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| CAS No.: | 738-70-5 |
|---|---|
| Name: | Trimethoprim |
| Molecular Structure: | |
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| Formula: | C14H18N4O3 |
| Molecular Weight: | 290.322 |
| Synonyms: | Bacidal;Sulthrim;Bactrim;Resprim Forte;Trimetoprim [DCIT];Deprim;5-(3,4,5-Trimethoxybenzyl)-2,4-diaminopyrimidine;Briscotrim;Salvatrim;Metoprim;Bacdan;Abaprim;Bencole;Bacticel;Trimez-IFSA;Trimethopim(TMP);Sulfamethoxazole Trimethoprim;Bethaprim;Trimexol;Sulfamethoprim;Streptoplus;Trimethoprim [USAN:BAN:INN:JAN];5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine;Tmp Smx;Trimethoprime [INN-French];NIH 204;Wellcoprin;Roubal;Trimpex (TN);Co-Trimoxizole;Trimetoprima [INN-Spanish];Syraprim;Monotrimin;Protrin;2,4-Diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine; |
| EINECS: | 212-006-2 |
| Density: | 1.252 g/cm3 |
| Melting Point: | 199-203 °C |
| Boiling Point: | 525.956 °C at 760 mmHg |
| Flash Point: | 271.889 °C |
| Solubility: | Soluble in DMSO |
| Appearance: | Odorless white powder. |
| Hazard Symbols: |
 T
|
| Risk Codes: | 25 |
| Safety: | 45 |
| Transport Information: | UN 3249 |
| PSA: | 105.51000 |
| LogP: | 2.42000 |
3-anilino-2-(3,4,5-trimethoxybenzyl)propenenitrile
guanidine nitrate
5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine
| Conditions | Yield |
|---|---|
| Stage #1: guanidine nitrate With sodium methylate at 30℃; for 0.5h; Reflux; Stage #2: 3-anilino-2-(3,4,5-trimethoxybenzyl)propenenitrile for 10h; Reflux; | 95% |
5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine
| Conditions | Yield |
|---|---|
| 90% |
2,4-dichloro-5-(3,4,5-trimethoxybenzyl)pyrimidine
5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine
| Conditions | Yield |
|---|---|
| With ammonia In methanol at 175℃; for 6h; | 85% |
| With ammonia In ethanol at 120℃; for 12h; | 83% |
6-methylsulfanyl-5-(3,4,5-trimethoxy-benzyl)-pyrimidine-2,4-diamine
5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine
| Conditions | Yield |
|---|---|
| With Raney nickel W-5 In ethanol; 2-methoxy-ethanol; water at 120℃; for 1h; | 83% |
2,4-diamino-5-(3,5-dimethoxy-4-hydroxybenzyl)pyrimidine
methyl iodide
5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine
| Conditions | Yield |
|---|---|
| With sodium methylate In dimethyl sulfoxide for 4h; Ambient temperature; | 66% |
2,4-dichloro-5-(3,4,5-trimethoxybenzyl)pyrimidine
B
5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine
| Conditions | Yield |
|---|---|
| With ammonia In ethanol at 120℃; for 8h; | A 22% B 55% |
3,4,5-trimethoxy-2'-(methoxymethyl)cinnamonitrile
sodium methylate
diguanidine carbonate
5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine
| Conditions | Yield |
|---|---|
| 1) DMSO, 70 to 75 deg C, 1.0 h, 2) DMSO, 110 deg C, 1.0 h; Yield given. Multistep reaction; |
| Conditions | Yield |
|---|---|
| With sodium ethanolate 1.) ethanol, RT, 20 min, 2.) ethanol, reflux, 12 h; Yield given. Multistep reaction; |
2,4-diamino-5-(3,4,5-trimethoxybenzyl)-6-chloropyrimidine
5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine
| Conditions | Yield |
|---|---|
| With hydrogen; acetic acid; palladium on activated charcoal In water |
3-morpholino-5-(3',4',5'-trimethoxybenzyl)acrylopyrimidine
guanidine nitrate
5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine
| Conditions | Yield |
|---|---|
| In ethanol; dimethyl sulfoxide for 18h; Heating; | |
| With dimethyl sulfoxide In ethanol |
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FOMULA: C14H18N4O3
Mol. mass: 290.32 g/mol
EINECS: 212-006-2
Index of Refraction: 1.608
Molar Refractivity: 80.25 cm3
Molar Volume: 231.8 cm3
Surface Tension: 53.9 dyne/cm
Density: 1.252 g/cm3
Flash Point: 271.9 °C
Enthalpy of Vaporization: 80.02 kJ/mol
Boiling Point: 526 °C at 760 mmHg
Vapour Pressure: 3.74E-11 mmHg at 25°C
Storage temp of Trimethoprim is 2-8°C.Trimethoprim,its melting point is about 199-203 °C;appearance is white powder|
Stability: Stable. Incompatible with strong oxidizing agents, acids
Water solubility is less than 0.1 g/100 mL at 24 oC
Product Categories: Pharmaceutical;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Peptide Synthesis/Antibiotics
2,4-Diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine (CAS NO.738-70-5) belongs to the class of chemotherapeutic agents known as dihydrofolate reductase inhibitors. It was formerly marketed by GlaxoSmithKline under trade names including Monotrim, Proloprim and Triprim.In clinical use it is often abbreviated TRI or TMP; its common laboratory abbreviation is W.
Following is the molecular structure of 2,4-Diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine (CAS NO.738-70-5):
Since 1980 in the UK,Trimethoprim was used as monotherapy,it is indicated for the prophylaxis and treatment of urinary tract infections. Co-trimoxazole, with its greater efficacy against a limited number of bacteria, remains indicated for some infections.
2,4-Diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine (CAS NO.738-70-5) is a bacteriostatic antibiotic mainly used in the prophylaxis and treatment of urinary tract infections. It was commonly used in a 1:5 combination with Sulfamethoxazole , a sulfonamide antibiotic , which inhibits an earlier step in the folate synthesis pathway.
Organism Test Type Route Reported Dose (Normalized Dose) Effect Source dog LDLo intravenous 90mg/kg (90mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION Chemotherapy Vol. 14, Pg. 37, 1969.
mouse LD50 intraperitoneal 400mg/kg (400mg/kg) Toksikologicheskii Vestnik. Vol. (2), Pg. 34, 1998. mouse LD50 intravenous 132mg/kg (132mg/kg) Journal of Chemotherapy. Vol. 5, Pg. 400, 1993.
mouse LD50 oral 2764mg/kg (2764mg/kg) United States Patent Document. Vol. #4180578, mouse LD50 subcutaneous > 5gm/kg (5000mg/kg) Chemotherapy Vol. 21, Pg. 175, 1973. rat LD50 intraperitoneal 500mg/kg (500mg/kg) Toksikologicheskii Vestnik. Vol. (2), Pg. 34, 1998. rat LD50 oral > 5300mg/kg (5300mg/kg) Toksikologicheskii Vestnik. Vol. (2), Pg. 34, 1998. rat LD50 subcutaneous > 5gm/kg (5000mg/kg) Chemotherapy Vol. 21, Pg. 175, 1973. women TDLo oral 56mg/kg/7D-I (56mg/kg) KIDNEY, URETER, AND BLADDER: HEMATURIA
BLOOD: OTHER CHANGES
MUSCULOSKELETAL: JOINTSPostgraduate Medical Journal. Vol. 68, Pg. 391, 1992. women TDLo oral 60mg/kg/10D-I (60mg/kg) BLOOD: THROMBOCYTOPENIA New Zealand Medical Journal. Vol. 106, Pg. 251, 1993.
Hazard Codes: 
T
Risk Statements: 25
R25: Toxic if swallowed
Safety Statements: 45
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: 3249
WGK Germany: 3
RTECS: UV8225000
F: 8-10-21
F 8: Photosensitive
F 10: Keep under argon
F 21: Sensitive to humidity
HazardClass: 6.1(b)
PackingGroup: III
Use of 2,4-Diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine (CAS NO.738-70-5) is contraindicated during pregnancy, especially the first trimester, and for sufferers of certain blood disorders. It is contraindicated to use trimethoprim during pregnancy, especially the first trimester, and for sufferers of certain blood disorders. 2,4-Diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine (CAS NO.738-70-5) also may be involved in a reaction similar to disulfiram when alcohol is consumed after it is used, particularly when used in combination with sulfamethoxazole .It can also reduce clearance of creatinine at renal tubules.
Tetrahydrofolic acid is an essential precursor in the de novo synthesis of the intermediate THYMIDINE monophoshpate (dTMP), precursor of DNA metabolite THYMIDINE triphosphate. 2,4-Diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine (CAS NO.738-70-5) is also called as Trimethoprim ; Bactrim ; Bactrim ; Cotrim ; SMZ/TMP ; Septra ; Sulfatrim ; 2,4-Pyrimidinediamine, 5-((3,4,5-trimethoxyphenyl)-methyl)- ; 5-((3,4,5-Trimethoxyphenyl)methyl)-2,4-pyrimidinediamine ; 5-25-13-00429 (Beilstein Handbook Reference) ; Abaprim ; Anitrim ; BRN 0625127 ; Bacidal ; Bacticel ; CCRIS 2410 ; Co-Trimoxizole ; Cotrimel ; EINECS 212-006-2 ; Espectrin ; Fortrim ; Kombinax ; Monoprim ; Pancidim ; Resprim Forte ; Sinotrim ; Sulmeprim ; Trimethoprime [INN-French] ; UNII-AN164J8Y0X ; Velaten ; component of Bactrim and so on.
