Trimethoprim Sulfate
Basic information
- CAS
56585-33-2- Standard SMILES
COc1cc(Cc2cnc(N)nc2N)cc(OC)c1OC.COc1cc(Cc2cnc(N)nc2N)cc(OC)c1OC.O=S(=O)(O)O- InChIKey
UILMMYFRNCCPLK-UHFFFAOYSA-N- Molecular formula
- C28H38N8O10S
- Average molar mass
- 678.7 g/mol
- Monoisotopic mass
- 678.24316061
Overview
Trimethoprim Sulfate is the sulfate salt form of trimethoprim, a synthetic substituted pyrimidine with antibacterial activity. Trimethoprim sulfate selectively binds to and reversibly inhibits dihydrofolate reductase, thereby blocking the production of tetrahydrofolic acid from dihydrofolic acid. This leads to an inhibition of bacterial synthesis of folic acid, thereby affecting nucleic acid and protein synthesis. Trimethoprim sulfate has a stronger binding affinity for the bacterial enzyme than for the corresponding mammalian enzyme.
Names & identifiers
- Preferred name
- Trimethoprim Sulfate
- IUPAC
- sulfuric acid;bis(5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine)
- English name
- Trimethoprim sulfate
- Molecular formula
- C14H20N4O7S
- Molecular weight
- 388.4
Names & synonyms
Trimethoprim sulfateBW 72UTrimethoprim sulphateE377MF8EQ8Trimethoprim sulfate [USAN]BW-72UTRIMETHOPRIM SULFATE [VANDF]TRIMETHOPRIM SULFATE [MART.]TRIMETHOPRIM SULFATE [WHO-DD]TRIMETHOPRIM SULFATE [ORANGE BOOK]2,4-Diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine sulfate (2:1)TRIMETHOPRIM SULFATE [USP MONOGRAPH]
Show more names
TRIMETHOPRIM SULFATE (MART.)TRIMETHOPRIM SULFATE (USP MONOGRAPH)RefChem:89972156585-33-2Trimethoprim sulfate [USAN:USP]sulfuric acid;5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamineUNII-E377MF8EQ8Trimethoprim sulfate (USP)
Database identifiers
- CAS
56585-33-2- PubChem CID
- 64936
- DTXSID
DTXSID40205138- ChEMBL
CHEMBL2110367- UNII
- E377MF8EQ8
Properties
Computed structural properties
- Topological polar surface area
- 294 Ų
- Hydrogen bond donors
- 6
- Hydrogen bond acceptors
- 18
- Rotatable bonds
- 10
- Heavy atoms
- 47
- Formal charge
- 0
- Complexity
- 388
Experimental & physicochemical properties
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physicochemical properties
- FDA UNII
- 377 MF8EQ8 · E377MF8EQ8
Chemistry & industry
Applications
UsesAntibacterial.
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Related reactions
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Compound notes
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