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

Stem definition	Drug id	CAS RN
systemic antifungal agents, miconazole derivatives	1187	86386-73-4

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: fluconazole difluconazole flunazol diflucan	Triazole antifungal agent that is used to treat oropharyngeal CANDIDIASIS and cryptococcal MENINGITIS in AIDS. Molecular weight: 306.28 Formula: C13H12F2N6O CLOGP: 0.10 LIPINSKI: 0 HAC: 7 HDO: 1 TPSA: 81.65 ALOGS: -2.34 ROTB: 5 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

fluconazole
difluconazole
flunazol
diflucan

Triazole antifungal agent that is used to treat oropharyngeal CANDIDIASIS and cryptococcal MENINGITIS in AIDS.

Molecular weight: 306.28
Formula: C13H12F2N6O
CLOGP: 0.10
LIPINSKI: 0
HAC: 7
HDO: 1
TPSA: 81.65
ALOGS: -2.34
ROTB: 5

Status: OFP

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

Drug dosage:

Dose	Unit	Route
0.20	g	O
0.20	g	P

ADMET properties:

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Property	Value	Reference
BA (Bioavailability)	90 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
MRTD (Maximum Recommended Therapeutic Daily Dose)	9.33 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
EoM (Fraction excreted unchanged in urine)	75 %	Benet LZ, Broccatelli F, Oprea TI
S (Water solubility)	6 mg/mL	Bocci G, Oprea TI, Benet LZ
t_half (Half-life)	30 hours	Lombardo F, Berellini G, Obach RS
BDDCS (Biopharmaceutical Drug Disposition Classification System)	3	Benet LZ, Broccatelli F, Oprea TI
fu (Fraction unbound in plasma)	0.89 %	Lombardo F, Berellini G, Obach RS
Vd (Volume of distribution)	0.75 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	0.31 mL/min/kg	Lombardo F, Berellini G, Obach RS

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Approvals:

Date	Agency	Company	Orphan
Jan. 29, 1990	FDA	PFIZER

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
Febrile neutropenia	610.85	9.91	812	93063	117637	63277510
Drug interaction	382.84	9.91	962	92913	228169	63166978
Candida infection	370.72	9.91	319	93556	28032	63367115
Mucosal inflammation	266.94	9.91	338	93537	46590	63348557
Pemphigus	235.83	9.91	8	93867	183718	63211429
Sepsis	215.84	9.91	604	93271	152519	63242628
Hand deformity	208.03	9.91	6	93869	159451	63235696
Thrombocytopenia	207.91	9.91	591	93284	150566	63244581
Glossodynia	206.77	9.91	15	93860	178861	63216286
Fungal infection	205.60	9.91	263	93612	36611	63358536

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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
Febrile neutropenia	493.19	10.76	962	72189	135887	34747893
Immune reconstitution inflammatory syndrome	315.82	10.76	208	72943	8551	34875229
Candida infection	285.81	10.76	261	72890	17454	34866326
Pyrexia	239.86	10.76	1346	71805	331667	34552113
Drug interaction	211.07	10.76	983	72168	224963	34658817
Pancytopenia	201.66	10.76	543	72608	94614	34789166
Mucormycosis	194.73	10.76	133	73018	5809	34877971
Cytokine release syndrome	175.96	10.76	228	72923	22649	34861131
Neutropenia	167.99	10.76	711	72440	156067	34727713
Drug abuse	158.62	10.76	13	73138	99083	34784697

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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
Febrile neutropenia	913.86	9.77	1537	139341	229462	79374048
Candida infection	599.65	9.77	515	140363	37699	79565811
Drug interaction	527.48	9.77	1771	139107	413412	79190098
Immune reconstitution inflammatory syndrome	369.85	9.77	256	140622	13585	79589925
Pancytopenia	367.04	9.77	866	140012	164879	79438631
Completed suicide	359.50	9.77	18	140860	245749	79357761
Cytokine release syndrome	349.02	9.77	372	140506	35626	79567884
Mucosal inflammation	337.51	9.77	532	140346	75048	79528462
Multiple organ dysfunction syndrome	315.09	9.77	672	140206	119574	79483936
Pyrexia	313.12	9.77	2159	138719	676550	78926960

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FDA Adverse Event Reporting System (Pediatric)

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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 ineffective	55.15	29.94	34	210	1018	88530

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Pharmacologic Action:

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Source	Code	Description
ATC	D01AC15	DERMATOLOGICALS ANTIFUNGALS FOR DERMATOLOGICAL USE ANTIFUNGALS FOR TOPICAL USE Imidazole and triazole derivatives
ATC	J01RA07	ANTIINFECTIVES FOR SYSTEMIC USE ANTIBACTERIALS FOR SYSTEMIC USE COMBINATIONS OF ANTIBACTERIALS Combinations of antibacterials
ATC	J02AC01	ANTIINFECTIVES FOR SYSTEMIC USE ANTIMYCOTICS FOR SYSTEMIC USE ANTIMYCOTICS FOR SYSTEMIC USE Triazole and tetrazole derivatives
CHEBI has role	CHEBI:35703	Xenobiotic
CHEBI has role	CHEBI:50183	P450 inhibitors
CHEBI has role	CHEBI:78298	environmental contaminants
FDA CS	M0002083	Azoles
FDA EPC	N0000175487	Azole Antifungal
FDA MoA	N0000182140	Cytochrome P450 2C19 Inhibitors
FDA MoA	N0000182141	Cytochrome P450 3A4 Inhibitors

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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
Cryptococcal meningitis	indication	14232007
Candidiasis of the esophagus	indication	20639004	DOID:13146
Mucocutaneous candidiasis	indication	29147005
Disseminated candidiasis	indication	70572005
Candidal vulvovaginitis	indication	72605008	DOID:2272
Candidiasis of mouth	indication	79740000	DOID:14262
Candidal septicemia	indication	187022007
Candidemia	indication	432261003
Prevention of Disseminated Candidiasis	indication
Candidal Urinary Tract Infection	indication

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	13.55	acidic
pKa2	1.84	Basic
pKa3	1.24	Basic

Orange Book patent data (new drug applications)

None

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
Cytochrome P450 2C9	Enzyme	P11712	CP2C9_HUMAN		IC50	4.54	CHEMBL
Cytochrome P450 2C19	Enzyme	P33261	CP2CJ_HUMAN		IC50	5.09	CHEMBL
Lanosterol 14-alpha demethylase	Enzyme	Q16850	CP51A_HUMAN		Kd	4.40	CHEMBL
Cytochrome P450 3A4	Enzyme	P08684	CP3A4_HUMAN		IC50	5.10	CHEMBL
Lanosterol 14-alpha demethylase	Enzyme		CP51_CANAL	INHIBITOR	IC50	6.70	WOMBAT-PK	CHEMBL
Lanosterol 14-alpha demethylase	Enzyme		CP51_MYCTU		Kd	6.70	CHEMBL
14-alpha sterol demethylase Cyp51A	Enzyme		Q4WNT5_ASPFU		Kd	4.92	CHEMBL
14-alpha sterol demethylase	Enzyme		Q96W81_ASPFM		Kd	5.39	CHEMBL
Mycocyclosin synthase	Enzyme		CP121_MYCTU		Kd	5.22	CHEMBL
Sterol 14-alpha demethylase	Enzyme		CP51_TRYCC		IC50	6.06	CHEMBL

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External reference:

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ID	Source
TPF	PDB_CHEM_ID
003534	NDDF
202813	RXNORM
31865003	SNOMEDCT_US
3365	PUBCHEM_CID
387174006	SNOMEDCT_US
3884	MMSL
4019493	VUID
4019493	VANDF
4732	MMSL

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Diflucan	HUMAN PRESCRIPTION DRUG LABEL	1	0049-3410	TABLET	50 mg	ORAL	NDA	27 sections
Diflucan	HUMAN PRESCRIPTION DRUG LABEL	1	0049-3410	TABLET	50 mg	ORAL	NDA	27 sections
Diflucan	HUMAN PRESCRIPTION DRUG LABEL	1	0049-3410	TABLET	50 mg	ORAL	NDA	27 sections
Diflucan	HUMAN PRESCRIPTION DRUG LABEL	1	0049-3410	TABLET	50 mg	ORAL	NDA	27 sections
Diflucan	HUMAN PRESCRIPTION DRUG LABEL	1	0049-3420	TABLET	100 mg	ORAL	NDA	27 sections
Diflucan	HUMAN PRESCRIPTION DRUG LABEL	1	0049-3420	TABLET	100 mg	ORAL	NDA	27 sections
Diflucan	HUMAN PRESCRIPTION DRUG LABEL	1	0049-3420	TABLET	100 mg	ORAL	NDA	27 sections
Diflucan	HUMAN PRESCRIPTION DRUG LABEL	1	0049-3420	TABLET	100 mg	ORAL	NDA	27 sections
Diflucan	HUMAN PRESCRIPTION DRUG LABEL	1	0049-3430	TABLET	200 mg	ORAL	NDA	27 sections
Diflucan	HUMAN PRESCRIPTION DRUG LABEL	1	0049-3430	TABLET	200 mg	ORAL	NDA	27 sections

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