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[ CAS No. 67-20-9 ] {[proInfo.proName]}

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Chemical Structure| 67-20-9
Chemical Structure| 67-20-9
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Product Citations

Product Citations

Boyao Zhang ; George-Eugen Maftei ; Bartosz Bartmanski , et al. DOI:

Abstract: Organic carcinogens, in particular DNA-reactive compounds, contribute to the irreversible initiation step of tumorigenesis through introduction of genomic instability. Although carcinogen bioactivation and detoxification by human enzymes has been extensively studied, carcinogen biotransformation by human-associated bacteria, the microbiota, has not yet been systematically investigated. We tested the biotransformation of 68 mutagenic carcinogens by 34 bacterial species representative for the upper and lower human gastrointestinal tract and found that the majority (41) of the tested carcinogens undergo bacterial biotransformation. To assess the functional consequences of microbial carcinogen metabolism, we developed a pipeline to couple gut bacterial carcinogen biotransformation assays with Ames mutagenicity testing and liver biotransformation experiments. This revealed a bidirectional crosstalk between gut microbiota and host carcinogen metabolism, which we validated in gnotobiotic mouse models. Overall, the systematic assessment of gut microbiota carcinogen biotransformation and its interplay with host metabolism highlights the gut microbiome as an important modulator of exposome-induced tumorigenesis.

Purchased from AmBeed: ; ; ; ; ; 117-39-5 ; ; ; ; 62-44-2 ; ; ; ; ; ; ; ; ; ; ; 101-61-1 ; ; ; ; ; ; 90-94-8 ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ;

Product Details of [ 67-20-9 ]

CAS No. :67-20-9 MDL No. :MFCD00003224
Formula : C8H6N4O5 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 238.16 Pubchem ID :-
Synonyms :
NSC 2107;Macrodantin;Nitrofurantoin, Macrobid, Macrodantin, 5-Nitrofurantoin, Furadantine, Furadonine;NSC 44150;Furadonine;Furadantine
Chemical Name :1-(((5-Nitrofuran-2-yl)methylene)amino)imidazolidine-2,4-dione

Calculated chemistry of [ 67-20-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.12
Num. rotatable bonds : 3
Num. H-bond acceptors : 6.0
Num. H-bond donors : 1.0
Molar Refractivity : 62.8
TPSA : 120.73 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -8.09 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.14
Log Po/w (XLOGP3) : -0.47
Log Po/w (WLOGP) : -0.69
Log Po/w (MLOGP) : -1.09
Log Po/w (SILICOS-IT) : -1.6
Consensus Log Po/w : -0.74

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.04
Solubility : 21.7 mg/ml ; 0.0912 mol/l
Class : Very soluble
Log S (Ali) : -1.6
Solubility : 6.0 mg/ml ; 0.0252 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.09
Solubility : 19.4 mg/ml ; 0.0817 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 4.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.1

Safety of [ 67-20-9 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P260-P264-P270-P272-P280-P285-P314-P330-P333+P313-P301+P312-P302+P352-P304+P341-P342+P311-P363-P403-P501 UN#:2811
Hazard Statements:H302-H317-H334 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 67-20-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 67-20-9 ]

[ 67-20-9 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 6301-02-6 ]
  • [ 92-55-7 ]
  • [ 67-20-9 ]
  • 2
  • [ 92-55-7 ]
  • [ 2827-56-7 ]
  • [ 67-20-9 ]
YieldReaction ConditionsOperation in experiment
Ca. 70% Add 90kg of aminohydantoin hydrochloride, 590kg of water and 66L of acetic acid in a 1000L reaction pot.Mechanical stirring was started, and ice water was cooled to a temperature below 20 C, and 106 L of concentrated sulfuric acid was slowly added thereto, and the dropwise addition was completed in about 1.5 hours.After stirring for 30 to 60 minutes, 160 kg of 5-Nitro-2-furaldehyde diacetate was gradually added, and finally 97 wt% of ethanol 118 L was added.The steam was heated to an internal temperature of 90 C.The reaction was kept warm and stirred for 3 hours, and the reaction solution became cloudy. Two gradients are cooled down to an internal temperature of 5 to 10 CSpecifically, in the present embodiment, first, the purified water is cooled to an internal temperature of 50 C, and then cooled to an internal temperature of 5 to 10 C with ice water.Gradually more yellow solids precipitated.The mash was filtered, and the filter cake was washed with a large amount of purified water in a near neutral state (pH = 6 to 7), and then washed with 95% by weight of ethanol.The crude product was placed in an oven and dried at 70 to 80 C for 3 hours.A yellow crystalline powder, i.e., 1-[[(5-nitro-2-furyl)methylene]amino]-2,4-imidazolidinedione, was obtained. Specifically, in the present embodiment, 1-[[(5-nitro-2-furyl)methylene]amino]-2,4-imidazolidinedione and N,N-dimethylformamide,The charge ratio of purified water and 95% by weight of ethanol is: 1-[[(5-nitro-2-furyl)methylene]amino]-2,4-imidazolidinedione (kg):N,N-dimethylformamide (L): purified water (L): 95% by weight of ethanol (L) = 1: 1.1: 2.2: 1.1.The above feed ratio of N,N-dimethylformamide was added to a 500 L reaction vessel, and 1-[[(5-nitro-2-furanyl)methylene]amino]-2,4-imidazolidine was added. The diketone was stirred at room temperature (23 C) for 40 minutes.Open compressed air for pressure filtration. The material was hydraulically poured into a crystallizing pot, stirred, and purified water was added dropwise to precipitate a yellow solid.Stirring was maintained for 30 minutes.The mash is filtered to obtain a filter cake.The filter cake was washed with a large amount of purified water, and then washed with three times or four times with 95 wt% of ethanol, and dried to obtain a cake.The filter cake was placed in an oven and dried at 70 to 80 C for 3 hours to obtain a yellow crystalline powder, that is, the target product nitrofurantoin.In the present embodiment, the total yield of the nitrofurantoin is about 70%.
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[ 67-20-9 ]

Chemical Structure| 1516934-90-9

A987331[ 1516934-90-9 ]

1-(((5-Nitrofuran-2-yl)methylene)amino-15N)imidazolidine-2,4-dione-2-13C-1,3-15N2

Reason: Stable Isotope

; ;