Products Categories
CAS No.: | 155213-67-5 |
---|---|
Name: | Ritonavir |
Article Data: | 12 |
Molecular Structure: | |
Formula: | C37H48N6O5S2 |
Molecular Weight: | 720.957 |
Synonyms: | 2,4,7,12-Tetraazatridecan-13-oicacid,10-hydroxy-2-methyl-5-(1-methylethyl)-1-[2-(1-methylethyl)-4-thiazolyl]-3,6-dioxo-8,11-bis(phenylmethyl)-,5-thiazolylmethyl ester, (5S,8S,10S,11S)- (9CI);A 84538;ABT 538;Abbott84538;NSC 693184;Norvir; |
EINECS: | 605-001-5 |
Density: | 1.239 g/cm3 |
Melting Point: | 120-122°C |
Boiling Point: | 947 °C at 760 mmHg |
Flash Point: | 526.6 °C |
Solubility: | 5mg/L(ms) |
Appearance: | white powder |
Hazard Symbols: | Xi,Xn |
Risk Codes: | 36/38-20/21/22-41 |
Safety: | 26-37/39-36/37-39 |
PSA: | 202.26000 |
LogP: | 7.07790 |
N-((N-Methyl-N-((2-isopropyl-4-thiazolyl)methyl)amino)-carbonyl)-L-valine
(2S,3S,5S)-5-Amino-2-(N-((5-thiazolyl)-methoxycarbonyl)amino)-3-hydroxy-1,6-diphenylhexane
ritonavir
Conditions | Yield |
---|---|
Stage #1: N-((N-Methyl-N-((2-isopropyl-4-thiazolyl)methyl)amino)-carbonyl)-L-valine With N-ethyl-N,N-diisopropylamine; diisopropyl-carbodiimide at 27℃; for 0.5h; Stage #2: (2S,3S,5S)-5-Amino-2-(N-((5-thiazolyl)-methoxycarbonyl)amino)-3-hydroxy-1,6-diphenylhexane for 7h; Temperature; | 91.5% |
With diethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In butanone at 41℃; for 0.666667h; Concentration; Temperature; | 87.4% |
With N-ethyl-N'-(3-diethylaminopropyl)-carbodiimide; 1-hydroxybenzotriazol-hydrate In tetrahydrofuran for 16h; Ambient temperature; Yield given; | |
Stage #1: N-((N-Methyl-N-((2-isopropyl-4-thiazolyl)methyl)amino)-carbonyl)-L-valine With pivaloyl chloride; triethylamine In dichloromethane at 0 - 10℃; Inert atmosphere; Large scale; Stage #2: With dmap In dichloromethane at 0 - 10℃; for 0.5h; Large scale; Stage #3: (2S,3S,5S)-5-Amino-2-(N-((5-thiazolyl)-methoxycarbonyl)amino)-3-hydroxy-1,6-diphenylhexane In dichloromethane at 25 - 35℃; Large scale; |
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In ethyl acetate at 50 - 60℃; for 9h; | 85.29% |
Conditions | Yield |
---|---|
Stage #1: C37H53N5O5S With hydrogenchloride In water; ethyl acetate at 0 - 20℃; for 6h; Green chemistry; Stage #2: (5-thiazolyl)methyl 2,2,2-trichloroethanol carbonate With triethylamine In ethyl acetate at 0 - 20℃; for 12h; Green chemistry; | 79% |
ritonavir
Conditions | Yield |
---|---|
With PBS In ethanol pH=7.4; Kinetics; Further Variations:; pH-values; |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 4-methylmorpholine / CH2Cl2 / Ambient temperature 2: DMAP, Et3N / tetrahydrofuran / 2 h / Heating 3: 0.50 M aq. LiOH / dioxane / 0.5 h / Ambient temperature 4: 1-hydroxybenzotriazole hydrate, N-ethyl-N'-<(dimethylamino)propyl>carbodiimide / tetrahydrofuran / 16 h / Ambient temperature View Scheme |
((5-thiazolyl)methyl)-(4-nitrophenyl)carbonate
ritonavir
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 16 percent / tetrahydrofuran / 4 h / Ambient temperature 2: 1-hydroxybenzotriazole hydrate, N-ethyl-N'-<(dimethylamino)propyl>carbodiimide / tetrahydrofuran / 16 h / Ambient temperature View Scheme |
N-methyl-N-<(2-isopropyl-4-thiazolyl)methyl>amine
ritonavir
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: DMAP, Et3N / tetrahydrofuran / 2 h / Heating 2: 0.50 M aq. LiOH / dioxane / 0.5 h / Ambient temperature 3: 1-hydroxybenzotriazole hydrate, N-ethyl-N'-<(dimethylamino)propyl>carbodiimide / tetrahydrofuran / 16 h / Ambient temperature View Scheme | |
Multi-step reaction with 3 steps 1.1: triethylamine / tetrahydrofuran / 6 h / 50 - 60 °C / Green chemistry 2.1: triethylamine; p-toluenesulfonyl chloride / dichloromethane / 3 h / 0 - 10 °C / Green chemistry 2.2: 6 h / 0 - 20 °C / Green chemistry 3.1: hydrogenchloride / ethyl acetate; water / 6 h / 0 - 20 °C / Green chemistry 3.2: 12 h / 0 - 20 °C / Green chemistry View Scheme |
N-<<(4-nitrophenyl)oxy>carbonyl>-L-valine methyl ester
ritonavir
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: DMAP, Et3N / tetrahydrofuran / 2 h / Heating 2: 0.50 M aq. LiOH / dioxane / 0.5 h / Ambient temperature 3: 1-hydroxybenzotriazole hydrate, N-ethyl-N'-<(dimethylamino)propyl>carbodiimide / tetrahydrofuran / 16 h / Ambient temperature View Scheme |
N-((N-methyl-N-((2-isopropyl-4-thiazolyl)methyl)amino)carbonyl)-L-valine methyl ester
ritonavir
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 0.50 M aq. LiOH / dioxane / 0.5 h / Ambient temperature 2: 1-hydroxybenzotriazole hydrate, N-ethyl-N'-<(dimethylamino)propyl>carbodiimide / tetrahydrofuran / 16 h / Ambient temperature View Scheme |
ritonavir
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: H2O / 1 h 2: DMAP, Et3N / tetrahydrofuran / 2 h / Heating 3: 0.50 M aq. LiOH / dioxane / 0.5 h / Ambient temperature 4: 1-hydroxybenzotriazole hydrate, N-ethyl-N'-<(dimethylamino)propyl>carbodiimide / tetrahydrofuran / 16 h / Ambient temperature View Scheme |
Molecular structure of Ritonavir (CAS NO.155213-67-5) is:
Product Name: Ritonavir
CAS Registry Number: 155213-67-5
IUPAC Name: 1,3-thiazol-5-ylmethylN-[(2S,3S,5S)-3-hydroxy-5-[[(2S)-3-methyl-2-[[methyl-[(2-propan-2-yl-1,3-thiazol-4-yl)methyl]carbamoyl]amino]butanoyl]amino]-1,66-diphenylhexan-2-yl]carbamate
Molecular Weight: 720.94422 [g/mol]
Molecular Formula: C37H48N6O5S2
XLogP3-AA: 6
H-Bond Donor: 4
H-Bond Acceptor: 7
Surface Tension: 53.7 dyne/cm
Density: 1.239 g/cm3
Flash Point: 526.6 °C
Enthalpy of Vaporization: 144.39 kJ/mol
Boiling Point: 947 °C at 760 mmHg
Classification Code: Anti-HIV Agents; Anti-Infective Agents; Anti-Retroviral Agents; Antiretroviral; Antiviral; Antiviral Agents; Enzyme Inhibitors; HIV Protease Inhibitors; Protease Inhibitors; Protease inhibitor
Ritonavir (CAS NO.155213-67-5) is manufactured as Norvir by Abbott Laboratories. Research that led to the drug's development was financed by a $3,500,000 federal grant through the National Institutes of Health (NIH) and over $200,000,000 by Abbott Labs. Most of the $200,000,000 figure cited by Abbott paid for clinical trials-despite NIH offering to pay for them-because Abbott was concerned about "public interest" responses to the high prices they projected Norvir would command.The FDA approved ritonavir on March 1, 1996, making it the seventh approved antiretroviral drug in the United States. In 2003, Abbott raised the price of a Norvir course from USD $1.71 per day to $8.57 per day, leading to claims of price gouging by patients' groups and some members of Congress. Consumer group Essential Inventions petitioned the NIH to override the Norvir patent, but the NIH announced on August 4, 2004 that it would not invoke its legal right to allow generic production of Norvir, citing potential adverse effects on the pharmaceutical market.
Ritonavir (CAS NO.155213-67-5) is an antiretroviral drug from the protease inhibitor class used to treat HIV infection and AIDS.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD | oral | > 2500mg/kg (2500mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 40, Pg. 2683, 1998. |
mouse | LDLo | intravenous | 65mg/kg (65mg/kg) | BEHAVIORAL: TREMOR BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: ATAXIA | Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 40, Pg. 2683, 1998. |
rat | LD | oral | > 2500mg/kg (2500mg/kg) | BEHAVIORAL: TREMOR BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 40, Pg. 2683, 1998. |
rat | LDLo | intravenous | 35mg/kg (35mg/kg) | BEHAVIORAL: TREMOR BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 40, Pg. 2683, 1998. |
Ritonavir , its cas register number is 155213-67-5. It also can be called Ritonavir [USAN] ; 5-Thiazolylmethyl ((alphaS)-alpha-((1S,3S)-1-hydroxy-3-((2S)-2-(3-((2-isopropyl-4-thiazolyl)methyl)-3-methylureido)-3-methylbutyramido)-4-phenylbutyl)phenethyl)carbamate ; 5-Thiazolylmethyl ((alphaS)-alpha-((1S,3S-1-hydroxy-3-((2S)-2-(3-((2-isopropyl-4-thiazolyl)methyl)-3-methylureido)-3-methylbutyramido)-4-phenylbutyl)phenethyl)carbamate ; 2,4,7,12-Tetraazatridecan-13-oic acid, 10-hydroxy-2-methyl-5-(1-methylethyl)-1-(2-(1-methylethyl)-4-thiazolyl)-3,6-dioxo-8,11-bis(phenylmethyl)-, 5-thiazolylmethyl ester, (5S-(5R*,8R*,10R*,11R*))- .It is a white powder.