5-(Aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoic acid 2-(2-呋喃甲基)氨基-5-(磺酰氨基)-4-氯苯甲酸
CAS 54-31-9 MFCD00010549
化学结构图
SMILES: NS(=O)(=O)C1C=C(C(O)=O)C(=CC=1Cl)NCC1=CC=CO1
化学属性
| Mol. Formula | C12H11ClN2O5S |
|---|---|
| Mol. Weight | 330.76 |
| Melting Point | 220 ºC |
| Density | 1.606 |
| Flash Point | 11 °C |
| Appearance | 白色或类白色结晶性粉末。熔点206℃。溶于丙酮，甲醇，二甲基甲酰胺，略溶于乙醇，不溶于水。无臭，几乎无味。 |
| Solubility | Soluble in DMSO (66 mg/ml at 25 °C), ethanol (<1 mg/ml at 25 °C), water (<1 mg/ml at 25 °C), methanol (50 mg/ml), and DMF. |
别名和识别编码
| Chemical Name | 5-(Aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]benzoic acid |
|---|---|
| CAS Number | 54-31-9 |
| Synonym | 5-(aminosulfonyl)-4-chloro-2-((2-furanylmethyl)amino)-benzoicaci Fuluvamide FRUSEMIDE arasemide NCI-C55936 2-furfurylamino-4-chloro-5-sulfamoylbenzoic acid 5-[AMINOSULFONYL] Furosemide "mita" Novosemi Hydrex {Chemica Diural Fusid Dryptal ######## endural Frusem 4-氯-N-呋喃基-5-氨磺酰邻氨基苯甲酸 5-(氨基磺酰基)-4-氯-2-([2-呋喃甲基]氨基)苯甲酸 { Chlor-N-(2-furylmethyl)-5-sulfamylanthranilsaeure Aqu 5-(AMINOSULPHONYL)-4-CHLOR Lowpstron 4-氯-N-呋喃基-5-氨磺酰邻氨基苯甲酸 5-(氨基磺酰基)-4-氯-2-([2-呋喃甲基]氨基)苯甲酸 5-(Aminosulfonyl)-4-chloro-2-[2-(furamyl-methyl)amino]-benzoicacid Neo-renal Discoid 2-(2-呋喃甲基)氨基-5-(磺酰氨基)-4-氯苯甲酸 4-chloro-n-(2-furylmethyl)-5-sulfanoylanthranilicacid Promedes 4-chloro-n-furfuryl-5-sulfamoyl- 4-CHLORO-N-FURFURYL-5-SULFAMOYLANTHRANILIC ACID diurolasa Furosemid 利尿灵 5-(Aminosulfonyl)-4-chloro-2-((2-furanylmethyl)amino)benzoic acid; 4-Chloro-N-furfuryl-5-sulfamoylanthranilic acid; 2-Furfurylamino-4-chloro-5-sulfamoylbenzoic acid 5-(Aminosulfonyl)-4-chloro-2-((2-furanylmethyl)amino)benzoic aci Furosemide Furose Fulsix al Benzoic acid, 5-(aminos Lasex {hazard aquasin 5-(aminosulfonyl)-4-chloro-2-[(2-furanylmethyl)amino]-benzoicaci {h FUROSEMID Odemase Urex 呋噻米;速尿;呋喃苯胺酸;利尿磺胺;4-氯-N-呋喃基-5-氨磺酰邻氨基苯甲酸;5-(氨基磺酰基)-4-氯-2-([2-呋喃甲基]氨基)苯甲酸;2-(2-呋喃甲基)氨基-5-(磺酰氨基)-4-氯苯甲酸 Furosedon Diur Laxur Trofurit |
| MDL Number | MFCD00010549 |
| EC Number | 200-203-6 |
| PubChem Substance ID | 24277714 |
| Alfabeta Name | AMINOSULFONYLCHLOROFURYLMETHYLAMINOBENZOICACID 5422[](())------ |
| Chemical Name Translation | 2-(2-呋喃甲基)氨基-5-(磺酰氨基)-4-氯苯甲酸 |
| Merck Number | 4309 |
| Wiswesser Line Notation | T5OJ B1MR CG FVQ DSZW |
| Beilstein Registry Number | 0840915 |
| LabNetwork Molecule ID | LN00176507 |
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分类
- Approved Therapeutics/Drug Candidates, Bioactive Small Molecules, Biochemicals and Reagents, Cell Biology, Cell Signaling and Neuroscience, Enzyme Inhibitors, Enzyme Inhibitors by Enzyme, Enzymes, Inhibitors, and Substrates, F, Ion Channels, Ion Pump Inhibitors, Monovalent Ion Channels, P to Q, Phosphodiesterase 3′,5′-Cyclic Nucleotide, Sanofi Aventis, Voltage-gated Ion Channels
- {SA} Approved Therapeutics/Drug Candidates, Bioactive Small Molecules, Biochemicals and Reagents, Cell Biology, Cell Signaling and Neuroscience, Enzyme Inhibitors, Enzyme Inhibitors by Enzyme,
产品应用
- An inhibitor of NKCC and a GABAA receptor antagonist.
相关文献及参考
- Goldenthal, E.I.: Toxicol. Appl. Pharmacol., 18, 185 (1971),
- Gutschmidt, K.U., et al. Neuroscience 91 , 1471, (1999) 摘要
- Thompson, S.A., et al. Mol. Pharmacol. 55 , 993, (1999) 摘要
- Zangen, A., et al. Eur. J. Pharmacol. 361 , 151, (1998) 摘要
- Crowe, A., et al., Identification Of Aminothienopyridazine Inhibitors Of Tau Assembly By Quantitative High-throughput Screening. Biochemistry 48 , 7732-45, (2009) 摘要
- Fong, J.E., et al., Tumor-supportive And Osteoclastogenic Changes Induced By Breast Cancer-derived Factors Are Reversed By Inhibition Of {gamma}-secretase. J. Thorac. Cardiovasc. Surg. 285 , 31427-34, (2010)
- Merck 14 ,4309
- Aldrich MSDS 1 , 985:A / Corp MSDS 1 (1), 1757:A / FT-IR 1 (2), 591:A / FT-IR 2 (3), 3465:B / FT-NMR 1 (3), 41:C / RegBook 1 (2), 2329:H / Sax 6 , 723 / Sigma FT-IR 1 (2), 587:D / Structure Index 1 , 366:B:6
安全信息
GHS Symbol
- P308+P313
- P201 Obtain special instructions before use. 使用前获取专门指示。
- P301+P310
- P210 Keep away from heat/sparks/open flames/hot surfaces. — No smoking. 远离热源/火花/明火/热的表面。——禁止吸烟。
- P260 Do not breathe dust/fume/gas/mist/vapours/spray. 不要吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
- P311 Call a POISON CENTER or doctor/physician. 呼叫解毒中心或医生/医师。
- P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
- H360 May damage fertility or the unborn child 可能对生育能力或未出生婴儿造成伤害
- H370 Causes damage to organs 导致器官损伤
- H331 Toxic if inhaled 吸入中毒
- H225 Highly flammable liquid and vapour 高度易燃液体和蒸气
- H301 Toxic if swallowed 吞食有毒
- H311 Toxic in contact with skin 皮肤接触中毒
- S22 Do not breathe dust 不要吸入粉尘；
- S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护；
- S53 Avoid exposure - obtain special instructions before use 避免接触，使用前获得特别指示说明；
- S45 In case of accident or if you feel unwell seek medical advice immediately (show the label where possible) 发生事故时或感觉不适时，立即求医（可能时出示标签）；
- S7 Keep container tightly closed 保存在严格密闭容器中；
- S16 Keep away from sources of ignition - No smoking 远离火源，禁止吸烟；
- S36/37 Wear suitable protective clothing and gloves 穿戴适当的防护服和手套；
- R61 May cause harm to the unborn child 可能对未出生的婴儿导致伤害
- R23/24/25 Toxic by inhalation, in contact with skin and if swallowed 吸入，皮肤接触及吞食都有毒
- R11 Highly flammable 非常易燃
- R39/23/24/25 Toxic: danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed 毒性：吸入，皮肤接触和吞食都会产生十分严重的不可逆危险
TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 15652 mg/kg/2Y-C TOXIC EFFECTS : Tumorigenic - Carcinogenic by RTECS criteria Skin and Appendages - tumors Blood - lymphoma, including Hodgkin's disease REFERENCE : NTPTR* National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No.206- Volume(issue)/page/year: NTP-TR-356,1989
TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 21112 mg/kg/2Y-C TOXIC EFFECTS : Tumorigenic - equivocal tumorigenic agent by RTECS criteria Brain and Coverings - tumors Kidney, Ureter, Bladder - Kidney tumors REFERENCE : NTPTR* National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No.206- Volume(issue)/page/year: NTP-TR-356,1989
TYPE OF TEST : TD - Toxic dose (other than lowest) ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 122 gm/kg/2Y-C TOXIC EFFECTS : Tumorigenic - Carcinogenic by RTECS criteria Skin and Appendages - tumors REFERENCE : JJATDK JAT, Journal of Applied Toxicology. (John Wiley & Sons Ltd., Baffins Lane, Chichester, W. Sussex PO19 1UD, UK) V.1- 1981- Volume(issue)/page/year: 10,369,1990
TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 308 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 14,44,1964
TYPE OF TEST : TDLo - Lowe
TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 800 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : APPHAX Acta Poloniae Pharmaceutica. For English translation, see APPFAR. (Ars Polona, POB 1001, 00-680 Warsaw 1, Poland) V.1- 1937- Volume(issue)/page/year: 42,199,1985
TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - rabbit DOSE/DURATION : 400 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,725,1982
TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Human - man DOSE/DURATION : 29 mg/kg TOXIC EFFECTS : Sense Organs and Special Senses (Ear) - change in acuity Sense Organs and Special Senses (Ear) - tinnitus Kidney, Ureter, Bladder - urine volume decreased REFERENCE : NEJMAG New England Journal of Medicine. (Massachusetts Medical Soc., 10 Shattuck St., Boston, MA 02115) V.198- 1928- Volume(issue)/page/year: 282,1413,1970
{hazard_TYPE OF TEST : Cytogenetic analysis TEST SYSTEM : Rodent - hamster Fibroblast DOSE/DURATION : 2 gm/L REFERENCE : ESKHA5 Eisei Shikenjo Hokoku. Bulletin of the Institute of Hygienic Sciences. (Kokuritsu Eisei Shikenjo Kagaku, 18-1 Bushitsu Johobu, Setagaya-ku, Tokyo 158, Japan) V.1- 1886- Volume(issue)/page/year: (96),55,1978
TYPE OF TEST : Cytogenetic analysis ROUTE OF EXPOSURE : Intraperitoneal TEST SYSTEM : Rodent - mouse DOSE/DURATION : 312 ug/kg REFERENCE : IJMRAQ Indian Journal of Medical Research. (Indian Council of Medical Research, Ansari Nagar, New Delhi 110 029, India) V.1- 1913- Volume(issue)/page/year: 66,104,1977
TYPE OF TEST : Cytogenetic analysis TEST SYSTEM : Rodent - hamster Lung DOSE/DURATION : 1 gm/L REFERENCE : ATSUDG Archives of Toxicology, Supplement. (Springer-Verlag New York, Inc., Service Center, 44 Hartz Way, Secaucus, NJ 07094) No.1- 1978- Volume(issue)/page/year: 4,41,1980
TYPE OF TEST : Cytogenetic analysis TEST SYSTEM : Rodent - hamster Ovary DOSE/DURATION : 200 mg/L REFERENCE : NTPTR* National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No.206- Volume(issue)/page/year: NTP-TR-356,1989
TYPE OF TEST : Mutation in microorganisms TEST SYSTEM : Rodent - mouse Lymphocyte DOSE/DURATION : 1 mg/L REFERENCE : NTPTR* National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No.206- Volume(issue)/page/year: NTP-TR-356,1989
TYPE OF TEST : Sister chromatid exchange TEST SYSTEM : Rodent - hamster Ovary DOSE/DURATION : 500 mg/L REFERENCE : NTPTR* National Toxicology Program Technical Report Series. (Researc
TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE : 122 mg/kg SEX/DURATION : male 6 week(s) pre-mating TOXIC EFFECTS : Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Paternal Effects - testes, epididymis, sperm duct REFERENCE : JRPFA4 Journal of Reproduction and Fertility. (Biochemical Soc. Book Depot, POB 32, Commerce Way, Colchester, Essex CO2 8HP, UK) V.1- 1960- Volume(issue)/page/year: 81,259,1987
TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE : 150 mg/kg SEX/DURATION : female 16 day(s) after conception TOXIC EFFECTS : Reproductive - Specific Developmental Abnormalities - musculoskeletal system REFERENCE : TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 40,668,1989
TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE : 300 mg/kg SEX/DURATION : female 16 day(s) after conception TOXIC
TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE : 150 mg/kg SEX/DURATION : female 12-14 day(s) after conception TOXIC EFFECTS : Reproductive - Specific Developmental Abnormalities - musculoskeletal system REFERENCE : TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 31,401,1985
其他信息
- 用途一:用作利尿药
- 类别:有毒物质
- 上游原料:2,4-二氯苯甲酸 --> 2,4-二氯-5-磺酰胺基苯甲酸 --> 2-呋喃甲胺
- 方法一:由2，4-二氯苯甲酸（见12740）经氯磺化，氨化，酸化得到2，4-二氯-5-氨磺酰基苯甲酸。然后与糠胺缩合制得速尿。
- TCI Shanghai:呋塞米 Furosemide,>;99.0%(T)(54-31-9)
- 呋塞米
- 急性毒性:口服- 大鼠 LD50: 2600 毫克/ 公斤; 口服- 小鼠 LD50: 2200 毫克/ 公斤
- 可燃性危险特性:可燃; 火场分解有毒氮氧化物; 硫氧化物和氯化物烟雾
- 毒性分级:中毒
- MOL 文件:54-31-9.mol
- 高效利尿药:呋塞米又称呋喃苯胺酸、速尿、速尿灵、利尿灵、利尿磺胺、腹安酸，是一种作用于髓袢升支髓质部的氨磺酰类高效利尿药，有强而短暂的利尿作用，能增加水、钠、氯、钾、钙、镁、磷酸盐等的排泄。主要抑制髓袢升支粗段的髓质部及皮质部对Na+及Cl-的重吸收，促进钠、氯、钾的排出和影响肾髓质高渗透压的形成，干扰尿液的浓缩和稀释过程，使尿量增加。本品能抑制前列腺素分解酶的活性，使前列腺素E2的含量升高，有扩张血管的作用，对近曲小管、肾小球滤过也有作用，能增加肾血流量，调整肾内血流分布，使髓质血流量减少，表层皮质的血流量增加，促进利尿，作用迅速强大，多用于其他利尿药无效的病例。临床上用于治疗心性水肿、肾性水肿、肝硬化腹水、机能障碍或血管障碍所引起的周围性水肿，并可促进上部尿道结石的排泄。静脉给药可治疗脑水肿，在脑水肿药物中毒时也可加速毒物的排泄。需要注意的是呋塞米利尿时，由于尿中Cl-、Na+、K+、H+排出的增加，HCO3-的排出并不增加，长期反复用药或大量用药可引发低盐综合征、低氯低钾性碱中毒。 近年研究人员发现呋塞米雾化吸入有明显平喘作用，与色甘酸钠相同，抑制过敏介质释放，抑制神经递质乙酰胆碱、P物质的释放，可能与其能抑制氯离子进入呼吸道细胞膜有关。临床试用于运动性哮喘、抗原引起的速发型和迟发型哮喘。
- Furosemide is a loop diuretic inhibitor of NKCC (Na+/2Cl-/K+) cotransporter. Furosemide acts as a non-competitive antagonist at GABAA receptors with ~ 100-fold greater selectivity for α6-containing receptors than α1-containing receptors.
- Sigma Aldrich:54-31-9(sigmaaldrich)
- 灭火剂:水, 二氧化碳, 干粉, 砂土
- 储运特性:库房低温, 通风, 干燥
- MSDS 信息:4-Chloro-N-furfuryl-5-sulfamoylanthranilic acid(54-31-9).msds
- 图谱信息:呋噻米(54-31-9)红外图谱(IR2) 呋噻米(54-31-9)核磁图( 1 HNMR) 呋噻米(54-31-9)红外图谱(IR1) 呋噻米(54-31-9)质谱(MS) 呋噻米(54-31-9)核磁图( 13 CNMR)
- 用途二:该品利尿作用强而短，为强效利尿药，用于治疗心，肝，肾等疾病引起的水肿，特别是对基他利尿药无效的病例；可用于治闻急性肺水肿，脑水肿，急性肾功能衰竭和高血压等疾病；配合补液该品可促进毒物非泄。大鼠口服LD50为2600-2820mg/kg。
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