1-(2'-deoxy-2'-fluoro-beta-arabinofuranosyl)-5-methylcytosine triphosphate profile

**1-(2'-deoxy-2'-fluoro-beta-arabinofuranosyl)-5-methylcytosine triphosphate (dFdCMP)** is a synthetic nucleoside triphosphate analogue. Here's a breakdown of its structure and significance:

**Structure:**

* **Base:** 5-methylcytosine (mC) - a modified base commonly found in DNA.
* **Sugar:** 2'-deoxy-2'-fluoro-beta-arabinofuranosyl - a modified sugar moiety. The arabino prefix indicates the sugar has an unusual configuration.
* The key modification is the fluorine atom at the 2' position.
* **Phosphate Groups:** Three phosphate groups attached to the sugar, making it a triphosphate.

**Importance in Research:**

dFdCMP is a potent inhibitor of several DNA polymerases, including those involved in DNA replication and repair. Its significance lies in its ability to:

* **Block DNA Synthesis:** The fluorine substitution at the 2' position alters the sugar's conformation, making it a poor substrate for DNA polymerases. When incorporated into DNA, dFdCMP terminates chain elongation.
* **Investigate DNA Replication and Repair:** By inhibiting DNA synthesis, dFdCMP is a valuable tool to study:
* The mechanism of DNA replication.
* The function of DNA polymerases.
* DNA repair pathways.
* The effect of DNA damage on cell growth and survival.
* **Develop Antiviral and Anticancer Drugs:**
* dFdCMP's ability to inhibit viral DNA replication has led to its use in treating viral infections, particularly those caused by herpesviruses (e.g., herpes simplex virus, varicella-zoster virus).
* The compound also shows potential as an anticancer drug, as it can inhibit the growth of tumor cells.

**Key Features that Make it Effective:**

* **High Affinity for DNA Polymerases:** The modified sugar moiety allows dFdCMP to bind strongly to DNA polymerase active sites.
* **Chain Termination:** Incorporation of dFdCMP into DNA prevents further elongation due to the fluorine modification.

**Summary:**

dFdCMP is a powerful research tool with significant applications in understanding DNA replication, repair, and the development of antiviral and anticancer therapies. Its unique structure and potent inhibitory activity make it a valuable resource for scientists.

1-(2'-deoxy-2'-fluoro-beta-arabinofuranosyl)-5-methylcytosine triphosphate: RN given refers to (D)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	157387
MeSH ID	M0136566

Synonym
2(1h)-pyrimidinone, 4-amino-1-[2-deoxy-2-fluoro-5-o-[hydroxy[[hydroxy(phosphonooxy)phosphinyl]oxy]phosphinyl]-.beta.-d-arabinofuranosyl]-5-methyl-
fmactp
[[(2r,3r,4s,5r)-5-(4-amino-5-methyl-2-oxo-pyrimidin-1-yl)-4-fluoro-3-hydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl] phosphono hydrogen phosphate
2(1h)-pyrimidinone, 4-amino-1-(2-deoxy-2-fluoro-5-o-(hydroxy((hydroxy(phosphonooxy)phosphinyl)oxy)phosphinyl)-beta-d-arabinofuranosyl)-5-methyl-
79570-62-0
1-(2'-deoxy-2'-fluoro-beta-l-arabinofuranosyl)-5-methyluracil 5'-triphosphate
1-dfamct
1-(2'-deoxy-2'-fluoro-beta-arabinofuranosyl)-5-methylcytosine triphosphate
DTXSID70229781
((2r,3r,4s,5r)-5-(4-amino-5-methyl-2-oxopyrimidin-1(2h)-yl)-4-fluoro-3-hydroxytetrahydrofuran-2-yl)methyl tetrahydrogen triphosphate

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	1 (20.00)	18.7374
1990's	1 (20.00)	18.2507
2000's	3 (60.00)	29.6817
2010's	0 (0.00)	24.3611
2020's	0 (0.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	1 (20.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	4 (80.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
adenine [no description available]	2	1	0	6-aminopurines; purine nucleobase	Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
cytidine triphosphate Cytidine Triphosphate: Cytidine 5'-(tetrahydrogen triphosphate). A cytosine nucleotide containing three phosphate groups esterified to the sugar moiety.	2.01	1	0	cytidine 5'-phosphate; pyrimidine ribonucleoside 5'-triphosphate	Escherichia coli metabolite; mouse metabolite
cytarabine [no description available]	1.96	1	0	beta-D-arabinoside; monosaccharide derivative; pyrimidine nucleoside	antimetabolite; antineoplastic agent; antiviral agent; immunosuppressive agent
thiophenes Thiophenes: A monocyclic heteroarene furan in which the oxygen atom is replaced by a sulfur.. thiophenes : Compounds containing at least one thiophene ring.	2.01	1	0	mancude organic heteromonocyclic parent; monocyclic heteroarene; thiophenes; volatile organic compound	non-polar solvent
arabinofuranosylcytosine triphosphate Arabinofuranosylcytosine Triphosphate: A triphosphate nucleotide analog which is the biologically active form of CYTARABINE. It inhibits nuclear DNA synthesis.	4.48	5	1
fiacitabine fiacitabine: anti-herpes virus agent which also inhibits growth of certain human tumor cell lines in vitro.	1.96	1	0
adefovir adefovir: inhibitor of African swine fever virus. adefovir(1-) : A organophosphonate oxoanion obtained by removal of a proton from the phosphonate group of adefovir, a nucleoside reverse transcriptase inhibitor. It is the major microspecies at pH 7.3 (according to Marvin v 6.2.0.).. adefovir : A member of the class of phosphonic acids that is methylphosphonic acid in which one of the methyl hydrogens has been replaced by a 2-(6-amino-9H-purin-9-yl)ethoxy group. An inhibitor of HIV-1 reverse transcriptase, the bis(t-butoxycarbonyloxymethyl) ester (dipivoxil ester) prodrug is used to treat chronic hepatitis B viral infection.	2	1	0	6-aminopurines; ether; phosphonic acids	antiviral drug; DNA synthesis inhibitor; drug metabolite; HIV-1 reverse transcriptase inhibitor; nephrotoxic agent
lamivudine [no description available]	2.01	1	0	monothioacetal; nucleoside analogue; oxacycle; primary alcohol	allergen; anti-HBV agent; antiviral drug; EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor; HIV-1 reverse transcriptase inhibitor; prodrug
amdoxovir amdoxovir: structure in first source; RN given refers to (2R-cis)-isomer	2.41	2	0
organophosphonates hydrogenphosphite : A divalent inorganic anion resulting from the removal of a proton from two of the hydroxy groups of phosphorous acid.	2	1	0	divalent inorganic anion; phosphite ion
2'-fluorothymidine [no description available]	4.07	3	1
tenofovir tenofovir (anhydrous) : A member of the class of phosphonic acids that is methylphosphonic acid in which one of the methyl hydrogens is replaced by a [(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy group. An inhibitor of HIV-1 reverse transcriptase, the bis(isopropyloxycarbonyloxymethyl) ester (disoproxil ester) prodrug is used as the fumaric acid salt in combination therapy for the treatment of HIV infection.	2	1	0	nucleoside analogue; phosphonic acids	antiviral drug; drug metabolite; HIV-1 reverse transcriptase inhibitor
arabinofuranosyluracil Arabinofuranosyluracil: A pyrimidine nucleoside formed in the body by the deamination of CYTARABINE.	4.07	3	1
acyclovir Acyclovir: A GUANOSINE analog that acts as an antimetabolite. Viruses are especially susceptible. Used especially against herpes.. acyclovir : An oxopurine that is guanine substituted by a (2-hydroxyethoxy)methyl substituent at position 9. Used in the treatment of viral infections.	2	1	0	2-aminopurines; oxopurine	antimetabolite; antiviral drug
guanine [no description available]	2	1	0	2-aminopurines; oxopurine; purine nucleobase	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
guanosine ribonucleoside : Any nucleoside where the sugar component is D-ribose.	2.01	1	0	guanosines; purines D-ribonucleoside	fundamental metabolite
penciclovir penciclovir : A member of the class of 2-aminopurines that is guanine in which the hydrogen at position 9 is substituted by a 4-hydroxy-3-(hydroxymethyl)but-1-yl group. An antiviral drug, it is administered topically for treatment of herpes labialis. A prodrug, famciclovir, is used for oral administration.	2	1	0	2-aminopurines; propane-1,3-diols	antiviral drug
2-aminopurine dioxolane (4-2-aminopurin-9-yl)-1,3-dioxolane-2-methanol: structure in first source	2.01	1	0
lobucavir lobucavir: inhibits the replication of HIV virus in T cells, monocytes & macrophages in vitro by inhibiting DNA polymerase and viral DNA synthesis	2	1	0

Condition	Relationship Strength	Studies	Trials
Hepatocellular Carcinoma [description not available]	2.01	1	0
Cancer of Liver [description not available]	2.01	1	0
Hepatitis, Viral, Animal INFLAMMATION of the LIVER in animals due to viral infection.	2.01	1	0
Infections, Hepadnaviridae [description not available]	2.01	1	0
Carcinoma, Hepatocellular A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.	2.01	1	0
Liver Neoplasms Tumors or cancer of the LIVER.	2.01	1	0
Hepadnaviridae Infections Virus diseases caused by the HEPADNAVIRIDAE.	2.01	1	0
Hepatitis B Virus Infection [description not available]	3.41	1	1
Hepatitis B INFLAMMATION of the LIVER in humans caused by a member of the ORTHOHEPADNAVIRUS genus, HEPATITIS B VIRUS. It is primarily transmitted by parenteral exposure, such as transfusion of contaminated blood or blood products, but can also be transmitted via sexual or intimate personal contact.	3.41	1	1
Cytomegalovirus A genus of the family HERPESVIRIDAE, subfamily BETAHERPESVIRINAE, infecting the salivary glands, liver, spleen, lungs, eyes, and other organs, in which they produce characteristically enlarged cells with intranuclear inclusions. Infection with Cytomegalovirus is also seen as an opportunistic infection in AIDS.	1.96	1	0

1-(2'-deoxy-2'-fluoro-beta-arabinofuranosyl)-5-methylcytosine triphosphate

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Research Demand Index: 12.59

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