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155213-67-5

Basic Information
CAS No.: 155213-67-5
Name: Ritonavir
Molecular Structure:
Molecular Structure of 155213-67-5 (Ritonavir)
Formula: C37H48N6O5S2
Molecular Weight: 720.94
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
Transport Information:
PSA: 202.26000
LogP: 7.07790
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
224631-15-6

N-[[N-methyl-N-[(2-isopropyl-4-thiazolyl)methyl]amino]carbonyl]-L-valinyl hydroxysuccinimide ester

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
In ethyl acetate at 0 - 20℃; for 18h;
In ethyl acetate at 0 - 20℃; for 18h;

N-[N-methyl-N-[(2-isopropyl-4-thiazolyl)methyl]aminocarbonyl]-L-valine chloride

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
In ethyl acetate Solvent;55.7 g
162849-95-8

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

155213-67-5

ritonavir

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / water; ethyl acetate / 3 h / 50 °C
2: ethyl acetate
View Scheme

N-[N-methyl-N-[(2-isopropyl-4-thiazolyl)methyl]aminocarbonyl]-L-valine chloride

155213-67-5

ritonavir

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: dichloromethane / 1 h / 10 °C
2: hydrogenchloride / ethyl acetate; water / 4 h / 10 - 20 °C
3: sodium hydrogencarbonate / ethyl acetate / 9 h / 50 - 60 °C
View Scheme
154212-61-0

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

155213-67-5

ritonavir

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 1 h / 0 - 10 °C
2: dichloromethane / 1 h / 10 °C
3: hydrogenchloride / ethyl acetate; water / 4 h / 10 - 20 °C
4: sodium hydrogencarbonate / ethyl acetate / 9 h / 50 - 60 °C
View Scheme
78221-33-7

(S)-3-methyl-2-[(2,2,2-trichloroethoxy)carbonylamino]butyric acid

155213-67-5

ritonavir

Conditions
ConditionsYield
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
75-18-3

dimethylsulfide

155213-67-5

ritonavir

875435-42-0

N1-((1S,3S,4S)-1-benzyl-3-[(methylthio)methoxy]-5-phenyl-4-{[(1,3-thiazol-5-ylmethoxy)carbonyl]amino}pentyl)-N2-{[[(2-isopropyl-1,3-thiazol-4-yl)methyl](methyl)amino]carbonyl}-L-valinamide

Conditions
ConditionsYield
With dibenzoyl peroxide In acetonitrile at 0 - 20℃; for 2.33333h;84%
With dibenzoyl peroxide In acetonitrile at 0 - 20℃; for 2.33333h;84%
875435-89-5

4-((di-tert-butoxyphosphoryl)oxy)-3,3-dimethylbutanoic acid

155213-67-5

ritonavir

(1S,3S)-3-[(N-{[[(2-isopropyl-1,3-thiazol-4-yl)methyl](methyl)amino]carbonyl}-L-valyl)amino]-4-phenyl-1-((1S)-2-phenyl-1-{[(1,3-thiazol-5-ylmethoxy)carbonyl]amino}ethyl)butyl 4-[(di-tert-butoxyphosphoryl)oxy]-3,3-dimethylbutanoate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 86h;81%
67746-43-4

dibenzyl N,N-diethylphosphoramidite

155213-67-5

ritonavir

875435-73-7

N1-((1S,3S,4S)-1-benzyl-3-{[bis(benzyloxy)phosphoryl]oxy}-5-phenyl-4-{[(1,3-thiazol-5-ylmethoxy)carbonyl]amino}pentyl)-N2-{[[(2-isopropyl-1,3-thiazol-4-yl)methyl](methyl)amino]carbonyl}-L-valinamide

Conditions
ConditionsYield
Stage #1: dibenzyl N,N-diethylphosphoramidite; ritonavir With 1H-tetrazole In tetrahydrofuran at 20℃; for 4h;
Stage #2: With 3-chloro-benzenecarboperoxoic acid In tetrahydrofuran; Dichlorodifluoromethane at -45 - 20℃; for 1h;
76%
352-93-2

diethyl sulphide

155213-67-5

ritonavir

875435-55-5

N1-((1S,3S,4S)-1-benzyl-3-[1-(ethylthio)ethoxy]-5-phenyl-4-{[(1,3-thiazol-5-ylmethoxy)carbonyl]amino}pentyl)-N2-{[[(2-isopropyl-1,3-thiazol-4-yl)methyl](methyl)amino]carbonyl}-L-valinamide

Conditions
ConditionsYield
With dibenzoyl peroxide In acetonitrile at 0 - 20℃; for 2.33333h;75%
With dibenzoyl peroxide In acetonitrile at 0℃; for 3h;75%
592-65-4

diisobutyl sulfide

155213-67-5

ritonavir

875436-09-2

N1-((1S,3S,4S)-1-benzyl-3-[1-(isobutylthio)-2-methylpropoxy]-5-phenyl-4-{[(1,3-thiazol-5-ylmethoxy)carbonyl]amino}pentyl)-N2-{[[(2-isopropyl-1,3-thiazol-4-yl)methyl](methyl)amino]carbonyl}-L-valinamide

Conditions
ConditionsYield
With dibenzoyl peroxide In acetonitrile at 0 - 20℃; for 2.33333h;75%
With dibenzoyl peroxide In acetonitrile at 0℃; for 1.5h;75%
18162-48-6

tert-butyldimethylsilyl chloride

155213-67-5

ritonavir

C43H62N6O5S2Si

Conditions
ConditionsYield
With dmap; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h;72%
41654-04-0

5-Methyl-4-oxohexanoic acid

155213-67-5

ritonavir

5-methyl-4-oxohexanoyl-ritonavir ester

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 5h;70.3%
544-40-1

Dibutyl sulfide

155213-67-5

ritonavir

875436-05-8

N1-((1S,3S,4S)-1-benzyl-3-[1-(butylthio)butoxy]-5-phenyl-4-{[(1,3-thiazol-5-ylmethoxy)carbonyl]amino}pentyl)-N2-{[[(2-isopropyl-1,3-thiazol-4-yl)methyl](methyl)amino]carbonyl}-L-valinamide

Conditions
ConditionsYield
With dibenzoyl peroxide In acetonitrile at 0 - 20℃; for 2.33333h;68%
With dibenzoyl peroxide In acetonitrile at 0 - 20℃; for 7h;68%
6160-65-2

1,1'-Thiocarbonyldiimidazole

155213-67-5

ritonavir

1004316-15-7

C41H50N8O5S3

Conditions
ConditionsYield
In 1,2-dichloro-ethane at 75℃; for 6h;
155213-67-5

ritonavir

C37H46N6O5S2

Conditions
ConditionsYield
With Dess-Martin periodane In dichloromethane at 20℃; for 6h;
With Dess-Martin periodane
67746-43-4

dibenzyl N,N-diethylphosphoramidite

155213-67-5

ritonavir

C51H61N6O7PS2

Conditions
ConditionsYield
With 1H-tetrazole In tetrahydrofuran at 20℃; for 4h;
155213-67-5

ritonavir

A

N-ritonavir

B

C30H39N5O5S

C

hydroxy ritonavir

D

C36H46N6O5S2

Conditions
ConditionsYield
With human CYP3A4; NADPH; NADPH-cytochrome P450 reductase In aq. phosphate buffer at 37℃; for 0.333333h; pH=7.7; Enzymatic reaction;
With cytochrome P450 monooxygenases from Actinosynnema mirum at 25℃; for 24h; pH=7.5; Reagent/catalyst; Enzymatic reaction;
155213-67-5

ritonavir

A

N-ritonavir

B

hydroxy ritonavir

Conditions
ConditionsYield
With human CYP2B6; NADPH; NADPH-cytochrome P450 reductase In aq. phosphate buffer at 37℃; for 0.333333h; pH=7.7; Enzymatic reaction;
70-18-8

GLUTATHIONE

155213-67-5

ritonavir

C39H51N7O11S2

Conditions
ConditionsYield
With human CYP3A4; NADPH; NADPH-cytochrome P450 reductase In aq. phosphate buffer at 37℃; for 0.333333h; pH=7.7; Enzymatic reaction;
155213-67-5

ritonavir

(2S,3S,5S)-5-(N-(N-((N-methyl-N-((2-isopropyl-4-thiazolyl)-methyl)amino)carbonyl)-L-valinyl)amino)-2-(N-((5-thiazolyl)-methoxy-carbonyl)-amino)-1,6-diphenyl-3-hydroxyhexane bis-hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In ethyl acetate Concentration; Temperature; Solvent; Inert atmosphere;
155213-67-5

ritonavir

C37H48N6O4S2

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 75 °C
2: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / 115 °C
View Scheme
6160-65-2

1,1'-Thiocarbonyldiimidazole

155213-67-5

ritonavir

C40H50N8O4S2

Conditions
ConditionsYield
at 75℃;
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    Ritonavir English name: Ritonavir Chemical name: 1,3-Thiazol-5-ylmethylN-[(2S,3S,5R)-3-hydroxy-5-[[(2S)-3-methyl-2-[[methyl-[(2-propan-2-yl-1,3-thiazol-4-yl)methyl]carbamoyl]amino]butanoyl]amino]-1,6-diph

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Chemistry

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

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.

Uses

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

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.

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.