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106463-17-6

Basic Information
CAS No.: 106463-17-6
Name: Tamsulosin hydrochloride
Molecular Structure:
Molecular Structure of 106463-17-6 (Tamsulosin hydrochloride)
Formula: C20H29ClN2O5S
Molecular Weight: 445.02
Synonyms: Benzenesulfonamide,5-[(2R)-2-[[2-(2-ethoxyphenoxy)ethyl]amino]propyl]-2-methoxy-,monohydrochloride (9CI);Benzenesulfonamide,5-[2-[[2-(2-ethoxyphenoxy)ethyl]amino]propyl]-2-methoxy-, monohydrochloride,(R)-;(-)-YM 12617;(R)-(-)-YM 12617;Flomax;Harnal;LY 253351;Omic;Omnic;YM 12617-1;YM 617;Yutanal;Tamsulosin HCl;
EINECS: 629-756-5
Density:
Melting Point: 228-230 °C
Boiling Point: 595.5 °C at 760 mmHg
Flash Point: 313.9 °C
Solubility:
Appearance: white to off-white solid
Hazard Symbols: Xn
Risk Codes: 22-36/37/38
Safety: 26
Transport Information:
PSA: 108.26000
LogP: 4.51290
Synthetic route

(S)-tamsulosin-(R)-BPA salt

106463-17-6

(+)-Tamsulosin

Conditions
ConditionsYield
With ammonia In water at 45 - 50℃; for 0.5h; pH=10.5; Product distribution / selectivity;83.4%

(R/S)-5-[2-[[2-(2-ethoxyphenoxy)ethyl]amino]propyl]-2-methoxybenzenesulfonamide D-10-camphorsulfonic acid salt

A

106463-17-6

(+)-Tamsulosin

B

106133-20-4

(R)-tamsulosin

Conditions
ConditionsYield
With sodium hydrogencarbonate In dichloromethane; water
882494-06-6

oxalate salt of tamsulosin

35193-63-6, 35193-64-7, 39648-67-4, 50574-52-2

(S)-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate

(R)-tamsulosin-(S)-BPA salt

B

106463-17-6

(+)-Tamsulosin

Conditions
ConditionsYield
In water; acetone at 27 - 55℃; for 5.41667h; Product distribution / selectivity;

(S)-tamsulosin-(S)-BPA salt

106463-17-6

(+)-Tamsulosin

Conditions
ConditionsYield
With ammonia In water at 45 - 50℃; for 0.5h; pH=10.5; Product distribution / selectivity;
852619-17-1

C20H26N2O5S

A

106463-17-6

(+)-Tamsulosin

B

106133-20-4

(R)-tamsulosin

Conditions
ConditionsYield
Stage #1: C20H26N2O5S; (S)-chloro[(1,2,3,4-η)-pentamethyl-2,4-cyclopentadien-1-yl] [N-(2-methoxy-3-dibenzofuranyl)-2-pyrrolidinecarboxamidato-κN1,κN2]iridium In acetonitrile at -3 - 3℃; for 0.5h;
Stage #2: With formic acid; triethylamine In acetonitrile at -3 - 20℃;
A n/a
B n/a
106463-17-6

(+)-Tamsulosin

(+)-Tamsulosin hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In methanol at 45℃; Product distribution / selectivity;77.5%
35963-20-3

(R)-10-camphorsulfonic acid

106463-17-6

(+)-Tamsulosin

106133-20-4

(R)-tamsulosin

521300-99-2

(R)-tamsarocin (-)-camphor-10-sulfonate

Conditions
ConditionsYield
Stage #1: (R)-10-camphorsulfonic acid; (+)-Tamsulosin; (R)-tamsulosin In water; acetone at 20℃; for 20 - 24h;
Stage #2:
Stage #3: at 20℃;
Raw Materials
852619-17-1
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    Product name: Tamsulosin HCL CAS No.:106463-17-6 Molecule Formula:C20H29ClN2O5S Molecule Weight:444.97 Purity: 99.0% Package: 25kg/drum Description: White crystalline powder Manufacture Standards:Enterprise Standard

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Chemistry

Molecular Structure of Tamsulosin hydrochloride (CAS NO.106463-17-6):

IUPAC Name: (7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione hydrochloride
CAS Registry Number : 106463-17-6
Empirical Formula: C20H29ClN2O5S
Molecular Weight: 444.9727
H bond acceptors: 7
H bond donors: 3
Freely Rotating Bonds: 11
Polar Surface Area: 76.69Å2
Flash Point: 313.9 °C
Enthalpy of Vaporization: 88.74 kJ/mol
Boiling Point: 595.5 °C at 760 mmHg
Vapour Pressure: 3.79E-14 mmHg at 25°C
Melting point : 228-230 oC
InChI
InChI=1/C20H28N2O5S.ClH/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);1H/t15-;/m1./s1
Smiles
c1(c(ccc(c1)C[C@H](NCCOc1c(cccc1)OCC)C)OC)S(N)(=O)=O.Cl
Product Categories: Active Pharmaceutical Ingredients; In treatment of benign prostatic hypertrophy; Treatment of BPH; Chiral Reagents; Intermediates & Fine Chemicals; Pharmaceuticals; Isotope Labeled Compounds; Tamsulosin; Adrenoceptor

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD oral > 1gm/kg (1000mg/kg) SENSE ORGANS AND SPECIAL SENSES: MIOSIS (PUPILLARY CONSTRICTION): EYE

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Kiso to Rinsho. Clinical Report. Vol. 24, Pg. 5085, 1990.
mouse LD50 intravenous 98mg/kg (98mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 35, Pg. 2169, 1993.
mouse LD50 oral 1023mg/kg (1023mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 35, Pg. 2169, 1993.
mouse LD50 subcutaneous 254mg/kg (254mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 35, Pg. 2169, 1993.
rat LD50 intravenous 70mg/kg (70mg/kg) SENSE ORGANS AND SPECIAL SENSES: CHROMODACYRORREA: EYE

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Kiso to Rinsho. Clinical Report. Vol. 24, Pg. 5071, 1990.
rat LD50 oral 650mg/kg (650mg/kg) SENSE ORGANS AND SPECIAL SENSES: CHROMODACYRORREA: EYE

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Kiso to Rinsho. Clinical Report. Vol. 24, Pg. 5071, 1990.
rat LD50 subcutaneous 347mg/kg (347mg/kg) SENSE ORGANS AND SPECIAL SENSES: CHROMODACYRORREA: EYE

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH
Kiso to Rinsho. Clinical Report. Vol. 24, Pg. 5071, 1990.

Safety Profile

A poison by subcutaneous and intravenous routes. Moderately toxic by ingestion. When heated to decomposition it emits toxic vapors of NOx, SOx, HCl, and Cl.

Specification

 Tamsulosin hydrochloride , with CAS number of 106463-17-6, can be called (-)-(R)-5-(2-((2-(o-Ethoxyphenoxy)ethyl)amino)propyl)-2-methoxybenzenesulfonamide monohydrochloride ; Benzenesulfonamide, 5-(2-((2-(2-ethoxyphenoxy)ethyl)amino)propyl)-2-methoxy-, monohydrochloride, (R)- ; R-(-)-5-(2-((2-(2-Ethoxyphenoxy)ethyl)amino)propyl)-2-methoxybenzenesulfonamide hydrochloride ; Tamsulosin HCl . It is a white to off-white solid, Tamsulosin hydrochloride (CAS NO.106463-17-6) extended-release tablets are marketed under the trade names Flomax, Flomaxtra and Urimax, though generic non-modified release capsules are still approved and marketed in many countries, such as Canada. The U.S. patent for Flomax is set to expire October 2009.