Thiopurine

Thiopurine is an analogue of a purine wherein a C=O/C-OH group has been replaced by a C=S/C-SH group. These organosulfur compounds are bioactive in beneficial and complicating manner. They interfere with purine biosynthesis. Thiopurine drugs antimetabolites widely used in the treatment of acute lymphoblastic leukemia, autoimmune disorders (e.g., Crohn's disease, rheumatoid arthritis), and organ transplant recipients. Azathioprine is a prodrug. 6-Mercaptopurine is substrate for three enzyme]]s: thiopurine methyltransferase (to give 6-methylmercaptopurine), xanthine oxidase (to give 6-thiouric acid], and hypoxanthine phosphoribosyltransferase (to give 6-thioisonine 5'-monphosphate).[1] They are also substrates for nudix hydrolase 15 (NUDT15).[2]

## Contents

* 1 Controversy
* 2 See also
* 3 References
* 4 External links

## Controversy

Litigation over patents covering diagnostic kits to monitor the dosing of these drugs led to a US Supreme Court case, Mayo Collaborative Services v. Prometheus Laboratories, Inc. that dramatically changed the nature of patent law in the United States.[3][4]

## See also

* 6-Mercaptopurine (6-MP)
* 6-Thioguanine (6-TG)
* Azathioprine (AZA)

## References

1. ↑ Dubinsky, Marla C.; Lamothe, Stéphanie; Yang, Hui Ying; Targan, Stephan R.; Sinnett, Daniel; Théorêt, Yves; Seidman, Ernest G. (2000). "Pharmacogenomics and metabolite measurement for 6-mercaptopurine therapy in inflammatory bowel disease". Gastroenterology 118 (4): 705–713. doi:10.1016/s0016-5085(00)70140-5. PMID 10734022.
2. ↑ "Clinical pharmacology and pharmacogenetics of thiopurines". Eur. J. Clin. Pharmacol. 64 (8): 753–67. August 2008. doi:10.1007/s00228-008-0478-6. PMID 18506437.
3. ↑ Supreme Court Decision. Mayo Collaborative Services v. Prometheus Laboratories, Inc., No. 10-1150, Slip Op. at 16. Decision
4. ↑ Gene Quinn, Killing Industry: The Supreme Court Blows Mayo v. Prometheus IP Watchdog (March 20, 2012).

## External links

* http://www.pharmgkb.org/do/serve?objId=PA2040

* v
* t
* e

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|

* Aminolevulinic acid / Methyl aminolevulinate
* Efaproxiral
* Porphyrin derivatives (Porfimer sodium
* Talaporfin
* Temoporfin
* Verteporfin)

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

* v
* t
* e

Specific antirheumatic products / DMARDs (M01C)

Quinolines|

* Oxycinchophen

Gold preparations|

* Sodium aurothiomalate
* Sodium aurothiosulfate
* Auranofin
* Aurothioglucose
* Aurotioprol

Other|

* [[Chemistry:PenicillPenicillamine]] #/Bucillamine
* Chloroquine #/Hydroxychloroquine
* Leflunomide
* Sulfasalazine #
* antifolate (Methotrexate #)
* thiopurine (Azathioprine) #

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

0.00

(0 votes)

Original source: https://en.wikipedia.org/wiki/Thiopurine. Read more

|

Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Thiopurine&oldid=4027782"
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template