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

Stem definition	Drug id	CAS RN
systemic antifungal agents, miconazole derivatives	1513	84625-61-6

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: itraconazole canditral itrizole oriconazole traconal triasporin R-51211	A triazole antifungal agent that inhibits cytochrome P-450-dependent enzymes required for ERGOSTEROL synthesis. Molecular weight: 705.64 Formula: C35H38Cl2N8O4 CLOGP: 6.84 LIPINSKI: 3 HAC: 12 HDO: 0 TPSA: 100.79 ALOGS: -4.86 ROTB: 11 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

itraconazole
canditral
itrizole
oriconazole
traconal
triasporin
R-51211

A triazole antifungal agent that inhibits cytochrome P-450-dependent enzymes required for ERGOSTEROL synthesis.

Molecular weight: 705.64
Formula: C35H38Cl2N8O4
CLOGP: 6.84
LIPINSKI: 3
HAC: 12
HDO: 0
TPSA: 100.79
ALOGS: -4.86
ROTB: 11

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
Vd (Volume of distribution)	7.40 L/kg	Lombardo F, Berellini G, Obach RS
BA (Bioavailability)	55 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
CL (Clearance)	5.10 mL/min/kg	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	25 hours	Lombardo F, Berellini G, Obach RS
BDDCS (Biopharmaceutical Drug Disposition Classification System)	2	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	14.17 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
EoM (Fraction excreted unchanged in urine)	0.03 %	Benet LZ, Broccatelli F, Oprea TI
S (Water solubility)	0.00 mg/mL	Benet LZ, Broccatelli F, Oprea TI
fu (Fraction unbound in plasma)	0.00 %	Lombardo F, Berellini G, Obach RS

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Approvals:

Date	Agency	Company	Orphan
Sept. 11, 1992	FDA	JANSSEN PHARMS

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 interaction	370.87	15.77	323	11751	228808	63248140
Febrile neutropenia	129.78	15.77	135	11939	118314	63358634
Aspergillus infection	129.17	15.77	51	12023	8042	63468906
Bronchopulmonary aspergillosis	122.54	15.77	50	12024	8585	63468363
Pseudohyponatraemia	103.86	15.77	16	12058	31	63476917
Symmetrical drug-related intertriginous and flexural exanthema	92.29	15.77	21	12053	483	63476465
Drug resistance	81.34	15.77	52	12022	22881	63454067
Rhabdomyolysis	74.77	15.77	64	12010	43887	63433061
Neutrophil count decreased	68.44	15.77	68	12006	56338	63420610
Myopathy	65.18	15.77	35	12039	11156	63465792

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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
Drug interaction	212.40	14.56	360	14593	225586	34716392
Aspergillus infection	132.64	14.56	76	14877	12178	34929800
Drug resistance	101.43	14.56	86	14867	25841	34916137
Bronchopulmonary aspergillosis	98.11	14.56	67	14886	14592	34927386
Febrile neutropenia	92.82	14.56	190	14763	136659	34805319
Pathogen resistance	92.54	14.56	55	14898	9427	34932551
Fungal infection	77.41	14.56	60	14893	15875	34926103
Cardiotoxicity	74.74	14.56	40	14913	5608	34936370
Neutrophil count decreased	72.60	14.56	99	14854	51005	34890973
Parathyroid gland enlargement	71.65	14.56	16	14937	141	34941837

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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
Drug interaction	511.10	13.86	623	23235	414560	79305970
Aspergillus infection	232.84	13.86	114	23744	19047	79701483
Bronchopulmonary aspergillosis	199.61	13.86	108	23750	22186	79698344
Drug resistance	174.43	13.86	125	23733	42088	79678442
Febrile neutropenia	162.44	13.86	266	23592	230733	79489797
Pathogen resistance	161.39	13.86	81	23777	14261	79706269
Neutrophil count decreased	113.14	13.86	140	23718	93819	79626711
Cardiotoxicity	111.51	13.86	60	23798	12179	79708351
Symmetrical drug-related intertriginous and flexural exanthema	107.44	13.86	29	23829	857	79719673
Ileus paralytic	101.42	13.86	52	23806	9568	79710962

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	J02AC02	ANTIINFECTIVES FOR SYSTEMIC USE ANTIMYCOTICS FOR SYSTEMIC USE ANTIMYCOTICS FOR SYSTEMIC USE Triazole and tetrazole derivatives
CHEBI has role	CHEBI:50183	P450 inhibitors
CHEBI has role	CHEBI:77748	steroid-transporting ATPase inhibitor
CHEBI has role	CHEBI:140921	Hedgehog pathway inhibitors
FDA CS	M0002083	Azoles
FDA EPC	N0000175487	Azole Antifungal
FDA MoA	N0000182141	Cytochrome P450 3A4 Inhibitors
FDA MoA	N0000185503	P-Glycoprotein Inhibitors
FDA MoA	N0000190113	Breast Cancer Resistance Protein Inhibitors
MeSH PA	D058888	14-alpha Demethylase 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
Invasive pulmonary aspergillosis	indication	3214003
Histoplasmosis	indication	12962009	DOID:1731
Candidiasis of the esophagus	indication	20639004	DOID:13146
Fusarium infection	indication	64250002
Aspergillosis	indication	65553006	DOID:13564
Blastomycosis	indication	69996000	DOID:12663
Disseminated candidiasis	indication	70572005
Onychomycosis of fingernails	indication	403058003
Onychomycosis of toenails	indication	403059006
Candidemia	indication	432261003

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🐶 Veterinary Drug Use

Species	Use	Relation
Cats	Dermatophytosis caused by Microsporum canis	Indication

🐶 Veterinary products

Product	Applicant	Ingredients
Itrafungol	Virbac AH Inc.	1

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	5.12	Basic
pKa2	5.0	Basic
pKa3	3.04	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
200MG	ONMEL	SEBELA IRELAND LTD	N022484	April 29, 2010	DISCN	TABLET	ORAL	8486456	Oct. 3, 2028	ONYCHOMYCOSIS OF THE TOENAIL CAUSED BY TRICOPHYTON RUBRUM OR TRICHOPHYTON MENTAGROPHYTES, ONCE DAILY USE FOR 12 CONSECUTIVE WEEKS
65MG	TOLSURA	MAYNE PHARMA	N208901	Dec. 11, 2018	RX	CAPSULE	ORAL	10463740	June 21, 2033	TREATMENT OF FUNGAL INFECTIONS, INCLUDING BLASTOMYCOSIS, HISTOPLASMOSIS, AND ASPERGILLOSIS
65MG	TOLSURA	MAYNE PHARMA	N208901	Dec. 11, 2018	RX	CAPSULE	ORAL	9713642	June 21, 2033	TREATMENT OF FUNGAL INFECTIONS, INCLUDING BLASTOMYCOSIS, HISTOPLASMOSIS, AND ASPERGILLOSIS

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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
Cytochrome P450 3A4	Enzyme	P08684	CP3A4_HUMAN		IC50	6.05	DRUG MATRIX
ATP-binding cassette sub-family G member 2	Transporter	Q9UNQ0	ABCG2_HUMAN		IC50	5.70	CHEMBL
Vasopressin V2 receptor	GPCR	P30518	V2R_HUMAN		IC50	6.10	CHEMBL
Tyrosine-protein kinase Fyn	Kinase	P06241	FYN_HUMAN		IC50	5.41	DRUG MATRIX
Lanosterol 14-alpha demethylase	Enzyme	Q16850	CP51A_HUMAN		IC50	5.44	CHEMBL
C-C chemokine receptor type 4	GPCR	P51679	CCR4_HUMAN		IC50	6.70	CHEMBL
C-X-C chemokine receptor type 1	GPCR	P25024	CXCR1_HUMAN		IC50	7	CHEMBL
Beta-2 adrenergic receptor	GPCR	P07550	ADRB2_HUMAN		Ki	6.30	CHEMBL
7-alpha-hydroxycholest-4-en-3-one 12-alpha-hydroxylase	Enzyme	Q9UNU6	CP8B1_HUMAN		IC50	5.33	CHEMBL
Lanosterol 14-alpha demethylase	Enzyme		CP51_CANAL	INHIBITOR	MIC	9.25	WOMBAT-PK	CHEMBL

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External reference:

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ID	Source
1YN	PDB_CHEM_ID
003915	NDDF
11426	IUPHAR_LIGAND_ID
28031	RXNORM
304NUG5GF4	UNII
387532006	SNOMEDCT_US
4020560	VUID
4020560	VANDF
4940	MMSL
5387	INN_ID

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Itraconazole	HUMAN PRESCRIPTION DRUG LABEL	1	0378-5100	CAPSULE	100 mg	ORAL	ANDA	24 sections
itraconazole	HUMAN PRESCRIPTION DRUG LABEL	1	10147-0150	SOLUTION	10 mg	ORAL	NDA	28 sections
itraconazole	HUMAN PRESCRIPTION DRUG LABEL	1	10147-0150	SOLUTION	10 mg	ORAL	NDA	28 sections
itraconazole	HUMAN PRESCRIPTION DRUG LABEL	1	10147-1700	CAPSULE	100 mg	ORAL	NDA	30 sections
itraconazole	HUMAN PRESCRIPTION DRUG LABEL	1	10147-1700	CAPSULE	100 mg	ORAL	NDA	30 sections
Itraconazole	HUMAN PRESCRIPTION DRUG LABEL	1	13668-463	CAPSULE	100 mg	ORAL	ANDA	14 sections
Itraconazole	HUMAN PRESCRIPTION DRUG LABEL	1	13668-463	CAPSULE	100 mg	ORAL	ANDA	14 sections
Itraconazole	HUMAN PRESCRIPTION DRUG LABEL	1	13668-463	CAPSULE	100 mg	ORAL	ANDA	14 sections
Itraconazole	HUMAN PRESCRIPTION DRUG LABEL	1	13668-463	CAPSULE	100 mg	ORAL	ANDA	14 sections
Itraconazole	Human Prescription Drug Label	1	16714-743	CAPSULE, COATED PELLETS	100 mg	ORAL	ANDA	21 sections

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