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Basic Information
CAS No.: 121268-17-5
Name: Alendronate sodium
Molecular Structure:
Molecular Structure of 121268-17-5 (Alendronate sodium)
Formula: C4H12NNaO7P2.3(H2O)
Molecular Weight: 271.079
Synonyms: (4-Amino-1-hydroxy-1-phosphono-butyl)phosphonic acid; sodium;Fosamax (TN);Alendronate sodium hydrate;sodium [4-amino-1-hydroxy-1-(hydroxy-oxido-phosphoryl)butyl]phosphonic acid trihydrate;Alendronate sodium hydrate (JAN);Alendronate Sodium (Fosamax);Alendronate Sodium BP;G-704,650;MK-217;
EINECS: 601-766-4
Density: 1.857 g/cm3
Melting Point: 245 °C(lit.)
Boiling Point: 616.7 °C at 760 mmHg
Flash Point: 326.7 °C
Solubility: Water, double-distilled: 10 mg/mL
Appearance: white crystalline solid
Hazard Symbols: Xn,Xi
Risk Codes: 22-36/37/38
Safety: 26-36-60
PSA: 211.45000
LogP: -0.32760
Synthetic route
56-12-2

4-amino-n-butyric acid

121268-17-5

sodium alendronate

Conditions
ConditionsYield
Stage #1: 4-amino-n-butyric acid With phosphonic Acid; methanesulfonic acid; phosphorus trichloride at 65℃;
Stage #2: With water Reflux;
Stage #3: With sodium hydroxide In water
91%
With phosphorous acid; phosphorus trichloride In methanesulfonic acid at 65℃;82%
Stage #1: 4-amino-n-butyric acid With 1-butyl-3-methylimidazolium Tetrafluoroborate; phosphorous acid; phosphorus trichloride In sulfolane at 75℃; for 3h;
Stage #2: With water In sulfolane at 105℃; for 3h;
Stage #3: With sodium hydroxide In sulfolane at 0 - 25℃; for 14h; pH=4.6; Reagent/catalyst;
80%
183959-44-6

tetraethyl 2-N-phthalimide-1-hydroxybutylidene-1,1-bisphosphonate

121268-17-5

sodium alendronate

Conditions
ConditionsYield
Stage #1: tetraethyl 2-N-phthalimide-1-hydroxybutylidene-1,1-bisphosphonate With hydrogenchloride Heating;
Stage #2: With sodium hydroxide pH=4.3 - 4.4;
90%
616-45-5

2-pyrrolidinon

121268-17-5

sodium alendronate

Conditions
ConditionsYield
Stage #1: 2-pyrrolidinon With phosphorus trichloride In water at 65 - 110℃; for 7.33333 - 7.41667h;
Stage #2: With methanesulfonic acid; phosphorus trichloride at 60 - 75℃; for 9h;
Stage #3: With sodium hydroxide; water Product distribution / selectivity; more than 3 stages;
82%
Stage #1: 2-pyrrolidinon With water; phosphorus trichloride at 65 - 110℃; for 7.33333 - 7.41667h; Heating / reflux;
Stage #2: With methanesulfonic acid; phosphorus trichloride at 60 - 75℃; for 9h;
Stage #3: With sodium hydroxide; methanesulfonic acid; water Product distribution / selectivity; more than 3 stages;
82%
Stage #1: 2-pyrrolidinon With methanesulfonic acid; water; phosphorus trichloride at 20 - 110℃; for 3.33333 - 8.41667h; Heating / reflux;
Stage #2: With methanesulfonic acid at 60 - 75℃; for 9h;
Stage #3: With sodium hydroxide; methanesulfonic acid; water Product distribution / selectivity; more than 3 stages;
81%
66376-36-1

4-amino-1-hydroxybutylidenebisphosphonic acid

121268-17-5

sodium alendronate

Conditions
ConditionsYield
With sodium carbonate In water for 3h; Heating;79%
With sodium hydroxide In water at 0 - 5℃; for 3h; pH=4.3;
With sodium hydroxide In water at 30 - 70℃;
1310-73-2

sodium hydroxide

121268-17-5

sodium alendronate

Conditions
ConditionsYield
Stage #1: 4-amino-n-butyric acid With phosphorous acid; phosphorus trichloride In acetonitrile at 55 - 75℃; for 6 - 9h;
Stage #2: With water In acetonitrile at 60 - 100℃; for 4 - 6h;
Stage #3: sodium hydroxide at 55 - 65℃; pH=4.4 - 4.8;
69.6%

C13H31NO8P2Si

121268-17-5

sodium alendronate

Conditions
ConditionsYield
Stage #1: C13H31NO8P2Si With hydrogenchloride In water for 17h; Reflux;
Stage #2: With sodium hydroxide In water at 25℃; pH=4.3;
26.84 g
75-15-0

carbon disulfide

121268-17-5

sodium alendronate

sodium alendronate dithiocarbamate

Conditions
ConditionsYield
Stage #1: sodium alendronate With sodium hydroxide In water Cooling with ice;
Stage #2: carbon disulfide In water for 24h; Cooling with ice;
95%
With sodium hydroxide In water at 0℃; for 24h;94%

C18H26N4O12

121268-17-5

sodium alendronate

C18H34N4O16P2

Conditions
ConditionsYield
With triethylamine In water at 20℃; for 24h;92%
132178-37-1

2,5-dioxopyrrolidin-1-yl pent-4-ynoate

121268-17-5

sodium alendronate

952615-43-9

1-hydroxy-4-pent-4-ynamidobutane-1,1-diyldiphosphonic acid

Conditions
ConditionsYield
Stage #1: sodium alendronate With sodium hydroxide In water pH=8.5;
Stage #2: 2,5-dioxopyrrolidin-1-yl pent-4-ynoate In water; acetonitrile at 22℃; for 8h; pH=8.5;
89.9%
122-04-3

4-nitro-benzoyl chloride

121268-17-5

sodium alendronate

Na(1+)*C11H15N2O10P2(1-)

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran; water at 20℃; for 2h; pH=11;86%
Downstream Products
66376-36-1
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    Alendronate sodium Basic information Product Name: Alendronate sodium Synonyms: G-704650;Fosamsx;4-amino-1-hydroxy-1-phosphonobutyl phosphonic acid, monosodium, MK-217;Alendronate trihydrate sodium;P,P'-(4-Amino-1-hydroxybutylidene)bis-ph

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Chemistry

Empirical Formula: C4H18NNaO10P2
Molecular Weight: 325.1237
Nominal Mass: 325 Da
Average Mass: 325.1237 Da
Monoisotopic Mass: 325.030363 Da 
Flash Point: 326.7 °C
Enthalpy of Vaporization: 104.87 kJ/mol
Boiling Point: 616.7 °C at 760 mmHg
Vapour Pressure: 8.72E-18 mmHg at 25 °C
Melting point: 245 °C(lit.)
Storage tempreture: -20 °C
Solubility: Water, double-distilled: 10 mg/mL
Appearance: White crystalline solid
Structure of Alendronate sodium (CAS NO.121268-17-5):
                            
IUPAC Name: Sodium (4-amino-1-hydroxy-1-phosphonobutyl)-hydroxyphosphinate trihydrate
Canonical SMILES: C(CC(O)(P(=O)(O)O)P(=O)(O)[O-])CN.O.O.O.[Na+]
InChI: InChI=1S/C4H13NO7P2.Na.3H2O/c5-3-1-2-4(6,13(7,8)9)14(10,11)12;;;;/h6H,1-3,5H2,(H2,7,8,9)(H2,10,11,12);;3*1H2/q;+1;;;/p-1
InChIKey: DCSBSVSZJRSITC-UHFFFAOYSA-M
Product Category of 2-Chloro-5-nitroanisole (CAS NO.1009-36-5): Miscellaneous Biochemicals;Osteoporosis;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Miscellaneous Compounds

Uses

 Alendronate sodium (CAS NO.121268-17-5)  is a bisphosphonate drug used for osteoporosis and several other bone diseases. And it used for prophylaxis and in treatment of female and male osteoporosis. It has been used for prevention and treatment of corticosteroid-associated osteoporosis together with supplements of calcium and vitamin D, and used for paget's disease.

Toxicity Data With Reference

1.    

ivn-rat LDLo:30 mg/kg

    KSRNAM    Kiso to Rinsho. Clinical Report. 28 (1994),3229.
2.    

ivn-dog LDLo:10 mg/kg

    KSRNAM    Kiso to Rinsho. Clinical Report. 28 (1994),3229.

Safety Profile

A poison by intravenous route. Experimental reproductive effects. When heated to decomposition it emits toxic vapors of NOx, POx, and NaO.
Hazard Codes: HarmfulXn,IrritantXi
The Risk Statements:
22:  Harmful if swallowed 
36/37/38:  Irritating to eyes, respiratory system and skin
The Safety Statements:
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 
36:  Wear suitable protective clothing  
WGK Germany: 3

Specification

 Alendronate sodium , its cas register number is 121268-17-5. It also can be called Fosamax ; Monosodium alendronate ; Alendronic acid monosodium salt ; Fosalan ; Alendros ; Bifosa ; NeoBon ; 4-Amino-1-hydroxybutylidene-1,1-bisphosphonic acid monosodium salt ; and Osteovan . It is marketed alone as well as in combination with vitamin D, and Merck's U.S. patent on alendronate expired in 2008 and Merck lost a series of appeals to block a generic version of the drug from being certified by the U.S. Food and Drug Administration (FDA). Alendronate inhibits osteoclast-mediated bone-resorption.