CAS 113852-37-2|Cidofovir

Introduction：Basic information about CAS 113852-37-2|Cidofovir, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Cidofovir BiologicalActivity
3. Chemical & Physical Properties
4. Safety Information
5. Customs
6. Synonyms

Common Name	Cidofovir
CAS Number	113852-37-2	Molecular Weight	279.187
Density	1.8±0.1 g/cm3	Boiling Point	609.5±65.0 °C at 760 mmHg
Molecular Formula	C₈H₁₄N₃O₆P	Melting Point	260ºC
MSDS	ChineseUSA	Flash Point	322.4±34.3 °C

Names

Name	cidofovir anhydrous
Synonym	More Synonyms

Cidofovir BiologicalActivity

Description	Cidofovir is an anti-CMV drug which can suppress CMV replication by selective inhibition of viral DNA polymerase and therefore prevention of viral replication and transcription.IC50 Value:Target: CMV DNA polymerasein vitro: The minimum concentrations of (S)-HPMPC required to inhibit CMV plaque formation by 50% was microgram/ml. The selectivity indices of (S)-HPMPC, as determined by the ratio of the 50% inhibitory concentration for cell growth to the 50% inhibitory concentration for plaque formation for CMV (AD-169 strain), was 1,500 [1]. The time course of uptake of HPMPC into Vero cells was linear between 10 and 75 min and proportional to the concentration in the medium from 10(-6) to 10(-2) M. HPMPC uptake was temperature sensitive and the rate of uptake was considerably lower at 27 degrees than at 37 degrees and almost totally inhibited at 4 degrees [2]. in vivo: Levels of cidofovirin serum following intravenous infusion were dose proportional over the dose range of 1.0 to 10.0 mg/kg of body weight and declined biexponentially with an overall mean +/- standard deviation terminal half-life of 2.6 +/- 1.2 h (n = 25). Approximately 90% of the intravenous dose was recovered unchanged in the urine in 24 h. The overall mean +/- standard deviation total clearance of the drug from serum (148 +/- 25 ml/h/kg; n = 25) approximated renal clearance (129 +/- 42 ml/h/kg; n = 25), which was significantly higher (P < 0.001) than the baseline creatinine clearance in the same patients (83 +/- 21 ml/h/kg; n = 12) [3]. Positive CMV urine cultures reverted to negative in 2 of 8 patients receiving doses of < or = 1.5 mg/kg twice weekly and 11 of 13 patients receiving higher doses. Cidofovir has in vivo anti-CMV activity demonstrated by prolonged clearing of CMV viruria, although this observation is tempered by the fact that clearance of viremia could not be demonstrated [4].Toxicity: Patients receiving 0.5 or 1.5 mg/kg twice weekly experienced no serious toxicity. The first two patients who received 5 mg/kg twice weekly developed glycosuria and 2+ proteinuria. Subsequent patients received concomitant probenecid to attempt to ameliorate renal toxicity [4].Clinical trial: FDA approved drug
Related Catalog	Signaling Pathways >>Anti-infection >>CMVResearch Areas >>Infection
References	[1]. Snoeck R, et al. (S)-1-(3-hydroxy-2-phosphonylmethoxypropyl)cytosine, a potent and selective inhibitor of human cytomegalovirus replication. Antimicrob Agents Chemother. 1988 Dec;32(12):1839-44. [2]. Connelly MC, et al. Mechanism of uptake of the phosphonate analog (S)-1-(3-hydroxy-2-phosphonylmethoxypropyl)cytosine (HPMPC) in Vero cells. Biochem Pharmacol. 1993 Sep 14;46(6):1053-7. [3]. Cundy KC, et al. Clinical pharmacokinetics of cidofovir in human immunodeficiency virus-infected patients. Antimicrob Agents Chemother. 1995 Jun;39(6):1247-52. [4]. Polis MA, et al. Anticytomegaloviral activity and safety of cidofovir in patients with human immunodeficiency virus infection and cytomegalovirus viruria. Antimicrob Agents Chemother. 1995 Apr;39(4):882-6.

Description

Cidofovir is an anti-CMV drug which can suppress CMV replication by selective inhibition of viral DNA polymerase and therefore prevention of viral replication and transcription.IC50 Value:Target: CMV DNA polymerasein vitro: The minimum concentrations of (S)-HPMPC required to inhibit CMV plaque formation by 50% was microgram/ml. The selectivity indices of (S)-HPMPC, as determined by the ratio of the 50% inhibitory concentration for cell growth to the 50% inhibitory concentration for plaque formation for CMV (AD-169 strain), was 1,500 [1]. The time course of uptake of HPMPC into Vero cells was linear between 10 and 75 min and proportional to the concentration in the medium from 10(-6) to 10(-2) M. HPMPC uptake was temperature sensitive and the rate of uptake was considerably lower at 27 degrees than at 37 degrees and almost totally inhibited at 4 degrees [2]. in vivo: Levels of cidofovirin serum following intravenous infusion were dose proportional over the dose range of 1.0 to 10.0 mg/kg of body weight and declined biexponentially with an overall mean +/- standard deviation terminal half-life of 2.6 +/- 1.2 h (n = 25). Approximately 90% of the intravenous dose was recovered unchanged in the urine in 24 h. The overall mean +/- standard deviation total clearance of the drug from serum (148 +/- 25 ml/h/kg; n = 25) approximated renal clearance (129 +/- 42 ml/h/kg; n = 25), which was significantly higher (P < 0.001) than the baseline creatinine clearance in the same patients (83 +/- 21 ml/h/kg; n = 12) [3]. Positive CMV urine cultures reverted to negative in 2 of 8 patients receiving doses of < or = 1.5 mg/kg twice weekly and 11 of 13 patients receiving higher doses. Cidofovir has in vivo anti-CMV activity demonstrated by prolonged clearing of CMV viruria, although this observation is tempered by the fact that clearance of viremia could not be demonstrated [4].Toxicity: Patients receiving 0.5 or 1.5 mg/kg twice weekly experienced no serious toxicity. The first two patients who received 5 mg/kg twice weekly developed glycosuria and 2+ proteinuria. Subsequent patients received concomitant probenecid to attempt to ameliorate renal toxicity [4].Clinical trial: FDA approved drug

Related Catalog

Signaling Pathways >>Anti-infection >>CMVResearch Areas >>Infection

References

[1]. Snoeck R, et al. (S)-1-(3-hydroxy-2-phosphonylmethoxypropyl)cytosine, a potent and selective inhibitor of human cytomegalovirus replication. Antimicrob Agents Chemother. 1988 Dec;32(12):1839-44.

[2]. Connelly MC, et al. Mechanism of uptake of the phosphonate analog (S)-1-(3-hydroxy-2-phosphonylmethoxypropyl)cytosine (HPMPC) in Vero cells. Biochem Pharmacol. 1993 Sep 14;46(6):1053-7.

[3]. Cundy KC, et al. Clinical pharmacokinetics of cidofovir in human immunodeficiency virus-infected patients. Antimicrob Agents Chemother. 1995 Jun;39(6):1247-52.

[4]. Polis MA, et al. Anticytomegaloviral activity and safety of cidofovir in patients with human immunodeficiency virus infection and cytomegalovirus viruria. Antimicrob Agents Chemother. 1995 Apr;39(4):882-6.

Chemical & Physical Properties

Density	1.8±0.1 g/cm3
Boiling Point	609.5±65.0 °C at 760 mmHg
Melting Point	260ºC
Molecular Formula	C₈H₁₄N₃O₆P
Molecular Weight	279.187
Flash Point	322.4±34.3 °C
Exact Mass	279.062012
PSA	157.71000
LogP	-3.37
Vapour Pressure	0.0±4.0 mmHg at 25°C
Index of Refraction	1.656
InChIKey	VWFCHDSQECPREK-LURJTMIESA-N
SMILES	Nc1ccn(CC(CO)OCP(=O)(O)O)c(=O)n1
Storage condition	room temp

Safety Information

Hazard Codes	T
Risk Phrases	25-38
Safety Phrases	S26-S36
WGK Germany	3
HS Code	2933599090

Customs

HS Code	2933599090
Summary	2933599090. other compounds containing a pyrimidine ring (whether or not hydrogenated) or piperazine ring in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Synonyms

Cidovir (S)-1-[3-hydroxy-2-(phosphonylmethoxy)propyl]cytosine HPMPC Vistide

Phosphonic acid, [[(1S)-2-(4-amino-2-oxo-1(2H)-pyrimidinyl)-1-(hydroxymethyl)ethoxy]methyl]-

({[(2S)-1-(4-Amino-2-oxo-1(2H)-pyrimidinyl)-3-hydroxy-2-propanyl]oxy}methyl)phosphonic acid

Vistide

({[(2S)-1-(4-Amino-2-oxopyrimidin-1(2H)-yl)-3-hydroxypropan-2-yl]oxy}methyl)phosphonic acid

Cidofovir

(S)-(3-(4-amino-2-oxopyrimidin-1(2H)-yl)-1-hydroxypropan-2-yloxy)methylphosphonic acid

(S)-[[2-(4-Amino-2-oxo-1(2H)-pyrimidinyl)-1-(hydroxymethyl)ethoxy]methyl]phosphonic Acid

MFCD00866936

Cidofovir hydrate

GS-504

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