Cyclopentenylcytosine
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Cyclopentenylcytosine
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CAS No:
90597-22-1
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Formula:
C10H13N3O4
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Chemical Name:
Cyclopentenylcytosine
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Synonyms:
2(1H)-Pyrimidinone,4-amino-1-[(1R,4R,5S)-4,5-dihydroxy-3-(hydroxymethyl)-2-cyclopenten-1-yl]-;2(1H)-Pyrimidinone,4-amino-1-[4,5-dihydroxy-3-(hydroxymethyl)-2-cyclopenten-1-yl]-,[1R-(1α,4β,5β)]-;4-Amino-1-[(1R,4R,5S)-4,5-dihydroxy-3-(hydroxymethyl)-2-cyclopenten-1-yl]-2(1H)-pyrimidinone;NSC 375575;CPEC;Cyclopentenylcytosine
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CAS No:
Description
Cyclopentenyl Cytosine is a pro-drug carbocyclic analogue of cytidine with antineoplastic and antiviral activities. Cyclopentenyl cytosine (CPEC) is converted to the active metabolite cyclopentenyl cytosine 5'-triphosphate (CPEC-TP); CPEC-TP competitively inhibits cytidine triphosphate (CTP) synthase, thereby depleting intracellular cytidine pools and inhibiting DNA and RNA synthesis. This agent may also induce differentiation of some tumor cell types. The antiviral activity of this agent is broad-spectrum.
Characteristics
121.60000
-2.02
1.7±0.1 g/cm3
508.4±60.0 °C at 760 mmHg
261.3±32.9 °C
1.743
Toluene < 1 (mg/mL)
(c = 0.3,0.1M phosphate buffer) [a]23D = -95 ± 5
Safety Information
Bulk: CPE-C was found to be stable under the following conditions: room temperature, dark; room temperature, light; 50 °C, dark; 50 °C, light. Solution: CPE-C was found to be stable at room temperature in 0.9% saline over a 75 hr period under exposure to light.
Drug Information
Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)|Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)
1-(4-hydroxymethyl-2,3-dihydroxy-4-cyclopenten-1-yl)cytosine
Computed Properties
Molecular Weight:239.23
XLogP3:-2.4
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:239.09060590
Monoisotopic Mass:239.09060590
Topological Polar Surface Area:119
Heavy Atom Count:17
Complexity:429
Defined Atom Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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