1953-02-2

Basic information

• Product Name: Tiopronin
• Synonyms: A-MERCAPTOPROPIONYL GLYCINE;ALPHA-MERCAPTO PROPIONYL GLYCINE;LABOTEST-BB LT00451995;TIOPRONIN;N-(2-MERCAPTOPROPIONYL)GLYCINE;Tiopronin, Vetranal;N-(2-MERCAPTOPROPIONYL)GLYCINE 99%;TOPRONIN
• CAS NO: 1953-02-2
• Molecular Formula: C₅H₉NO₃S
• Molecular Weight: 163.19
• EINECS: 217-778-4
• Product Categories: Pharmaceutical material and intermeidates;API;Amino Acids & Derivatives;Intermediates & Fine Chemicals;Isotope Labelled Compounds;Pharmaceuticals;Sulfur & Selenium Compounds;ACADIONE
• Mol File: 1953-02-2.mol

Chemical Properties

• Melting Point: 93-98 °C
• Boiling Point: 418.3 °C at 760 mmHg
• Flash Point: 206.8 °C
• Appearance: /solid
• Density: 1.249 (estimate)
• Vapor Pressure: 3.6E-08mmHg at 25°C
• Refractive Index: 1.5216 (estimate)
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 3.36±0.10(Predicted)
• Merck: 14,9453
• BRN: 1859822
• CAS DataBase Reference: Tiopronin(CAS DataBase Reference)
• NIST Chemistry Reference: Tiopronin(1953-02-2)
• EPA Substance Registry System: Tiopronin(1953-02-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36/37
• WGK Germany: 3
• RTECS: MC0596500
• Hazardous Substances Data: 1953-02-2(Hazardous Substances Data)

Usage

Uses

Used in Biolistic Delivery:
Tiopronin is used in the preparation of polyethylenimine (PEI)-coated gold microparticles (PEI-gold) for biolistic delivery of nucleic acids, facilitating efficient gene transfer and expression in various applications.
Used in Neuroprotection Research:
Tiopronin serves as a reactive oxygen species (ROS) inhibitor in studying its effect on lysophosphatidylcholine (LPC)-induced inflammasome activation and the role of ROS at the reperfusion stage in in vivo isoflurane preconditioning-induced neuroprotection.
Used in Antidote Therapy:
Tiopronin is used as an antidote against heavy metal poisoning, protecting the body from the toxic effects of heavy metals.
Used as a Hepatoprotectant:
Tiopronin acts as a hepatoprotectant, increasing the activity of antioxidant enzymes such as superoxide dismutase and glutathione peroxidase, and reversing hepatocyte degeneration in a rat model of high-fat diet-induced non-alcoholic steatohepatitis.
Used as a Mucolytic:
Tiopronin is used as a mucolytic, helping to break down and thin mucus in the respiratory tract, making it easier to expel.
Used in the Treatment of Cystine Urolithiasis:
Tiopronin is used in the treatment of cystine urolithiasis in children, helping to dissolve cystine stones and prevent their recurrence.
Used in the Management of Rheumatoid Polyarthritis:
Tiopronin is used in the management of rheumatoid polyarthritis, possibly due to its inhibitory effect on the free oxygen radicals produced by inflammatory macrophages and granulocytes.
Brand Name:
Thiola

Originator

Roussel-Uclaf (Japan)

Manufacturing Process

α-Benzylmercaptopropionic acid (melting point 76°C to 78°C; 100 g) prepared by condensation of α-mercaptopropionic acid with benzyl chloride is allowed to stand overnight with 80 g of thionyl chloride. After removal of excess thionyl chloride distillation in vacuo gives 70 g of α-benzylmercaptopropionic acid chloride of boiling point 138°C to 139°C/7 to 8 mm Hg. Then, 25 g of glycine is dissolved in 165 ml of 2 N sodium hydroxide solution and 70 g of α-benzylmercaptopropionic acid chloride and 100 ml of 2 N sodium hydroxide solution are dropped thereinto simultaneously at 3°C to 5°C. The solution is then stirred at room temperature for 3 to 4 hours to complete the reaction, the reaction solution is washed with ether, the aqueous layer is acidified with hydrochloric acid, and the resulting crystals are collected by filtration. These are recrystallized from a mixture of methanol and ethyl acetate to give 60 g of α-benzylmercaptopropionylglycine of melting point 133°C to 134°C. This α-benzylmercaptopropionylglycine (60 g) is dissolved in 400 ml of liquid ammonia, kept at about -50°C, and 12 g of sodium metal is gradually added thereto. After the reaction, excess ammonia is removed therefrom, the residue is dissolved in water, washed with ether and the residual aqueous layer is adjusted to pH 1 with hydrochloric acid and concentrated in vacuo in a stream of hydrogen sulfide. The crystalline residue is dried and recrystallized from ethyl acetate to give 25 g of α-mercaptopropionylglycine of melting point 95°C to 97°C.

Therapeutic Function

Antidote (heavy metal)

Biochem/physiol Actions

N-(2-Mercaptopropionyl)glycine (NMPG) is a thiol compound associated with autoimmune hypoglycemia. It is a diffusible antioxidant and reduces the severity of colonic injury. NMPG also relieves myeloperoxidase activity and stimulates hypoxia-inducible factor-1 (HIF-1) - vascular endothelial growth factor (VEGF) pathway for ulcer healing.

Veterinary Drugs and Treatments

Tiopronin is indicated for the prevention of cystine urolithiasis in patients where dietary therapy combined with urinary alkalinization is not completely effective. It may also be useful in combination with urine alkalinization to dissolve stones.

InChI:InChI=1/C5H9NO3S/c1-3(10)5(9)6-2-4(7)8/h3,10H,2H2,1H3,(H,6,9)(H,7,8)

Synthetic route

2-chloropropionylglycine (85038-45-5) → N-(2-mercaptopropionyl)glycine (1953-02-2)

Conditions	Yield
Stage #1: 2-chloropropionylglycine With sodium disulfide; sulfuric acid; sodium carbonate In water at 45℃; for 0.05h; Large scale; Stage #2: With sulfuric acid; zinc at 5 - 20℃; for 1.05h; Temperature; Large scale;	76.5%

N-(2-bromo-propionyl)-glycine (25413-03-0) → N-(2-mercaptopropionyl)glycine (1953-02-2)

Conditions	Yield
With hydrogen sulfide; sodium methylate In methanol

α-Ethylxanthogenpropionylglycin (6182-95-2) → N-(2-mercaptopropionyl)glycine (1953-02-2)

Conditions	Yield
With ammonium hydroxide In ethanol

bis-2,2-mercaptopropionylglycine → N-(2-mercaptopropionyl)glycine (1953-02-2)

Conditions	Yield
With sulfuric acid; zinc

α-Benzoylmercaptopropionylglycin (6183-01-3) → N-(2-mercaptopropionyl)glycine (1953-02-2)

Conditions	Yield
With ammonium hydroxide for 1h; Ambient temperature;

α-Benzylmercaptopropionylglycin (6183-04-6) → N-(2-mercaptopropionyl)glycine (1953-02-2)

Conditions	Yield
With ammonia; sodium

C38H43N5O9S → N-(2-mercaptopropionyl)glycine (1953-02-2) + biliverdin IXα (902268-70-6)

Conditions	Yield
In dimethyl sulfoxide at 27.5℃; Equilibrium constant; further solvent;

2-methylmercaptoacetyl chloride (144122-68-9) + glycine (56-40-6) → N-(2-mercaptopropionyl)glycine (1953-02-2)

Conditions	Yield
With sodium carbonate at 0℃; for 5h;	190 g

conc. aqueous HCl + diethyl ether (60-29-7) + N-(2-mercaptopropionyl)glycine (1953-02-2) + N-(hydroxymethyl)benzamide (6282-02-6) → N-[2-(S-benzamidomethyl)mercaptopropionyl]glycine

Conditions	Yield
In water	94.4%

4-(3-Oxo-3H-benzo[d)-isothiazol-2-yl)benzenesulfonamide (4369-80-6) + N-(2-mercaptopropionyl)glycine (1953-02-2) → {2-[2-(4-Sulfamoylphenylcarbamoyl)phenyldisulfanyl]propionylamino}-acetic acid

Conditions	Yield
In tetrahydrofuran; methanol at 60℃; for 0.5h;	93%

N-(2-mercaptopropionyl)glycine (1953-02-2) + N-methyl bromomaleimide (65060-93-7) → S-(N-methylmaleimide-3-yl)-tiopronin

Conditions	Yield
Stage #1: N-(2-mercaptopropionyl)glycine; N-methyl bromomaleimide With triethylamine In tetrahydrofuran at 20℃; for 0.5h; Stage #2: With sodium hydrogen sulfate; magnesium sulfate In tetrahydrofuran at 20℃; for 1h;	92%

N-(2-mercaptopropionyl)glycine (1953-02-2) + hematoporphyrin IX dihydrochloride (17696-69-4) → 7,12-bis<1-<1-(glycinocarbonyl)ethylthio>ethyl>-3,8,13,17-tetramethyl-21H,23H-porphine-2,18-dipropanoic acid

Conditions	Yield
With L-valine; acetic acid for 0.666667h; Ambient temperature;	90%

ethanol (64-17-5) + N-(2-mercaptopropionyl)glycine (1953-02-2) + beta-pinene (18172-67-3, 19902-08-0) → {2-[1-methyl-1-(4-methyl-cyclohex-3-enyl)-ethylsulfanyl]-propionylamino}-acetic acid ethyl ester

Conditions	Yield
With zinc(II) chloride In dichloromethane at 20℃; for 0.5h;	87%

N-(2-mercaptopropionyl)glycine (1953-02-2) + 7-methoxy-3-(1H-benzotriazol-1-ylcarbonyl)-2H-chromene-2-one (1286276-26-3) → 2-{2-[(7-methoxy-2-oxo-2H-chromene-3-carbonyl)thio]propanamido}acetic acid (1286277-50-6)

Conditions	Yield
Stage #1: N-(2-mercaptopropionyl)glycine; 7-methoxy-3-(1H-benzotriazol-1-ylcarbonyl)-2H-chromene-2-one In methanol; water at 20℃; for 0.0833333h; Stage #2: With potassium hydrogencarbonate In methanol; water at 20℃; for 0.0833333h;	85%

N-(2-mercaptopropionyl)glycine (1953-02-2) + 3-(1H-benzotriazol-1-ylcarbonyl)-7-(diethylamino)-2H-chromen-2-one (1286276-78-5) → 2-(2-{[7-(diethylamino)-2-oxo-2H-chromene-3-carbonyl]thio}propanamido)acetic acid (1327278-89-6)

Conditions	Yield
Stage #1: N-(2-mercaptopropionyl)glycine; 3-(1H-benzotriazol-1-ylcarbonyl)-7-(diethylamino)-2H-chromen-2-one In methanol; water at 20℃; for 0.0833333h; Stage #2: With potassium hydrogencarbonate In methanol; water at 20℃; for 0.0833333h;	80%

dimethyl-4-nitrophenylsulfonium trifluoromethanesulfonate + N-(2-mercaptopropionyl)glycine (1953-02-2) → (2-((4-nitrophenyl)thio)propanoyl)glycine

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 3h; Inert atmosphere; Schlenk technique;	78%

ethanol (64-17-5) + N-(2-mercaptopropionyl)glycine (1953-02-2) + D-limonene (5989-27-5) → {2-[1-methyl-1-(4-methyl-cyclohex-3-enyl)-ethylsulfanyl]-propionylamino}-acetic acid ethyl ester

Conditions	Yield
With zinc(II) chloride In dichloromethane at 20℃; for 0.5h;	76%

1,10-Phenanthroline (66-71-7) + VOCl2*2CH3CN + N-(2-mercaptopropionyl)glycine (1953-02-2) + triethylamine (121-44-8) → HN(C2H5)3(1+)*VO(C12H8N2)(SCH2CH2CONCH2CO2)(1-) = [HN(C2H5)3][VO(C12H8N2)(SCH2CH2CONCH2CO2)]

Conditions	Yield
In acetonitrile (argon); addn. of 1,10-phenanthroline to VOCl2*2MeCN in MeCN at -15°C, stirring (15 min), addn. of the dipeptide and NEt3 in MeCN, stirring (6 h); filtration, washing (Et2O), drying; elem. anal.;	75%

N-(2-mercaptopropionyl)glycine (1953-02-2) → N-propionylglycine (21709-90-0)

Conditions	Yield
With triethyl borane; tributylphosphine; triethyl phosphite In acetonitrile for 36h; Irradiation;	71%

methanol (67-56-1) + [2,2]bipyridinyl (366-18-7) + sodium acetate dihydrate + vanadyl(IV) sulphate pentahydrate + N-(2-mercaptopropionyl)glycine (1953-02-2) → [(V(IV)O)2(μ-OH)(μ-OAc)(μ-(N-2-mercapto-propionyl-glycine disulfide-H2)(2,2'-bipyridine)2]*1.68MeOH*0.75H2O

Conditions	Yield
With O2 In methanol byproducts: Na2SO4, CH3COOH; by treating V-contg. compd. (0.8 mmol) in CH3OH with 2,2'-bipyridine (0.8 mmol), S-contg. compd. (0.8 mmol) and CH3CO2Na*2H2O (1.6 mmol); stirring for ca. 1 h; the soln. was filtered in order to remove Na2SO4; the filtrate was allowed to stand for 3-4 d; elem. anal.;	71%

hexaamminenickel (II) chloride + N-(2-mercaptopropionyl)glycine (1953-02-2) → 3NH4(1+)*Ni3(C5H6NO3S)3(3-)*3CH3OH*0.5(C2H5)2O=(NH4)3{Ni3(C5H6NO3S)3}*3CH3OH*0.5(C2H5)2O

Conditions	Yield
In water; N,N-dimethyl-formamide byproducts: NH4Cl; Addn. of MPG-soln. in DMF to a soln. of Ni-complex im DMF/H2O with stirring (N2), stirring (1 h, 50°C).; Concg., filtn. of NH4Cl, addn. of CH3Cn to the filtrate, storing (12 h, -20°C), filtn., recrystn. (CH3OH/diethyl ether), elem. anal.;	70%

methanol (67-56-1) + 1,10-Phenanthroline (66-71-7) + sodium acetate dihydrate + vanadyl(IV) sulphate pentahydrate + N-(2-mercaptopropionyl)glycine (1953-02-2) → [(V(IV)O)2(μ-OH)(μ-OAc)(μ-(N-2-mercapto-propionyl-glycine disulfide-H2)(1,10-phenanthroline)2]*1.40MeOH*0.81H2O

Conditions	Yield
With O2 In methanol byproducts: Na2SO4, CH3COOH; by treating V-contg. compd. (0.8 mmol) in CH3OH with 1,10-phenanthroline(0.8 mmol), S-contg. compd. (0.8 mmol) and CH3CO2Na*2H2O (1.6 mmol); st irring for ca. 1 h; the soln. was filtered in order to remove Na2SO4; the filtrate was allowed to stand for 3-4 d; elem. anal.;	66%

N-(2-mercaptopropionyl)glycine (1953-02-2) + 8-bromocaffeine (10381-82-5) → C13H17N5O5S

Conditions	Yield
With diisopropylammonium bis(catecholato)isobutylsilicate; Ni[(4,4′-di-tert-butyl-2,2′-bipyridine)(H2O)4]Cl2; [Ru(bpy)3](PF6)2 In N,N-dimethyl-formamide at 20℃; Irradiation;	66%

[(n-C4H9)4N][ReOCl3(o-OC6H4P(C6H5)2)] + N-(2-mercaptopropionyl)glycine (1953-02-2) → ReO(tioproninato)(o-diphenylphosphinophenolato)[(n-C4H9)4N]

Conditions	Yield
In methanol; acetonitrile ligand/MeOH added to Re complex/MeCN, refluxed for 60 min; solvent removed (vac.), residue dissolved in CH2Cl2, chromd. (SiO2, CH2Cl2/MeOH), concd., MeOH added, crystd. by slow evapn. at room remp.; elem. anal.;	65%

N-(2-mercaptopropionyl)glycine (1953-02-2) + 3-(1H-benzotriazol-1-ylcarbonyl)-2H-chromene-2-one (312929-01-4) → 2-{2-[(2-oxo-2H-chromene-3-carbonyl)thio]propanamido}acetic acid (1286329-96-1)

Conditions	Yield
Stage #1: N-(2-mercaptopropionyl)glycine; 3-(1H-benzotriazol-1-ylcarbonyl)-2H-chromene-2-one In methanol; water at 20℃; for 0.0833333h; Stage #2: With potassium hydrogencarbonate In methanol; water at 20℃; for 0.0833333h;	65%

N-(2-mercaptopropionyl)glycine (1953-02-2) + para-bromoacetophenone (99-90-1) → C13H15NO4S

Conditions	Yield
With diisopropylammonium bis(catecholato)isobutylsilicate; Ni[(4,4′-di-tert-butyl-2,2′-bipyridine)(H2O)4]Cl2; [Ru(bpy)3](PF6)2 In N,N-dimethyl-formamide at 20℃; Irradiation;	64%

N-(2-mercaptopropionyl)glycine (1953-02-2) + 4-bromobenzenecarbonitrile (623-00-7) → C12H12N2O3S

Conditions	Yield
With diisopropylammonium bis(catecholato)isobutylsilicate; Ni[(4,4′-di-tert-butyl-2,2′-bipyridine)(H2O)4]Cl2; [Ru(bpy)3](PF6)2 In N,N-dimethyl-formamide at 20℃; Irradiation;	61%

3-bromo-5-chloropyridine (73583-39-8) + N-(2-mercaptopropionyl)glycine (1953-02-2) → C10H11ClN2O3S

Conditions	Yield
With diisopropylammonium bis(catecholato)isobutylsilicate; Ni[(4,4′-di-tert-butyl-2,2′-bipyridine)(H2O)4]Cl2; [Ru(bpy)3](PF6)2 In N,N-dimethyl-formamide at 20℃; Irradiation;	56%

5-bromopyrimidine (4595-59-9) + N-(2-mercaptopropionyl)glycine (1953-02-2) → C9H11N3O3S

Conditions	Yield
With diisopropylammonium bis(catecholato)isobutylsilicate; Ni[(4,4′-di-tert-butyl-2,2′-bipyridine)(H2O)4]Cl2; [Ru(bpy)3](PF6)2 In N,N-dimethyl-formamide at 20℃; Irradiation;	56%

ethyl Bromopyruvate (70-23-5) + N-(2-mercaptopropionyl)glycine (1953-02-2) → 3-[1-(carboxymethyl-carbamoyl)-ethylsulfanyl]-2-hydroxy-acrylic acid ethyl ester

Conditions	Yield
In ethanol; water; acetonitrile	53.3%
In ethanol; water; acetonitrile	53.3%

2-chloro-1-(thiazolidin-3-yl)-1-oxoethane (52837-50-0) + N-(2-mercaptopropionyl)glycine (1953-02-2) → 2-[2-[(3-thiazolidyl)carbonylmethylthio]-propionamide]acetic acid

Conditions	Yield
	52%
	52%

diethyl ether (60-29-7) + N-(2-mercaptopropionyl)glycine (1953-02-2) + N-(hydroxymethyl)acetamide (625-51-4) → N-[2-(S-acetamidomethyl)mercaptopropionyl]glycine

Conditions	Yield
With hydrogenchloride In water	50.2%

4-[4-(1,1'-biphenyl-4-ylcarbonyl)piperazin-1-yl]-2-chloro-6-ethylthieno[2,3-d]pyrimidine (902765-53-1) + N-(2-mercaptopropionyl)glycine (1953-02-2) → N-[2-({4-[4-(1,1'-biphenyl-4-ylcarbonyl)piperazin-1-yl]-6-ethylthieno[2,3-d]pyrimidin-2-yl}thio)propanoyl]glycine

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide for 24h;	43%

N-(2-mercaptopropionyl)glycine (1953-02-2) + 2-bromo-5-(trifluoromethyl)pyridine (50488-42-1) → C11H11F3N2O3S

Conditions	Yield
With diisopropylammonium bis(catecholato)isobutylsilicate; Ni[(4,4′-di-tert-butyl-2,2′-bipyridine)(H2O)4]Cl2; [Ru(bpy)3](PF6)2 In N,N-dimethyl-formamide at 20℃; Irradiation;	43%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + N-(2-mercaptopropionyl)glycine (1953-02-2) → (2-mercapto-propionylamino)acetic acid 2,5-dioxopyrrolidin-1-ylester (753457-40-8)

Conditions	Yield
With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 24h;	32%

N-(2-mercaptopropionyl)glycine (1953-02-2) + 5-bromo-2'-deoxyuridine (59-14-3) → C14H19N3O8S

Conditions	Yield
With diisopropylammonium bis(catecholato)isobutylsilicate; Ni[(4,4′-di-tert-butyl-2,2′-bipyridine)(H2O)4]Cl2; [Ru(bpy)3](PF6)2 In N,N-dimethyl-formamide at 20℃; Irradiation;	31%

N-(2-mercaptopropionyl)glycine (1953-02-2) → 6-Methyl-thiomorpholine-2,5-dione (80142-35-4)

Conditions	Yield
With chloroformic acid ethyl ester; triethylamine In dichloromethane for 16h; Ambient temperature;	30%

Upstream product

• 25413-03-0 N-(2-bromo-propionyl)-glycine 
• 21269-37-4 bis-2,2-mercaptopropionylglycine 
• 6183-01-3 α-Benzoylmercaptopropionylglycin 
• 6183-04-6 α-Benzylmercaptopropionylglycin 
• 144122-68-9 2-methylmercaptoacetyl chloride 
• 56-40-6 glycine 
• 85038-45-5 2-chloropropionylglycine 
• 6182-95-2 α-Ethylxanthogenpropionylglycin 

Downstream Products

• 554-68-7 triethylamine hydrochloride 
• 104030-69-5 S-(2-phenylcarbamoyl-phenylselenyl)-DL-2-mercaptopropionylglycine 
• 104030-78-6 S-(2-phenylcarbamoyl-6-methoxy-phenylselenyl)-DL-2-mercaptopropionylglycine 
• 14333-24-5 perrhenate 
• 21269-37-4 bis-2,2-mercaptopropionylglycine 
• 64728-93-4 {2-[5-(Benzoyl-hydrazono)-3-hydroxy-1-methyl-6-oxo-1,2,3,4,5,6-hexahydro-indol-3a-ylsulfanyl]-propionylamino}-acetic acid 

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Preparation method of tiopronin

The invention relates to a preparation method of tiopronin. The tiopronin is prepared by the following steps: (1) reacting glycine, 2-chloropropionyl chloride and ethyl acetate according to a weight ratio of 12.5: 21.5: 98 to obtain 2-chloropropionyl glycine; and (2) reacting 2-chloropropionyl glycine, sodium carbonate, sodium sulfide, sublimed sulfur and zinc powder according to a weight ratio of15:5.5:8:3:12 to obtain the tiopronin. According to the tiopronin obtained by the method, the yield is remarkably improved, the purity is high, the stability is high, and the quality of tiopronin isremarkably improved.

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A method for inhibiting and/or ameliorating the occurrence of diseases associated with reactive oxygen species, reactive nitrogen species, radicals and/or non-radicals in a subject whereby a subject is administered a carotenoid analog or derivative, either alone or in combination with another carotenoid analog or derivative, or co-antioxidant formulation. The analog or derivative is administered such that the subject's risk of experiencing diseases associated with reactive oxygen species, reactive nitrogen species, radicals and/or non-radicals may be thereby reduced. The analog or analog combination may be administered to a subject for the inhibition and/or amelioration of any disease that involves production of reactive oxygen species, reactive nitrogen species, radicals and/or non-radicals. In some embodiments, the invention may include a pharmaceutical composition including a carotenoid analog or derivative. The carotenoid analog may include a conjugated polyene with between 7 to 14 double bonds. The conjugated polyene may include a cyclic ring including at least one substituent. In some embodiments, a cyclic ring of a carotenoid analog or derivative may include at least one substituent. The substituent may be coupled to the cyclic ring with an ether functionality. In some embodiments, a pharmaceutical composition may include a biologically inactive carrier. The pharmaceutical composition may be adapted to be administered to a human subject.

Pharmaceutical compositions including carotenoid ester analogs or derivatives for the inhibition and amelioration of disease

A method for inhibiting and/or ameliorating the occurrence of diseases associated with reactive oxygen species, reactive nitrogen species, radicals and/or non-radicals in a subject whereby a subject is administered a carotenoid analog or derivative, either alone or in combination with another carotenoid analog or derivative, or co-antioxidant formulation. The analog or derivative is administered such that the subject's risk of experiencing diseases associated with reactive oxygen species, reactive nitrogen species, radicals and/or non-radicals may be thereby reduced. The analog or analog combination may be administered to a subject for the inhibition and/or amelioration of any disease that involves production of reactive oxygen species, reactive nitrogen species, radicals and/or non-radicals. In some embodiments, the invention may include a pharmaceutical composition including a carotenoid analog or derivative. The carotenoid analog may include a conjugated polyene with between 7 to 14 double bonds. The conjugated polyene may include a cyclic ring including at least one substituent. In some embodiments, a cyclic ring of a carotenoid analog or derivative may include at least one substituent. The substituent may be coupled to the cyclic ring with an ester functionality. In some embodiments, a pharmaceutical composition may include a biologically inactive carrier. The pharmaceutical composition may be adapted to be administered to a human subject.

Carotenoid ester analogs or derivatives for the inhibition and amelioration of liver disease

A method of treating liver disease in a subject may include administering to the subject an effective amount of a pharmaceutically acceptable formulation. The pharmaceutically acceptable formulation may include a synthetic analog or derivative of a carotenoid. The subject may be administered a carotenoid analog or derivative, either alone or in combination with another carotenoid analog or derivative, or co-antioxidant formulation. The carotenoid analog may include a conjugated polyene with between 7 to 14 double bonds. The conjugated polyene may include a cyclic ring including at least one substituent. In some embodiments, a cyclic ring of a carotenoid analog or derivative may include at least one substituent. The substituent may be coupled to the cyclic ring with an ester functionality.

Carotenoid analogs or derivatives for the inhibition and amelioration of disease

A method for inhibiting and/or ameliorating the occurrence of diseases associated with reactive oxygen species, reactive nitrogen species, radicals and/or non-radicals in a subject whereby a subject is administered a carotenoid analog or derivative, either alone or in combination with another carotenoid analog or derivative, or co-antioxidant formulation. The analog or derivative is administered such that the subject's risk of experiencing diseases associated with reactive oxygen species, reactive nitrogen species, radicals and/or non-radicals may be thereby reduced. The analog or analog combination may be administered to a subject for the inhibition and/or amelioration of any disease that involves production of reactive oxygen species, reactive nitrogen species, radicals and/or non-radicals. In some embodiments, the invention may include a chemical compound including an analog or derivative of a carotenoid. The carotenoid analog or derivative may be synthetic. The carotenoid analog may include a conjugated polyene with between 7 to 14 double bonds. The conjugated polyene may include an acyclic alkene including at least one substituent and/or a cyclic ring including at least one substituent. In some embodiments, a carotenoid analog or derivative may include at least one substituent. The substituent may enhance the solubility of the carotenoid analog or derivative such that the carotenoid analog or derivative at least partially dissolves in water.

Carotenoid analogs or derivatives for the inhibition and amelioration of ischemic reperfusion injury

A method of treating ischemic reperfusion injury in a subject. The method may include administering to the subject an effective amount of a pharmaceutically acceptable formulation. The pharmaceutically acceptable formulation may include a synthetic analog or derivative of a carotenoid. The subject may be administered a carotenoid analog or derivative, either alone or in combination with another carotenoid analog or derivative, or co-antioxidant formulation. The carotenoid analog may include a conjugated polyene with between 7 to 14 double bonds. The conjugated polyene may include an acyclic alkene including at least one substituent and/or a cyclic ring including at least one substituent. In some embodiments, a carotenoid analog or derivative may include at least one substituent.