-7-17-19(21(16)31-23(24)25)27(14-3-4-14)10-18(20(17)28)22(29)30/h2,5-8,10-11,14,23,26H,3-4,9H2,1H3,(H,29,30)/t11-/m1/s1 Key:NJDRXTDGYFKORP-LLVKDONJSA-N
(what is this?) (verify)

Garenoxacin (INN) is a quinolone antibiotic for the treatment of Gram-positive and Gram-negative bacterial infections.

Garenoxacin was discovered by Toyama Chemical Co., Ltd. of Tokyo, Japan, and is currently being marketed in Japan under the tradename Geninax. Schering-Plough holds worldwide rights for garenoxacin, except for Japan, South Korea, and China.

On February 13, 2006, Schering-Plough announced that the United States Food and Drug Administration had accepted the New Drug Application (NDA) for garenoxacin, and had been granted a 10-month review. As of 2015, however, it has not been approved in the US.

Schering-Plough later withdrew its application to the United States Food and Drug Administration, FDA, (August 20, 2006) for approval of the antibiotic Garenoxacin.

The European Medicines Agency (EMA) had also been formally notified by Schering-Plough Europe (July 25, 2007) of its decision to withdraw the application for a centralized marketing authorization for garenoxacin as well. Based on the CHMP review of the data regarding safety and efficacy (risk/benefit), the CHMP considered the application for garenoxacin to be unapprovable.

References

Takagi H, Tanaka K, Tsuda H, Kobayashi H (December 2008). "Clinical studies of garenoxacin". International Journal of Antimicrobial Agents. 32 (6): 468–74. doi:10.1016/j.ijantimicag.2008.06.032. PMID 18790608.
"Drugs.com, Schering-Plough Reports Garenoxacin NDA Accepted for FDA Review". Retrieved 2008-03-25.
"Schering-Plough pulls its garenoxacin app". 20 August 2006.
"Schering-Plough Europe Withdraws Its Marketing Authorisation Application For Garenoxacin Mesylate". MediLexicon International Ltd. 28 July 2007. Archived from the original on 2007-08-08. Retrieved 2009-05-30.
"Garenoxacin mesylate: Withdrawn application". European Medicines Agency (EMA). 17 September 2018. Retrieved 13 July 2020.
"Schering-Plough Europe withdraws its marketing authorisation applicationfor Garenoxacin mesylate". European Medicines Agency (EMA) (Press release). Retrieved 13 July 2020.
"Withdrawal Assessment report for Garenoxacin Mesylate (garenoxacin)" (PDF). European Medicines Agency. 18 October 2007.

Antibacterials that inhibit nucleic acid (J01E, J01M)

Antifolates
(inhibit bacterial
purine metabolism,
thereby inhibiting
DNA and RNA
synthesis)

DHFR inhibitor

2,4-Diaminopyrimidine

Sulfonamides
(DHPS inhibitor)

Short-acting	Sulfaisodimidine Sulfamethizole Sulfadimidine (Sulfamethazine, Sulfadimerazine, Sulfadimezine) Sulfapyridine (Sulfasalazine) Sulfafurazole (Acetyl sulfisoxazole) Sulfanilamide Prontosil Sulfathiazole (Phthalylsulfathiazole, Succinylsulfathiazole) Sulfathiourea
Intermediate-acting	Sulfamethoxazole Sulfadiazine Sulfamoxole
Long-acting	Sulfadimethoxine Sulfadoxine Sulfalene Sulfametomidine Sulfametoxydiazine Sulfamethoxypyridazine Sulfaperin Sulfamerazine Sulfaphenazole Sulfamazone
Other/ungrouped	Mafenide Sulfacetamide Sulfaclozine Sulfadicramide Sulfaguanidine Sulfametrole Sulfanitran

Combinations

Other DHPS inhibitors

Quinolones
(inhibit bacterial
topoisomerase
and/or DNA gyrase,
thereby inhibiting
DNA replication)

1st generation

Fluoroquinolones

2nd generation	Ciprofloxacin Ofloxacin Enoxacin Fleroxacin Lomefloxacin Nadifloxacin/Levonadifloxacin/Alalevonadifloxacin Norfloxacin Pefloxacin Rufloxacin
3rd generation	Levofloxacin Balofloxacin Grepafloxacin Pazufloxacin Sparfloxacin Temafloxacin Tosufloxacin
4th generation	Besifloxacin Delafloxacin Gatifloxacin Finafloxacin Gemifloxacin Moxifloxacin Clinafloxacin Garenoxacin Prulifloxacin Sitafloxacin Trovafloxacin/Alatrofloxacin
Veterinary	Danofloxacin Difloxacin Enrofloxacin Ibafloxacin Marbofloxacin Orbifloxacin Pradofloxacin Sarafloxacin

Newer non-fluorinated

Related (DG)

Aminocoumarins: Novobiocin

Anaerobic DNA
inhibitors

Nitroimidazole derivatives	Secnidazole

RNA synthesis

Rifamycins/ RNA polymerase	Rifampicin Rifabutin Rifapentine Rifaximin Rifalazil
Lipiarmycins	Fidaxomicin

WHO-EM
Withdrawn from market
Clinical trials:
- Phase III
- Never to phase III

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