Tamsulosin hydrochloride

Bezeichnung:Tamsulosin hydrochloride

CAS-Nr106463-17-6

Englisch Name:Tamsulosin hydrochloride

CBNumberCB3410080

SummenformelC20H29ClN2O5S

Molgewicht444.97

MOL-Datei106463-17-6.mol

Tamsulosin hydrochloride physikalisch-chemischer Eigenschaften

Schmelzpunkt	228-230°C
alpha	D24 -4.0° (c = 0.35 in methanol)
RTECS-Nr.	DB2430000
storage temp.	2-8°C
Löslichkeit	DMSO: >10mg/mL
Aggregatzustand	white powder
Farbe	White to Off-White
Merck	14,9049
InChIKey	ZZIZZTHXZRDOFM-XFULWGLBSA-N
SMILES	C1(S(=O)(=O)N)=CC(=CC=C1OC)C[C@@H](C)NCCOC1C=CC=CC=1OCC.Cl \|&1:13,r\|
CAS Datenbank	106463-17-6(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	22-36/37/38
S-Sätze:	26
WGK Germany	3
HS Code	29350090

Gefahreninformationscode (GHS)

Tamsulosin hydrochloride Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung
Tamsulosin is a potent antagonist of α₁-adrenergic receptors (α₁-ARs; K_i = 0.229 nM in a radioligand binding assay). It is 3,800-fold selective for α₁-ARs over α₂-ARs (K_i = 871 nM). Tamsulosin antagonizes norepinephrine-induced contraction of isolated rabbit aorta (pA₂ = 10.11) but has no effect on contraction stimulated by histamine, serotonin , angiotensin II , or prostaglandin F_2α . In vivo, tamsulosin reverses the pressor effect of phenylephrine (Item Nos. 17205 | 18619) in pithed rats. It reversibly reduces fertility in male rats when administered at a dose of 0.15 mg/kg. Tamsulosin (1-100 μg/kg) also reduces prostatic pressure in a dose-dependent manner with minimal hypotensive effects in anesthetized dogs. Formulations containing tamsulosin have been used for the treatment of benign prostatic hyperplasia.
Chemische Eigenschaften
White to Off-White Solid
Originator
Contiflo OD,Ranbaxy Laboratories,India
Verwenden
An α1-adrenoceptor antagonist
Verwenden
(R)-Tamsulosin is a specific α1-adrenoceptor antagonist. It is used in the treatment of benign prostatic hypertrophy.
Verwenden
Specific α1-adrenoceptor antagonist. Used in the treatment of benign prostatic hypertrophy.
Verwenden
antineoplastic, alkylating agent
Verwenden
Specific a1-adrenoceptor antagonist. Used in the treatment of benign prostatic hypertrophy
Definition
ChEBI: Tamsulosin hydrochloride is a hydrochloride resulting from the reaction of equimolar amounts of tamulosin and hydrogen chloride. It has a role as an alpha-adrenergic antagonist and an antineoplastic agent. It contains a tamsulosin(1+). It is an enantiomer of an ent-tamsulosin hydrochloride.
Manufacturing Process
In 1,000 ml of acetonitrile was suspended 17 g of 5-{2-[2-(2- ethoxyphenoxy)ethylamino]-1-hydroxy-2-methylethyl}-2- methoxybenzenesulfonamide hydrochloride and while stirring the suspension, 9 g of thionyl chloride was added dropwise to the suspension at room temperature, whereby the product first dissolved and then began to crystallize gradually. After stirring the mixture for two days, the crystals formed were recovered by filtration, washed with chloroform and dried to provide 15 g of 5-{1-chloro-2-[2-(2-ethoxyphenoxy)ethylamino]-2-methylethyl}-2- methoxybenzenesulfonamide hydrochloride. Melting point: 197°-200°C.
In methanol was dissolved the 5-{1-chloro-2-[2-(2- ethoxyphenoxy)ethylamino]ethyl}-2-methoxybenzenesulfonamide hydrochloride and after adding thereto 10% palladium carbon, dechlorination was performed under hydrogen stream at normal temperature and pressure. The palladium carbon was filtered away and the filtrate was concentrated under reduced pressure to provide the 2-methoxy-5-{2-[2-(2- ethoxyphenoxy)ethylamino]ethyl}benzenesulfonamide hydrochloride, which was recrystallized from 120 ml of a mixture of methanol and ethanol (1:4 by volume ratio) to provide the colorless crystals thereof. The melting point of the 5-{2-[2-(2-ethoxyphenoxy)ethylamino]-2-methylethyl}-2- methoxybenzenesulfonamide hydrochloride: 254°-256°C.
Therapeutic Function
Antihypertensive
Allgemeine Beschreibung
Tamsulosin hydrochloride is a subtypeselective a₁A and a₁D adrenoceptor antagonist, which exists in two enantiomeric forms, of which the R-isomer is the pharmaceutically active component. It is used to reduce urinary obstruction and is also involved in relieving the symptoms associated with symptomatic benign prostatic hyperplasia.
Hazard
Moderately toxic by ingestion.
Biologische Aktivität
Selective α 1A -adrenoceptor antagonist (pK i values are 9.97, 9.64 and 8.86 for α 1A , α 1B and α 1D subtypes respectively). Decreases resting maximal urethral pressure with negligable effect on mean arterial blood pressure in vivo .
Biochem/physiol Actions
Tamsulosin is an α1A/1D-adrenoceptor antagonist used as a treatment of benign prostatic hypertrophy (BPH). Its activity as an ? blocker also affects the iris, and has led to complications during cataract surgery, a condition called "floppy iris" syndrome.
Lager
Desiccate at RT

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