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ciprofloxacin 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
antibacterials, nalidixic acid derivatives	659	85721-33-1

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: ciprofloxacin ciprofloxacin hydrochloride ciprofloxacillin ciprofloxacine ciprofloxacin hydrochloride monohydrate ciprofloxacin HCl ciprofloxacin lactate	A broad-spectrum antimicrobial carboxyfluoroquinoline. Molecular weight: 331.35 Formula: C17H18FN3O3 CLOGP: -0.47 LIPINSKI: 0 HAC: 6 HDO: 2 TPSA: 72.88 ALOGS: -2.39 ROTB: 3 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

ciprofloxacin
ciprofloxacin hydrochloride
ciprofloxacillin
ciprofloxacine
ciprofloxacin hydrochloride monohydrate
ciprofloxacin HCl
ciprofloxacin lactate

A broad-spectrum antimicrobial carboxyfluoroquinoline.

Molecular weight: 331.35
Formula: C17H18FN3O3
CLOGP: -0.47
LIPINSKI: 0
HAC: 6
HDO: 2
TPSA: 72.88
ALOGS: -2.39
ROTB: 3

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

Dose	Unit	Route
1	g	O
0.80	g	P

ADMET properties:

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Property	Value	Reference
CL (Clearance)	8.30 mL/min/kg	Lombardo F, Berellini G, Obach RS
EoM (Fraction excreted unchanged in urine)	65 %	Benet LZ, Broccatelli F, Oprea TI
BA (Bioavailability)	60 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
BDDCS (Biopharmaceutical Drug Disposition Classification System)	4	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	34.49 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
t_half (Half-life)	3.80 hours	Lombardo F, Berellini G, Obach RS
Vd (Volume of distribution)	2.10 L/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.70 %	Lombardo F, Berellini G, Obach RS
S (Water solubility)	0.15 mg/mL	Bocci G, Oprea TI, Benet LZ

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Approvals:

Date	Agency	Company	Orphan
Oct. 22, 1987	FDA	BAYER HLTHCARE

FDA Adverse Event Reporting System (Female)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Drug hypersensitivity	1323.83	9.68	2311	127182	308376	63051153
Tendon pain	665.97	9.68	252	129241	3074	63356455
Tendonitis	536.27	9.68	389	129104	19226	63340303
Abortion spontaneous	419.02	9.68	499	128994	46696	63312833
Drug reaction with eosinophilia and systemic symptoms	372.31	9.68	400	129093	33436	63326093
Pemphigus	348.68	9.68	5	129488	183721	63175808
Hand deformity	304.04	9.68	4	129489	159453	63200076
Tendon disorder	285.89	9.68	167	129326	5676	63353853
Glossodynia	284.34	9.68	21	129472	178855	63180674
Drug interaction	278.46	9.68	1062	128431	228069	63131460

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FDA Adverse Event Reporting System (Male)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Tendon pain	711.36	10.52	278	94988	2717	34858948
Tendonitis	568.87	10.52	338	94928	8802	34852863
Tendon rupture	456.53	10.52	267	94999	6745	34854920
Tendon disorder	254.38	10.52	134	95132	2741	34858924
Pathogen resistance	235.27	10.52	200	95066	9282	34852383
Death	226.21	10.52	467	94799	397582	34464083
Toxic epidermal necrolysis	210.66	10.52	277	94989	21369	34840296
Tendon discomfort	188.18	10.52	56	95210	210	34861455
Drug hypersensitivity	167.12	10.52	541	94725	79988	34781677
Drug abuse	155.87	10.52	39	95227	99057	34762608

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FDA Adverse Event Reporting System (Geriatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Tendon pain	1159.11	9.48	458	194569	5200	79544161
Tendonitis	855.70	9.48	599	194428	23231	79526130
Drug hypersensitivity	771.49	9.48	2023	193004	296893	79252468
Tendon rupture	546.29	9.48	351	194676	11775	79537586
Drug reaction with eosinophilia and systemic symptoms	482.92	9.48	686	194341	63558	79485803
Pathogen resistance	467.60	9.48	340	194687	14002	79535359
Tendon disorder	439.45	9.48	253	194774	6933	79542428
Toxic epidermal necrolysis	395.57	9.48	516	194511	44065	79505296
Drug interaction	350.71	9.48	1966	193061	413217	79136144
Tubulointerstitial nephritis	288.31	9.48	409	194618	37826	79511535

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	J01MA02	ANTIINFECTIVES FOR SYSTEMIC USE ANTIBACTERIALS FOR SYSTEMIC USE QUINOLONE ANTIBACTERIALS Fluoroquinolones
ATC	J01RA10	ANTIINFECTIVES FOR SYSTEMIC USE ANTIBACTERIALS FOR SYSTEMIC USE COMBINATIONS OF ANTIBACTERIALS Combinations of antibacterials
ATC	J01RA11	ANTIINFECTIVES FOR SYSTEMIC USE ANTIBACTERIALS FOR SYSTEMIC USE COMBINATIONS OF ANTIBACTERIALS Combinations of antibacterials
ATC	J01RA12	ANTIINFECTIVES FOR SYSTEMIC USE ANTIBACTERIALS FOR SYSTEMIC USE COMBINATIONS OF ANTIBACTERIALS Combinations of antibacterials
ATC	S01AE03	SENSORY ORGANS OPHTHALMOLOGICALS ANTIINFECTIVES Fluoroquinolones
ATC	S02AA15	SENSORY ORGANS OTOLOGICALS ANTIINFECTIVES Antiinfectives
ATC	S03AA07	SENSORY ORGANS OPHTHALMOLOGICAL AND OTOLOGICAL PREPARATIONS ANTIINFECTIVES Antiinfectives
CHEBI has role	CHEBI:35441	antiinfective agents
CHEBI has role	CHEBI:36047	antibacterial drugs
CHEBI has role	CHEBI:50750	inhibitors of type II topoisomerase

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Drug Use | Suggest Off label Use Form| |View source of the data|

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Disease	Relation	SNOMED_ID	DOID
Otitis externa	indication	3135009
Typhoid fever	indication	4834000	DOID:13258
Septicemia due to Escherichia coli	indication	9323009
Prostatitis	indication	9713002	DOID:14654
Infection due to Pseudomonas aeruginosa	indication	11218009
Enteric campylobacteriosis	indication	18081009
Infectious diarrheal disease	indication	19213003	DOID:13250
Infection of skin AND/OR subcutaneous tissue	indication	19824006
Acute gonococcal cervicitis	indication	20943002	DOID:10615
Acute gonococcal urethritis	indication	29864006

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

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Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	6.12	acidic
pKa2	8.54	Basic
pKa3	1.37	Basic

Orange Book patent data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
0.3%;0.1%	CIPRODEX	NOVARTIS	N021537	July 18, 2003	RX	SUSPENSION/DROPS	OTIC	8846650	June 4, 2025	TREATMENT OF ACUTE OTITIS MEDIA
6% (60MG/ML)	OTIPRIO	ALK ABELLO	N207986	Dec. 10, 2015	DISCN	INJECTABLE, SUSPENSION	OTIC	9205048	April 21, 2029	TREATMENT OF PEDIATRIC PATIENTS WITH OTITIS MEDIA WITH EFFUSION UNDERGOING TYMPANOSTOMY TUBE PLACEMENT
6% (60MG/ML)	OTIPRIO	ALK ABELLO	N207986	Dec. 10, 2015	DISCN	INJECTABLE, SUSPENSION	OTIC	9603796	April 21, 2029	THE TREATMENT OF ACUTE OTITIS EXTERNA IN PATIENTS 6 MONTHS OF AGE AND OLDER DUE TO PSEUDOMONAS AERUGINOSA AND STAPHYLOCOCCUS AUREUS
6% (60MG/ML)	OTIPRIO	ALK ABELLO	N207986	Dec. 10, 2015	DISCN	INJECTABLE, SUSPENSION	OTIC	8318817	April 27, 2030	TREATMENT OF OTIC INFECTION OR INFLAMMATION
6% (60MG/ML)	OTIPRIO	ALK ABELLO	N207986	Dec. 10, 2015	DISCN	INJECTABLE, SUSPENSION	OTIC	11040004	Nov. 12, 2037	THE TREATMENT OF ACUTE OTITIS EXTERNA IN PATIENTS 6 MONTHS OF AGE AND OLDER DUE TO PSEUDOMONAS AERUGINOSA AND STAPHYLOCOCCUS AUREUS
EQ 0.3% BASE;0.025%	OTOVEL	LABORATORIOS SALVAT	N208251	April 29, 2016	RX	SOLUTION/DROPS	OTIC	8932610	March 24, 2030	TREATMENT OF ACUTE OTITIS MEDIA

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Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
DNA topoisomerase II	Enzyme	P11388 Q02880	TOP2A_HUMAN TOP2B_HUMAN		EC50	7.52	CHEMBL
DNA gyrase subunit A	Enzyme		GYRA_ECOLI	INHIBITOR	IC50	5.75	WOMBAT-PK	CHEMBL
DNA topoisomerase 4 subunit A	Enzyme		PARC_BACSU		IC50	5.66	WOMBAT-PK
DNA topoisomerase 4 subunit A	Enzyme		PARC_STAAU	INHIBITOR	IC50	6	WOMBAT-PK
DNA gyrase subunit A	Enzyme		GYRA_MYCTU		IC50	6.20	WOMBAT-PK
Histamine H3 receptor	GPCR		HRH3_RAT		Ki	9.18	CHEMBL
GABA-A receptor; anion channel	Ion channel		GBRP_RAT GBRB1_RAT GBRD_RAT GBRG2_RAT GBRA5_RAT GBRA3_RAT GBRG1_RAT GBRA2_RAT GBRA4_RAT GBRG3_RAT GBRA6_RAT GBRA1_RAT GBRB3_RAT GBRB2_RAT Q91ZM7_RAT GBRE_RAT		IC50	6.39	CHEMBL
DNA topoisomerase 4 subunit A	Enzyme		PARC_ECOLI		IC50	5.60	WOMBAT-PK
Multidrug resistance protein mdtK	Unclassified		MDTK_ECOLI		Kd	4.04	CHEMBL

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External reference:

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ID	Source
CPF	PDB_CHEM_ID
002882	NDDF
003577	NDDF
004125	NDDF
10902	IUPHAR_LIGAND_ID
20450009	SNOMEDCT_US
235851	RXNORM
2764	PUBCHEM_CID
31644	MMSL
372840008	SNOMEDCT_US

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Ciloxan	HUMAN PRESCRIPTION DRUG LABEL	1	0065-0656	SOLUTION/ DROPS	3 mg	OPHTHALMIC	NDA	21 sections
Ciloxan	HUMAN PRESCRIPTION DRUG LABEL	1	0065-0656	SOLUTION/ DROPS	3 mg	OPHTHALMIC	NDA	21 sections
CILOXAN	HUMAN PRESCRIPTION DRUG LABEL	1	0078-0841	OINTMENT	3 mg	OPHTHALMIC	NDA	20 sections
CILOXAN	HUMAN PRESCRIPTION DRUG LABEL	1	0078-0841	OINTMENT	3 mg	OPHTHALMIC	NDA	20 sections
CILOXAN	HUMAN PRESCRIPTION DRUG LABEL	1	0078-0841	OINTMENT	3 mg	OPHTHALMIC	NDA	20 sections
CIPRODEX	HUMAN PRESCRIPTION DRUG LABEL	2	0078-0799	SUSPENSION/ DROPS	3 mg	AURICULAR (OTIC)	NDA	28 sections
CIPRODEX	HUMAN PRESCRIPTION DRUG LABEL	2	0078-0799	SUSPENSION/ DROPS	3 mg	AURICULAR (OTIC)	NDA	28 sections
CIPRODEX	HUMAN PRESCRIPTION DRUG LABEL	2	0078-0799	SUSPENSION/ DROPS	3 mg	AURICULAR (OTIC)	NDA	28 sections
Ciprofloxacin	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9927	TABLET, FILM COATED	250 mg	ORAL	ANDA	30 sections
Ciprofloxacin	HUMAN PRESCRIPTION DRUG LABEL	1	0143-9927	TABLET, FILM COATED	250 mg	ORAL	ANDA	30 sections

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