Cidofovir Dihydrate

Basic Information

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CAS Number

149394-66-1

Molecular Formula

C8H18N3O8P

Molecular Weight

315.22 g/mol

EINECS

814-987-8

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Ethers

Basic Chemical Raw Materials Organic Chemicals Amines

Basic Chemical Raw Materials Organic Chemicals Heterocyclic Compounds

Pharmaceutical Chemicals Pharmaceutical Intermediates Heterocyclic Intermediates

Fine Chemicals Dyes and Pigments Organic Dyes

Agricultural Chemicals Pesticides Insecticides

Basic Physical Properties

Physical State

White

Melting Point

>250°C (dec.)

Boiling Point

609.5±65.0 °C at 760 mmHg

Flash Point

322.4±34.3 °C

Solubility

DMSO (Sparingly), Water (Sparingly)

Specific Rotation

-97.3° (c=0.80, in H2O)

SMILES

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C1=CN(C(=O)N=C1N)CC(CO)OCP(=O)(O)O.O.O

InChI

InChI=1S/C8H14N3O6P.2H2O/c9-7-1-2-11(8(13)10-7)3-6(4-12)17-5-18(14,15)16;;/h1-2,6,12H,3-5H2,(H2,9,10,13)(H2,14,15,16);2*1H2/t6-;;/m0../s1

InChIKey

FPKARFMSZDBYQF-ILKKLZGPSA-N

LogP

-1.08060

Complexity

417

Safety Information

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Hazard Statement

H315 Causes skin irritation
Skin corrosion/irritation

H317 May cause an allergic skin reaction
Sensitization, Skin

H319 Causes serious eye irritation
Serious eye damage/eye irritation

H335 May cause respiratory irritation
Specific target organ toxicity, single exposure; Respiratory tract irritation

Hazard Class

Class 6.1 Class 6.1

Synonyms & References

English

SCHEMBL2946561
DTXSID6041002
({[(2S)-1-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxypropan-2-yl]oxy}methyl)phosphonic acid dihydrate
CHEBI:59495
F90391
JIL713Q00N
BCP07716
CIDOFOVIR [ORANGE BOOK]
Cidofovir hydrate
Cidofovir (USAN/INN)
({[(2S)-1-(4-amino-2-oxopyrimidin-1(2H)-yl)-3-hydroxypropan-2-yl]oxy}methyl)phosphonic acid--water (1/2)
A808887
Vistide (TN)
AKOS015892576
CIDOFOVIR [EMA EPAR]
Cidofovir dihydrate
CIDOFOVIR [USP MONOGRAPH]
Phosphonic acid, P-[[(1S)-2-(4-amino-2-oxo-1(2H)-pyrimidinyl)-1-(hydroxymethyl)ethoxy]methyl]-, hydrate (1:2)
NSC 742135
(S)-(((1-(4-Amino-2-oxopyrimidin-1(2H)-yl)-3-hydroxypropan-2-yl)oxy)methyl)phosphonic acid dihydrate
Cidofovir (dihydrate)
Hpmpc dihydrate
[(2S)-1-(4-amino-2-oxopyrimidin-1-yl)-3-hydroxypropan-2-yl]oxymethylphosphonic acid;dihydrate
BC166672
(((S)-2-(4-Amino-2-oxo-1(2H)-pyrimidinyl)-1-(hydroxymethyl)ethoxy)methyl)phosphonic acid, dihydrate
CS-1908
Q27126748
({[(2S)-1-(4-amino-2-oxopyrimidin-1(2H)-yl)-3-hydroxypropan-2-yl]oxy}methyl)phosphonic acid dihydrate
GS-0504
Cidofovir dihydrate- Bio-X
P-[[(1S)-2-(4-Amino-2-oxo-1(2H)-pyrimidinyl)-1-(hydroxymethyl)ethoxy]methyl]phosphonic acid dihydrate

MDL Number

MFCD16556167

EC Number

814-987-8

Customs Code

2933599550

FAQ

What are the physical and chemical properties of Cidofovir Dihydrate (CAS: 149394-66-1)?

Cidofovir dihydrate is a white crystalline solid with a molecular weight of approximately 597.62 g/mol. It has a high solubility in water and is poorly soluble in organic solvents. Chemically, it is a nucleoside analog with antiviral activity. It is reactive towards nucleophilic attack and can form stable complexes with metal ions, making it useful in various pharmaceutical applications.

How is Cidofovir Dihydrate (CAS: 149394-66-1) typically synthesized?

Cidofovir dihydrate is typically synthesized through a multistep process involving the condensation of 2'-deoxyguanosine with 2-hydroxy-5-nitroimidazole-1-ylidene, followed by reduction and hydration. The synthesis involves the use of reagents such as sodium hydride and acetic anhydride. The yield is moderate, around 50-60%, and the reaction conditions are optimized for selectivity and purity.

What industries use Cidofovir Dihydrate (CAS: 149394-66-1)?

Cidofovir dihydrate is primarily used in the pharmaceutical industry for the treatment of viral infections, particularly CMV retinitis in AIDS patients. It is also explored for its potential in other applications such as topical treatments for viral infections in the skin and mucous membranes. Limited use is seen in research and development for its reactivity and complex chemistry in various industries.

What precautions should be taken when handling Cidofovir Dihydrate (CAS: 149394-66-1)?

When handling Cidofovir dihydrate, it is important to wear appropriate personal protective equipment (PPE) including gloves and safety goggles. Work should be conducted in a well-ventilated area or fume hood to avoid inhalation of dust. Spills should be cleaned up with appropriate absorbents and disposed of according to local regulations. Always refer to the Safety Data Sheet (SDS) for specific handling and disposal instructions to ensure safety and compliance.