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

Stem definition	Drug id	CAS RN
antimicrobials, dihydrofolate reductase (DHFR) inhibitors, trimethoprim analogues	2755	738-70-5

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: trimethoprim trimethoprim sulfate trimethoprim hydrochloride trimethioprim trimetoprim trimopan trimethoprim HCl	A pyrimidine inhibitor of dihydrofolate reductase, it is an antibacterial related to PYRIMETHAMINE. It is potentiated by SULFONAMIDES and the TRIMETHOPRIM, SULFAMETHOXAZOLE DRUG COMBINATION is the form most often used. It is sometimes used alone as an antimalarial. TRIMETHOPRIM RESISTANCE has been reported. Molecular weight: 290.32 Formula: C14H18N4O3 CLOGP: 1.08 LIPINSKI: 0 HAC: 7 HDO: 2 TPSA: 105.51 ALOGS: -2.67 ROTB: 5 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

trimethoprim
trimethoprim sulfate
trimethoprim hydrochloride
trimethioprim
trimetoprim
trimopan
trimethoprim HCl

A pyrimidine inhibitor of dihydrofolate reductase, it is an antibacterial related to PYRIMETHAMINE. It is potentiated by SULFONAMIDES and the TRIMETHOPRIM, SULFAMETHOXAZOLE DRUG COMBINATION is the form most often used. It is sometimes used alone as an antimalarial. TRIMETHOPRIM RESISTANCE has been reported.

Molecular weight: 290.32
Formula: C14H18N4O3
CLOGP: 1.08
LIPINSKI: 0
HAC: 7
HDO: 2
TPSA: 105.51
ALOGS: -2.67
ROTB: 5

Status: OFP

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

Drug dosage:

Dose	Unit	Route
0.40	g	O
0.40	g	P

ADMET properties:

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Property	Value	Reference
BA (Bioavailability)	98 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
t_half (Half-life)	9.60 hours	Lombardo F, Berellini G, Obach RS
EoM (Fraction excreted unchanged in urine)	70 %	Benet LZ, Broccatelli F, Oprea TI
BDDCS (Biopharmaceutical Drug Disposition Classification System)	3	Benet LZ, Broccatelli F, Oprea TI
CL (Clearance)	2.10 mL/min/kg	Lombardo F, Berellini G, Obach RS
MRTD (Maximum Recommended Therapeutic Daily Dose)	15.75 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution)	1.50 L/kg	Lombardo F, Berellini G, Obach RS
S (Water solubility)	1.37 mg/mL	Benet LZ, Broccatelli F, Oprea TI
fu (Fraction unbound in plasma)	0.50 %	Lombardo F, Berellini G, Obach RS

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Approvals:

Date	Agency	Company	Orphan
July 30, 1973	FDA	MUTUAL PHARM

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
Soft tissue disorder	178.45	10.84	81	49266	4341	63435334
Acute kidney injury	160.23	10.84	509	48838	262906	63176769
Drug ineffective	122.82	10.84	411	48936	1044354	62395321
Liver function test abnormal	121.79	10.84	168	49179	48013	63391662
Swelling face	119.80	10.84	193	49154	63282	63376393
Pre-engraftment immune reaction	102.78	10.84	26	49321	212	63439463
Leukopenia	98.42	10.84	198	49149	77092	63362583
Pneumonia viral	96.75	10.84	66	49281	7856	63431819
Hyperkalaemia	94.45	10.84	159	49188	54044	63385631
Pancytopenia	93.46	10.84	222	49125	96711	63342964

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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
Off label use	178.29	11.27	118	37687	419406	34499720
Hyperkalaemia	159.03	11.27	276	37529	69113	34850013
Drug ineffective	156.23	11.27	159	37646	456592	34462534
Pyrexia	154.26	11.27	739	37066	332274	34586852
Acute kidney injury	126.30	11.27	656	37149	304332	34614794
Neutropenia	110.14	11.27	396	37409	156382	34762744
Death	95.25	11.27	179	37626	397870	34521256
Blood creatinine increased	92.10	11.27	268	37537	94708	34824418
Pancytopenia	87.02	11.27	263	37542	94894	34824232
Drug abuse	86.98	11.27	5	37800	99091	34820035

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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
Acute kidney injury	246.16	10.31	1009	69558	518395	79155426
Hyperkalaemia	235.13	10.31	388	70179	114010	79559811
Drug ineffective	177.54	10.31	439	70128	1080474	78593347
Pyrexia	145.44	10.31	1062	69505	677647	78996174
Pre-engraftment immune reaction	141.25	10.31	37	70530	304	79673517
Off label use	139.87	10.31	380	70187	906835	78766986
Completed suicide	136.52	10.31	26	70541	245741	79428080
Stevens-Johnson syndrome	130.38	10.31	167	70400	38999	79634822
Pancytopenia	113.87	10.31	364	70203	165381	79508440
Product dose omission issue	111.26	10.31	40	70527	247497	79426324

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	J01EA01	ANTIINFECTIVES FOR SYSTEMIC USE ANTIBACTERIALS FOR SYSTEMIC USE SULFONAMIDES AND TRIMETHOPRIM Trimethoprim and derivatives
ATC	J01EE01	ANTIINFECTIVES FOR SYSTEMIC USE ANTIBACTERIALS FOR SYSTEMIC USE SULFONAMIDES AND TRIMETHOPRIM Combinations of sulfonamides and trimethoprim, incl. derivatives
ATC	J01EE02	ANTIINFECTIVES FOR SYSTEMIC USE ANTIBACTERIALS FOR SYSTEMIC USE SULFONAMIDES AND TRIMETHOPRIM Combinations of sulfonamides and trimethoprim, incl. derivatives
ATC	J01EE03	ANTIINFECTIVES FOR SYSTEMIC USE ANTIBACTERIALS FOR SYSTEMIC USE SULFONAMIDES AND TRIMETHOPRIM Combinations of sulfonamides and trimethoprim, incl. derivatives
ATC	J01EE04	ANTIINFECTIVES FOR SYSTEMIC USE ANTIBACTERIALS FOR SYSTEMIC USE SULFONAMIDES AND TRIMETHOPRIM Combinations of sulfonamides and trimethoprim, incl. derivatives
ATC	J01EE05	ANTIINFECTIVES FOR SYSTEMIC USE ANTIBACTERIALS FOR SYSTEMIC USE SULFONAMIDES AND TRIMETHOPRIM Combinations of sulfonamides and trimethoprim, incl. derivatives
ATC	J01EE07	ANTIINFECTIVES FOR SYSTEMIC USE ANTIBACTERIALS FOR SYSTEMIC USE SULFONAMIDES AND TRIMETHOPRIM Combinations of sulfonamides and trimethoprim, incl. derivatives
ATC	J04AM08	ANTIINFECTIVES FOR SYSTEMIC USE ANTIMYCOBACTERIALS DRUGS FOR TREATMENT OF TUBERCULOSIS Combinations of drugs for treatment of tuberculosis
CHEBI has role	CHEBI:35498	diuretics
CHEBI has role	CHEBI:35703	Xenobiotic

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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
Acute otitis media	indication	3110003
Haemophilus Influenzae Acute Otitis Media	indication	19021002
Shigellosis	indication	36188001
Klebsiella cystitis	indication	60867007
Urinary tract infectious disease	indication	68566005
Blepharoconjunctivitis	indication	68659002	DOID:2456
Bacterial conjunctivitis	indication	128350005	DOID:9700
Escherichia coli urinary tract infection	indication	301011002
Proteus urinary tract infection	indication	301012009
Bacterial urinary infection	indication	312124009

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🐶 Veterinary Drug Use

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Species	Use	Relation
Dogs	Systemic antibacterial action against sensitive organisms to surgery	Indication
Dogs	Systemic antibacterial action against sensitive organisms to debridement	Indication
Dogs	Control of bacterial infection during the treatment of acute urinary tract infections	Indication
Dogs	Control of bacterial infection during the treatment of acute bacterial complications of distemper	Indication
Dogs	Control of bacterial infection during the treatment of acute respiratory tract infections	Indication
Dogs	Control of bacterial infection during the treatment of acute alimentary tract infections	Indication
Dogs	Control of bacterial infection during the treatment of wound infections	Indication
Dogs	Control of bacterial infection during the treatment of abscesses	Indication
Horses	Systemic antibacterial action against sensitive organisms during treatment of acute strangles	Indication
Horses	Systemic antibacterial action against sensitive organisms during treatment of respiratory tract infections	Indication

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🐶 Veterinary products

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Product	Applicant	Ingredients
Di-Trim 24%	Zoetis Inc.	2
Di-Trim 400 Paste	Zoetis Inc.	2
Di-Trim 48% Injection	Zoetis Inc.	2
Di-Trim Tablets	Zoetis Inc.	2
EQUISUL-SDT	Aurora Pharmaceutical Inc.	2
Tribrissen 120 Tablets, Tribrissen 30 Tablets, Tribrissen 480 Tablets, Tribrissen 960 Tablets	Intervet Inc.	2
Tribrissen 24% Injection	Intervet Inc.	2
Tribrissen 400 Oral Paste	Intervet Inc.	2
Tribrissen 48% Injection	Intervet Inc.	2
Tribrissen 60 Oral Suspension	Intervet Inc.	2

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Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	7.01	Basic
pKa2	0.6	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
Dihydrofolate reductase	Enzyme	P00374	DYR_HUMAN		Ki	8	CHEMBL
Solute carrier family 22 member 1	Transporter	O15245	S22A1_HUMAN		IC50	4.25	CHEMBL
Dihydrofolate reductase	Enzyme		DYR_ECOLI	INHIBITOR	IC50	5.57	CHEMBL	CHEMBL
Bifunctional dihydrofolate reductase-thymidylate synthase	Enzyme		DRTS_TOXGO		IC50	8.14	CHEMBL
Dihydrofolate reductase	Enzyme		DYR_PNECA		Ki	6.82	CHEMBL
Bifunctional dihydrofolate reductase-thymidylate synthase	Enzyme		DRTS_PLABA		IC50	6.92	CHEMBL
Bifunctional dihydrofolate reductase-thymidylate synthase	Enzyme		DRTS_PLAFK		Ki	7.99	CHEMBL
Dihydrofolate reductase	Enzyme		DYR_MOUSE		Ki	6.30	CHEMBL
Dihydrofolate reductase	Enzyme		DYR_RAT		Ki	4.84	CHEMBL
Dihydrofolate reductase	Enzyme		DYR_LACCA		Ki	6.88	CHEMBL

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External reference:

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ID	Source
TOP	PDB_CHEM_ID
002873	NDDF
008281	NDDF
1047	INN_ID
10829	RXNORM
10931	IUPHAR_LIGAND_ID
3055	MMSL
32792001	SNOMEDCT_US
387179001	SNOMEDCT_US
4017735	VUID

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Polytrim	HUMAN PRESCRIPTION DRUG LABEL	2	0023-7824	SOLUTION/ DROPS	1 mg	OPHTHALMIC	NDA	19 sections
Polytrim	HUMAN PRESCRIPTION DRUG LABEL	2	0023-7824	SOLUTION/ DROPS	1 mg	OPHTHALMIC	NDA	19 sections
Sulfamethoxazole and Trimethoprim	HUMAN PRESCRIPTION DRUG LABEL	2	0121-0853	SUSPENSION	40 mg	ORAL	NDA	28 sections
Sulfamethoxazole and Trimethoprim	HUMAN PRESCRIPTION DRUG LABEL	2	0121-4793	SUSPENSION	40 mg	ORAL	ANDA	28 sections
Sulfamethoxazole and Trimethoprim	HUMAN PRESCRIPTION DRUG LABEL	2	0440-2406	TABLET	160 mg	ORAL	ANDA	13 sections
Sulfamethoxazole and Trimethoprim	HUMAN PRESCRIPTION DRUG LABEL	2	0527-5180	SUSPENSION	40 mg	ORAL	ANDA	21 sections
Sulfamethoxazole and Trimethoprim	HUMAN PRESCRIPTION DRUG LABEL	2	0527-5180	SUSPENSION	40 mg	ORAL	ANDA	21 sections
Sulfamethoxazole and Trimethoprim	HUMAN PRESCRIPTION DRUG LABEL	2	0527-5181	SUSPENSION	40 mg	ORAL	ANDA	21 sections
Sulfamethoxazole and Trimethoprim	HUMAN PRESCRIPTION DRUG LABEL	2	0527-5181	SUSPENSION	40 mg	ORAL	ANDA	21 sections
Sulfamethoxazole and Trimethoprim	HUMAN PRESCRIPTION DRUG LABEL	2	0615-8121	TABLET	160 mg	ORAL	ANDA	26 sections

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