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Ritonavir

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Name

Ritonavir

EINECS 605-001-5
CAS No. 155213-67-5 Density 1.239 g/cm3
PSA 202.26000 LogP 7.07790
Solubility 5mg/L(ms) Melting Point 120-122°C
Formula C37H48N6O5S2 Boiling Point 947 °C at 760 mmHg
Molecular Weight 720.957 Flash Point 526.6 °C
Transport Information N/A Appearance white powder
Safety 26-37/39-36/37-39 Risk Codes 36/38-20/21/22-41
Molecular Structure Molecular Structure of 155213-67-5 (Ritonavir) Hazard Symbols Xi,Xn
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;

Article Data 12

Ritonavir Synthetic route

154212-61-0

N-((N-Methyl-N-((2-isopropyl-4-thiazolyl)methyl)amino)-carbonyl)-L-valine

144164-11-4

(2S,3S,5S)-5-Amino-2-(N-((5-thiazolyl)-methoxycarbonyl)amino)-3-hydroxy-1,6-diphenylhexane

155213-67-5

ritonavir

Conditions
ConditionsYield
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;

N-ritonavir

144163-97-3

((5-thiazolyl)methyl)-(4-nitrophenyl)carbonate

155213-67-5

ritonavir

Conditions
ConditionsYield
With sodium hydrogencarbonate In ethyl acetate at 50 - 60℃; for 9h;85.29%

C37H53N5O5S

(5-thiazolyl)methyl 2,2,2-trichloroethanol carbonate

155213-67-5

ritonavir

Conditions
ConditionsYield
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%

(2S,3S,5S)-5-amino-3-[O-[N-[N-methyl-N-[(2-isopropyl-4-thiazolyl)methyl]amino]carbonyl]-L-valyloxy]-2-[N-[(5-thiazolyl)methoxycarbonyl]amino]-1,6-diphenyl-3-hydroxyhexane hydrochloride

155213-67-5

ritonavir

Conditions
ConditionsYield
With PBS In ethanol pH=7.4; Kinetics; Further Variations:; pH-values;
6306-52-1

L-valine methylester hydrochloride

Sasrin Fmoc-valine

Sasrin Fmoc-valine

155213-67-5

ritonavir

Conditions
ConditionsYield
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
144163-97-3

((5-thiazolyl)methyl)-(4-nitrophenyl)carbonate

155213-67-5

ritonavir

Conditions
ConditionsYield
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
154212-60-9

N-methyl-N-<(2-isopropyl-4-thiazolyl)methyl>amine

155213-67-5

ritonavir

Conditions
ConditionsYield
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
162537-10-2

N-<<(4-nitrophenyl)oxy>carbonyl>-L-valine methyl ester

155213-67-5

ritonavir

Conditions
ConditionsYield
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
154248-99-4

N-((N-methyl-N-((2-isopropyl-4-thiazolyl)methyl)amino)carbonyl)-L-valine methyl ester

155213-67-5

ritonavir

Conditions
ConditionsYield
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

4-(Chloromethyl)-2-isopropylthiazole Hydrochloride

155213-67-5

ritonavir

Conditions
ConditionsYield
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

Ritonavir Chemical Properties

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 History

 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 Uses

 Ritonavir (CAS NO.155213-67-5) is an antiretroviral drug from the protease inhibitor class used to treat HIV infection and AIDS.

Ritonavir Toxicity Data With Reference

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 Specification

 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.

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