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Chemistry

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Also known as: 6-thioguanine, 154-42-7, Tioguanine, 2-amino-6-mercaptopurine, 6-mercaptoguanine, Tioguanin
Molecular Formula
C5H5N5S
Molecular Weight
167.19  g/mol
InChI Key
WYWHKKSPHMUBEB-UHFFFAOYSA-N
FDA UNII
WIX31ZPX66

Thioguanine
An antineoplastic compound which also has antimetabolite action. The drug is used in the therapy of acute leukemia.
Thioguanine anhydrous is an Antimetabolite.
1 2D Structure

Thioguanine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-amino-3,7-dihydropurine-6-thione
2.1.2 InChI
InChI=1S/C5H5N5S/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)
2.1.3 InChI Key
WYWHKKSPHMUBEB-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=NC2=C(N1)C(=S)N=C(N2)N
2.2 Other Identifiers
2.2.1 UNII
WIX31ZPX66
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2 Amino 6 Purinethiol

2. 2-amino-6-purinethiol

3. 6 Thioguanine

4. 6-thioguanine

5. Anhydrous, Thioguanine

6. Lanvis

7. Tabloid

8. Thioguanin Gsk

9. Thioguanin-gsk

10. Thioguanine Anhydrous

11. Thioguanine Hemihydrate

12. Thioguanine Monosodium Salt

13. Thioguanine Tabloid

14. Thioguaningsk

15. Tioguanina Wellcome

16. Tioguanine

2.3.2 Depositor-Supplied Synonyms

1. 6-thioguanine

2. 154-42-7

3. Tioguanine

4. 2-amino-6-mercaptopurine

5. 6-mercaptoguanine

6. Tioguanin

7. Tabloid

8. 2-amino-6-purinethiol

9. Lanvis

10. 2-amino 6mp

11. 2-aminopurin-6-thiol

12. 2-aminopurine-6-thiol

13. 2-aminopurine-6(1h)-thione

14. Wellcome U3b

15. 6-mercapto-2-aminopurine

16. 2-amino-9h-purine-6-thiol

17. 6-tg

18. 2-amino-6-merkaptopurin

19. Tioguaninum

20. Guanine, Thio-

21. Tioguanina

22. 6h-purine-6-thione, 2-amino-1,7-dihydro-

23. 2-amino-1,7-dihydro-6h-purine-6-thione

24. Thioguanine Anhydrous

25. Nsc-752

26. Bw 5071

27. Purine-6-thiol, 2-amino-

28. Purine-6(1h)-thione, 2-amino-

29. 2-amino-1,9-dihydro-6h-purine-6-thione

30. Tg

31. Thioguanine, Anhydrous

32. Thg

33. Nsc 752

34. 2-amino-1,7-dihydro-6h-purin-6-thion

35. X 27

36. Tioguanine (inn)

37. Tioguanine [inn]

38. 2-amino-6,7-dihydro-3h-purine-6-thione

39. 2-amino-1,9-dihydropurine-6-thione

40. Chembl727

41. Wix31zpx66

42. 2-amino-3,7-dihydro-6h-purine-6-thione

43. Chebi:9555

44. Nsc752

45. Thioguanine2-amino-6-purinethiol

46. 2-thioguanine

47. 2-amino-1h-purine-6(9h)-thione

48. 2-amino-1,7-dihydropurine-6-thione

49. Nsc-76504

50. Ncgc00094792-01

51. Dsstox_cid_3652

52. 2-amino-6-mp

53. Tioguanine Hemihydrate

54. Dsstox_rid_77129

55. Dsstox_gsid_23652

56. Tioguaninum [inn-latin]

57. C5h5n5s

58. 2-aminopurin-6-thiol [czech]

59. Guanine, Thio- (van)

60. 2-amino-6-merkaptopurin [czech]

61. 6-tioguanine

62. Tioguanina [inn-spanish]

63. Cas-154-42-7

64. Dx4

65. Smr000857244

66. Lanvis (tn)

67. Ccris 8997

68. 9h-purine-6-thiol, 2-amino-

69. Hsdb 2504

70. Sr-05000002077

71. Einecs 205-827-2

72. Thioguanine [usan:usp]

73. 2-amino-1,7-dihydro-6h-purin-6-thion [czech]

74. Unii-wix31zpx66

75. Thioquanine

76. Ai3-26078

77. 6-thioguano-sine

78. 6-tg/thioguanine

79. Mfcd00233553

80. 1330266-29-9

81. Spectrum_000235

82. Thioguanine [mi]

83. Spectrum2_000695

84. Spectrum3_000577

85. Spectrum4_000926

86. Spectrum5_001455

87. Purine Antimetabolite: Antimetabolite: Inhibits Nucleic Acid Replication

88. Thioguanine [hsdb]

89. 2-amino-6-mercapto-purin

90. 6-thioguanine, >=98%

91. Schembl3701

92. Schembl5898

93. Nciopen2_004153

94. Tioguanine [who-dd]

95. Bspbio_001994

96. Kbiogr_001452

97. Kbiogr_002476

98. Kbioss_000715

99. Kbioss_002483

100. Mls001333131

101. Mls001333132

102. Mls006010896

103. Divk1c_000428

104. Spectrum1500573

105. Spbio_000849

106. 154-42-7

107. 6-thioguanine

108. 2-amino-6-mercapto-9h-purine

109. Gtpl6845

110. Thioguanine (tn) (glaxosmith)

111. Dtxsid6023652

112. Hms501f10

113. Kbio1_000428

114. Kbio2_000715

115. Kbio2_002476

116. Kbio2_003283

117. Kbio2_005044

118. Kbio2_005851

119. Kbio2_007612

120. Kbio3_001494

121. Kbio3_002954

122. Cmap_000061

123. Ninds_000428

124. Bcpe000001

125. Hms1921e09

126. Hms2092m11

127. Hms2235f05

128. Hms3865g13

129. Pharmakon1600-01500573

130. Albb-023493

131. Bcp27718

132. Zinc6382803

133. Tox21_111035

134. Tox21_113184

135. Tox21_202401

136. Tox21_300275

137. Bdbm50200099

138. Ccg-39890

139. Nsc757348

140. S1774

141. Akos003389499

142. Akos015901298

143. Tox21_111035_1

144. 2-amino-1,7-dihydro-purine-6-thione

145. 2-amino-1,9-dihydro-purine-6-thione

146. Ac-8421

147. Bcp9000197

148. Ccg-213953

149. Ccg-266338

150. Cs-1497

151. Db00352

152. Nsc-757348

153. Ps-5007

154. Wln: T56 Bnm Fym Inj Fus Hz

155. Idi1_000428

156. Smp2_000326

157. Ncgc00094792-02

158. Ncgc00094792-03

159. Ncgc00094792-05

160. Ncgc00094792-06

161. Ncgc00094792-17

162. Ncgc00188976-01

163. Ncgc00188976-02

164. Ncgc00254082-01

165. Ncgc00259950-01

166. Ncgc00263442-01

167. Ncgc00263442-02

168. Ncgc00263442-05

169. Ac-23020

170. Bt166463

171. Hy-13765

172. Nci60_041643

173. Smr004701808

174. Sbi-0051533.p003

175. Ft-0611217

176. T0212

177. 2-amino-1,7-dihydro-6h-purine-6-thione #

178. C07648

179. D08603

180. T71841

181. Ab00174074_06

182. Ab00918694_06

183. Ab01273926-01

184. Ab01273926-02

185. Ab01273926_03

186. 154t427

187. A809532

188. Q385347

189. Sr-05000002077-1

190. Sr-05000002077-5

191. W-108030

192. W-205813

193. Z2768769146

194. 6-thioguanine;6-tg;2-amino-6-mercaptopurine;2-amino-6-purinethiol

195. Thioguanine, United States Pharmacopeia (usp) Reference Standard

196. Thioguanine;6-tg; 2-amino-6-mercaptopurine; 2-amino-6-purinethiol

197. 6-thioguanine, Hybri-max(tm), 50 X, Gamma-irradiated, Lyophilized Powder, Bioxtra, Suitable For Hybridoma

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 167.19 g/mol
Molecular Formula C5H5N5S
XLogP3-0.1
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count2
Rotatable Bond Count0
Exact Mass167.02656635 g/mol
Monoisotopic Mass167.02656635 g/mol
Topological Polar Surface Area111 Ų
Heavy Atom Count11
Formal Charge0
Complexity225
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameThioguanine
PubMed HealthThioguanine (By mouth)
Drug ClassesAntineoplastic Agent
Drug LabelTABLOID brand Thioguanine was synthesized and developed by Hitchings, Elion, and associates at the Wellcome Research Laboratories. It is one of a large series of purine analogues which interfere with nucleic acid biosynthesis, and has been found acti...
Active IngredientThioguanine
Dosage FormTablet
RouteOral
Strength40mg
Market StatusPrescription
CompanyAspen Global

2 of 2  
Drug NameThioguanine
PubMed HealthThioguanine (By mouth)
Drug ClassesAntineoplastic Agent
Drug LabelTABLOID brand Thioguanine was synthesized and developed by Hitchings, Elion, and associates at the Wellcome Research Laboratories. It is one of a large series of purine analogues which interfere with nucleic acid biosynthesis, and has been found acti...
Active IngredientThioguanine
Dosage FormTablet
RouteOral
Strength40mg
Market StatusPrescription
CompanyAspen Global

4.2 Therapeutic Uses

Antimetabolites, Antineoplastic

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


CLINICALLY, THIOGUANINE HAS BEEN USED IN THE TREATMENT OF ACUTE LEUKEMIA AND, IN COMBINATION WITH CYTARABINE, IS ONE OF THE MOST EFFECTIVE AGENTS FOR INDUCTION OF REMISSIONS IN ACUTE GRANULOCYTIC LEUKEMIA; IT HAS NOT BEEN USEFUL IN THE TREATMENT OF PATIENTS WITH SOLID TUMORS. THIS CMPD HAS BEEN USED AS AN IMMUNOSUPPRESSIVE AGENT, PARTICULARLY IN PATIENTS WITH NEPHROSIS AND WITH COLLAGEN-VASCULAR DISORDERS. TOXIC MANIFESTATIONS INCLUDE BONE MARROW DEPRESSION AND GI EFFECTS, ALTHOUGH THE LATTER MAY BE LESS PRONOUNCED THAN WITH MERCAPTOPURINE.

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1236


SHORT TERM TREATMENT WITH DOXORUBICIN, CYTARABINE, & 6-THIOGUANINE WAS GIVEN TO 90 PATIENTS WITH ACUTE MYELOGENOUS LEUKEMIA. FIFTY PATIENTS RECEIVED HIGH DOSES (REGIMEN 1) & 41 RECEIVED VERY HIGH DOSES (REGIMEN 2). REMISSION RATE WAS SIGNIFICANTLY HIGHER WITH REGIMEN 1 THAN WITH REGIMEN 2. DURATION OF REMISSION WAS, HOWEVER, SIGNIFICANTLY LONGER WITH REGIMEN 2.

BELL R ET AL; BR MED J 284 (APR 24): 221-24 (1982)


IN ADVANCED COLORECTAL ADENOCARCINOMA, TWO DIFFERENT SCHEDULES OF COMBINATION METHYL-CCNU, 6-THIOGUANINE, & 5-FLUOROURACIL EXHIBITED SIMILAR EFFICACIES, WITH A COMBINED COMPLETE & PARTIAL REMISSION RATE OF 17% & A MEDIAN SURVIVAL OF 53+ WK. SIGNIFICANT SYMPTOMATIC BENEFIT WAS SEEN IN 52% OF PATIENTS. TOXICITY WAS PREDOMINATELY HEMOPOIETIC & GI.

PMID:7231364 ARONEY RS ET AL; MED PEDIATR ONCOL 9 (2): 181-6 (1981)


For more Therapeutic Uses (Complete) data for THIOGUANINE (14 total), please visit the HSDB record page.


4.3 Drug Warning

Risk-benefit should be considered when the following medical problems exist: Bone marrow depression; chickenpox, existing or recent (including recent exposure; herpes zoster (risk of severe generalized disease); gout, history of; urate renal stones, history of (risk of hyperuricemia); hepatic function impairment (reduced biotransformation; lower dosage is recommended); infection; renal function impairment (reduced elimination; lower dosage is recommended); or sensitivity to thioguanine. Caution should be used also in patients who have had cytotoxic drug therapy and radiation therapy within 4 to 6 weeks.

USP Convention. USPDI-Drug Information for the Health Care Professional. 14th ed. Volume I. Rockville, MD: United States Pharmacopeial Convention, Inc., 1994. (Plus Updates)., p. 2653


Because normal defense mechanisms may be suppressed by thioguanine therapy, concurrent use with alive virus vaccine may potentiate the replication of the vaccine virus, may increase the side/adverse effects of the vaccine virus, and/or may decrease the patient's antibody response to the vaccine; immunization of these patients should be undertaken only with extreme caution after careful review of the patient's hematologic status and only with the knowledge and consent of the physician managing the thioguanine therapy. The interval between discontinuation of medication that cause immunosuppression and restoration of the patient's ability to respond to the vaccine depends on the intensity and type of immunosuppression-causing medication used, the underlying disease, and other factors; estimates vary from 3 months to 1 year. Patients with leukemia in remission should not receive live virus vaccine until at least 3 months after their last chemotherapy. Immunization with oral poliovirus vaccine should also be postponed in persons in close contact with the patient, especially family members.

USP Convention. USPDI-Drug Information for the Health Care Professional. 14th ed. Volume I. Rockville, MD: United States Pharmacopeial Convention, Inc., 1994. (Plus Updates)., p. 2653


Because normal defense mechanisms may be suppressed by thioguanine therapy, the patient's antibody response to the vaccine may be decreased. The interval between discontinuation of medications that cause immunosuppression and restoration of the patient's ability to respond to the vaccine depends on the intensity and type of immunosuppression-causing medication used, the underlying disease, and other factors; estimates vary from 3 months to 1 year.

USP Convention. USPDI-Drug Information for the Health Care Professional. 14th ed. Volume I. Rockville, MD: United States Pharmacopeial Convention, Inc., 1994. (Plus Updates)., p. 2653


TOXIC MANIFESTATIONS INCL BONE MARROW DEPRESSION & GI EFFECTS ... .

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1236


For more Drug Warnings (Complete) data for THIOGUANINE (9 total), please visit the HSDB record page.


4.4 Drug Indication

For remission induction and remission consolidation treatment of acute nonlymphocytic leukemias.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Thioguanine is an antineoplastic anti-metabolite used in the treatment of several forms of leukemia including acute nonlymphocytic leukemia. Anti-metabolites masquerade as purine or pyrimidine - which become the building blocks of DNA. They prevent these substances becoming incorporated in to DNA during the "S" phase (of the cell cycle), stopping normal development and division. Thioguanine was first synthesized and entered into clinical trial more than 30 years ago. It is a 6-thiopurine analogue of the naturally occurring purine bases hypoxanthine and guanine. Intracellular activation results in incorporation into DNA as a false purine base. An additional cytotoxic effect is related to its incorporation into RNA. Thioguanine is cross-resistant with mercaptopurine. Cytotoxicity is cell cycle phase-specific (S-phase).


5.2 MeSH Pharmacological Classification

Antimetabolites, Antineoplastic

Antimetabolites that are useful in cancer chemotherapy. (See all compounds classified as Antimetabolites, Antineoplastic.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
THIOGUANINE ANHYDROUS
5.3.2 FDA UNII
WIX31ZPX66
5.3.3 Pharmacological Classes
Antimetabolite [EPC]
5.4 ATC Code

L - Antineoplastic and immunomodulating agents

L01 - Antineoplastic agents

L01B - Antimetabolites

L01BB - Purine analogues

L01BB03 - Tioguanine


5.5 Absorption, Distribution and Excretion

Absorption

Absorption of an oral dose is incomplete and variable, averaging approximately 30% of the administered dose (range: 14% to 46%)


Incompletely and variably (about 30%) absorbed from the gastrointestinal tract.

USP Convention. USPDI-Drug Information for the Health Care Professional. 14th ed. Volume I. Rockville, MD: United States Pharmacopeial Convention, Inc., 1994. (Plus Updates)., p. 2652


THIOGUANINE IS INCOMPLETELY ABSORBED WHEN GIVEN ORALLY, AVERAGING ABOUT 30% OF AN ADMIN DOSE. ... THE ELIMINATION HALF-LIFE OF THE PARENT DRUG IS 1.5 HR, BUT PEAK PLASMA LEVELS OF METABOLITES ARE REACHED IN 6-8 HR. BETWEEN 24% & 46% IS EXCRETED IN THE URINE AS METABOLITES WITHIN 24 HR. ... THIS DRUG IS CLEARED RAPIDLY FROM PLASMA AFTER IV ADMINISTRATION; MORE THAN 80% EXCRETED WITHIN 24 HR. ALTHOUGH THIOGUANINE.../SRP: HAS LIMITED ACCESS ACROSS/ THE BLOOD-BRAIN BARRIER IN ANIMALS AFTER LARGE DOSES, VERY LITTLE ENTERS THE CEREBROSPINAL FLUID OF HUMANS AFTER THE USUAL CLINICAL DOSES ARE EMPLOYED.

American Medical Association, Council on Drugs. AMA Drug Evaluations Annual 1994. Chicago, IL: American Medical Association, 1994., p. 2046


THE METABOLISM AND PHARMACOKINETICS OF 6-THIOGUANINE WERE STUDIED IN DOGS AFTER IV ADMIN OF 5 MG/KG (35)S-THIOGUANINE (TG). THIOGUANINE WAS RAPIDLY & EXTENSIVELY DEGRADED. METABOLITES WERE NOT FOUND IN THE CEREBROSPINAL FLUID IN SIGNIFICANT CONCENTRATIONS.

PMID:7307231 LOO TL ET AL; CANCER CHEMOTHER PHARMACOL 6 (2): 131-6 (1981)


5.6 Metabolism/Metabolites

Hepatic. First converted to 6-thioguanilyic acid (TGMP). TGMP is further converted to the di- and tri-phosphates, thioguanosine diphosphate (TGDP) and thioguanosine triphosphate (TGTP) by the same enzymes that metabolize guanine nucleotides.


... WHEN THIOGUANINE IS ADMIN TO MAN, THE S-METHYLATION PRODUCT, 2-AMINO-6-METHYLTHIOPURINE, RATHER THAN FREE THIOGUANINE APPEARS IN URINE; INORGANIC SULFATE IS ALSO A MAJOR URINARY METABOLITE. LESSER AMT OF 6-THIOURIC ACID ARE FORMED, SUGGESTING THAT DEAMINATION CATALYZED BY THE ENZYME GUANASE DOES NOT HAVE A MAJOR ROLE IN THE METABOLIC INACTIVATION OF THIOGUANINE.

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1236


THE PHARMACOKINETICS OF RADIOLABELED 6-THIOGUANINE (TG) WERE COMPARED WITH THAT OF BETA-2'-DEOXYTHIOGUANOSINE (BETA-TGDR) AFTER IV ADMIN. URINARY EXCRETION OF THE RADIOLABEL WAS 75% OF THE DOSE 24 HR AFTER ADMIN. BOTH THIOPURINES WERE RAPIDLY & EXTENSIVELY DEGRADED & EXCRETED AS 6-THIOXANTHINE, INORGANIC SULFATE, S-METHYL-6-THIOXANTHINE, & 6-THIOURIC ACID IN ADDITION TO OTHER PRODUCTS. SMALL AMOUNTS OF UNCHANGED DRUG WERE ALSO EXCRETED. STUDIES SUGGEST THAT BETA-TGDR IS A LATENT FORM OF TG. SINCE RESISTANCE TO ANTILEUKEMIC AGENT 6-THIOGUANINE INEVITABLY DEVELOPS IN ANIMAL TUMORS, THIS NEW AGENT BETA-TGDR IS OF POTENTIAL CLINICAL USE.

LU K ET AL; PHARMACOKINETICS AND METABOLISM OF BETA-2'-DEOXYTHIOGUANOSINE AND 6-THIOGUANINE IN MAN; CANCER CHEMOTHER PHARMACOL 8 (1): 119-23 (1982)


5.7 Biological Half-Life

When the compound was given in singles doses of 65 to 300 mg/m^2, the median plasma half-disappearance time was 80 minutes (range 25-240 minutes)


5.8 Mechanism of Action

Thioguanine competes with hypoxanthine and guanine for the enzyme hypoxanthine-guanine phosphoribosyltransferase (HGPRTase) and is itself converted to 6-thioguanilyic acid (TGMP), which reaches high intracellular concentrations at therapeutic doses. TGMP interferes with the synthesis of guanine nucleotides by its inhibition of purine biosynthesis by pseudofeedback inhibition of glutamine-5-phosphoribosylpyrophosphate amidotransferase, the first enzyme unique to the de novo pathway of purine ribonucleotide synthesis. TGMP also inhibits the conversion of inosinic acid (IMP) to xanthylic acid (XMP) by competition for the enzyme IMP dehydrogenase. Thioguanine nucleotides are incorporated into both the DNA and the RNA by phosphodiester linkages, and some studies have shown that incorporation of such false bases contributes to the cytotoxicity of thioguanine. Its tumor inhibitory properties may be due to one or more of its effects on feedback inhibition of de novo purine synthesis; inhibition of purine nucleotide interconversions; or incorporation into the DNA and RNA. The overall result of its action is a sequential blockade of the utilization and synthesis of the purine nucleotides.


THIOGUANINE, THE 6-THIO ANALOGUE OF GUANINE, IS A PRODRUG THAT IS CONVERTED TO 6-THIOGUANINE-RIBOSE-PHOSPHATE, AN ACTIVE METABOLITE. ... 6-THIOGUANINE-RIBOSE-PHOSPHATE IS A FEEDBACK INHIBITOR OF THE INITIAL (AMIDOTRANSFERASE) STEP IN PURINE BIOSYNTHESIS. THIS METABOLITE ALSO BLOCKS CONVERSIONS OF INOSINIC ACID TO GUANYLIC ACID & OF GUANYLIC ACID TO GDP. THIOGUANINE ALSO IS CONVERTED TO THE DEOXYNUCLEOTIDE TRIPHOSPHATE, WHICH CAN BE INCORPORATED INTO TUMOR CELL DNA. ALTHOUGH SOME INVESTIGATORS BELIEVE THAT THIS IS THE MAJOR MECHANISM OF CYTOTOXICITY, THE RELATIVE IMPORTANCE OF THE VARIOUS SITES OF ACTION HAS NOT BEEN DETERMINED. ... THIOGUANINE IS CELL-CYCLE SPECIFIC FOR THE S PHASE.

American Medical Association, Council on Drugs. AMA Drug Evaluations Annual 1994. Chicago, IL: American Medical Association, 1994., p. 2046


APPARENTLY, THE METABOLISM OF 6-THIOGUANINE TO 6-THIOGUANOSINE IN SARCOMA 180 & 180/TG CELLS IS MEDIATED BY PURINE NUCLEOSIDE PHOSPHORYLASE & NEWLY SYNTHESIZED 6-THIOGUANOSINE IS READILY EFFLUXED INTO THE CELLULAR ENVIRONMENT. THE FORMATION OF 6-THIOGUANINE, BY PURINE NUCLEOSIDE PHOSPHORYLASE, MAY BE IMPORTANT TO THE EXPRESSION OF CELLULAR SENSITIVITY TO 6-THIOGUANINE, IN THAT IT DECR THE AVAIL OF 6-THIOGUANINE FOR DIRECT CONVERSION BY HYPOXANTHINE-GUANINE PHOSPHORIBOSYLTRANSFERASE TO THE NUCLEOTIDE LEVEL, A PHENOMENON CRITICAL TO THE EXPRESSION OF THE ANTINEOPLASTIC ACTIVITY OF THE 6-THIOPURINES.

PMID:7459851 LEE SH, SARTORELLI AC; CANCER RES 41 (3): 1086-90 (1981)


PHENYL SUBSTITUTION AT C-8 OF 2-AMINO-6-MERCAPTOPURINE ABOLISHED THE IMMUNOSUPPRESSIVE ACTIVITY. THEREFORE, A NONSUBSTITUTED 8 POSITION OF 2-AMINO-6-MERCAPTOPURINE IS ESSENTIAL FOR IMMUNOSUPPRESSIVE ACTION.

PMID:6031686 FU SC J ET AL; J MED CHEM 10 (1): 109-10 (1967)


SPONTANEOUSLY CYCLING LYMPHOCYTES (IN CELL DIVISION IN CULTURES WITHOUT ADDITION OF PHYTOHEMAGGLUTININ, PHA) GO THROUGH VARIOUS PHASES OF 1ST DIVISION WITH THE SAME KINETICS AS PHA-STIMULATED CELLS. IN SAMPLES FROM 10 REFERENTS, THE FREQUENCY OF SPONTANEOUSLY CYCLING LYMPHOCYTES VARIED FROM 8.9X10-5 TO 9.5X10-3 AS INDICATED WITH AUTORADIOGRAPHY ON CELLS IN (S + G2) PHASE DETERMINED BY FLOW SORTING. IN PHA-STIMULATED SAMPLES FROM THE SAME PERSONS THE FREQUENCY OF 6-THIOGUANINE (TG)-RESISTANT VARIANTS WAS BETWEEN 4X10-7 & 2.6X10-6, WHICH INDICATES THAT MOST OF THE SPONTANEOUSLY CYCLING CELLS WERE TG-SENSITIVE.

PMID:6690915 AMNEUS H ET AL; MUTAT RES 139 (1): 41-4 (1984)


For more Mechanism of Action (Complete) data for THIOGUANINE (7 total), please visit the HSDB record page.


API Reference Price

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04-Feb-2021
01-Oct-2022
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