CAS 908-54-3|diminazene aceturate
Introduction：Basic information about CAS 908-54-3|diminazene aceturate, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | diminazene aceturate | ||
|---|---|---|---|
| CAS Number | 908-54-3 | Molecular Weight | 515.52200 |
| Density | / | Boiling Point | 463.3ºC at 760mmHg |
| Molecular Formula | C22H29N9O6 | Melting Point | / |
| MSDS | ChineseUSA | Flash Point | 234ºC |
Names
| Name | diminazene diaceturate |
|---|---|
| Synonym | More Synonyms |
diminazene aceturate BiologicalActivity
| Description | Diminazene aceturate (Diminazene diaceturate) is an anti-trypanosome agent for livestock. The main biochemical mechanism of the trypanocidal actions of Diminazene aceturate is by binding to trypanosomal kinetoplast DNA (kDNA) in a non-intercalative manner through specific interaction with sites rich in adenine-thymine base pairs. Diminazene aceturate is also an angiotensin-converting enzyme 2 (ACE2) activator and has strong and potent anti-inflammatory properties[1][2][3]. |
|---|---|
| Related Catalog | Research Areas >>Infection |
| Target | Parasite[1][2]; Angiotensin-converting enzyme 2 (ACE2)[3] |
| In Vitro | Pre-treatment of bone marrow-derived macrophages (BMDM) and dendritic cells (BMDC) with Diminazene aceturate (Berenil) downregulats LPS-, CpG- and Poly I:C-induced proinflammatory cytokine production, suggesting that it may be affecting common pathways through which these molecules stimulate proinflammatory cytokine production. Indeed, Diminazene aceturate does not alter the expression of different TLRs (including TLR2, TLR4 and TLR9), on macrophages and DCs when assessed by flow cytometry. Instead, Diminazene aceturate dramatically downregulats the phosphorylation of MAPKs (ERK, p38 and JNK), STATs (STAT1 and STAT3) and NFκB p65 subunit, which are key signaling molecules and transcription factors involved in the production of proinflammatory cytokines[2]. |
| In Vivo | Diminazene aceturate (14 mg/kg; intraperitoneal injection; female BALB/c mice and C57BL/6 mice) treatment significantly reduces the percentages of CD25+ cells, a concomitant reduction in the percentage of regulatory (CD4+Foxp3+) T cells and a striking reduction in serum levels of disease exacerbating pro-inflammatory cytokines including IL-6, IL-12, TNF and IFN-γ[1]. Animal Model: Female BALB/c mice and C57BL/6 mice (6-8 week old) infected with T. congolense variant antigenic type TC1[1] Dosage: 14 mg/kg Administration: Intraperitoneal injection Result: Significantly reduced the percentages of CD25+ cells, a concomitant reduction in the percentage of regulatory (CD4+Foxp3+) T cells and a striking reduction in serum levels of disease exacerbating pro-inflammatory cytokines including IL-6, IL-12, TNF and IFN-γ. |
| References | [1]. Kuriakose S, et al. Diminazene aceturate (Berenil) modulates the host cellular and inflammatory responses to Trypanosoma congolense infection. PLoS One. 2012;7(11):e48696. [2]. Kuriakose S, et al. Diminazene aceturate (Berenil), a new use for an old compound? Int Immunopharmacol. 2014 Aug;21(2):342-5. [3]. Castardeli C, et al. The ACE 2 activator diminazene aceturate (DIZE) improves left ventricular diastolic dysfunction following myocardial infarction in rats. Biomed Pharmacother. 2018 Nov;107:212-218. |
Chemical & Physical Properties
| Boiling Point | 463.3ºC at 760mmHg |
|---|---|
| Molecular Formula | C22H29N9O6 |
| Molecular Weight | 515.52200 |
| Flash Point | 234ºC |
| Exact Mass | 515.22400 |
| PSA | 269.29000 |
| LogP | 3.23460 |
| InChIKey | OKQSSSVVBOUMNZ-UHFFFAOYSA-N |
| SMILES | CC(=O)NCC(=O)O.CC(=O)NCC(=O)O.N=C(N)c1ccc(N=NNc2ccc(C(=N)N)cc2)cc1 |
| Storage condition | 0-6°C |
| Stability | Stable. Incompatible with strong oxidizing agents. |
Toxicological Information
CHEMICAL IDENTIFICATION |
ACUTE TOXICITY DATA - TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 663 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 258 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Mammal - species unspecified
- DOSE/DURATION :
- 300 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 20 mg/kg/5D-I
- TOXIC EFFECTS :
- Kidney, Ureter, Bladder - other changes Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - true cholinesterase Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - dehydrogenases
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 8 gm/kg
- SEX/DURATION :
- female 8-15 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
MUTATION DATA - TYPE OF TEST :
- Micronucleus test
- TEST SYSTEM :
- Rodent - mouse Lymphocyte
- DOSE/DURATION :
- 10 umol/L
- REFERENCE :
- MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 300,165,1993
- TYPE OF TEST :
- Micronucleus test
- TEST SYSTEM :
- Rodent - mouse Lymphocyte
- DOSE/DURATION :
- 10 umol/L
- REFERENCE :
- MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 300,165,1993
Safety Information
| Personal Protective Equipment | Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter |
|---|---|
| RIDADR | NONH for all modes of transport |
| WGK Germany | 3 |
| RTECS | MB7605000 |
Articles34
More Articles| A validated and stability indicating HPLC method for analysis of diminazene aceturate and antipyrine combination in a ready injectable solution. Drug Res. (Stuttg.) 63(6) , 300-4, (2013) Diminazene aceturate and Antipyrine combination therapy is widely used in veterinary medicine. A simple reverse HPLC method for the analysis of samples of a ready injectable formulation containing a m... | |
| A sensitive and reproducible in vivo imaging mouse model for evaluation of drugs against late-stage human African trypanosomiasis. J. Antimicrob. Chemother. 70(2) , 510-7, (2015) To optimize the Trypanosoma brucei brucei GVR35 VSL-2 bioluminescent strain as an innovative drug evaluation model for late-stage human African trypanosomiasis.An IVIS® Lumina II imaging system was us... | |
| Inhibition of spermidine/spermine N1-acetyltransferase activity: a new therapeutic concept in rheumatoid arthritis. Arthritis Rheumatology 66(7) , 1723-33, (2014) Changes in polyamine-modulated factor 1 (PMF-1) promoter methylation might favor the expression of spermidine/spermine N1-acetyltransferase 1 (SSAT-1), causing excessive consumption of S-adenosyl meth... |
Synonyms
| EINECS 212-999-2 |
| MFCD00058386 |
| DIMINAZENE ACETURATE |
| Diminazene Diaceturate |
