Ethacrynic Acid
에타크린산 · ETACRYNIC ACID · edecrin · mingit · mk-595 · reomax · uregit · edecril
식별자 및 물리적 특성
| CAS No. | 58-54-8 |
|---|---|
| 분자식 | C13H12Cl2O4 |
| 평균 분자량 | 303.13 g/mol |
| 단동위원소 질량 | 302.01126422 g/mol |
| SMILES | C=C(CC)C(=O)c1ccc(OCC(=O)O)c(Cl)c1Cl |
| InChIKey | AVOLMBLBETYQHX-UHFFFAOYSA-N |
| PubChem CID | 3278 |
| ChEMBL | CHEMBL456 |
| ChEBI | CHEBI:4876 |
| EC No. | 200-384-1 |
| DTXSID | DTXSID3025257 |
화학 및 물리적 성질
| XLogP | 3.8 |
|---|---|
| 극성 표면적 | 63.6 |
| 수소 결합 공여자 수 | 1 |
| 수소 결합 수용자 수 | 4 |
| 회전 가능 결합 수 | 6 |
| 무거운 원자 수 | 19 |
| 형식 전하 | 0 |
| 복잡도 | 370 |
| 의약품 | Pharmaceuticals -> Listed in ZINC15 |
| LogP(분배 계수) | 3.3 |
| Color/Form | CrystalsWhite, or practically white, crystalline powder |
| 용해도 | less than 1 mg/mL at 75 °F (NTP, 1992)Sparingly soluble in water, aq acidssoluble in chloroformVery slightly soluble in water but soluble in most organic solvents such as alcohols, chloroform, and benzene1.94e-02 g/LDMSO: 용해성20mg/mL, 투명 |
| Human Drugs | Breast FeedingLactationAntihypertensive AgentsLoop DiureticsFDA approved drugs -> Active ingredientPharmaceuticals |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Decomposition | When heated to decomp it emits toxic fumes of /hydrogen chloride/. |
| 녹는점 | 252 °F (NTP, 1992)118.5-120.5121-122 °C122.5 °C125 °C |
| Physical Description | Ethacrynic acid is a white solid. (NTP, 1992) |
| Stability/Shelf Life | Solns at pH 7 at 25 °C stable for short periods of time. Stability decreased with an incr in pH, temp and time. /sodium salt/This compound is stable under normal laboratory conditions. |
| Dissociation Constants | 3.53.1pKa'= 3.50 |
| Other Experimental Properties | UV max (water): 225 nm(E=15287)Soluble in water at 25 °C: up to 9%Solutions at pH 7 @ 25 °C stable for short periods of time. Stability decreased with increase in pH, temperature, and time. /Ethacrynate sodium/Soluble in water @ 25 °C to the extent of about 7%solutions of the sodium salt are relatively stable at pH 7 at room temperature for short periods but as the pH or temperature increase solutions are less stable /Ethacrynate sodium/ |
| 끓는 점 | 480.0±45.0 °C(Predicted) |
| 밀도 | 1.3562 (estimate) |
| 저장 조건 | 2-8°C |
| 물리적 상태 | 가루 |
| pKa(산도 계수) | 3.50(at 25℃) |
| 색상 | 흰색에서 베이지색 |
| 용해도 | 에탄올, 클로로포름, 에테르, 암모니아, 탄산염 및 메탄올에 용해됩니다. 물에 불용성. |
| Merck | 3717 |
| InChI | 1S/C13H12Cl2O4/c1-3-7(2)13(18)8-4-5-9(12(15)11(8)14)19-6-10(16)17/h4-5H,2-3,6H2,1H3,(H,16,17) |
| InChIKey | AVOLMBLBETYQHX-UHFFFAOYSA-N |
| SMILES | ClC1=C(Cl)C(C(C(CC)=C)=O)=CC=C1OCC(O)=O |
| EPA | Ethacrynic acid (58-54-8) |
화학적 성질
White Solid
안전 및 규제
| GHS 분류 | WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 41 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 기타 안전 정보 | IMAP assessments - Acetic acid, [2,3-dichloro-4-(2-methylene-1-oxobutyl)phenoxy]-: Human health tier I assessment |
| 화재 위험 | This chemical is probably combustible. (NTP, 1992) |
| 화재 가능성 | The flash point of this chemical is not available, but it is probably combustible. |
| 건강 유해성 | SYMPTOMS: Symptoms associated with exposure to this chemical may include fluid and electrolyte imbalances, gout, gastrointestinal disturbances, depression of formed elements of the blood, skin rashes, paresthesias and hepatic dysfunction. It may also cause transient or permanent deafness in rare cases. |
| FDA 요건 | The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl ethacrynic acid, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. |
| 반응성 그룹 | Acids, Carboxylic |
| Special Reports | JONES HCINTRAUTERINE OTOTOXICITY CASE REPORT AND REVIEW OF LITERATUREJ NATL MED ASSOC 65: 201 (1973) INTRAUTERINE OTOTOXICITY & REVIEW OF LITERATURE, INCLUDING ETHACRYNIC ACID IS DISCUSSED.RAHN KHCLINICAL PHARMACOLOGY OF DIURETICSCLIN EXP HYPERTENS (A) 5(2): 157 (1983) A REVIEW OF THE CLINICAL PHARMACOLOGY OF DIURETICS, INCLUDING PHARMACODYNAMIC DRUG INTERACTIONS WITH DIURETICS.KOECHEL DAETHACRYNIC ACID AND RELATED DIURETICS: RELATIONSHIP OF STRUCTURE TO BENEFICIAL AND DETRIMENTAL ACTIONSANNU REV PHARMACOL TOXICOL 21: 265 (1981) A REVIEW WITH 186 REFERENCES ON THE BENEFICIAL & DETRIMENTAL EFFECTS OF PHENOXYACETIC ACID-TYPE DIURETICS SUCH AS ETHACRYNIC ACID. |
용도
개요
Ethacrynic acid is a loop diuretic with anticancer activity., It inhibits the Na-K-2Cl (NKCC) cotransporter in duck erythrocytes (IC50 = 0.18 mM) and ATP-dependent chloride uptake in rat renal plasma membrane vesicles when used at a concentration of 0.3 mM., Ethacrynic acid also inhibits glutathione S-transferase P1-1 (GSTP1-1) and GSTA3-3 (IC50s = 4.9 and ~0.4 μM, respectively), and inhibits Wnt/β-catenin signaling in a cell-based reporter assay. It is cytotoxic to primary chronic lymphocytic leukemia cells (IC50 = 8.56 μM), as well as MCF-7, MDA-MB-231, and 4T1 cancer cells (IC50s = 45.53, 39.64, and 25.23 μM, respectively). Ethacrynic acid (250 μg per day) increases tumor growth reduction induced by the EGFR family inhibitors afatinib (Item Nos. 11492 | 21567) or neratinib in a 4T1 murine breast cancer model. Formulations containing ethacrynic acid have been used in the treatment of edema.
용도
Ethacrynic acid is a powerful diuretic prescribed for edema associated with cardiac insufficiency, renal edema that does not respond to other diuretics, and edema of the brain and lungs.
일반 설명
White solid.