2-(2,6-Dioxo-3-piperidinyl)-1H-isoindol-1,3(2H)-dion

2-(2,6-Dioxopiperidin-3-yl)isoindoline-1,3-dione · Neo · Celgene · 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione · k17 · Contergan · α-Phthalimidoglutarimide · K 17

https://huagongshe.com/de/chemical/5426

Molekülstruktur von 2-(2,6-Dioxo-3-piperidinyl)-1H-isoindol-1,3(2H)-dion

Identifikatoren & physikalische Daten

CAS No.	2614-06-4
Summenformel	C13H10N2O4
Durchschnittliche Molmasse	258,23 g/mol
Monoisotopische Masse	258,0640568 g/mol
SMILES	O=C1CCC(N2C(=O)c3ccccc3C2=O)C(=O)N1
InChIKey	UEJJHQNACJXSKW-UHFFFAOYSA-N
PubChem CID	5426
ChEMBL	CHEMBL468
ChEBI	CHEBI:74947
EC No.	200-031-1
DTXSID	DTXSID9022524
Lokaler Name	2-(2,6-Dioxo-3-piperidinyl)-1H-isoindol-1,3(2H)-dion

Chemische & physikalische Eigenschaften

XLogP	0,3
Polarare Oberfläche (TPSA)	83,6
H-Brücken-Donoren	1
H-Brücken-Akzeptoren	4
Frei drehbare Bindungen	1
Schwere Atome	19
Formalladung	0
Komplexität	449
LogP (Verteilungskoeffizient)	log Kow = 0.330.49
Color/Form	Needles
Löslichkeit	less than 1 mg/mL at 72 °F (NTP, 1992)In water, approximately 2X10-4 mol/L45-60 mg/L at 25 °CSparingly soluble in methanol, ethanol, acetone, ethyl acetate, butyl acetate, glacial acetic acid. Very soluble in DMF. Practically insoluble in ether, chloroform, benzene.Very soluble in dioxane, pyridine2.55e+00 g/L45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 0.6 mg/mL<0.1 g/100 mL at 22 ºC
Human Drugs	Breast FeedingLactationMilk, HumanImmunosuppressive AgentsLeprostatic AgentsAngiogenesis InhibitorsFDA approved drugs -> Active ingredientEMA approved medicines: Human medicineImmunomodulators
Decomposition	When heated to decomposition it emits toxic fumes of /nitrogen oxides/.
Schmelzpunkt	516 to 520 °F (NTP, 1992)270 °C269-271°C
Physical Description	Thalidomide appears as needles or white powder. (NTP, 1992)Solid
Stability/Shelf Life	Stable under recommended storage conditions.
Collision Cross Section	149.91 Å² [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]
Siedepunkt	401.48°C (rough estimate)
Dichte	1.2944 (rough estimate)
Brechungsindex	1.5300 (estimate)
Lagerbedingungen	Keep in dark place,Sealed in dry,Room Temperature
Aggregatzustand	White solid
pKa (Säurekonstante)	10.70±0.40(Predicted)
Farbe	white
Merck	14,9255
Stabilität	Stable. Combustible. Incompatible with strong oxidizing agents.
InChI	1S/C13H10N2O4/c16-10-6-5-9(11(17)14-10)15-12(18)7-3-1-2-4-8(7)13(15)19/h1-4,9H,5-6H2,(H,14,16,17)
InChIKey	UEJJHQNACJXSKW-UHFFFAOYSA-N
SMILES	O=C1CCC(N2C(=O)c3ccccc3C2=O)C(=O)N1
CAS Datenbank	50-35-1(CAS DataBase Reference)
NIST chemische Informationen	Phthalimide, n-(2,6-dioxo-3-piperidyl)-(50-35-1)
EPA chemische Informationen	Thalidomide (50-35-1)

Sicherheit & Vorschriften

GHS-Einstufung	DangerH302 (88.2%): Harmful if swallowed [Warning Acute toxicity, oral]P203, P264, P270, P280, P301+P317, P318, P330, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 76 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H302: Harmful if swallowed [Warning Acute toxicity, oral]
Regulatorische Informationen	Hazard Traits - Developmental Toxicity
DOT-Kennzeichnung	Poison
Brandgefahren	Flash point data for this chemical are not availablehowever, it is probably combustible. (NTP, 1992)
Gesundheitsgefahren	SYMPTOMS: Symptoms of exposure to this compound include peripheral neuritis, numbness, paresthesias in the extremities and signs of motor neuron disease. Other symptoms include teratogenic effects and peripheral neuropathy. Exposure to this type of compound may lead to sleepiness, mental confusion, unsteadiness, coma with slow, shallow respiration, flaccid muscles, cyanosis, hypotension, hypothermia or hyperthermia, absent reflexes, pulmonary edema, atelectasis or aspiration pneumonia with signs of lung consolidation and fever, acidosis and fetal injury. Death occurs most often from pneumonia, pulmonary edema or refractory hypotension.
FDA-Anforderungen	The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including thalidomide, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.U.S. Food & Drug Administration. ... Because of /its/ toxicity and in an effort to make the chance of fetal exposure to thalidomide as negligible as possible, thalidomide is approved for marketing only under a special restricted distribution program approved by the Food and Drug Administration. This program is called the "System for thalidomide education and prescribing safety (S.T.E.P.S.)". Under this restricted distribution program, only prescribers and pharmacists registered with the program are allowed to prescribe and dispense the product. In addition, patients must be advised of, agree to, and comply with the requirements of the S.T.E.P.S. program in order to receive product.If thalidomide is taken during pregnancy, it can cause severe birth defects or embryo-fetal death. Thalidomide should never be used by females who are pregnant or who could become pregnant while taking the drug. Even a single dose (1 capsule (regardless of strength)) taken by a pregnant woman during her pregnancy can cause severe birth defects. Because of this toxicity and in an effort to make the chance of embryo-fetal exposure to Thalomid (thalidomide) as negligible as possible, Thalomid (thalidomide) is approved for marketing only through a special restricted distribution program: Thalomid REMS program, approved by the Food and Drug Administration. This program was formerly known as the "System for Thalidomide Education and Prescribing Safety (S.T.E.P.S. program)".

Anwendungen & Verwendung

History

Thalidomide was introduced in 1957 as a tranquilizer, and was later marketed by the West German pharmaceutical company Chemie Grünenthal under the trade name Contergan as a medication for anxiety, trouble sleeping, tension, and morning sickness. It was introduced as a sedative and medication for morning sickness without having been tested on pregnant women. While initially deemed to be safe in pregnancy, concerns regarding birth defects were noted in 1961, and the medication was removed from the market in Europe that year.In the late 1950s and early 1960s, thalidomide was prescribed to women in 46 countries who were pregnant or who subsequently became pregnant, and consequently resulted in the "biggest anthropogenic medical disaster ever," with more than 10,000 children born with a range of severe deformities, such as phocomelia, as well as thousands of miscarriages.

Verwenden

Inhibits FGF-induced angiogenesis. Inhibits replication of human immunodeficiency virus type 1. Teratogenic sedative. There is now a growing clinical interest in Thalidomide, and it is introduced as an immunomodulatory agent used primarily in combination with dexamethasone to treat multiple myeloma.