CAS No.155213-67-5,Ritonavir Suppliers

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Basic Information

Molecular Structure:
CAS No.:	155213-67-5
Name:	Ritonavir
Article Data:	12

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

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

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;

: N-ritonavir

: 144163-97-3
((5-thiazolyl)methyl)-(4-nitrophenyl)carbonate

: 155213-67-5
ritonavir

Conditions

Conditions	Yield
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

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%

: (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

Conditions	Yield
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

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

: 144163-97-3
((5-thiazolyl)methyl)-(4-nitrophenyl)carbonate

: 155213-67-5
ritonavir

Conditions

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

: 154212-60-9
N-methyl-N-<(2-isopropyl-4-thiazolyl)methyl>amine

: 155213-67-5
ritonavir

Conditions

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

: 162537-10-2
N-<<(4-nitrophenyl)oxy>carbonyl>-L-valine methyl ester

: 155213-67-5
ritonavir

Conditions

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

: 154248-99-4
N-((N-methyl-N-((2-isopropyl-4-thiazolyl)methyl)amino)carbonyl)-L-valine methyl ester

: 155213-67-5
ritonavir

Conditions

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

: 4-(Chloromethyl)-2-isopropylthiazole Hydrochloride

: 155213-67-5
ritonavir

Conditions

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

Raw Materials

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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.