Compound: trimethoprim
SMILES: O(c1c(OC)cc(Cc2c(nc(N)nc2)N)cc1OC)C
InChIKey: IEDVJHCEMCRBQM-UHFFFAOYSA-N
Synonyms: trimethoprim, 738-70-5, Proloprim, Trimpex, 2,4-Diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine, Trimetoprim, Monotrim, Trimopan, Wellcoprim, Syraprim, Monoprim, Uretrim, Trimethoprime, Trimethoprimum, Trimetoprima, 5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine, Tiempe, Trimpex 200, NSC-106568, BW 56-72, NIH 204, Trimogal, Infectotrimet, 2,4-Pyrimidinediamine, 5-[(3,4,5-trimethoxyphenyl)methyl]-, BW-56-72, DTXSID3023712, NIH-204, 5-(3,4,5-Trimethoxybenzyl)-2,4-diaminopyrimidine, 5-[(3,4,5-Trimethoxyphenyl)methyl]-2,4-pyrimidinediamine, AN164J8Y0X, 2,4-Pyrimidinediamine, 5-((3,4,5-trimethoxyphenyl)methyl)-, CHEBI:45924, Pyrimidine, 2,4-diamino-5-(3,4,5-trimethoxybenzyl)-, 5-((3,4,5-Trimethoxyphenyl)methyl)-2,4-pyrimidinediamine, NSC106568, DTXCID803712, 5-((3,4,5-trimethoxyphenyl)methyl)pyrimidine-2,4-diamine, Ledatrim, Proloprin, Triprimix 200, RefChem:6327, J01EA01, 212-006-2, Monotrimin, Triprim, 5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine, component of Bactrim, TCMDC-125538, MFCD00036761, NSC 106568, CHEMBL22, Trimethoprim-d3 (Major), Trimpex (TN), Abaprim, BW 5672, 5-(3,4,5-Trimethoxybenzyl)-2,4-pyrimidinediamine, MLS000079023, Briscotrim, Novotrimel, Streptoplus, Sulfoxaprim, Trimethioprim, Urobactrim, Wellcoprin, Anitrim, Antrima, Antrimox, Bacidal, Bacticel, Bactoprim, Bencole, Bethaprim, Biosulten, Chemotrin, Colizole, Conprim, Cotrimel, Duocide, Esbesul, Espectrin, Euctrim, Exbesul, Fermagex, Fortrim, Ikaprim, Kombinax, Lagatrim, Lastrim, Metoprim, Pancidim, Protrin, Resprim, Salvatrim, Setprin, Sinotrim, Sugaprim, Sulfamar, Sulthrim, Sultrex, Trimexol, Trimezol, Trimono, Trisulcom, Trisulfam, Trisural, Utetrin, Velaten, Xeroprim, Zamboprim, Bacdan, Bacide, Deprim, Omstat, Purbal, Roubac, Roubal, Stopan, Toprim, Trisul, Bacin, Bacta, Futin, Co-Trimoxizole, Lagatrim Forte, Septrin Forte, Alcorim-F, Colizole DS, Septrin S, Septrin DS, Smz-Tmp, Trimez-IFSA, U-Prin, component of Septra, NCGC00016055-05, Trimethopriom, Bactifor, CAS-738-70-5, Dosulfin, Instalac, SMR000035999, Trimetoprim [DCIT], Lescot, Trimetoprim [Polish], Resprim Forte, Trimethoprim 100 microg/mL in Acetonitrile, Uro-D S, Tmp Smx, Trimethoprime [INN-French], Trimethoprimum [INN-Latin], Trimetoprima [INN-Spanish], Bacterial [Antibiotic], NIH 204 (VAN), Proloprim (TN), WR 5949, CCRIS 2410, HSDB 6781, Trimethoprim D3 (4-methoxy D3), SR-01000075652, EINECS 212-006-2, 5-(3, 4, 5-Trimethoxybenzyl)-2, 4-pyrimidinediamine, Trimethoprim & VRC3375, BRN 0625127, UNII-AN164J8Y0X, Trimethoprim (JAN/USP/INN), AI3-52594, Trimethoprim RS, Syraprim;, Trimethoprim CRS, B-Lock, KUC103659N, Trimethoprim(TMP), Prestwick_485, KSC-4-158, Trimethoprim (TMP), Bactrim (Salt/Mix), Spectrum_000167, Tocris-0650, Trimethoprim [USAN:USP:INN:BAN:JAN], 2w9h, 3fl9, 3n0h, 3s3v, 4km2, Trimethoprim (Standard), Trimethoprim D3 (4-methoxy D3) 100 microg/mL in Acetonitrile, 2,4-Pyrimidinediamine, 5-((3,4,5-trimethoxyphenyl)-methyl)-, Opera_ID_1760, Prestwick0_000208, Prestwick1_000208, Prestwick2_000208, Prestwick3_000208, Spectrum2_000937, Spectrum3_000643, Spectrum4_000372, Spectrum5_001559, Lopac-T-7883, TRIMETHOPRIM [MI], TRIMETHOPRIM [INN], TRIMETHOPRIM [JAN], Epitope ID:119684, UPCMLD-DP132, T 7883, TRIMETHOPRIM [HSDB], TRIMETHOPRIM [USAN], TRIMETHOPRIM [VANDF], Lopac0_001271, Oprea1_495058, SCHEMBL24506, BSPBio_000195, BSPBio_002245, KBioGR_000863, KBioSS_000647, TRIMETHOPRIM [MART.], 5-25-13-00429 (Beilstein Handbook Reference), MLS001201740, MLS002303068, MLS002548881, BIDD:GT0190, DivK1c_000589, SPECTRUM1500595, TRIMETHOPRIM [USP-RS], TRIMETHOPRIM [WHO-DD], SPBio_000874, SPBio_002116, BPBio1_000215, orb1309588, orb3140219, SCHEMBL28042088, SCHEMBL28636448, SCHEMBL29462189, UPCMLD-DP132:001, BDBM18069, GTPL10931, HMS501N11, HY-B0510R, KBio1_000589, KBio2_000647, KBio2_003215, KBio2_005783, KBio3_001465, MSK4009, TRIMETHOPRIM [GREEN BOOK], Trimethoprim, >=98% (HPLC), NINDS_000589, 2,4,5-trimethoxybenzyl)pyrimidine, HMS1568J17, HMS1921I03, HMS2090D14, HMS2092A10, HMS2095J17, HMS2230L06, HMS3259I11, HMS3263P04, HMS3371O18, HMS3652E03, HMS3712J17, HMS5081C18, Pharmakon1600-01500595, TRIMETHOPRIM [EP IMPURITY], TRIMETHOPRIM [ORANGE BOOK], Trimethoprim for system suitability, TRIMETHOPRIM [EP MONOGRAPH], 2,4,5-trimethoxyphenzyl)pyrimidine, ALBB-028968, COTRIM COMPONENT TRIMETHOPRIM, HY-B0510, PXB92338, SEPTRA COMPONENT TRIMETHOPRIM, Co-trimoxazole component trimethoprim, Tox21_110291, Tox21_200157, Tox21_501271, TRIMETHOPRIM [USP MONOGRAPH], BACTRIM COMPONENT TRIMETHOPRIM, BBL005584, CCG-40335, EBC-03787, MSK4009-100M, NSC752719, NSC757370, s3129, SBB080617, STK177322, STL455117, UROPLUS COMPONENT TRIMETHOPRIM, TRIMETHOPRIMUM [WHO-IP LATIN], AKOS001650069, MSK4009-1000M, SULFATRIM COMPONENT TRIMETHOPRIM, SULMEPRIM COMPONENT TRIMETHOPRIM, Tox21_110291_1, AC-8427, BW-5672, DB00440, KS-1145, LP01271, NC00483, NSC-752719, NSC-757370, SDCCGSBI-0051237.P004, BACTRIM DS COMPONENT TRIMETHOPRIM, IDI1_000589, SMP2_000262, NCGC00016055-01, NCGC00016055-02, NCGC00016055-03, NCGC00016055-04, NCGC00016055-06, NCGC00016055-07, NCGC00016055-08, NCGC00016055-09, NCGC00016055-10, NCGC00016055-11, NCGC00016055-12, NCGC00016055-13, NCGC00016055-14, NCGC00016055-16, NCGC00016055-17, NCGC00016055-27, NCGC00024707-01, NCGC00024707-03, NCGC00024707-04, NCGC00024707-05, NCGC00024707-06, NCGC00024707-07, NCGC00024707-08, NCGC00257711-01, NCGC00261956-01, COTRIM D.S. COMPONENT TRIMETHOPRIM, ST024737, SY031734, SBI-0051237.P003, DB-055812, SULFAMETHOPRIM COMPONENT TRIMETHOPRIM, 2, 5-[(3,4,5-trimethoxyphenyl)methyl]-, AB00052118, EU-0101271, NS00000211, SW196690-3, T2286, Trimethoprim 1000 microg/mL in Acetonitrile, Trimethoprim Solution in Methanol, 100ug/mL, Trimethoprim Solution in Methanol, 1000ug/mL, BACTRIM PEDIATRIC COMPONENT TRIMETHOPRIM, C01965, D00145, EN300-118703, Trimethoprim, crystallized, >=99.0% (HPLC), WLN: T6N CNJ BZ DZ E1R CO1 DO1 EO1, 5-(3,5-Trimethoxybenzyl)-2,4-diaminopyrimidine, AB00052118-30, AB00052118-32, AB00052118_33, AB00052118_34, Trimethoprim, VETRANAL(TM), analytical standard, Q422665, 2,4-diamino-5-(3,4,5-trimethoxybenzyl)-pyrimidine, Pyrimidine,4-diamino-5-(3,4,5-trimethoxybenzyl)-, SR-01000075652-1, SR-01000075652-3, SR-01000075652-6, 5-(3,4,5-Trimethoxybenzyl)-2,4-pyrimidinediamine #, BRD-K07208025-001-06-5, BRD-K07208025-001-29-7, BRD-K07208025-001-31-3, SR-01000075652-10, 2,4-Diamino-5-(3',4',5'-trimethoxybenzyl)pyrimidine, F0914-5266, Trimethoprim, certified reference material, TraceCERT(R), Z1515385071, 5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4(1H,3H)-diimine, pyrimidine, 2,4-diamino-5-(3',4',5'-trimethoxybenzyl)-, Trimethoprim, British Pharmacopoeia (BP) Reference Standard, Trimethoprim, European Pharmacopoeia (EP) Reference Standard, 5-{[3,4,5-tris(methyloxy)phenyl]methyl}pyrimidine-2,4-diamine, Trimethoprim, United States Pharmacopeia (USP) Reference Standard, Trimethoprim for system suitability, European Pharmacopoeia (EP) Reference Standard, Trimethoprim, Pharmaceutical Secondary Standard; Certified Reference Material
Theoretical properties:
molecular_formula: C14H18N4O3
molecular_weight: 290.32 g/mol
exact_mass: 290.13789045 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 7
rotatable_bond_count: 5
heavy_atom_count: 21
topological_polar_surface_area: 106 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: White to cream, crystalline powder
color: White to cream, crystalline powder
odor: Odorless
melting_point: 390 to 397 °F (NTP, 1992)
solubility: less than 1 mg/mL at 75 °F (NTP, 1992)
Descriptions:
pubchem: Trimethoprim is an aminopyrimidine antibiotic whose structure consists of pyrimidine 2,4-diamine and 1,2,3-trimethoxybenzene moieties linked by a methylene bridge. It has a role as a diuretic, a xenobiotic, an antibacterial drug, an EC 1.5.1.3 (dihydrofolate reductase) inhibitor, an environmental contaminant and a drug allergen. It is an aminopyrimidine and a member of methoxybenzenes.
chebi: An aminopyrimidine antibiotic whose structure consists of pyrimidine 2,4-diamine and 1,2,3-trimethoxybenzene moieties linked by a methylene bridge.
chembl: TRIMETHOPRIM is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Trimethoprim (TMP) is an antibiotic used mainly in the treatment of bladder infections. Other uses include for middle ear infections and travellers' diarrhoea. With sulfamethoxazole or dapsone it may be used for Pneumocystis pneumonia in people with HIV/AIDS. It is taken orally (swallowed by mouth).
Common side effects include nausea, changes in taste, and rash. Rarely it may result in blood problems such as not enough platelets or white blood cells. Trimethoprim may cause sun sensitivity. There is evidence of potential harm during pregnancy in some animals but not humans. It works by blocking folate metabolism via dihydrofolate reductase in some bacteria, preventing creation of bacterial DNA and RNA and leading to bacterial cell death.
Trimethoprim was first used in 1962. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication.