| Record Information |
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| Version | 5.0 |
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| Status | Expected but not Quantified |
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| Creation Date | 2013-05-17 01:02:10 UTC |
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| Update Date | 2019-07-23 07:14:19 UTC |
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| HMDB ID | HMDB0060428 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Acetylhydrazine |
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| Description | The acetylhydrazine metabolite was found to be much less cytotoxic than hydrazine in this hepatocyte inflammation model. (PMID: 18295292 ) In the pathogenesis of isoniazid-induced hepatic injury, cytochrome P450-dependent metabolic activation of the metabolite, acetylhydrazine (AcHz), is the crucial step. (PMID: 8852701 ) The mechanism of action of acetylphosphabenzide is likely to involve the formation of acetylhydrazine, capable of producing active electrophiles attacking DNA. (PMID: 9589859 ) |
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| Structure | InChI=1S/C2H6N2O/c1-2(5)4-3/h3H2,1H3,(H,4,5) |
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| Synonyms | | Value | Source |
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| Acethydrazide | ChEBI | | Acetic acid hydrazide | ChEBI | | Acetic hydrazide | ChEBI | | Acetyl hydrazide | ChEBI | | Ethanehydrazonic acid | ChEBI | | Monoacetyl hydrazine | ChEBI | | Monoacetylhydrazine | ChEBI | | N-Acetylhydrazine | ChEBI | | Acetate hydrazide | Generator | | Ethanehydrazonate | Generator | | Acethydrazine | HMDB | | Acetylhydrazine monohydrochloride | HMDB | | Acetylhydrazide | HMDB | | Acetylhydrazine, (e)-2-fumarate (1:1) | HMDB | | Acetylhydrazine | ChEBI |
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| Chemical Formula | C2H6N2O |
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| Average Molecular Weight | 74.0818 |
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| Monoisotopic Molecular Weight | 74.048012824 |
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| IUPAC Name | acetohydrazide |
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| Traditional Name | acetohydrazide |
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| CAS Registry Number | Not Available |
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| SMILES | CC(O)=NN |
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| InChI Identifier | InChI=1S/C2H6N2O/c1-2(5)4-3/h3H2,1H3,(H,4,5) |
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| InChI Key | OFLXLNCGODUUOT-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as acetamides. These are organic compounds with the general formula RNHC(=O)CH3, where R= organyl group. |
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| Kingdom | Organic compounds |
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| Super Class | Organic acids and derivatives |
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| Class | Carboxylic acids and derivatives |
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| Sub Class | Carboxylic acid derivatives |
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| Direct Parent | Acetamides |
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| Alternative Parents | |
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| Substituents | - Acetamide
- Carboxylic acid hydrazide
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Carbonyl group
- Aliphatic acyclic compound
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Physiological effect | Not Available |
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| Disposition | |
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| Process | Not Available |
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| Role | Not Available |
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| Physical Properties |
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| State | Not Available |
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| Experimental Molecular Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Experimental Chromatographic Properties | Not Available |
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| Predicted Molecular Properties | |
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| Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Retention Times Underivatized| Chromatographic Method | Retention Time | Reference |
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| Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022. | 0.52 minutes | 32390414 | | Predicted by Siyang on May 30, 2022 | 8.3142 minutes | 33406817 | | Predicted by Siyang using ReTip algorithm on June 8, 2022 | 4.23 minutes | 32390414 | | Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid | 619.0 seconds | 40023050 | | Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid | 341.0 seconds | 40023050 | | Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid | 83.5 seconds | 40023050 | | Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid | 244.7 seconds | 40023050 | | RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 75.8 seconds | 40023050 | | Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid | 257.8 seconds | 40023050 | | BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid | 258.3 seconds | 40023050 | | HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate) | 534.9 seconds | 40023050 | | UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid | 550.5 seconds | 40023050 | | BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid | 53.5 seconds | 40023050 | | UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid | 609.7 seconds | 40023050 | | SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 209.0 seconds | 40023050 | | RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 263.6 seconds | 40023050 | | MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate | 580.4 seconds | 40023050 | | KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA | 374.7 seconds | 40023050 | | Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water | 235.8 seconds | 40023050 |
Predicted Kovats Retention IndicesUnderivatizedDerivatized| Derivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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| Acetylhydrazine,1TMS,isomer #1 | CC(=NN)O[Si](C)(C)C | 1013.8 | Semi standard non polar | 33892256 | | Acetylhydrazine,1TMS,isomer #2 | CC(O)=NN[Si](C)(C)C | 1217.2 | Semi standard non polar | 33892256 | | Acetylhydrazine,2TMS,isomer #1 | CC(=NN[Si](C)(C)C)O[Si](C)(C)C | 1172.6 | Semi standard non polar | 33892256 | | Acetylhydrazine,2TMS,isomer #1 | CC(=NN[Si](C)(C)C)O[Si](C)(C)C | 1135.2 | Standard non polar | 33892256 | | Acetylhydrazine,2TMS,isomer #1 | CC(=NN[Si](C)(C)C)O[Si](C)(C)C | 1424.0 | Standard polar | 33892256 | | Acetylhydrazine,2TMS,isomer #2 | CC(O)=NN([Si](C)(C)C)[Si](C)(C)C | 1384.2 | Semi standard non polar | 33892256 | | Acetylhydrazine,2TMS,isomer #2 | CC(O)=NN([Si](C)(C)C)[Si](C)(C)C | 1129.9 | Standard non polar | 33892256 | | Acetylhydrazine,2TMS,isomer #2 | CC(O)=NN([Si](C)(C)C)[Si](C)(C)C | 1558.4 | Standard polar | 33892256 | | Acetylhydrazine,3TMS,isomer #1 | CC(=NN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C | 1321.0 | Semi standard non polar | 33892256 | | Acetylhydrazine,3TMS,isomer #1 | CC(=NN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C | 1227.6 | Standard non polar | 33892256 | | Acetylhydrazine,3TMS,isomer #1 | CC(=NN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C | 1351.6 | Standard polar | 33892256 | | Acetylhydrazine,1TBDMS,isomer #1 | CC(=NN)O[Si](C)(C)C(C)(C)C | 1206.5 | Semi standard non polar | 33892256 | | Acetylhydrazine,1TBDMS,isomer #2 | CC(O)=NN[Si](C)(C)C(C)(C)C | 1375.2 | Semi standard non polar | 33892256 | | Acetylhydrazine,2TBDMS,isomer #1 | CC(=NN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 1555.5 | Semi standard non polar | 33892256 | | Acetylhydrazine,2TBDMS,isomer #1 | CC(=NN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 1513.9 | Standard non polar | 33892256 | | Acetylhydrazine,2TBDMS,isomer #1 | CC(=NN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 1592.5 | Standard polar | 33892256 | | Acetylhydrazine,2TBDMS,isomer #2 | CC(O)=NN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 1636.5 | Semi standard non polar | 33892256 | | Acetylhydrazine,2TBDMS,isomer #2 | CC(O)=NN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 1540.7 | Standard non polar | 33892256 | | Acetylhydrazine,2TBDMS,isomer #2 | CC(O)=NN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 1674.5 | Standard polar | 33892256 | | Acetylhydrazine,3TBDMS,isomer #1 | CC(=NN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 1893.5 | Semi standard non polar | 33892256 | | Acetylhydrazine,3TBDMS,isomer #1 | CC(=NN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 1832.8 | Standard non polar | 33892256 | | Acetylhydrazine,3TBDMS,isomer #1 | CC(=NN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 1705.4 | Standard polar | 33892256 |
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| GC-MS Spectra| Spectrum Type | Description | Splash Key | Deposition Date | Source | View |
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| Predicted GC-MS | Predicted GC-MS Spectrum - Acetylhydrazine GC-MS (Non-derivatized) - 70eV, Positive | splash10-001l-9000000000-c0c6a35bac1462ff7d95 | 2017-09-20 | Wishart Lab | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - Acetylhydrazine GC-MS (1 TMS) - 70eV, Positive | splash10-00gi-9300000000-e17deff9b9942fd000e9 | 2017-10-06 | Wishart Lab | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - Acetylhydrazine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS Spectra| Spectrum Type | Description | Splash Key | Deposition Date | Source | View |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Acetylhydrazine 10V, Positive-QTOF | splash10-004i-9000000000-cf2f4be4db94a1740dc1 | 2017-10-06 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Acetylhydrazine 20V, Positive-QTOF | splash10-056r-9000000000-e240ca6a723c0fe333ef | 2017-10-06 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Acetylhydrazine 40V, Positive-QTOF | splash10-066u-9000000000-252f13e42ab532c8fb3a | 2017-10-06 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Acetylhydrazine 10V, Negative-QTOF | splash10-00di-9000000000-62fb398f4ac53e9a12dd | 2017-10-06 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Acetylhydrazine 20V, Negative-QTOF | splash10-05fr-9000000000-5bb4307ab62748b28a21 | 2017-10-06 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Acetylhydrazine 40V, Negative-QTOF | splash10-0a4i-9000000000-716ce61fe4c7b1100d2f | 2017-10-06 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Acetylhydrazine 10V, Positive-QTOF | splash10-004i-9000000000-83c14c6a559e41e3fc4a | 2021-10-12 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Acetylhydrazine 20V, Positive-QTOF | splash10-0a7i-9000000000-2ff9a771cebd96ee8310 | 2021-10-12 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Acetylhydrazine 40V, Positive-QTOF | splash10-0a4i-9000000000-03118a48b6476710028b | 2021-10-12 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Acetylhydrazine 10V, Negative-QTOF | splash10-00di-9000000000-87753cf4baa848fb8803 | 2021-10-12 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Acetylhydrazine 20V, Negative-QTOF | splash10-00dl-9000000000-2fa51eccd4ca4be2742b | 2021-10-12 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Acetylhydrazine 40V, Negative-QTOF | splash10-0006-9000000000-c6e9b14dd1c3f7143a15 | 2021-10-12 | Wishart Lab | View Spectrum |
NMR Spectra| Spectrum Type | Description | Deposition Date | Source | View |
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| Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum |
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| General References | - Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
- Morike K, Koch M, Fritz P, Urban W, Eichelbaum M: Identification of N2 as a metabolite of acetylhydrazine in the rat. Arch Toxicol. 1996;70(5):300-5. [PubMed:8852701 ]
- Jenner PJ, Ellard GA: Isoniazid-related hepatotoxicity: a study of the effect of rifampicin administration on the metabolism of acetylisoniazid in man. Tubercle. 1989 Jun;70(2):93-101. [PubMed:2617692 ]
- Tafazoli S, Mashregi M, O'Brien PJ: Role of hydrazine in isoniazid-induced hepatotoxicity in a hepatocyte inflammation model. Toxicol Appl Pharmacol. 2008 May 15;229(1):94-101. doi: 10.1016/j.taap.2008.01.002. Epub 2008 Jan 17. [PubMed:18295292 ]
- Il'inskaia ON, Ivanchenko OB, Trubnikova GG, Valimukhametova DA, Tarasova RI, Bagautdinova DB: [Genotoxic effects of metabolic derivatives of the new drug phosphabenzide]. Genetika. 1998 Feb;34(2):308-12. [PubMed:9589859 ]
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