Sertraline

Zoloft · Sertraline for peak identification CRS · Tatig · Gladem · cp51974 · Adjuvin · Sealdin · Atruline

https://huagongshe.com/de/chemical/68617

Identifikatoren & physikalische Daten

CAS No.	79617-95-1
Summenformel	C17H17Cl2N
Durchschnittliche Molmasse	306,2 g/mol
Monoisotopische Masse	305,0738049 g/mol
SMILES	CN[C@H]1CC[C@@H](c2ccc(Cl)c(Cl)c2)c2ccccc21
InChIKey	VGKDLMBJGBXTGI-SJCJKPOMSA-N
PubChem CID	68617
ChEMBL	CHEMBL809
ChEBI	CHEBI:9123
EC No.	616-708-3
DTXSID	DTXSID6023577

Chemische & physikalische Eigenschaften

XLogP	4,8
Polarare Oberfläche (TPSA)	12
H-Brücken-Donoren	1
H-Brücken-Akzeptoren	1
Frei drehbare Bindungen	2
Schwere Atome	20
Formalladung	0
Komplexität	322
Stoffklassen	Pharmaceutical
Arzneimittel	DEA NFLIS-Drug Category -> AntidepressantsPharmaceuticals -> Synthetic Cannabinoids or Psychoactive CompoundsPharmaceuticals -> Listed in ZINC15Pharmaceuticals -> SSRIs (Selective Serotonin Reuptake Inhibitors)Pharmaceuticals -> Used in Switzerland
Löslichkeit	3.8mg/mL>45.9 [ug/mL] (The mean of the results at pH 7.4)<0.1g/L(room temperature)
Human Drugs	Antidepressants -> Selective serotonin reuptake inhibitors (SSRI)Breast FeedingLactationMilk, HumanAntidepressive AgentsSerotonin Uptake InhibitorsPharmaceuticals
Endocrine Disruptors	Potential endocrine disrupting compound
Siedepunkt	416.3±45.0 °C416.3±45.0 °C(Predicted)
Schmelzpunkt	245-246
Physical Description	Solid
Dissociation Constants	89.16
Collision Cross Section	167.7 Å² [M+H]+ [CCS Type: DTBuffer gas: N2Ionization: ESI+Dataset: Antidepressants]166.47 Å² [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]167.3 Å² [M+H]+ [CCS Type: DTMethod: single field calibrated]
Other Experimental Properties	MW: 342.70. Crystals, mp 243-245 °C. Specific optical rotation at 23 °C = +37.9 deg (c = 2 in methanol). Solubility at room temperature (mg/ml): water 3.80.1N HCl 0.510.1N NaOH 0.002ethanol 15.7isopropyl alcohol 4.3chloroform 110acetone 1.1N,N-dimethylformamide 88dimethylsulfoxide 147ethyl acetate 0.20acetonitrile 0.85methanolic 0.1N HCl 47chloroform/methanol (1:1) 134. pKa (ethanol:water, 1:1 v/v): 8.5. density = 1.37 /Sertraline hydrochloride/
Dichte	1.25±0.1 g/cm3(Predicted)
pKa (Säurekonstante)	pKa 9.48±0.04(H2O I > 0)(Approximate)
InChI	InChI=1S/C17H17Cl2N/c1-20-17-9-7-12(13-4-2-3-5-14(13)17)11-6-8-15(18)16(19)10-11/h2-6,8,10,12,17,20H,7,9H2,1H3/t12-,17-/m0/s1
InChIKey	VGKDLMBJGBXTGI-SJCJKPOMSA-N
SMILES	[C@@H]1(NC)C2=C(C=CC=C2)[C@H](C2=CC=C(Cl)C(Cl)=C2)CC1
CAS Datenbank	79617-96-2(CAS DataBase Reference)
NIST chemische Informationen	Sertraline(79617-96-2)
EPA chemische Informationen	Sertraline (79617-96-2)

Sicherheit & Vorschriften

GHS-Einstufung	WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Entsorgungsverfahren	SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Treatment	Treatment should consist of those general measures employed in the management of overdosage with any antidepressant. Ensure an adequate airway, oxygenation and ventilation. Monitor cardiac rhythm and vital signs. General supportive and symptomatic measures are also recommended. Induction of emesis is not recommended. Gastric lavage with a large-bore orogastric tube with appropriate airway protection, if needed, may be indicated if performed soon after ingestion, or in symptomatic patients. Activated charcoal should be administered. Due to large volume of distribution of this drug, forced diuresis, dialysis, hemoperfusion and exchange transfusion are unlikely to be of benefit. No specific antidotes for sertraline are known. (L1712)
Wechselwirkungen	Examples of drug interactions with serotonin-reuptake inhibitors include potentiation of agents metabolized prominently by CYP1A2 (e.g. beta-adrenergic receptor antagonists, caffeine, several antipsychotic agents, & most tricyclic antidepressants)CYP2C9 (carbamazepine)CYP2C19 (barbiturates, imipramine, propranolol, phenyltoin)CYP2D6 (beta-adrenergic receptor antagonists, some antipsychotics, many antidepressants)CYP3A3/4 (benzodiazepines, carbamazepine, many antidepressants, & several antibiotics). /Serotonin-reuptake inhibitors/Antidepressants potentiate the effects of alcohol & probably other sedatives. The anticholinergic activity of tricyclic antidepressants can add to that of antiparkinsonism agents, antipsychotic drugs of low potency (especially clozapine & thioridazine), or other compounds with antimuscarinic activity to produce toxic effects. Tricyclic antidepressants have prominent & potentially dangerous interactions with biogenic amines, such as norepinephrine, which normally are removed from their site of action by neuronal uptake. However, drugs that inhibit norepinephrine transport also block the effects of indirectly acting amines, such as tyramine, which must be taken up by sympathetic neurons to release norepinephrine. Presumable by a similar mechanism, tricyclic antidepressants prevent the antihypertensive action of adrenergic neuron blocking agents such as guanadrel. Tricyclic agents & trazodone also can block the centrally mediated antihypertensive action of clonidine. /Antidepressants/

Anwendungen & Verwendung

History

The history of sertraline dates back to the early 1970s when Pfizer chemist Reinhard Sarges invented a novel series of psychoactive compounds, including lometraline, based on the structures of the neuroleptics thiothixene and pinoxepin. Further work on these compounds led to tametraline, a norepinephrine and weaker dopamine reuptake inhibitor. A few years later, in 1977, pharmacologist Kenneth Koe, after comparing the structural features of a variety of reuptake inhibitors, became interested in the tametraline series. He asked another Pfizer chemist, Willard Welch, to synthesize some previously unexplored tametraline derivatives. Welch generated several potent norepinephrine and triple reuptake inhibitors, but to the surprise of the scientists, one representative of the generally inactive cis-analogs was a serotonin reuptake inhibitor. Welch then prepared stereoisomers of this compound, which were tested in vivo by animal behavioral scientist Albert Weissman. The most potent and selective (+)-isomer[a] was taken into further development and eventually named sertraline.

Verwenden

Antidepressant;5-HT uptake inhibitor