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Tamsulosin(CAS No. 106133-20-4)

Tamsulosin C20H28N2O5S (cas 106133-20-4) Molecular Structure

106133-20-4 Structure

Identification and Related Records

【Name】
Tamsulosin
【Iupac name】
5-[(2R)-2-[2-(2-ethoxyphenoxy)ethylamino]propyl]-2-
methoxybenzenesulfonamide
【CAS Registry number】
106133-20-4
【Synonyms】
Benzenesulfonamide,5-[(2R)-2-[[2-(2-ethoxyphenoxy) ethyl]amino]propyl]-2-methoxy-
Amsulosin
Tamsulosine [INN-French]
Tamsulosinum [INN-Latin]
Tamsulosina [INN-Spanish]
5-[(2R)-2-[2-(2-ethoxyphenoxy)ethylamino]propyl]-2-methoxy-benzenesulfonamide
Benzenesulfonamide, 5-(2-((2-(2-ethoxyphenoxy)ethyl)amino)propyl)-2-methoxy-, (R)-
(R)-5-(2-((2-(2-Ethoxyphenoxy)ethyl)amino)propyl)-2-methoxybenzenesulfonamide
Tamsulosin Hydrochloride
【Molecular Formula】
C20H28N2O5S (Products with the same molecular formula)
【Molecular Weight】
408.51172
【Inchi】
InChI=1S/C20H28N2O5S/c1-4-26-17-7-5-6-8-18(17)27-12-11-22-15(2)13-16-9-10-19(25-3)20(14-16)28(21,23)24/h5-10,14-15,22H,4,11-13H2,1-3H3,(H2,21,23,24)/t15-/m1/s1
【InChIKey】
DRHKJLXJIQTDTD-OAHLLOKOSA-N
【Canonical SMILES】
CCOC1=CC=CC=C1OCCNC(C)CC2=CC(=C(C=C2)OC)S(=O)(=O)N
【Isomers smiles】
CCOC1=CC=CC=C1OCCN[C@H](C)CC2=CC(=C(C=C2)OC)S(=O)(=O)N
【MOL File】
106133-20-4.mol

Chemical and Physical Properties

【Appearance】
White crystals
【Density】
1.191 g/cm3
【Melting Point】
226-228℃
【Boiling Point】
595.5 °C at 760 mmHg
【Vapour】
3.79E-14mmHg at 25°C
【Refractive Index】
1.553
【Flash Point】
313.9 °C
【Water】
sparingly soluble in water and in methanol
【Solubilities】
sparingly soluble in water and in methanol
【Computed Properties】
Molecular Weight:408.51172 [g/mol]
Molecular Formula:C20H28N2O5S
XLogP3-AA:2.7
H-Bond Donor:2
H-Bond Acceptor:7
Rotatable Bond Count:11
Exact Mass:408.171893
MonoIsotopic Mass:408.171893
Topological Polar Surface Area:108
Heavy Atom Count:28
Formal Charge:0
Complexity:539
Isotope Atom Count:0
Defined Atom Stereocenter Count:1
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:5
Feature 3D Donor Count:2
Feature 3D Cation Count:1
Feature 3D Ring Count:2
Effective Rotor Count:11
Conformer Sampling RMSD:1
CID Conformer Count:121

Safety and Handling

【Formulations/Preparations】
Formulations: (AHFS, 2009) Formulations: (AHFS, 2009) Route Dosage Form Strength Brand (Manufacturer) Oral capsules 0.4 mg Flomax; (Boehringer Ingelheim)
【Exposure Standards and Regulations】
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl tamsulosin hydrochloride, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Tamsulosin hydrochloride/
【Specification】

The Tamsulosin ,?with cas registry number of 106133-20-4, belongs to?the classification codes of?(1)adrenergic agents ; (2)adrenergic antagonists ; (3)adrenergic alpha-antagonists ; (4)antineoplastic agents ; (5)neurotransmitter agents. It is also called (R)-5-(2-((2-(2-Ethoxyphenoxy)ethyl)amino)propyl)-2-methoxybenzenesulfonamide ; Benzenesulfonamide, 5-(2-((2-(2-ethoxyphenoxy)ethyl)amino)propyl)-2-methoxy-, (R)- . Its IUPAC name is 5-[(2R)-2-[2-(2-ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulfonamide?. Its systematic name is 5-[(2R)-2-{[2-(2-ethoxyphenoxy)ethyl]amino}propyl]-2-methoxybenzenesulfonamide .

Physical properties of?Tamsulosin are:?(1) ACD/LogP: 2.24 ; (2) # of Rule of 5 Violations: 0 ; (3) ACD/LogD (pH 5.5): -0.66 ; (4) ACD/LogD (pH 7.4): 0.79 ; (5) ACD/BCF (pH 5.5): 1 ; (6) ACD/BCF (pH 7.4): 1.06 ; (7) ACD/KOC (pH 5.5): 1 ; (8) ACD/KOC (pH 7.4): 14.13 ; (9) #H bond acceptors: 7 ; (10) #H bond donors: 3 ; (11) #Freely Rotating Bonds: 11 ; (12) Index of Refraction: 1.553 ; (13) Molar Refractivity: 109.78 cm3 ; (14) Molar Volume: 342.8 cm3 ; (15) Surface Tension: 45.2 dyne/cm ; (16) Density: 1.191 g/cm3 ; (17) Flash Point: 313.9 °C ; (18) Enthalpy of Vaporization: 88.74 kJ/mol ; (19) Boiling Point: 595.5 °C at 760 mmHg ; (20) Vapour Pressure: 3.79E-14 mmHg at 25°C.

Uses of?Tamsulosin : this chemical has been used as a drug. It is an alpha 1 adrenoreceptor blocker which?is used for treatment of?benign prostatic hyperplasia and?kidney stones.

You can still convert the following datas into molecular structure:
(1) SMILES:O=S(=O)(N)c1c(OC)ccc(c1)C[C@H](NCCOc2ccccc2OCC)C;
(2) InChI:InChI=1/C20H28N2O5S/c1-4-26-17-7-5-6-8-18(17)27-12-11-22-15(2)13-16-9-10-19(25-3)20(14-16)28(21,23)24/h5-10,14-15,22H,4,11-13H2,1-3H3,(H2,21,23,24)/t15-/m1/s1;
(3) InChIKey:DRHKJLXJIQTDTD-OAHLLOKOBW

【Octanol/Water Partition Coefficient】
log Kow = 2.47 (est)
【Disposal Methods】
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.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Preparation: K. Imai et al., EP 34432; eidem, US 4703063 (1981, 1987 both to Yamanouchi).

Biomedical Effects and Toxicity

【Pharmacological Action】
- Drugs that bind to and block the activation of ADRENERGIC ALPHA-1 RECEPTORS.
【Therapeutic Uses】
Sulfonamides; Adrenergic alpha-Antagonists
Tamsulosin hydrochloride capsules are indicated for the treatment of the signs and symptoms of benign prostatic hyperplasia (BPH). /Included in US product label/
Tamsulosin hydrochloride capsules are not intended for use as an antihypertensive drug. /Included in US product label/
Tamsulosin hydrochloride capsules are not indicated for use in women. /Included in US product label/
/EXPTL Ther:/ ...Meta-analysis was performed of randomized clinical trials of alpha-blockers for the treatment of ureteral stones. The primary outcome was overall stone expulsion rate. Risk ratios and risk differences were estimated using DerSimonian and Laird random effects models. Eleven trials (911 participants) met inclusion criteria for this study. Pooled analysis demonstrated significantly increased rates of stone expulsion with alpha-blocker therapy. Compared to patients receiving conservative therapy only, patients receiving conservative therapy plus alpha-blockers were 44% more likely to spontaneously expel the stones (RR 1.44, 95% CI 1.31 to 1.59, p<0.001), and stone expulsion incidence increased significantly (RD 0.28, 95% CI 0.22 to 0.34, p<0.001). Sensitivity and subgroup analyses categorized by specific alpha-blocker, prior use of shock wave lithotripsy and stone size produced similar effect estimates, but were generally less precise due to smaller sample sizes. The largest subgroup of trials (664 participants) studied tamsulosin without prior shock wave lithotripsy (RR 1.44, 95% CI 1.32 to 1.58; RD 0.29, 95% CI 0.23 to 0.35). alpha-Blocker therapy is associated with significantly increased rates of distal ureteral stone expulsion. [Parsons J et al; J Urol 177 (3): 983-7(2007). Available from, as of July 7, 2009:]
【Biomedical Effects and Toxicity】
In patients with moderate hepatic impairment, protein binding is altered, resulting in changes in overall plasma concentrations; however, no substantial alterations in intrinsic clearance and concentrations of unbound drug.
In patients with renal impairment, protein binding is altered, resulting in changes in overall plasma concentrations, however, no substantial alterations in intrinsic clearance and concentrations of unbound drug.
Absorption of tamsulosin hydrochloride ... is essentially complete (>90%) following oral administration under fasting conditions. Tamsulosin hydrochloride exhibits linear kinetics following single and multiple dosing, with achievement of steady-state concentrations by the fifth day of once-a-day dosing.
Essentially completely absorbed following oral administration under fasting conditions; peak plasma concentrations attained within 4-5 hours.
Food delays time to peak plasma concentration by about 2 hours. When administered under fasting conditions, bioavailability and peak plasma concentration are increased by 30 and 40-70%, respectively, compared with fed state.
The mean steady-state apparent volume of distribution of tamsulosin hydrochloride after intravenous administration to ten healthy male adults was 16L, which is suggestive of distribution into extracellular fluids in the body.
Appears to distribute into extracellular fluids in humans. In animals, distributed into kidney, prostate, liver, gallbladder, heart, aorta, and brown fat, with minimal distribution into brain, spinal cord, and testes.
94-99% /protein bound/ (mainly to alpha1-acid glycoprotein).
Tamsulosin hydrochloride undergoes restrictive clearance in humans, with a relatively low systemic clearance (2.88 L/hr).
In males 55-75 years of age, intrinsic clearance is decreased and elimination half-life is prolonged, resulting in a 40% increase in AUC compared with males 20-32 years of age.
On administration of the radiolabeled dose of tamsulosin hydrochloride to four healthy volunteers, 97% of the administered radioactivity was recovered, with urine (76%) representing the primary route of excretion compared to feces (21%) over 168 hours.
Excreted in urine (76%) and feces (21%).
The pharmacokinetics of tamsulosin hydrochloride was investigated after single iv and oral dosing to rats and dogs, and oral dosing to healthy male volunteers. After iv dosing, plasma tamsulosin concentrations declined in an apparent biexponential manner with terminal half-lives of 0.32 hr in rats and 1.13 hr in dogs. Values for total blood clearance (CLB) were 6.57 L/hr/kg in rats and 1.61 L/hr/kg in dogs, suggesting "hepatic blood flow-limited" and "intermediate flow-dependent" clearance, respectively. After oral dosing, tamsulosin was rapidly absorbed and reached maximum levels within 1 hr in rats and dogs, and at 1.0-1.8 hr in humans. Values for oral clearance (CLoral) in rats, dogs, and humans were 34.5-113.6, 3.01-3. 99, and 0.031-0.041 L/hr/kg, respectively, showing wide variation among these species. The absolute bioavailability (F) increased with dose in rats (from 6.9% at 1 mg/kg to 22.8% at 10 mg/kg), but was almost constant in dogs (29.7-42.0% over the 0.3-3 mg/kg dose range). The plasma protein binding of 14C-tamsulosin in humans was much higher (98.9-99.1%) than that in rats and dogs (79.0-80.6% and 90. 2-90.3%, respectively). The ratio of blood to plasma concentrations (RB) value in rats, dogs, and humans decreased in this order (1.2, 0. 72, and 0.53, respectively), corresponding to the decrease in plasma unbound fraction (fu) in these species. These results imply that the large interspecies difference in CLoral is attributable to a difference not only in hepatic metabolism but also in protein binding among these species. [Matsushima H et al; Drug Metab Dispos. 1998 Mar;26(3):240-5 (1998). Available from, as of July 7, 2009:] PubMed Abstract
The present study was undertaken to simultaneously measure alpha1 adrenoceptors in rat tissues by (3H)tamsulosin in vivo. In vivo specific (3H)tamsulosin binding was observed in the prostate, vas deferens, aorta, submaxillary gland, spleen, heart, lung, and kidney after i.v. injection of the ligand but not in the cerebral cortex and liver. Specific (3H)tamsulosin binding in the kidney, lung, heart, and spleen was greatest at 3 min after iv injection and declined rapidly with the disappearance of (3H)tamsulosin from the plasma. On the other hand, (3H)tamsulosin binding in the prostate and aorta peaked at 10 to 60 min after i.v. injection, and a considerable level of specific binding in both tissues persisted up to 240 min. The most sustained binding of (3H)tamsulosin occurred in the submaxillary gland. In vivo specific (3H)tamsulosin binding in rat tissues was effectively inhibited by the coinjection of low doses of unlabeled tamsulosin, prazosin, and terazosin with the radioligand but not by relatively high doses of yohimbine and propranolol. Based on estimated ID50 values, in vivo inhibitory effect of tamsulosin compared with prazosin was 5 to 14 times greater in rat tissues except the spleen, which showed 1.6 times less potent than prazosin. From ratios of ID50 (spleen) to ID50 (submaxillary gland) or ID50 (prostate), tamsulosin was 9 and 19 times, respectively, greater than prazosin in selectivity of alpha1 adrenoceptors in the submaxillary gland and prostate versus the spleen, respectively, suggesting that tamsulosin binds to alpha1A subtype with higher affinity than alpha1B subtype in vivo. ... [Yamada S et al; J Pharmacol Exp Ther 289 (3): 1575-83 (1999). Available from, as of July 7, 2009:] PubMed Abstract

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 3.0X10+4(SRC), determined from a structure estimation method(2), indicates that tamsulosin is expected to be immobile in soil(SRC). Volatilization of tamsulosin from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.9X10-15 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Tamsulosin is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.0X10-11 mm Hg at 25 deg C(SRC), determined from a fragment constant method(4). Biodegradation data were not available(SRC, 2009).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 3.0X10+4(SRC), determined from a structure estimation method(2), indicates that tamsulosin is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 4.9X10-15 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 20(SRC), from an estimated log Kow of 2.5(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2009).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), tamsulosin, which has an estimated vapor pressure of 4.0X10-11 mm Hg at 25 deg C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase tamsulosin may be removed from the air by wet or dry deposition(SRC). Tamsulosin does not contain chromophores that absorb at wavelengths >290 nm(3) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

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