Biology:Pyrimidine analogue

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

Examples

Nucleobase analogues
- Fluorouracil (5FU), which inhibits thymidylate synthase
- Floxuridine (FUDR)
- 6-azauracil (6-AU)
Nucleoside analogues
- Cytarabine (Cytosine arabinoside)
- Gemcitabine
Nucleotide analogues

Medical uses

Pyrimidine antimetabolites are commonly used to treat cancer by interfering with DNA replication.^[1]

References

↑ Parker, William B. (2009). "Enzymology of Purine and Pyrimidine Antimetabolites Used in the Treatment of Cancer". Chem Rev 109 (7): 2880–2893. doi:10.1021/cr900028p. PMID 19476376.

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) Nelarabine Thiopurine (Tioguanine^# Mercaptopurine^#)
Pyrimidine	Thymidylate synthase inhibitor (Fluorouracil^# Capecitabine^# Doxifluridine Tegafur (+gimeracil/oteracil) 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 Cositecan^† Belotecan Gimatecan Exatecan Irinotecan^# Lurtotecan^‡ Silatecan^§ Topotecan Rubitecan^‡)
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: Chlormethine Cyclophosphamide^# (Ifosfamide^# Trofosfamide) Chlorambucil^# (Melphalan Prednimustine) Bendamustine^# Uramustine Nitrosoureas: Carmustine Lomustine (Semustine) Fotemustine Nimustine Ranimustine Streptozocin Alkyl sulfonates: Busulfan (Mannosulfan Treosulfan) Aziridines: Carboquone Thiotepa Triaziquone Triethylenemelamine
Platinum-based	Carboplatin^# Cisplatin^# Dicycloplatin Nedaplatin Oxaliplatin^# Satraplatin
Nonclassical	Hydrazines (Procarbazine^#) Triazenes (Dacarbazine^# Temozolomide) Altretamine Mitobronitol Pipobroman
Intercalation	Streptomyces (Actinomycin^# Bleomycin^# Mitomycins Plicamycin)

Photosensitizers/PDT

Other

Enzyme inhibitors	FI (Tipifarnib^§) CDK inhibitors (Abemaciclib Alvocidib^† Palbociclib Ribociclib Seliciclib^†) PrI Bortezomib Carfilzomib Ixazomib PhI (Anagrelide) IMPDI (Tiazofurin^§) LI (Masoprocol) PARP inhibitor (Niraparib Olaparib Rucaparib) HDAC (Belinostat Panobinostat Romidepsin Vorinostat) PIKI (Idelalisib)
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 Estramustine phosphate Etoglucid Lonidamine Lucanthone Mitoguazone Mitotane Oblimersen^† Omacetaxine mepesuccinate Eribulin

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^‡Withdrawn from market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

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

DNA-synthesis
inhibitor

TK activated

Purine analogue	guanine (Aciclovir^#/Valaciclovir Ganciclovir/Valganciclovir^# Penciclovir/Famciclovir) adenine (Vidarabine)
Pyrimidine analogue	uridine (Idoxuridine Trifluridine (+tipiracil) Edoxudine) thymine Brivudine Sorivudine [[Chemistry:Cytocytosine (Cytarabine\|Cytarabine]])

Not TK activated

Foscarnet

Other

assembly: Rifampicin

Methisazone

Hepatitis B (VII)

Nucleoside analogues/NARTIs: Entecavir^#
Lamivudine
Telbivudine
Clevudine

Multiple/general

Nucleic acid inhibitors	Cidofovir
Interferon	Interferon alfa 2b Peginterferon alfa-2a
Multiple/unknown	Ribavirin^#/Taribavirin^† Moroxydine

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

Nucleic acid constituents

Ribonucleoside	Adenosine Guanosine 5-Methyluridine Uridine 5-Methylcytidine Cytidine Pseudouridine Inosine N⁶-Methyladenosine Xanthosine Wybutosine
Deoxyribonucleoside	Deoxyadenosine Deoxyguanosine Thymidine Deoxyuridine Deoxycytidine Deoxyinosine Deoxyxanthosine

Nucleotide
(Nucleoside monophosphate)

Ribonucleotide	AMP GMP m⁵UMP UMP CMP IMP XMP
Deoxyribonucleotide	dAMP dGMP dTMP dUMP dCMP dIMP dXMP
Cyclic nucleotide	cAMP cGMP c-di-GMP c-di-AMP cADPR

Nucleoside diphosphate

ADP GDP m⁵UDP UDP CDP
dADP dGDP dTDP dUDP dCDP

Nucleoside triphosphate

ATP GTP m⁵UTP UTP CTP ITP XTP
dATP dGTP dTTP dUTP dCTP dITP dXTP

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