シタロプラム
1-[3-(ジメチルアミノ)プロピル]-1-(4-フルオロフェニル)-1,3-ジヒドロイソベンゾフラン-5-カルボニトリル · ニタラプラム · シプラミル · シタロプラム · 1-(4-フルオロフェニル)-1-[3-(ジメチルアミノ)プロピル]-1,3-ジヒドロイソベンゾフラン-5-カルボニトリル · 1-[3-(ジメチルアミノ)プロピル]-1-(4-フルオロフェニル)-1,3-ジヒドロ-5-イソベンゾフランカルボニトリル · 1-[3-(ジメチルアミノ)プロピル]-1-(4-フルオロフェニル)-1,3-ジヒドロ-2-ベンゾフラン-5-カルボニトリル · 1-(4-フルオロフェニル)-1-(3-ジメチルアミノプロピル)1,3-ジヒドロイソベンゾフラン-5-カルボニトリル
識別子と物理属性
| CAS No. | 59729-33-8 |
|---|---|
| 分子式 | C20H21FN2O |
| 平均分子量 | 324.4 g/mol |
| 単同位体質量 | 324.16379146 g/mol |
| SMILES | CN(C)CCCC1(c2ccc(F)cc2)OCc2cc(C#N)ccc21 |
| InChIKey | WSEQXVZVJXJVFP-UHFFFAOYSA-N |
| PubChem CID | 2771 |
| ChEMBL | CHEMBL1628605 |
| ChEBI | CHEBI:77397 |
| EC No. | 261-891-1 |
| DTXSID | DTXSID8022826 |
| 現地名 | シタロプラム |
化学・物理的性質
| XLogP | 3.2 |
|---|---|
| 極性表面積 | 36.3 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 4 |
| 回転可能結合数 | 5 |
| 重原子数 | 24 |
| 形式電荷 | 0 |
| 複雑度 | 466 |
| LogP（分配係数） | 3.76 |
| LogS | -4.7 |
| Color/Form | Fine white to off-white powder |
| 溶解度 | Sparingly solublelog Kow = 1.39 at 22 °C.Solubility in water = 15,460 mg/L at 22 °C /Citalopram hydrobromide/... Sparingly soluble in water and soluble in ethanol.メタノール（微量）、水（微量） |
| 沸点 | 347-358BP: 175-181 °C at 0.03 mm Hg /Citalopram/bp0.03 175-181° |
| Decomposition | When heated to decomposition it emits very toxic fumes of /nitrogen oxides, hydrogen fluoride and hydrogen bromides/ |
| 融点 | 182-188Crystals from isopropanol. MP: 182-183. Freely soluble in water, ethanol, chloroform /Citolapram hydrobromide/178 °C156-157 °C |
| Optical Rotation | Specific optical rotation: +12.33 at 25 °C/D (c = 1 in methanol) /Citolapram escitalopram/ |
| Physical Description | Solid |
| Stability/Shelf Life | Stable under recommended storage conditions. /Citalopram hydrobromide/ |
| Dissociation Constants | 9.389.78 |
| Kovats Retention Index | 2393.42408.62406.52391.3 |
| 密度 | 1.18±0.1 g/cm3(Predicted) |
| 貯蔵条件 | Sealed in dry,2-8°C |
| pKa（酸解離定数） | pKa 9.38(H2O) (Uncertain) |
| 外観・状態 | 個体 |
| 色 | ホワイトからオフホワイト |
| CAS データベース | 59729-33-8(CAS DataBase Reference) |
| NISTの化学物質情報 | Citalopram(59729-33-8) |
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 20% (1 of 5) of reports.WarningH302 (60%): Harmful if swallowed [Warning Acute toxicity, oral]H312 (20%): Harmful in contact with skin [Warning Acute toxicity, dermal]H315 (20%): Causes skin irritation [Warning Skin corrosion/irritation]H317 (40%): May cause an allergic skin reaction [Warning Sensitization, Skin]H319 (40%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H332 (20%): Harmful if inhaled [Warning Acute toxicity, inhalation]H335 (20%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]H361 (20%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]H410 (40%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]P203, P261, P264, P264+P265, P270, P271, P272, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P318, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 5 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Reported as not meeting GHS hazard criteria per 1 of 5 reports by companies.There are 3 notifications provided by 4 of 5 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| 規制情報 | Status: Active Update: 24-07-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/22357Citalopram: Does not have an individual approval but may be used under an appropriate group standard |
| FDA 要件 | The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including citalopram hydrobromide, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Citalopram hydrobromide/ |
用途
説明
Citalopram is a specific serotonin-uptake inhibitor useful in the treatment of depression. In endogenous depression citalopram was reported to be as effective as amitriptyline and mianserin, while being inferior to clomipramine in both endogenous and non-endogenous depression.
来歴
The invention of citalopram dates back to 1972, when Klaus Bøgesø, a chemist at H. Lundbeck A/S in Denmark, and his team, while searching for new antidepressants, rationally designed and synthesized a compound called 1-(3-dimethylaminopropyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxynitrile, based on their previous research on the norepinephrine reuptake inhibitor talopram. They quickly completed a patent application, marking the pharmacological starting point for citalopram as a selective serotonin reuptake inhibitor (SSRI). In the late 1970s, the compound entered a systematic preclinical research phase, and its unique highly selective inhibition of the serotonin transporter (SERT) was gradually confirmed, exhibiting good antidepressant activity in animal models. In the early 1980s, citalopram entered clinical trials. Multiple double-blind controlled studies confirmed its significant efficacy and good tolerability for major depressive disorder. It was finally launched in Denmark in 1989 under the brand name Cipramil®, becoming the first domestically developed SSRI antidepressant in the Nordic market. In the 1990s, H. Lundbeck entered into a collaboration agreement with Forest Laboratories in the United States to jointly advance the registration of citalopram in the US. After a series of clinical trials that met FDA requirements, the drug received FDA approval on July 17, 1998, and officially entered the US market in September of the same year under the brand name Celexa®, quickly becoming one of the fastest-growing antidepressants in terms of prescription volume at the time. With the expiration of the citalopram patent in 2003, several generic drugs were launched, further expanding its global usage. This also spurred the development of its S-enantiomer, escitalopram, which was initiated in 1997 and approved in 2002, becoming Lundbeck's next-generation core antidepressant product.
使用
scabicide
一般的な説明
Citalopram (Celexa) is a racemic mixture and is very SERTselective. The N-monodemethylated compound is slightlyless potent but is as selective. The aryl substituents are importantfor activity. The ether function is important andprobably interacts with the protonated amino group to givea suitable shape for SERT binding.