CAS No.30516-87-1,Zidovudine Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	30516-87-1
Name:	Zidovudine
Article Data:	72
Cas Database

Formula:	C₁₀H₁₃N₅O₄
Molecular Weight:	267.244
Synonyms:	3-Azido-3-deoxythymidine;3'-Azido-3'-deoxythymidine;3'-Azidothymidine;3'-Deoxy-3'-azidothymidine;AZT;AZT (pharmaceutical);Azidothymidine;Azitidin;BW-A 509U;Compound S;NSC602670;Retrovir;Retrovir IV;Retrovis;Timazid;Viro-Z;ZDV;ZVD;Zido-H;
EINECS:	623-849-4
Density:	1.3382 (rough estimate)
Melting Point:	106-112 °C
Boiling Point:	410.43°C (rough estimate)
Flash Point:	9℃
Solubility:	1-5 g/100 mL at 17 °C in water
Appearance:	Off -white crystalline powder
Hazard Symbols:	Xn
Risk Codes:	40-36/37/38-20/21/22
Safety:	36/37/39-45-36-26
PSA:	134.07000
LogP:	-0.74354

Synthetic route

: 106060-78-0
3'-azido-5'-O-benzoyl-3'-deoxythymidine

: 30516-87-1
3'-azido-2',3'-deoxythymidine

Conditions

Conditions	Yield
With sodium methylate In methanol for 24h; Ambient temperature;	95%
With ammonia In methanol at 20℃;	81%
With sodium methylate In methanol	71%
With ammonia In methanol

: 29706-84-1
1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine

: 30516-87-1
3'-azido-2',3'-deoxythymidine

Conditions

Conditions	Yield
With silica gel; trifluoroacetic acid In methanol; chloroform	95%
With hydrogenchloride In methanol; water at 20℃; for 3h;	95%
With hydrogenchloride In acetic acid at 20℃; for 2h;	49%
With sodium periodate In acetone at 50℃; for 20h;

: 134077-32-0
3'-Azido-5'-O-(4-methoxybenzoyl)-3'-deoxythymidine

: 30516-87-1
3'-azido-2',3'-deoxythymidine

Conditions

Conditions	Yield
With sodium methylate In methanol for 12h; Ambient temperature;	94%
With sodium methylate In methanol

: 162404-30-0
AZT guanidine salt

: 30516-87-1
3'-azido-2',3'-deoxythymidine

Conditions

Conditions	Yield
With hydrogenchloride In water at 75℃; Large scale reaction;	88.5%

: 126441-74-5
3’-azido-5’-O-(4,4’-dimethoxytrityl)-3’-deoxythymidine

: 30516-87-1
3'-azido-2',3'-deoxythymidine

Conditions

Conditions	Yield
In methanol; tetrachloromethane at 25 - 40℃; for 12h; ultrasonic;	87%

: 3'-azido-3'-deoxy-5'-O-pivaloylthymidine

: 30516-87-1
3'-azido-2',3'-deoxythymidine

Conditions

Conditions	Yield
With sodium methylate In methanol at 20℃; for 1h;	86%

: 52450-18-7
3'-amino-3'-deoxythymidine

: 30516-87-1
3'-azido-2',3'-deoxythymidine

Conditions

Conditions	Yield
With fluorosulfonyl azide; potassium hydrogencarbonate In tert-butyl methyl ether; water; N,N-dimethyl-formamide at 20℃; for 4h;	83%

: 15981-92-7
2,3'-anhydrothymidine

: 30516-87-1
3'-azido-2',3'-deoxythymidine

Conditions

Conditions	Yield
With sodium azide In N,N-dimethyl-formamide for 3h; Heating;	71%

: 15981-92-7
2,3'-anhydrothymidine

A: 30516-87-1
3'-azido-2',3'-deoxythymidine

B: 3-(3-azido-2,3-dideoxy-β-D-ribofuranosyl)thymine

Conditions

Conditions	Yield
With lithium azide In N,N-dimethyl-formamide at 110℃; for 24h;	A 56% B n/a
With lithium azide In N,N-dimethyl-formamide at 110℃; for 24h; Title compound not separated from byproducts;

: 1-[(4S,5S)-4-Azido-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

A: 30516-87-1
3'-azido-2',3'-deoxythymidine

B: 66323-40-8
alpha-3'-azido-2',3'-dideoxythymidine

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran for 0.5h; Ambient temperature;	A 31% B 45%
With tetrabutyl ammonium fluoride In tetrahydrofuran Yield given. Yields of byproduct given;
With tetrabutyl ammonium fluoride In tetrahydrofuran Yield given;
With tetrabutyl ammonium fluoride In tetrahydrofuran

Raw Materials

91926-90-8

50-89-5

65-71-4

Downstream Products

67-56-1

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History

Usage of Zidovudine was major breakthrough in AIDS therapy in the 1990s that significantly altered the course of the illness and helped destroy the notion of the 1980s and early 90s that HIV/AIDS was an instant death sentence.
Jerome Horwitz of Barbara Ann Karmanos Cancer Institute and Wayne State University School of Medicine first synthesized Zidovudine in 1964, under a US National Institutes of Health (NIH) grant. Zidovudine was originally intended as an anticancer drug, but was shelved after it proved insufficiently toxic to cancer tumours in mice.

Specification

The IUPAC name of Zidovudine is 1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione. With the CAS registry number 30516-87-1, it is also named as 1-(3-Azido-2,3-dideoxy-beta-D-ribofuranosyl)-5-methylpyrimidine-2,4-(1H,3H)-dione. It is off -white crystalline powder which is a dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. When burns, it will produce toxic nitrogen oxide fumes. Additionally, this chemical should be sealed in the container and stored at -20 °C.

The other characteristics of this product can be summarized as: (1)ACD/LogP: -0.53; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.53; (4)ACD/LogD (pH 7.4): -0.53; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 12.29; (8)ACD/KOC (pH 7.4): 12.12; (9)#H bond acceptors: 9; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 71.44 Å²; (13)Rotatable Bond Count: 3; (14)Tautomer: Count 3; (15)Exact Mass: 267.096754; (16)MonoIsotopic Mass: 267.096754; (17)Topological Polar Surface Area: 93.2; (18)Heavy Atom Count: 19; (19)Complexity: 484; (20)Defined Atom StereoCenter Count: 3.

Preparation of Zidovudine: It can be obtained by thymidine, triphenylphosphine, p-methoxybenzo and Diethyl azodicarboxylate.

Uses of Zidovudine: It is a type of antiretroviral drug used for the treatment of HIV/AIDS. Its use was a major breakthrough in AIDS therapy in the 1990s that significantly altered the course of the illness and helped destroy the notion that HIV/AIDS was a death sentence. This drug is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Chronic, high-dose therapy with Zidovudine is associated with significant side effects, including anemia, neutropenia, hepatotoxicity, cardiomyopathy, and myopathy.

When you are using this chemical, please be cautious about it as the following:
It is not only harmful by inhalation, in contact with skin and if swallowed, but also irritating to eyes, respiratory system and skin. It also has limited evidence of a carcinogenic effect. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

People can use the following data to convert to the molecule structure.
1. Smiles:n1([C@H]2C[C@H](N=[N+]=[N-])[C@H](O2)CO)c([nH]c(=O)c(c1)C)=O
2. InChI:InChI=1/C10H13N5O4/c1-5-3-15(10(18)12-9(5)17)8-2-6(13-14-11)7(4-16)19-8/h3,6-8,16H,2,4H2,1H3,(H,12,17,18)/t6-,7+,8+/m0/s1

The following are the toxicity data which has been tested.

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
man	LDLo	oral	86mg/kg/1W-I (86mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: HEADACHE	Lancet. Vol. 2, Pg. 1392, 1986.
man	TDLo	oral	434mg/kg/38D- (434mg/kg)	BLOOD: CHANGES IN CELL COUNT (UNSPECIFIED) BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE BLOOD: APLASTIC ANEMIA	Annals of Internal Medicine. Vol. 107, Pg. 502, 1987.
man	TDLo	unreported	69mg/kg (69mg/kg)	SENSE ORGANS AND SPECIAL SENSES: "RETINAL CHANGES (PIGMENTARY DEPOSITIONS, RETINITIS, OTHER): EYE"	Annals of Internal Medicine. Vol. 114, Pg. 297, 1991.
mouse	LD50	intravenous	> 70mg/kg (70mg/kg)		United States Patent Document. Vol. #4804651,
mouse	LD50	oral	3062mg/kg (3062mg/kg)	SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)	Fundamental and Applied Toxicology. Vol. 32, Pg. 129, 1996.
mouse	LD50	unreported	> 750mg/kg (750mg/kg)		United States Patent Document. Vol. #4857511,
rat	LD50	intravenous	> 70mg/kg (70mg/kg)		United States Patent Document. Vol. #4804651,
rat	LD50	oral	3084mg/kg (3084mg/kg)	SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)	Fundamental and Applied Toxicology. Vol. 32, Pg. 129, 1996.
rat	LD50	unreported	> 750mg/kg (750mg/kg)		United States Patent Document. Vol. #4857511,
women	TDLo	oral	1gm/kg/6W-I (1000mg/kg)	SKIN AND APPENDAGES (SKIN): NAILS: OTHER	Annals of Internal Medicine. Vol. 107, Pg. 350, 1987.