Scroll

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

Stem definition	Drug id	CAS RN
	2332	58-14-0

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: pyrimethamine chloridin chloridine diaminopyritamin pirimecidan pirimetamin pyrimethamin	One of the FOLIC ACID ANTAGONISTS that is used as an antimalarial or with a sulfonamide to treat toxoplasmosis. Molecular weight: 248.71 Formula: C12H13ClN4 CLOGP: 3 LIPINSKI: 0 HAC: 4 HDO: 2 TPSA: 77.82 ALOGS: -3.14 ROTB: 2 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

pyrimethamine
chloridin
chloridine
diaminopyritamin
pirimecidan
pirimetamin
pyrimethamin

One of the FOLIC ACID ANTAGONISTS that is used as an antimalarial or with a sulfonamide to treat toxoplasmosis.

Molecular weight: 248.71
Formula: C12H13ClN4
CLOGP: 3
LIPINSKI: 0
HAC: 4
HDO: 2
TPSA: 77.82
ALOGS: -3.14
ROTB: 2

Status: OFP

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

Drug dosage:

Dose	Unit	Route
75	mg	O
75	mg	O
75	mg	P

ADMET properties:

Show entries

Search:

Property	Value	Reference
BA (Bioavailability)	90 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
EoM (Fraction excreted unchanged in urine)	65 %	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	5.03 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
t_half (Half-life)	140 hours	Lombardo F, Berellini G, Obach RS
BDDCS (Biopharmaceutical Drug Disposition Classification System)	1	Bocci G, Oprea TI, Benet LZ
Vd (Volume of distribution)	0.43 L/kg	Lombardo F, Berellini G, Obach RS
S (Water solubility)	0.18 mg/mL	Bocci G, Oprea TI, Benet LZ
fu (Fraction unbound in plasma)	0.10 %	Lombardo F, Berellini G, Obach RS
CL (Clearance)	0.05 mL/min/kg	Lombardo F, Berellini G, Obach RS

Showing 1 to 9 of 9 entries

Previous1Next

Approvals:

Date	Agency	Company	Orphan
Jan. 23, 1953	FDA	AMEDRA PHARMS

FDA Adverse Event Reporting System (Female)

Show entries

Search:

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
Pancytopenia	93.62	37.10	40	942	96893	63391147
Drug reaction with eosinophilia and systemic symptoms	84.34	37.10	28	954	33808	63454232
Cerebral toxoplasmosis	55.01	37.10	10	972	968	63487072
Bone marrow failure	48.89	37.10	18	964	29272	63458768
Hepatocellular injury	42.66	37.10	16	966	27365	63460675
Neutropenia	38.11	37.10	27	955	174978	63313062

Showing 1 to 6 of 6 entries

Previous1Next

FDA Adverse Event Reporting System (Male)

Show entries

Search:

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
Pancytopenia	61.04	36.65	41	1347	95116	34860427
Enterocutaneous fistula	45.02	36.65	10	1378	1025	34954518
Immune reconstitution inflammatory syndrome	41.89	36.65	15	1373	8744	34946799
Urinary tract inflammation	41.39	36.65	7	1381	169	34955374
Neuropsychiatric symptoms	40.80	36.65	9	1379	893	34954650
Myopia	38.74	36.65	9	1379	1127	34954416

Showing 1 to 6 of 6 entries

Previous1Next

FDA Adverse Event Reporting System (Geriatric)

Show entries

Search:

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
Pancytopenia	137.12	33.40	74	2144	165671	79576499
Drug reaction with eosinophilia and systemic symptoms	80.26	33.40	38	2180	64206	79677964
Cerebral toxoplasmosis	66.58	33.40	15	2203	2347	79739823
Bone marrow failure	63.09	33.40	30	2188	51077	79691093
Neutropenia	53.76	33.40	52	2166	287658	79454512
Hepatocellular injury	49.91	33.40	25	2193	47568	79694602
Immune reconstitution inflammatory syndrome	47.84	33.40	17	2201	13824	79728346
Mycobacterial infection	45.34	33.40	12	2206	3656	79738514
Enterocutaneous fistula	42.19	33.40	10	2208	1951	79740219
Urinary tract inflammation	41.15	33.40	7	2211	253	79741917

Showing 1 to 10 of 16 entries

Previous1 2Next

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

Show entries

Search:

Source	Code	Description
ATC	P01BD01	ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS ANTIPROTOZOALS ANTIMALARIALS Diaminopyrimidines
ATC	P01BD51	ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS ANTIPROTOZOALS ANTIMALARIALS Diaminopyrimidines
ATC	P01BF04	ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS ANTIPROTOZOALS ANTIMALARIALS Artemisinin and derivatives, combinations
ATC	P01BF09	ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS ANTIPROTOZOALS ANTIMALARIALS Artemisinin and derivatives, combinations
CHEBI has role	CHEBI:35820	antiprotozoal drugs
CHEBI has role	CHEBI:38068	antimalarials
CHEBI has role	CHEBI:50683	dihydrofolic acid reductase inhibitors
FDA EPC	N0000175934	Dihydrofolate Reductase Inhibitor Antimalarial
FDA MoA	N0000000191	Dihydrofolate Reductase Inhibitors
MeSH PA	D000890	Anti-Infective Agents

Showing 1 to 10 of 15 entries

Previous1 2Next

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

Show entries

Search:

Disease	Relation	SNOMED_ID	DOID
Malaria	indication	61462000	DOID:12365
Toxoplasmosis	indication	187192000	DOID:9965
Toxoplasmosis associated with acquired immunodeficiency syndrome	indication	421666009
Chloroquine-Resistant Plasmodium Falciparum Malaria Prevention	indication
Chloroquine Resistant Plasmodium Falciparum Malaria	indication
Encephalitis due to Toxoplasmosis	indication
Toxoplasmosis Prevention	off-label use
Pneumocystis Carinii Pneumonia Prevention	off-label use
Third trimester pregnancy	contraindication	41587001
Acute nephropathy	contraindication	58574008

Showing 1 to 10 of 22 entries

Previous1 2 3Next

🐶 Veterinary Drug Use

Species	Use	Relation
Horses	Myeloencephalitis (EPM) caused by Sarcocystis neurona	Indication

🐶 Veterinary products

Product	Applicant	Ingredients
ReBalance	Pegasus Laboratories Inc.	2

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	6.94	Basic
pKa2	0.6	Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

Show entries

Search:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Dihydrofolate reductase	Enzyme	P00374	DYR_HUMAN		Ki	8.10	CHEMBL
Cytochrome P450 2C9	Enzyme	P11712	CP2C9_HUMAN		Ki	4.29	WOMBAT-PK
Solute carrier family 22 member 1	Transporter	O15245	S22A1_HUMAN		IC50	4.87	CHEMBL
Multidrug and toxin extrusion protein 1	Transporter	Q96FL8	S47A1_HUMAN	INHIBITOR	Ki	7.10	IUPHAR
Beta-hexosaminidase subunit alpha	Enzyme	P06865	HEXA_HUMAN		IC50	5.51	CHEMBL
Beta-hexosaminidase subunit beta	Enzyme	P07686	HEXB_HUMAN		IC50	5.35	CHEMBL
Muscarinic acetylcholine receptor M1	GPCR	P11229	ACM1_HUMAN		Ki	8.72	PDSP
Bifunctional dihydrofolate reductase-thymidylate synthase	Enzyme		DRTS_PLAFK	INHIBITOR	Ki	9.72	CHEMBL	CHEMBL
Bifunctional dihydrofolate reductase-thymidylate synthase	Enzyme		DRTS_TOXGO		IC50	6.41	WOMBAT-PK
Dihydrofolate reductase	Enzyme		DYR_PNECA		Ki	8.01	CHEMBL

Showing 1 to 10 of 23 entries

Previous1 2 3Next

External reference:

Show entries

Search:

ID	Source
CP6	PDB_CHEM_ID
002948	NDDF
2215	INN_ID
373769001	SNOMEDCT_US
4017802	VUID
4017802	VANDF
4800	IUPHAR_LIGAND_ID
4993	PUBCHEM_CID
5396	MMSL
59589008	SNOMEDCT_US

Showing 1 to 10 of 21 entries

Previous1 2 3Next

Pharmaceutical products:

Show entries

Search:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Daraprim	HUMAN PRESCRIPTION DRUG LABEL	1	69413-330	TABLET	25 mg	ORAL	NDA	23 sections
Pyrimethamine	HUMAN PRESCRIPTION DRUG LABEL	1	0480-3720	TABLET	25 mg	ORAL	ANDA	18 sections
Pyrimethamine	HUMAN PRESCRIPTION DRUG LABEL	1	43598-672	TABLET	25 mg	ORAL	ANDA	24 sections
Pyrimethamine	HUMAN PRESCRIPTION DRUG LABEL	1	43598-672	TABLET	25 mg	ORAL	ANDA	24 sections
pyrimethamine	HUMAN PRESCRIPTION DRUG LABEL	1	47781-925	TABLET	25 mg	ORAL	ANDA	22 sections
pyrimethamine	HUMAN PRESCRIPTION DRUG LABEL	1	47781-925	TABLET	25 mg	ORAL	ANDA	22 sections
Pyrimethamine	HUMAN PRESCRIPTION DRUG LABEL	1	48102-026	TABLET	25 mg	ORAL	ANDA	23 sections
Pyrimethamine	Human Prescription Drug Label	1	59651-590	TABLET	25 mg	ORAL	ANDA	22 sections
Pyrimethamine	HUMAN PRESCRIPTION DRUG LABEL	1	72647-330	TABLET	25 mg	ORAL	NDA authorized generic	23 sections
Pyrimethamine Leucovorin	HUMAN PRESCRIPTION DRUG LABEL	2	70260-426	CAPSULE	25 mg	ORAL	unapproved drug other	1 sections

Showing 1 to 10 of 21 entries

Previous1 2 3Next