(E)-Nitrofurazone

Absorption, Distribution and Excretion
Well absorbed.
ABOUT 1% OF (14)C WAS RECOVERED FROM URINE, FECES & BILE AS UNCHANGED 5-NITRO-2-FURALDEHYDE SEMICARBAZONE, SUGGESTING SUBSTANTIAL METABOLISM OF THIS SUBSTANCE IN RAT /AFTER ORAL DOSAGE OF 100 MG/KG/.
RATS DOSED WITH 100 MG/KG 5-NITRO-2-FURALDEHYDE SEMICARBAZONE- [FORMYL-(14)C] ... EXCRETED ABOUT 66%, 35% & 1% OF ACTIVITY IN URINE, FECES & IN RESPIRED AIR AS CO2, RESPECTIVELY, WITHIN 96 HR, & MAJORITY OF (14)C ACTIVITY WAS ELIMINATED WITHIN 48 HR. RECOVERY OF (14)C IN BILE WAS ABOUT 27% AFTER 48 HR.
IN RATS DOSED WITH 100 MG/KG, PLASMA LEVELS OF 4.5 MG/L ... WERE FOUND AFTER 4 HR, 34% OF WHICH WAS BOUND TO PROTEINS. RATS DOSED WITH 200 MG/KG ... EXCRETED ABOUT 4.6% IN URINE & 0.5% IN FECES WITHIN 48 HR. ORALLY ADMIN 5-NITRO-2-FURALDEHYDE SEMICARBAZONE WAS DETECTED IN CEREBROSPINAL FLUID OF DOGS WITHIN 2 HR.

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Metabolism / Metabolites
Nitrofurans, including nitrofural, undergo metabolic reduction at the nitro group to generate reactive species which can covalently bind to cellular macromolecules (Polnaszek et al., 1984; Kutcher & McCalla, 1984; McCalla 1979; McCalla et al., 1975).
/NITROFURAZONE HAS/ BEEN SHOWN TO BE REDUCED BY ENZYMES & PREPN FROM MAMMALIAN LIVER. ... ISOLATION OF A HYDROXYLAMINE INTERMEDIATE IS NOT UNCOMMON IN IN VITRO STUDIES.
The disposition of the antibiotic nitrofurazone was studied in the singlepass isolated perfused rat liver. Both the effects of the steady state level of drug and the composition of the perfusate were evaluated. The higher level (120 ug/ml) of nitrofurazone in a perfusion medium lacking the glutathione precursors, glycine, glutamic acid and cysteine, caused a marked increase in bile flow (from 1.01 + or - 0.07 to 2.33 + or - 1.07 ul/min/g), massiv biliary efflux of glutathione disulfide (from 0.55 + or - 0.07 to 60.6 + or - 25.4 nmol/min/g) and a sharp decline in the caval efflux of glutathione (to undetectable levels) and the tissue level of glutathione (from 5.74 + or - 0.20 to 2.68 + or - 0.13 umol/g). Even after the drug was discontinued, these parameters were not restored to control levels. The lower level (30 ug/ml) of nitrofurazone with or without amino acid supplementatio and the higher level with supplementation induced less dramatic effects. Using (35)S methionine, a new conjugated metabolite of nitrofurazone and glutathione was detected. The data suggest that the toxicity of the reactive oxygen species generated by the redox cycling of the nitro group and the reactive metabolites generated by further reduction of nitrofurazone can be mitigated by adequate glutathione levels, but that livers lacking sufficient glutathione to scavenge these reactive species may be damaged.
Nitrofurans, including nitrofural, undergo metabolic reduction at the nitro group to generate reactive species which can covalently bind to cellular macromolecules.
Half Life: 5 hours

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Biological Half-Life
5 hours

Toxicity Summary
The exact mechanism of action is unknown. Nitrofurazone inhibits several bacterial enzymes, especially those involved in the aerobic and anaerobic degradation of glucose and pyruvate. This activity is believed also to affect pyruvate dehydrogenase, citrate synthetase, malate dehydrogenase, glutathione reductase, and pyruvate decarboxylase.

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Toxicity Data
Rat LD₅₀ = 590 mg/kg

[1]. A new FTIR-based technique in the polymorphic analysis of Nitrofural[J]. Journal of Molecular Structure, 2021, 1233: 130098.

[2]. Nitrofural (nitrofurazone). IARC Monogr Eval Carcinog Risks Hum. 1990;50:195-209. PMID: 2292799; PMCID: PMC7681543.

Nitrofurazone can cause cancer according to The Environmental Protection Agency (EPA).
Nitrofurazone appears as odorless pale yellow needles or yellow powder. pH (saturated aqueous solution) 6.0 - 6.5. Alkaline solutions are dark orange. (NTP, 1992)
Nitrofurazone is a semicarbazone resulting from the formal condensation of semicarbazide with 5-nitrofuraldehyde. A broad spectrum antibacterial drug, although with little activity against Pseudomonas species, it is used as a local application for burns, ulcers, wounds and skin infections. It has a role as an antibacterial drug. It is a semicarbazone and a nitrofuran antibiotic.
Nitrofural or nitrofurazone is a topical anti-infective agent effective against gram-negative and gram-positive bacteria. It is used for superficial wounds, burns, ulcers, and skin infections. Nitrofural has also been administered orally in the treatment of trypanosomiasis. Except for topical drug products formulated for dermatologic application, the FDA withdrew its approval for the use of drug products containing nitrofurazone.
A topical anti-infective agent effective against gram-negative and gram-positive bacteria. It is used for superficial wounds, burns, ulcers, and skin infections. Nitrofurazone has also been administered orally in the treatment of trypanosomiasis.
A topical anti-infective agent effective against gram-negative and gram-positive bacteria. It is used for superficial WOUNDS AND INJURIES and skin infections. Nitrofurazone has also been administered orally in the treatment of TRYPANOSOMIASIS.
See also: Butacaine Sulfate; Nitrofurazone (component of) ... View More ...

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Drug Indication
For the treatment of bacterial skin infections including pyodermas, infected dermatoses and infections of cuts, wounds, burns and ulcers due to susceptible organisms.

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Mechanism of Action
The exact mechanism of action is unknown. Nitrofurazone inhibits several bacterial enzymes, especially those involved in the aerobic and anaerobic degradation of glucose and pyruvate. This activity is believed also to affect pyruvate dehydrogenase, citrate synthetase, malate dehydrogenase, glutathione reductase, and pyruvate decarboxylase.
MECHANISM OF ANTIBACTERIAL ACTION OF FURAN DERIV IS UNKNOWN, BUT IT IS PRESUMED THAT THE COMPD INTERFERES WITH ENZYMATIC PROCESSES ESSENTIAL TO BACTERIAL GROWTH. /FURAN DERIV/
The exact mechanism of action of nitrofurazone is not known. It appears, howeverthat the drug acts by inhibiting bacterial enzymes involved in carbohydrage metabolism. Oragnic matter (eg, blood pus, serum) and aminobenzoic acid (p-aminobenzoic acid) inhibit the antibacterial action of nitrofurazone.

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Therapeutic Uses
Anti-Infective Agents, Local; Anti-Infective Agents, Urinary; Trypanocidal Agents
/NITROFURAZONE/ IS BACTERICIDAL FOR MANY GRAM POSITIVE & GRAM NEGATIVE ORGANISMS PRESENT IN SURFACE INFECTIONS ... IT HAS BEEN USED TOPICALLY TO TREAT INFECTIONS OF SKIN & MUCOUS MEMBRANES.
NITROFURAZONE MAY BE TRIED IN ... /LATE-STAGE TRYPANOSOMIASIS/ WITH SOME CHANCE OF SUCCESS. SINGLE COURSE OF TREATMENT ... AT 6 HR INTERVALS FOR 1 WK. 3 COURSES MAY BE GIVEN WITH A WEEK'S REST BETWEEN EACH.
IT FINDS USE, ESP, IN TREATMENT OF 2ND & 3RD DEGREE BURNS & IN SKIN GRAFTING IN WHICH THERE ARE COMPLICATIONS FROM BACTERIAL INFECTIONS THAT ARE REFRACTORY TO USUAL DRUGS OF CHOICE BUT IN WHICH SENSITIVITY TO NITROFURAZONE IS DEMONSTRABLE. ... NITROFURAZONE IS USED IN MGMNT OF SUSCEPTIBLE INFECTIONS OF EYE, EAR, NOSE, URETHRA & VAGINA. ... /IT/ RETAINS ITS ANTIBACTERIAL ACTIVITY IN BLOOD, SERUM & PUS; PHAGOCYTOSIS IS NOT INHIBITED & NITROFURAZONE DOES NOT INTERFERE WITH HEALING.
For more Therapeutic Uses (Complete) data for NITROFURAZONE (14 total), please visit the HSDB record page.

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Drug Warnings
... /TREATMENT AS IN LATE-STAGE TRYPANOSOMIASIS/ IS UNSUITABLE FOR FEBRILE OR DEBILITATED PATIENTS. ... IT PRODUCES HEMOLYTIC ANEMIA IN PATIENTS WITH GLUCOSE-6-PHOSPHATE DEHYDROGENASE DEFICIENCY.
WHEN USED TOPICALLY IN EAR ... /NITROFURAZONE/ MAY PRODUCE CUTANEOUS SENSITIVITY REACTIONS. ... THIS TYPE OF REACTION ... FREQUENTLY MIMICS DISEASE BEING TREATED. ... /THIS DRUG REACTION/ CAN USUALLY BE RECOGNIZED BECAUSE THE INFLAMMATORY PROCESS BEGINS TO SPREAD TO LOBULE OF EAR & INFECTION DOES NOT RESPOND TO TREATMENT.
... STRAINS OF PSEUDOMONAS & PROTEUS ARE OFTEN RESISTANT.
IT HAS NOT YET BEEN SHOWN TO BE USEFUL IN TREATMENT OF MINOR BURNS, WOUNDS, OR CUTANEOUS ULCERS WHICH ARE INFECTED. IT IS PROBABLY NOT EFFECTIVE IN TREATMENT OF PYODERMA. ... APPROX 0.5-2% OF PATIENTS BECOME SENSITIZED TO DRUG, SOMETIMES WITHIN 5 DAYS OF INITIATION OF TREATMENT. ... FOR ALL NITROFURAZONE DOSAGE FORMS, AVOID EXPOSURE AT ALL TIMES TO DIRECT SUNLIGHT, EXCESSIVE HEAT & ALKALINE MATERIALS.
For more Drug Warnings (Complete) data for NITROFURAZONE (8 total), please visit the HSDB record page.

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Pharmacodynamics
Nitrofurazone is a topical antibacterial agent indicated as an adjunctive therapy for second and third degree burns when resistance to other agents is a real or potential problem. Nitrofurazone is also indicated in skin grafting when bacterial contamination may cause graft rejection or donor site infection, especially in hospitals with a history of resistant bacteria.

C6H6N4O4

198.14

198.039

112574-44-4

5447130

PALE YELLOW NEEDLES
LEMON-YELLOW CRYSTALLINE POWDER

457 to 464 °F (decomposes) (NTP, 1992)

1.617

127.43

2

5

2

14

261

0

C1=C(OC(=C1)[N+](=O)[O-])/C=N/NC(=O)N

IAIWVQXQOWNYOU-FPYGCLRLSA-N

InChI=1S/C6H6N4O4/c7-6(11)9-8-3-4-1-2-5(14-4)10(12)13/h1-3H,(H3,7,9,11)/b8-3+

[(E)-(5-nitrofuran-2-yl)methylideneamino]urea

(E)-Nitrofural

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples

注意: 如下所列的是一些常用的体内动物实验溶解配方，主要用于溶解难溶或不溶于水的产品（水溶度<1 mg/mL）。 建议您先取少量样品进行尝试，如该配方可行，再根据实验需求增加样品量。

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注射用配方1: DMSO : Tween 80： Saline = 10 : 5 : 85 (如： 100 μL DMSO → 50 μL Tween 80 → 850 μL Saline)
*生理盐水/Saline的制备：将0.9g氯化钠/NaCl溶解在100 mL ddH ₂ O中，得到澄清溶液。
注射用配方 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (如： 100 μL DMSO → 400 μL PEG300 → 50 μL Tween 80 → 450 μL Saline)
注射用配方 3: DMSO : Corn oil = 10 : 90 (如： 100 μL DMSO → 900 μL Corn oil)
示例: 以注射用配方 3 (DMSO : Corn oil = 10 : 90) 为例说明, 如果要配制 1 mL 2.5 mg/mL的工作液, 您可以取 100 μL 25 mg/mL 澄清的 DMSO 储备液，加到 900 μL Corn oil/玉米油中, 混合均匀。

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注射用配方 4: DMSO : 20% SBE-β-CD in Saline = 10 : 90 [如：100 μL DMSO → 900 μL (20% SBE-β-CD in Saline)]
*20% SBE-β-CD in Saline的制备（4°C，储存1周）：将2g SBE-β-CD (磺丁基-β-环糊精) 溶解于10mL生理盐水中，得到澄清溶液。
注射用配方 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (如： 500 μL 2-Hydroxypropyl-β-cyclodextrin (羟丙基环胡精)→ 500 μL Saline)
注射用配方 6: DMSO : PEG300 : Castor oil : Saline = 5 : 10 : 20 : 65 (如： 50 μL DMSO → 100 μL PEG300 → 200 μL Castor oil → 650 μL Saline)
注射用配方 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (如： 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline)
注射用配方 8: 溶解于Cremophor/Ethanol (50 : 50), 然后用生理盐水稀释。
注射用配方 9: EtOH : Corn oil = 10 : 90 (如： 100 μL EtOH → 900 μL Corn oil)
注射用配方 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (如： 100 μL EtOH → 400 μL PEG300 → 50 μL Tween 80 → 450 μL Saline)

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口服配方 1: 悬浮于0.5% CMC Na (羧甲基纤维素钠)
口服配方 2: 悬浮于0.5% Carboxymethyl cellulose (羧甲基纤维素)
示例: 以口服配方 1 (悬浮于 0.5% CMC Na)为例说明, 如果要配制 100 mL 2.5 mg/mL 的工作液, 您可以先取0.5g CMC Na并将其溶解于100mL ddH2O中，得到0.5%CMC-Na澄清溶液；然后将250 mg待测化合物加到100 mL前述 0.5%CMC Na溶液中，得到悬浮液。

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口服配方 3: 溶解于 PEG400 (聚乙二醇400)
口服配方 4: 悬浮于0.2% Carboxymethyl cellulose (羧甲基纤维素)
口服配方 5: 溶解于0.25% Tween 80 and 0.5% Carboxymethyl cellulose (羧甲基纤维素)
口服配方 6: 做成粉末与食物混合

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注意: 以上为较为常见方法，仅供参考， InvivoChem并未独立验证这些配方的准确性。具体溶剂的选择首先应参照文献已报道溶解方法、配方或剂型，对于某些尚未有文献报道溶解方法的化合物，需通过前期实验来确定（建议先取少量样品进行尝试），包括产品的溶解情况、梯度设置、动物的耐受性等。

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请根据您的实验动物和给药方式选择适当的溶解配方/方案：
1、请先配制澄清的储备液(如：用DMSO配置50 或 100 mg/mL母液(储备液));
2、取适量母液，按从左到右的顺序依次添加助溶剂，澄清后再加入下一助溶剂。以 下列配方为例说明 (注意此配方只用于说明，并不一定代表此产品 的实际溶解配方):
10% DMSO → 40% PEG300 → 5% Tween-80 → 45% ddH2O (或 saline);
假设最终工作液的体积为 1 mL, 浓度为5 mg/mL: 取 100 μL 50 mg/mL 的澄清 DMSO 储备液加到 400 μL PEG300 中，混合均匀/澄清；向上述体系中加入50 μL Tween-80，混合均匀/澄清；然后继续加入450 μL ddH2O (或 saline)定容至 1 mL；
3、溶剂前显示的百分比是指该溶剂在最终溶液/工作液中的体积所占比例;
4、 如产品在配制过程中出现沉淀/析出，可通过加热(≤50℃)或超声的方式助溶;
5、为保证最佳实验结果，工作液请现配现用！
6、如不确定怎么将母液配置成体内动物实验的工作液，请查看说明书或联系我们;
7、 以上所有助溶剂都可在 Invivochem.cn网站购买。