Tamsulosin

Structural formula
General
Non-proprietary name	Tamsulosin
other names	( R ) - (-) - 5- {2- [2- (2-Ethoxyphenoxy) ethylamino] propyl} -2-methoxy-benzenesulfonamide
Molecular formula	C 20 H 28 N 2 O 5 S
Brief description	white to almost white powder (tamsulosin hydrochloride)
External identifiers / databases
EC number	600-716-9
ECHA InfoCard	100.109.780
PubChem	129211
ChemSpider	114457
DrugBank	DB00706
Wikidata	Q418480
Drug information
ATC code	G04 CA02
Drug class	Alpha blockers
Mechanism of action	α 1 -adrenoceptor - antagonist
properties
Molar mass	408.51 g · mol -1 (Tamsulosin) ; 444.97 g · mol -1 (Tamsulosin Hydrochloride) ;
Physical state	firmly
Melting point	228–230 ° C (tamsulosin hydrochloride)
solubility	poorly soluble in water, slightly soluble in formic acid , poorly soluble in ethanol (tamsulosin hydrochloride)
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Hydrochloride; Caution
H and P phrases	H: 302-315-319-335
	P: 261-305 + 351 + 338
Toxicological data	650 mg kg −1 ( LD 50 , rat , oral , hydrochloride)
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Tamsulosin is a drug from the class of alpha-receptor blockers used to treat symptoms of benign prostatic hyperplasia (BPH) and requires a doctor's prescription. Tamsulosin is used in pharmaceuticals as tamsulosin hydrochloride .

pharmacology

Applications and clinical effects

Tamsulosin is approved for the treatment of symptoms of the lower urinary tract in benign prostatic hyperplasia and is considered the first choice for this indication. Compared to other alpha blockers such as doxazosin and alfuzosin , it has a lower effect on blood pressure (which, however, cannot always be ruled out).

A clinical study with kidney stone patients after ESWL treatment showed that patients treated with tamsulosin were better able to pass stone debris.

In the treatment of prostate cancer with low-dose-rate brachytherapy , so-called seeds are permanently inserted into the prostate . Urination, dysuria, and polyuria are common in the first 6 months after the procedure . The urological symptoms can be reduced by a prophylactic administration of tamsulosin.

Mechanism of action

Tamsulosin is an antagonist at α ₁ -adrenoceptors . In contrast to other alpha blockers, it shows a comparatively high antagonistic selectivity for prostatic α _{1A / 1L} adrenoceptors. On the one hand, this receptor selectivity leads to a relaxation of the smooth muscles of the bladder neck, the urethra and the prostate, combined with an easier urine outflow and, on the other hand, is associated with a lower rate of side effects.

Since alpha blockade leads to relaxation of the smooth muscles in a gender-unspecific manner, it also improves the flow of urine in women, which has been proven in studies. Nevertheless, the approved indication for tamsulosin is still “Treatment of symptoms of the lower urinary tract ( LUTS ) in benign prostatic hyperplasia” and its use in women suffering from urinary retention associated with narrowing of the bladder and urethra is an off-label use .

Side effects

Despite the prostate selectivity of this alpha blocker, dizziness can occur frequently (1 to 10%) and occasionally (<1%) hypotension and orthostatic complaints; ejaculation disorders ( retrograde ejaculation ) are also frequently observed. Ejaculation disorder can be avoided in many cases by adjusting the dose. Rarely there may be a vascular -related syncope come to a sudden loss of power with loss of consciousness, further occasional to rare non-specific complaints of the gastrointestinal tract, such as nausea, diarrhea or constipation. In ophthalmology, a connection with the intraoperative “floppy iris syndrome” has been reported in cataract operations.

Interactions

Clinically relevant interactions are not known.

Trade names

Monopreparations

Aglandin (A), Alna (D, A), Flomax (USA), Omnic (D), Omix (CH), Pradif (CH), Prostacure (D), Prostadil (D), Prostalitan (D), Tamsublock (D ), Stichtulosin (A), tadin (D), numerous generics (D, A, CH)

literature

Lyseng-Williamson, KA (2002): Tamsulosin: an update of its role in the management of lower urinary tract symptoms. In: Drugs . 62 (1): 135-167. PMID 11790159

Individual evidence

^ The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, ISBN 0-911910-00-X , p. 1555.
↑ Entry on tamsulosin. In: Römpp Online . Georg Thieme Verlag, accessed on May 30, 2014.
↑ European Pharmacopoeia Commission (Ed.): EUROPEAN PHARMACOPOE 5TH EDITION . tape 5.0-5.8 , 2006.
↑ ^a ^b ^c data sheet Tamsulosin hydrochloride from Sigma-Aldrich , accessed on April 23, 2011 ( PDF ).
↑ EE Salem, WM Gamal, AE Abuzeid: Tamsulosin as an Expulsive Therapy for Steinstrasse After Extracorporeal Shock Wave Lithotripsy: A Randomized Controlled Study. In: UroToday Int J. (2010) Feb; 3 (1).
↑ Ralph C. Wang, Rebecca Smith-Bindman, Evans Whitaker, Jersey Neilson, Isabel Elaine Allen: Effect of Tamsulosin on Stone Passage for Ureteral Stones: A Systematic Review and Meta-analysis . In: Annals of Emergency Medicine . tape 69 , no. 3 , March 2017, p. 353–361.e3 , doi : 10.1016 / j.annemergmed.2016.06.044 ( elsevier.com [accessed November 23, 2019]).
↑ Mohamed A. Elshaikh, James C. Ulchaker, Chandana A. Reddy, Kenneth W. Angermeier, Eric A. Klein: Prophylactic tamsulosin (Flomax) in patients undergoing prostate 125I brachytherapy for prostate carcinoma: Final report of a double-blind placebo- controlled randomized study . In: International Journal of Radiation Oncology * Biology * Physics . tape 62 , no. 1 , May 2005, p. 164–169 , doi : 10.1016 / j.ijrobp.2004.09.036 ( elsevier.com [accessed November 23, 2019]).
↑ Gregory S Merrick, Wayne M Butler, Kent E Wallner, Zachariah Allen, Robert W Galbreath: Brachytherapy-related dysuria . In: BJU international . tape 95 , no. 4 , March 2005, ISSN 1464-4096 , p. 597-602 , doi : 10.1111 / j.1464-410X.2005.05346.x , PMID 15705087 .
↑ Laura E. Meyer, Jamie N. Brown: Tamsulosin for voiding dysfunction in women. In: International Urology and Nephrology. 44, No. 6, September 16, 2012, pp. 1649-1656, doi: 10.1007 / s11255-012-0275-0 , PMID 22983886 .
↑ Mohamed G. Soliman, Ahmed R. Abou-Ramadan, Ahmed S. El-Abd, Hassan H. El-Tatawy, Shawky A. El-Abd: Outcome of Modification of Dose and Time of Administration of Tamsulosin in Men with Abnormal Ejaculation . In: Urologia Internationalis . tape 102 , no. 4 , 2019, ISSN 0042-1138 , p. 482-486 , doi : 10.1159 / 000497295 ( karger.com [accessed November 23, 2019]).
↑ Core Safety Profiles of Tamsulosin 0.4 mg modified release hard capsules (PDF) and Tamsulosin 0.4 mg film coated prolonged release tablets (PDF) NL / H / PSUR / 0014/001 of March 23, 2010.
↑ PR Brogden et al .: Intraoperative floppy iris syndrome associated with tamsulosin. In: Can Fam Physician. July 2007; 53 (7), p. 1148.

[MerckIndex-1] The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, ISBN 0-911910-00-X , p. 1555.

[RÖMPP_Online-2] Entry on tamsulosin. In: Römpp Online . Georg Thieme Verlag, accessed on May 30, 2014.

[3] European Pharmacopoeia Commission (Ed.): EUROPEAN PHARMACOPOE 5TH EDITION . tape 5.0-5.8 , 2006.

[Sigma-4] ta sheet Tamsulosin hydrochloride from Sigma-Aldrich , accessed on April 23, 2011 ( PDF ).

[5] EE Salem, WM Gamal, AE Abuzeid: Tamsulosin as an Expulsive Therapy for Steinstrasse After Extracorporeal Shock Wave Lithotripsy: A Randomized Controlled Study. In: UroToday Int J. (2010) Feb; 3 (1).

[6] Ralph C. Wang, Rebecca Smith-Bindman, Evans Whitaker, Jersey Neilson, Isabel Elaine Allen: Effect of Tamsulosin on Stone Passage for Ureteral Stones: A Systematic Review and Meta-analysis . In: Annals of Emergency Medicine . tape 69 , no. 3 , March 2017, p. 353–361.e3 , doi : 10.1016 / j.annemergmed.2016.06.044 ( elsevier.com [accessed November 23, 2019]).

[7] Mohamed A. Elshaikh, James C. Ulchaker, Chandana A. Reddy, Kenneth W. Angermeier, Eric A. Klein: Prophylactic tamsulosin (Flomax) in patients undergoing prostate 125I brachytherapy for prostate carcinoma: Final report of a double-blind placebo- controlled randomized study . In: International Journal of Radiation Oncology * Biology * Physics . tape 62 , no. 1 , May 2005, p. 164–169 , doi : 10.1016 / j.ijrobp.2004.09.036 ( elsevier.com [accessed November 23, 2019]).

[8] Gregory S Merrick, Wayne M Butler, Kent E Wallner, Zachariah Allen, Robert W Galbreath: Brachytherapy-related dysuria . In: BJU international . tape 95 , no. 4 , March 2005, ISSN 1464-4096 , p. 597-602 , doi : 10.1111 / j.1464-410X.2005.05346.x , PMID 15705087 .

[9] Laura E. Meyer, Jamie N. Brown: Tamsulosin for voiding dysfunction in women. In: International Urology and Nephrology. 44, No. 6, September 16, 2012, pp. 1649-1656, doi: 10.1007 / s11255-012-0275-0 , PMID 22983886 .

[10] Mohamed G. Soliman, Ahmed R. Abou-Ramadan, Ahmed S. El-Abd, Hassan H. El-Tatawy, Shawky A. El-Abd: Outcome of Modification of Dose and Time of Administration of Tamsulosin in Men with Abnormal Ejaculation . In: Urologia Internationalis . tape 102 , no. 4 , 2019, ISSN 0042-1138 , p. 482-486 , doi : 10.1159 / 000497295 ( karger.com [accessed November 23, 2019]).

[11] Core Safety Profiles of Tamsulosin 0.4 mg modified release hard capsules (PDF) and Tamsulosin 0.4 mg film coated prolonged release tablets (PDF) NL / H / PSUR / 0014/001 of March 23, 2010.

[12] PR Brogden et al .: Intraoperative floppy iris syndrome associated with tamsulosin. In: Can Fam Physician. July 2007; 53 (7), p. 1148.