HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acemetacin
aximeixin · AceMetacin (EMflex) · k-708 · Solart · Emflex · acemix · tv1322 · rantudil
Identifiers & Physical Properties
| CAS No. | 53164-05-9 |
|---|---|
| Molecular formula | C21H18ClNO6 |
| Average molar mass | 415.8 g/mol |
| Monoisotopic mass | 415.08226498 g/mol |
| SMILES | COc1ccc2c(c1)c(CC(=O)OCC(=O)O)c(C)n2C(=O)c1ccc(Cl)cc1 |
| InChIKey | FSQKKOOTNAMONP-UHFFFAOYSA-N |
| PubChem CID | 1981 |
| ChEMBL | CHEMBL189171 |
| ChEBI | CHEBI:31162 |
| EC No. | 258-403-4 |
| DTXSID | DTXSID7022540 |
Chemical & Physical Properties
| XLogP | 4.2 |
|---|---|
| Topological polar surface area | 94.8 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 6 |
| Rotatable bonds | 7 |
| Heavy atoms | 29 |
| Formal charge | 0 |
| Complexity | 620 |
| Drugs | Pharmaceuticals -> Analgesics and anti-inflammatoriesPharmaceuticals -> Listed in ZINC15Pharmaceuticals -> Used in Switzerland |
| Solubility | Slightly soluble>62.4 [ug/mL] (The mean of the results at pH 7.4)Practically insoluble in water, soluble in acetone, slightly soluble in anhydrous ethanol. |
| Human Drugs | Breast FeedingLactationMilk, HumanAnalgesic AgentsAnti-inflammatory Agents, NonsteroidalPharmaceuticals |
| Boiling point | 637ºC565.5±50.0 °C(Predicted) |
| Melting point | 151.5ºC151.5°C |
| Dissociation Constants | 2.6 |
| Collision Cross Section | 197.64 Ų [M+Na]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]191 Ų [M+H]+ [CCS Type: TW |
| Density | 1.2387 (rough estimate) |
| Refractive index | 1.6000 (estimate) |
| RTECS number | NL3521400 |
| Storage conditions | Sealed in dry,Store in freezer, under -20°C |
| pKa (acidity coefficient) | 2.60±0.10(Predicted) |
| Physical state | Solid |
| Color | Very fine, pale-yellow crystals from pet eth |
| Merck | 14,27 |
| Major applications | pharmaceutical (small molecule) |
| InChI | InChI=1S/C21H18ClNO6/c1-12-16(10-20(26)29-11-19(24)25)17-9-15(28-2)7-8-18(17)23(12)21(27)13-3-5-14(22)6-4-13/h3-9H,10-11H2,1-2H3,(H,24,25) |
| InChIKey | FSQKKOOTNAMONP-UHFFFAOYSA-N |
| SMILES | N1(C(=O)C2=CC=C(Cl)C=C2)C2=C(C=C(OC)C=C2)C(CC(OCC(O)=O)=O)=C1C |
| CAS DataBase Reference | 53164-05-9(CAS DataBase Reference) |
| FDA UNII | 5V141XK28X |
| ATC code | M01AB11 |
| UNSPSC Code | 41116107 |
| NACRES | NA.24 |
| GHS pictogram | GHS06 |
| Signal word | Danger |
| GHS hazard statements | H300+H310+H330 |
| GHS precautionary statements | P260-P262-P264-P280-P302+P352+P310-P304+P340+P310 |
| Hazard symbols | T+ |
| Risk statements (R) | 26/27/28 |
| Safety statements (S) | 22-25-36/37/39-45-24/25 |
| UN transport number | UN 2811 |
| Water hazard class (WGK) | 3 |
| Hazard class | 6.1(a)Acute Tox. 1 InhalationAcute Tox. 2 DermalAcute Tox. 2 Oral |
| Packing group | II |
| Customs code | 29339900 |
| Storage class | 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials |
| Toxicity | LD50 in male, female mice, male, female rats (mg/kg): 55.5, 18.42, 24.2, 30.1 orally34.1, 51.1, 38.1, 28.3 i.v. (Jacobi, Dell) |
| Limited quantities | 0.5 Kg (solid) |
| Excepted quantities | Max Inner Pack (1g or 1ml) and Max Outer Pack (500g or 500ml) |
Safety & Regulations
| GHS classification | DangerH300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]P260, P262, P264, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P316, P320, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 65 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 2 (100%) |
| Drug Induced Liver Injury | Drug-Induced Liver Injury Severity and Toxicity (DILIst)ACEMETACINDILI PositiveDOI:10.1016/j.drudis.2019.09.022 |
| Effects During Pregnancy and Lactation | ◉ Summary of Use during Lactation |
| Water hazard class (WGK) | 3 |
| UN transport number | UN 2811 |
| Customs code | 29339900 |
| Toxicity | LD50 in male, female mice, male, female rats (mg/kg): 55.5, 18.42, 24.2, 30.1 orally34.1, 51.1, 38.1, 28.3 i.v. (Jacobi, Dell) |
| Risk statements (R) | 26/27/28 |
| Signal word | Danger |
| GHS pictogram | GHS06 |
| Hazard symbols | T+ |
| Safety statements (S) | 22-25-36/37/39-45-24/25 |
| Hazard class | 6.1(a)Acute Tox. 1 InhalationAcute Tox. 2 DermalAcute Tox. 2 Oral |
| Storage class | 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials |
| Packing group | II |
| GHS hazard statements | H300+H310+H330 |
| Limited quantities | 0.5 Kg (solid) |
| Excepted quantities | Max Inner Pack (1g or 1ml) and Max Outer Pack (500g or 500ml) |
| GHS precautionary statements | P260-P262-P264-P280-P302+P352+P310-P304+P340+P310 |
Applications & Uses
Description
Acemetacin is used in the treatment of pain and restricted mobility resulting from chronic articular rheumatism, degenerative articular disease, gout, and inflammation of muscle, joints, and tendons. Acemetacin causes less gastrointestinal blood loss than indomethacin. Its anti-inflammatory activity results from liberation of the parent compound, indomethacin.
Uses
Cyclo-oxygenase inhibitor; analgesic; anti-inflammatory.
Uses
A potent inhibitor of COX-2 found to have anti-tumor activity in the colon