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(Redirected from Pyrimidine analog) Chemicals that inhibit the use of a metabolite

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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.

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. PMC 2827868. PMID 19476376.

Intracellular chemotherapeutic agents / antineoplastic agents (L01)

SPs/MIs
(M phase)

Block microtubule assembly	Vinca alkaloids (Vinblastine Vincristine Vindesine Vinflunine 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 (Pemetrexed Raltitrexed)
Purine	Adenosine deaminase inhibitor (Pentostatin) Halogenated/ribonucleotide reductase inhibitors (Cladribine Clofarabine Fludarabine) Nelarabine Rabacfosadine Thiopurine (Mercaptopurine Tioguanine)
Pyrimidine	Thymidylate synthase inhibitor (Capecitabine Carmofur Doxifluridine Floxuridine Fluorouracil Tegafur (+gimeracil/oteracil)) DNA polymerase inhibitor (Cytarabine +daunorubicin) Ribonucleotide reductase inhibitor (Gemcitabine) Hypomethylating agent (Azacitidine Decitabine)
Deoxyribonucleotide	Ribonucleotide reductase inhibitor (Hydroxycarbamide)

Topoisomerase inhibitors
(S phase)

I	Camptotheca (Belotecan Camptothecin Cositecan Etirinotecan pegol Exatecan Gimatecan Irinotecan Lurtotecan Rubitecan Silatecan Topotecan)
II	Podophyllum (Etoposide Teniposide)
II+Intercalation	Anthracyclines (Aclarubicin Amrubicin Daunorubicin (+cytarabine) Doxorubicin Epirubicin Idarubicin Pirarubicin Valrubicin Zorubicin) Anthracenediones (Losoxantrone Mitoxantrone Pixantrone) Amsacrine Bisantrene Crisnatol Menogaril

Crosslinking of DNA
(CCNS)

Alkylating	Nitrogen mustards: Bendamustine Chlormethine Cyclophosphamide (Ifosfamide Trofosfamide) Chlorambucil Melphalan (Melphalan flufenamide) Prednimustine Uramustine Nitrosoureas: Carmustine Fotemustine Lomustine (Semustine) Nimustine Ranimustine Streptozocin Alkyl sulfonates: Busulfan (Mannosulfan Treosulfan) Aziridines: Carboquone Thiotepa Triaziquone Triethylenemelamine
Platinum-based	Carboplatin Cisplatin Dicycloplatin Nedaplatin Oxaliplatin Satraplatin
Nonclassical	Altretamine Hydrazines (Procarbazine) Etoglucid Mitobronitol Pipobroman Triazenes (Dacarbazine Mitozolomide Temozolomide)
Intercalation	Streptomyces (Dactinomycin Bleomycin Mitomycins Plicamycin)

Photosensitizers/PDT

Other

Enzyme inhibitors	FI (Tipifarnib) CDK inhibitors (Abemaciclib Alvocidib Palbociclib Ribociclib Seliciclib) PrI Bortezomib Carfilzomib Oprozomib Ixazomib PhI (Anagrelide) IMPDI (Tiazofurin) LI (Masoprocol) PARP inhibitor (Fuzuloparib Niraparib +abiraterone acetate Olaparib Rucaparib) HDAC (Belinostat Entinostat Panobinostat Romidepsin Vorinostat) PIKI (Pi3K) (Alpelisib Copanlisib Duvelisib Idelalisib Inavolisib Umbralisib) IDH (Enasidenib Ivosidenib Olutasidenib Vorasidenib)
Receptor antagonists	ERA (Atrasentan) Retinoid X receptor (Bexarotene) Sex steroid (Testolactone)
Other/ungrouped	Adagrasib Aflibercept Arsenic trioxide Asparagine depleters (Asparaginase/Pegaspargase) Axicabtagene ciloleucel Belzutifan Bexarotene Brexucabtagene autoleucel Celecoxib Ciltacabtagene autoleucel Demecolcine Denileukin diftitox Eflornithine Elesclomol Elsamitrucin Epacadostat Eribulin Estramustine Glasdegib Idecabtagene vicleucel Imetelstat Lifileucel Lisocabtagene maraleucel Lonidamine Lucanthone Lurbinectedin Mitoguazone Mitotane Nadofaragene firadenovec Navitoclax Obecabtagene autoleucel Oblimersen Omacetaxine mepesuccinate Plitidepsin Tabelecleucel Retinoids (Alitretinoin Tretinoin) Selinexor Sitimagene ceradenovec Sotorasib Tagraxofusp Talimogene laherparepvec Tazemetostat Tebentafusp Tiazofurine Tigilanol tiglate Tisagenlecleucel Trabectedin Veliparib Venetoclax Verdinexor Vosaroxin

WHO-EM
Withdrawn from market
Clinical trials:
- Phase III
- Never to phase III

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

Baltimore I

Herpesvirus

DNA-synthesis
inhibitor

TK activated

Purine analogue

adenine (Vidarabine)

Pyrimidine analogue

thymine

cytosine (Cytarabine)

Not TK activated

Foscarnet

Other

HPV/MC

Vaccinia

assembly: Rifampicin

Poxviridae

Hepatitis B (VII)

Multiple/general

Nucleic acid inhibitors	Cidofovir Brincidofovir
Interferon	Interferon alfa 2b Peginterferon alfa-2a
Multiple/unknown	Filociclovir Ribavirin/Taribavirin Moroxydine

WHO-EM
Withdrawn from market
Clinical trials:
- Phase III
- Never to phase III

Nucleic acid constituents

Nucleobase

Nucleoside

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

Nucleotide
(Nucleoside monophosphate)

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

Nucleoside diphosphate

ADP GDP mUDP UDP CDP Xanthosine diphosphate
dADP dGDP dTDP dUDP dCDP

Nucleoside triphosphate

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

Purine receptor modulators

Receptor
(ligands)

P0 (adenine)

Agonists: 8-Aminoadenine
Adenine

P1
(adenosine)

Agonists: 2-(1-Hexynyl)-N-methyladenosine
2-Cl-IB-MECA
2-Chloroadenosine
2'-MeCCPA
4'-O-β-D-Glucosyl-9-O-(6''-deoxysaccharosyl)olivil
5'-N-ethylcarboxamidoadenosine
Adenosine
ADP
AMP
Apadenoson
ATL-146e
ATP
BAY 60–6583
Binodenoson
Capadenoson
CCPA
CGS-21680
CP-532,903
CV-1808
Evodenoson
GR 79236
HENECA
LUF-5835
LUF-5845
N-Cyclopentyladenosine
Namodenoson
NECA
Neladenoson dalanate
Piclidenoson
Regadenoson
SDZ WAG 994
Selodenoson
Sonedenoson
Tecadenoson
Trabodenoson
UK-432,097

Antagonists: 3-Chlorostyrylcaffeine (CSC)
7-Methylxanthine
8-Chlorotheophylline
8-Phenyl-1,3-dipropylxanthine
8-Phenyltheophylline
Acefylline
Aminophylline
ATL-444
AZD-4635
Bamifylline
Cafedrine
Caffeine
Caffeine citrate
Cartazolate
CGH-2466
CGS-15943
Choline theophyllinate
Ciforadenant
CPX
CVT-6883
Dimethazan
DMPX
DPCPX
Dyphylline
Enprofylline
Etazolate
Etrumadenant
Fenethylline
IBMX
Imaradenant
Inupadenant
ISAM-140
ISAM-R316
Isovaleric acid
Istradefylline
KF-26777
Lu AA41063
Lu AA47070
MRE3008F20
MRS-1191
MRS-1220
MRS-1334
MRS-1523
MRS-1706
MRS-1754
MRS-3777
MSX-2
MSX-3
MSX-4
Muvadenant
Paraxanthine
Pentoxifylline
Preladenant
Propentofylline
Proxyphylline
PSB-10
PSB-11
PSB-36
PSB-603
PSB-788
PSB-1115
PSB-1901
Reversine
Rolofylline
SCH-442,416
SCH-58261
Sipagladenant
Taminadenant
Theacrine
Theobromine
Theodrenaline
Theophylline
Tozadenant
Tracazolate
Vipadenant
VUF-5574
ZM-241,385

P2
(nucleotide)

P2X
(ATPTooltip Adenosine triphosphate)

Antagonists: 5-BDBD
A-317491
A-438079
A-740003
A-804598
A-839977
AF-353
AZ-10606120
AZ-11645373
BBG
Calcium
Calmidazolium
Chelerythrine
Copper
Emodin (Rheum officinale)
Evans blue
Gefapixant
GW-791343
HMA
Ip5I
isoPPADS
JNJ-47965567
KN-04
KN-62
Magnesium
MRS-2159
NF-023
NF-110
NF-157
NF-279
NF-449
Opiranserin (VVZ-149)
Oxidized-ATP
Phenol Red
Phenolphthalein
PPADS
PPNDS
PSB-12062
Puerarin (Radix puerariae)
Purotoxin 1
RB-2
Ro 0437626
Ro 51
RO-3
Sodium ferulate (Angelica sinensis, Ligusticum wallichii)
Suramin
TC-P 262
Tetramethylpyrazine (ligustrazine) (Ligusticum wallichii)
TNP-ATP
Zinc

P2Y

Transporter
(blockers)

CNTsTooltip Concentrative nucleoside transporters	6-Hydroxy-7-methoxyflavone Adenosine dMeThPmR Estradiol KGO-2142 KGO-2173 MeThPmR Phloridzin Progesterone
ENTsTooltip Equilibrative nucleoside transporters	Barbiturates Benzodiazepines Cilostazol Dilazep Dipyridamole Estradiol Ethanol Hexobendine NBMPR Pentoxifylline Progesterone Propentofylline
PMATTooltip Plasma membrane monoamine transporter	Decynium-22

Enzyme
(inhibitors)

XOTooltip Xanthine oxidase	Allopurinol Amflutizole Benzbromarone Caffeic acid Cinnamaldehyde Cinnamomum osmophloeum Febuxostat Myo-inositol Kaempferol Myricetin Niraxostat Oxipurinol Phytic acid Pistacia integerrima Propolis Quercetin Tisopurine Topiroxostat
Others	Aminopterin Azathioprine Methotrexate Mycophenolic acid Pemetrexed Pralatrexate Many others

Others

Others: Chrysophanol (rhubarb)

See also: Receptor/signaling modulators

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