Pyrimidine analogue

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Pyrimidine analogue

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Pyrimidine analogues are antimetabolites which mimic the structure of metabolic pyrimidines.

Examples

Examples include:

5-fluorouracil (5FU) which inhibits thymidylate synthase.
Floxuridine (FUDR)
Cytosine arabinoside (Cytarabine)
6-azauracil

Intracellular chemotherapeutic agents / antineoplastic agents (L01)

SPs/MIs
(M phase)

Block microtubule assembly	Vinca alkaloids (Vinblastine Vincristine Vinflunine Vindesine Vinorelbine)

Block microtubule disassembly	Taxanes (Cabazitaxel Docetaxel Larotaxel Ortataxel Paclitaxel Tesetaxel) Epothilones (Ixabepilone)

DNA replication
inhibitor

DNA precursors/
antimetabolites
(S phase)

Folic acid	Dihydrofolate reductase inhibitor (Aminopterin Methotrexate Pemetrexed Pralatrexate) Thymidylate synthase inhibitor (Raltitrexed Pemetrexed)

Purine	Adenosine deaminase inhibitor (Pentostatin) Halogenated/ribonucleotide reductase inhibitors (Cladribine Clofarabine Fludarabine) Thiopurine (Thioguanine Mercaptopurine)

Pyrimidine	Thymidylate synthase inhibitor (Fluorouracil Capecitabine Tegafur Carmofur Floxuridine) DNA polymerase inhibitor (Cytarabine) Ribonucleotide reductase inhibitor (Gemcitabine) Hypomethylating agent (Azacitidine Decitabine)

Deoxyribonucleotide	Ribonucleotide reductase inhibitor (Hydroxycarbamide)

Topoisomerase inhibitors
(S phase)

I	Camptotheca (Camptothecin Topotecan Irinotecan Rubitecan Belotecan)

II	Podophyllum (Etoposide Teniposide)

II+Intercalation	Anthracyclines (Aclarubicin Daunorubicin Doxorubicin Epirubicin Idarubicin Amrubicin Pirarubicin Valrubicin Zorubicin) Anthracenediones (Mitoxantrone Pixantrone)

Crosslinking of DNA
(CCNS)

Alkylating	Nitrogen mustards: Mechlorethamine Cyclophosphamide (Ifosfamide Trofosfamide) Chlorambucil (Melphalan Prednimustine) Bendamustine Uramustine Estramustine Nitrosoureas: Carmustine Lomustine (Semustine) Fotemustine Nimustine Ranimustine Streptozocin Alkyl sulfonates: Busulfan (Mannosulfan Treosulfan) Aziridines: Carboquone ThioTEPA Triaziquone Triethylenemelamine

Alkylating-like	Platinum (Carboplatin Cisplatin Nedaplatin Oxaliplatin Triplatin tetranitrate Satraplatin)

Nonclassical	Hydrazines (Procarbazine) Triazenes (Dacarbazine Temozolomide) Altretamine Mitobronitol

Intercalation	Streptomyces (Actinomycin Bleomycin Pingyangmycin Mitomycin Plicamycin)

Photosensitizers/PDT

Other

Enzyme inhibitors	FI (Tipifarnib) CDK inhibitors (Alvocidib Seliciclib) PrI (Bortezomib) PhI (Anagrelide) IMPDI (Tiazofurine) LI (Masoprocol) PARP inhibitor (Olaparib) HDAC (Panobinostat Vorinostat Romidepsin)

Receptor antagonists	ERA (Atrasentan) Retinoid X receptor (Bexarotene) Sex steroid (Testolactone)

Other/ungrouped	Amsacrine Trabectedin Retinoids (Alitretinoin Tretinoin) Arsenic trioxide Asparagine depleters (Asparaginase/Pegaspargase) Celecoxib Demecolcine Elesclomol Elsamitrucin Etoglucid Lonidamine HAMLET (human alpha-lactalbumin made lethal to tumor cells) Lucanthone Mitoguazone Mitotane Oblimersen Omacetaxine mepesuccinate mTOR inhibitors (Everolimus Temsirolimus)

M: NEO

tsoc, mrkr

tumr, epon, para

drug (L1i/1e/V03)

DNA virus antivirals (primarily J05, also S01AD and D06BB)

Baltimore I

Herpesvirus

DNA-synthesis
inhibitor

TK activated

Purine analogue	guanine (Aciclovir^#/Valacyclovir Ganciclovir/Valganciclovir Penciclovir/Famciclovir) adenine (Vidarabine)

Pyrimidine analogue	uridine (Idoxuridine Trifluridine Edoxudine) thymine (Brivudine) cytosine (Cytarabine)

Not TK activated

Foscarnet

Other

HPV/MC

Vaccinia

assembly: Rifampicin

Poxviridae

Methisazone

Hepatitis B (VII)

Multiple/general

Nucleic acid inhibitors	Cidofovir

Interferon	Interferon alfa-2b Peginterferon alfa-2a

Multiple/unknown	Ribavirin^#/Taribavirin^†

ErbB2/PI3K Pathway	NOV-205^§ NOV-002^†

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

M: VIR

virs(prot)/clss

cutn/syst (hppv/hiva, infl/zost/zoon)/epon

drugJ(dnaa, rnaa, rtva, vacc)

Nucleic acid constituents

Nucleobase

Purine (Adenine, Guanine, Purine analogue) · Pyrimidine (Uracil, Thymine, Cytosine, Pyrimidine analogue)

Nucleoside

Ribonucleoside	Adenosine · Guanosine · 5-Methyluridine · Uridine · Cytidine

Deoxyribonucleoside	Deoxyadenosine · Deoxyguanosine · Thymidine · Deoxyuridine · Deoxycytidine

Nucleotide
(Nucleoside monophosphate)

Ribonucleotide	AMP, GMP, m⁵UMP, UMP, CMP

Deoxyribonucleotide	dAMP, dGMP, dTMP, dUMP, dCMP

Cyclic nucleotide	cAMP, cGMP, c-di-GMP, cADPR

Nucleoside diphosphate

ADP, GDP, m⁵UDP, UDP, CDP · dADP, dGDP, dTDP, dUDP, dCDP

Nucleoside triphosphate

ATP, GTP, m⁵UTP, UTP, CTP · dATP, dGTP, dTTP, dUTP, dCTP

biochemical families: proteins (amino acids/intermediates) · nucleic acids (constituents/intermediates) · carbohydrates (glycoproteins, alcohols, glycosides)
lipids (fatty acids/intermediates, phospholipids, steroids, sphingolipids, eicosanoids) · tetrapyrroles/intermediates

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