Metioprim

Modify Date: 2025-08-25 19:21:34

Metioprim Structure
Metioprim structure
Common Name Metioprim
CAS Number 68902-57-8 Molecular Weight 306.38300
Density 1.31g/cm3 Boiling Point 563.3ºC at 760 mmHg
Molecular Formula C14H18N4O2S Melting Point N/A
MSDS N/A Flash Point 294.5ºC

 Use of Metioprim


Metioprim is a competitive inhibitor of bacterial Dihydrofolate reductase (DHFR). Metioprim has inhibitory activity against anaerobic bacteria. Metioprim shows synergistic activity in combination with DDS (HY-B0688) against E. coli. and various mycobacteria[1][2].

 Names

Name 5-[(3,5-dimethoxy-4-methylsulfanylphenyl)methyl]pyrimidine-2,4-diamine
Synonym More Synonyms

 Metioprim Biological Activity

Description Metioprim is a competitive inhibitor of bacterial Dihydrofolate reductase (DHFR). Metioprim has inhibitory activity against anaerobic bacteria. Metioprim shows synergistic activity in combination with DDS (HY-B0688) against E. coli. and various mycobacteria[1][2].
Related Catalog
In Vitro Metioprim 对部分厌氧菌有抑制作用,平均 MIC 值为 3.2 μg/mL[1]。 Metioprim (0-1.0 μM;0-8 h) 抑制细菌生长动力学,抑制大肠杆菌的 MIC 值为 0.7 μg/mL[2]。
In Vivo Metioprim (5 mg/kg or 10 mg/kg; 静脉注射; 单剂量) 在羊中的消除半衰期比猪的短 (23 min vs 169 min),它的主要代谢产物为蛋氨酸亚砜和甲氧磷磺酸[3]。 药代动力学分析[1] Animal Route Dose (mg/kg) C0 (μg/mL) A (μg/mL) α (1/min) t1/2α (min) B (μg/mL) β (1/min) t1/2β (min) VC (1/kg) Vp (1/kg) Vd,ss (1/kg) Clβ (mL/min/kg) Pigs i.v. 5 3.6 2.1 0.032 25 1.5 0.00415 169 1.45 0.74 2.19 10.0 Goats i.v. 10 12.2 6.4 0.220 4 5.6 0.03138 23 0.85 0.44 1.28 49
References

[1]. Wüst J, et al. Activity of brodimoprim and metioprim alone and in combination with sulfonamides against anaerobic bacteria. Antimicrob Agents Chemother. 1983 Mar;23(3):490-2.  

[2]. Seydel JK, et al. Bacterial growth kinetics of Escherichia coli and mycobacteria in the presence of brodimoprim and metioprim alone and in combination with sulfamerazine and dapsone (VI). Chemotherapy. 1983;29(4):249-61.  

[3]. Nielsen P, et al. Pharmacokinetics and metabolism of metioprim in pigs and goats. Pharmacol Toxicol. 1987 Nov;61(5):330-4.  

 Chemical & Physical Properties

Density 1.31g/cm3
Boiling Point 563.3ºC at 760 mmHg
Molecular Formula C14H18N4O2S
Molecular Weight 306.38300
Flash Point 294.5ºC
Exact Mass 306.11500
PSA 123.04000
LogP 1.83110
Index of Refraction 1.642
InChIKey HRZQMMXCASMDBP-UHFFFAOYSA-N
SMILES COc1cc(Cc2cnc(N)nc2N)cc(OC)c1SC

 Synonyms

Metioprim
He 909
Ro 12-6995
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