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

Stem definition	Drug id	CAS RN
	258	95233-18-4

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: 566C80 atovaquone mepron	A hydroxynaphthoquinone that has antimicrobial activity and is being used in antimalarial protocols. Molecular weight: 366.84 Formula: C22H19ClO3 CLOGP: 6.03 LIPINSKI: 1 HAC: 3 HDO: 1 TPSA: 54.37 ALOGS: -5.66 ROTB: 2 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

566C80
atovaquone
mepron

A hydroxynaphthoquinone that has antimicrobial activity and is being used in antimalarial protocols.

Molecular weight: 366.84
Formula: C22H19ClO3
CLOGP: 6.03
LIPINSKI: 1
HAC: 3
HDO: 1
TPSA: 54.37
ALOGS: -5.66
ROTB: 2

Status: OFP

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

Drug dosage:

Dose	Unit	Route
2.25	g	O

ADMET properties:

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Property	Value	Reference
t_half (Half-life)	63 hours	Lombardo F, Berellini G, Obach RS
MRTD (Maximum Recommended Therapeutic Daily Dose)	58.41 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BDDCS (Biopharmaceutical Drug Disposition Classification System)	4	Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine)	3 %	Benet LZ, Broccatelli F, Oprea TI
BA (Bioavailability)	23 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution)	0.60 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	0.15 mL/min/kg	Lombardo F, Berellini G, Obach RS
S (Water solubility)	0.00 mg/mL	Bocci G, Oprea TI, Benet LZ
fu (Fraction unbound in plasma)	0.00 %	Lombardo F, Berellini G, Obach RS

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Approvals:

Date	Agency	Company	Orphan
Nov. 25, 1992	FDA

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
Malaria	83.09	17.33	15	6257	205	63482545
Pyrexia	68.39	17.33	146	6126	470332	63012418
Pancytopenia	58.05	17.33	59	6213	96874	63385876
Babesiosis	57.09	17.33	11	6261	218	63482532
Cerebellar stroke	54.34	17.33	11	6261	283	63482467
Rash maculo-papular	50.10	17.33	34	6238	31862	63450888
Encephalopathy	46.47	17.33	35	6237	38585	63444165
Cytokine release syndrome	42.60	17.33	23	6249	14291	63468459
Stevens-Johnson syndrome	42.56	17.33	28	6244	24922	63457828
Agranulocytosis	39.96	17.33	27	6245	25107	63457643

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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
Nocardiosis	158.89	16.80	53	8742	3898	34944238
Malacoplakia	114.82	16.80	26	8769	436	34947700
Immune reconstitution inflammatory syndrome	108.43	16.80	50	8745	8709	34939427
Pancytopenia	70.13	16.80	102	8693	95055	34853081
Pneumocystis jirovecii pneumonia	66.03	16.80	48	8747	19662	34928474
Malaria	63.34	16.80	14	8781	209	34947927
Pyrexia	63.06	16.80	205	8590	332808	34615328
Thrombocytopenia	61.68	16.80	127	8668	156120	34792016
Neutropenia	61.38	16.80	127	8668	156651	34791485
Mucormycosis	52.66	16.80	27	8768	5915	34942221

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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
Nocardiosis	198.31	15.34	62	13244	5617	79725465
Malacoplakia	117.16	15.34	26	13280	610	79730472
Pancytopenia	116.82	15.34	141	13165	165604	79565478
Pyrexia	107.83	15.34	301	13005	678408	79052674
Immune reconstitution inflammatory syndrome	100.03	15.34	48	13258	13793	79717289
Malaria	98.74	15.34	21	13285	401	79730681
Neutropenia	98.67	15.34	174	13132	287536	79443546
Thrombocytopenia	89.09	15.34	159	13147	265100	79465982
Cytokine release syndrome	81.91	15.34	59	13247	35939	79695143
Babesiosis	78.90	15.34	17	13289	346	79730736

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	P01AX06	ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS ANTIPROTOZOALS AGENTS AGAINST AMOEBIASIS AND OTHER PROTOZOAL DISEASES Other agents against amoebiasis and other protozoal diseases
ATC	P01BB51	ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS ANTIPROTOZOALS ANTIMALARIALS Biguanides
CHEBI has role	CHEBI:35718	antifungal agents
CHEBI has role	CHEBI:38068	antimalarials
CHEBI has role	CHEBI:38503	NADH-coenzyme Q oxidoreductase inhibitors
CHEBI has role	CHEBI:77103	DHODH inhibitor
CHEBI has role	CHEBI:77106	inhibitor of quinol--cytochrome-c reductase (EC 1.10.2.2)
FDA EPC	N0000175482	Antimalarial
FDA EPC	N0000175485	Antiprotozoal
MeSH PA	D000890	Anti-Infective Agents

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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
Falciparum malaria	indication	62676009	DOID:14067
Pneumocystosis jiroveci pneumonia	indication	415125002	DOID:11339
Chloroquine-Resistant Plasmodium Falciparum Malaria Prevention	indication
Plasmodium Falciparum Malaria Prevention	indication
Pneumocystis Carinii Pneumonia Prevention	indication
Babesiosis	off-label use	21061004	DOID:9643
Vivax malaria	off-label use	27052006	DOID:12978
Toxoplasmosis	off-label use	187192000	DOID:9965
Toxoplasmosis associated with acquired immunodeficiency syndrome	off-label use	421666009
Toxoplasmosis Prevention	off-label use

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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	5.18	acidic

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
ATP-binding cassette sub-family G member 2	Transporter	Q9UNQ0	ABCG2_HUMAN		IC50	6.64	CHEMBL
Dihydroorotate dehydrogenase (quinone), mitochondrial	Enzyme	Q02127	PYRD_HUMAN		IC50	5.03	WOMBAT-PK
Cytochrome b	Enzyme		CYB_PLAFA	INHIBITOR			CHEMBL	CHEMBL
Ubiquinol-cytochrome-c reductase complex core protein I, mitochondrial	Enzyme		QCR1_EUGGR				WOMBAT-PK
Dihydroorotate dehydrogenase (quinone), mitochondrial	Enzyme		PYRD_RAT		IC50	6.15	CHEMBL
Dihydroorotate dehydrogenase	Enzyme		Q54A96_PLAFA		Ki	4.57	CHEMBL
Dihydroorotate dehydrogenase	Enzyme		G4VFD7_SCHMA		IC50	6.37	CHEMBL

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External reference:

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ID	Source
AOQ	PDB_CHEM_ID
004112	NDDF
108718008	SNOMEDCT_US
114972	RXNORM
1907	MMSL
213467	MMSL
386899002	SNOMEDCT_US
4020594	VUID
4020594	VANDF
4227	MMSL

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Atovaquone	HUMAN PRESCRIPTION DRUG LABEL	1	0121-0888	SUSPENSION	750 mg	ORAL	ANDA	29 sections
Atovaquone	HUMAN PRESCRIPTION DRUG LABEL	1	0121-0888	SUSPENSION	750 mg	ORAL	ANDA	29 sections
Atovaquone	HUMAN PRESCRIPTION DRUG LABEL	1	0121-0898	SUSPENSION	750 mg	ORAL	ANDA	29 sections
Atovaquone	HUMAN PRESCRIPTION DRUG LABEL	1	0121-0898	SUSPENSION	750 mg	ORAL	ANDA	29 sections
Atovaquone	HUMAN PRESCRIPTION DRUG LABEL	1	0121-1796	SUSPENSION	1500 mg	ORAL	ANDA	29 sections
Atovaquone	HUMAN PRESCRIPTION DRUG LABEL	1	0121-1796	SUSPENSION	1500 mg	ORAL	ANDA	29 sections
Atovaquone	HUMAN PRESCRIPTION DRUG LABEL	1	0904-7064	SUSPENSION	750 mg	ORAL	ANDA	24 sections
atovaquone	HUMAN PRESCRIPTION DRUG LABEL	1	16714-900	SUSPENSION	750 mg	ORAL	ANDA	25 sections
Atovaquone	Human Prescription Drug Label	1	31722-629	SUSPENSION	750 mg	ORAL	ANDA	24 sections
Atovaquone and Proguanil Hydrochloride	HUMAN PRESCRIPTION DRUG LABEL	2	0378-4160	TABLET, FILM COATED	62.50 mg	ORAL	ANDA	27 sections

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