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Details

Stereochemistry ACHIRAL
Molecular Formula C5H4N4S
Molecular Weight 152.177
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MERCAPTOPURINE ANHYDROUS

SMILES

S=C1NC=NC2=C1N=CN2

InChI

InChIKey=GLVAUDGFNGKCSF-UHFFFAOYSA-N
InChI=1S/C5H4N4S/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10)

HIDE SMILES / InChI

Molecular Formula C5H4N4S
Molecular Weight 152.177
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Mercaptopurine, marketed under the brand name Purinethol among others, is a medication used for cancer and autoimmune diseases. Mercaptopurine competes with hypoxanthine and guanine for the enzyme hypoxanthine-guanine phosphoribosyltransferase (HGPRTase) and is itself converted to thioinosinic acid (TIMP). This intracellular nucleotide inhibits several reactions involving inosinic acid (IMP), including the conversion of IMP to xanthylic acid (XMP) and the conversion of IMP to adenylic acid (AMP) via adenylosuccinate (SAMP). In addition, 6-methylthioinosinate (MTIMP) is formed by the methylation of TIMP. Both TIMP and MTIMP have been reported to inhibit glutamine-5-phosphoribosylpyrophosphate amidotransferase, the first enzyme unique to the de novo pathway for purine ribonucleotide synthesis. Experiments indicate that radiolabeled mercaptopurine may be recovered from the DNA in the form of deoxythioguanosine. Some mercaptopurine is converted to nucleotide derivatives of 6-thioguanine (6-TG) by the sequential actions of inosinate (IMP) dehydrogenase and xanthylate (XMP) aminase, converting TIMP to thioguanylic acid (TGMP). PURINETHOL (mercaptopurine) is indicated for maintenance therapy of acute lymphatic (lymphocytic, lymphoblastic) leukemia as part of a combination regimen. The response to this agent depends upon the particular subclassification of acute lymphatic leukemia and the age of the patient (pediatric or adult).

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Pharmacogenetics: the therapeutic drug monitoring of the future?
2001
Pharmacokinetic considerations in the treatment of inflammatory bowel disease.
2001
Mechanism of azathioprine-induced injury to hepatocytes: roles of glutathione depletion and mitochondrial injury.
2001 Dec
Comparative pharmacokinetics of oral 6-mercaptopurine and intravenous 6-mercaptopurine riboside in children.
2001 Dec
Evolving medical therapies for ulcerative colitis.
2001 Dec
Results of a randomized phase III trial in children and adolescents with advanced stage diffuse large cell non Hodgkin's lymphoma: a Pediatric Oncology Group study.
2001 Jul
Prognostic impact of CD45 antigen expression in high-risk, childhood B-cell precursor acute lymphoblastic leukemia.
2001 Jul
Management of fistulas in patients with Crohn's disease: antibiotic to antibody.
2001 Nov
Azathioprine for prevention of postoperative recurrence in Crohn's disease.
2001 Nov
Review article: the treatment of inflammatory bowel disease with 6-mercaptopurine or azathioprine.
2001 Nov
Pitfalls in the determination of mutant alleles of the thiopurine methyltransferase gene.
2001 Nov
Possible implication of thiopurine S-methyltransferase in occurrence of infectious episodes during maintenance therapy for childhood lymphoblastic leukemia with mercaptopurine.
2001 Nov
Azathioprine treatment and male fertility in inflammatory bowel disease.
2001 Nov
Diagnosis and treatment of perianal fistulas in Crohn disease.
2001 Nov 20
Medical management of ulcerative proctitis, proctosigmoiditis, and left-sided colitis.
2001 Oct
Managing the glucocorticoid dependent inflammatory bowel disease patient.
2001 Oct
A variant form of acute promyelocytic leukemia with marked myelofibrosis.
2001 Oct
6-mercaptopurine metabolite levels in children with inflammatory bowel disease.
2001 Oct
Single-agent therapy with oral mercaptopurine for nonlymphoid blast crisis of chronic myeloid leukemia.
2001 Sep
Therapy-related CD7+ acute myeloid leukemia with trisomy 8 following acute monocytic leukemia.
2001 Sep
Patents

Sample Use Guides

In Vivo Use Guide
Usual Adult Dose for Intestinal Arterial Insufficiency Initial Dosage: Oral: 2.5 mg/kg of body weight per day (100 to 200 mg in the average adult). This dose may be continued daily for several weeks or more in some patients. If, after 4 weeks at this dosage, there is no clinical improvement and no definite evidence of leukocyte or platelet depression, the dosage may be increased up to 5 mg/kg daily. A dosage of 2.5 mg/kg per day may result in a rapid fall in leukocyte count within 1 to 2 weeks in some adults with acute lymphatic leukemia and high total leukocyte counts. The total daily dosage may be given at one time. It is calculated to the nearest multiple of 25 mg. Maintenance Therapy: Once a complete hematologic remission is obtained, maintenance therapy is considered essential. A usual daily maintenance dose of mercaptopurine is 1.5 to 2.5 mg/kg per day as a single dose. Mercaptopurine should rarely be relied upon as a single agent for the maintenance of remissions induced in acute leukemia. Usual Adult Dose for Acute Lymphoblastic Leukemia Initial Dosage: Oral: 2.5 mg/kg of body weight per day (100 to 200 mg in the average adult). This dose may be continued daily for several weeks or more in some patients. If, after 4 weeks at this dosage, there is no clinical improvement and no definite evidence of leukocyte or platelet depression, the dosage may be increased up to 5 mg/kg daily. A dosage of 2.5 mg/kg per day may result in a rapid fall in leukocyte count within 1 to 2 weeks in some adults with acute lymphatic leukemia and high total leukocyte counts. The total daily dosage may be given at one time. It is calculated to the nearest multiple of 25 mg. Maintenance Therapy: Once a complete hematologic remission is obtained, maintenance therapy is considered essential. A usual daily maintenance dose of mercaptopurine is 1.5 to 2.5 mg/kg per day as a single dose. Mercaptopurine should rarely be relied upon as a single agent for the maintenance of remissions induced in acute leukemia. Usual Adult Dose for Crohn's Disease - Acute Oral: 1.0 to 1.5 mg/kg of body weight per day Usual Adult Dose for Crohn's Disease - Maintenance Oral: 1.0 to 1.5 mg/kg of body weight per day Usual Adult Dose for Ulcerative Colitis - Maintenance Oral: 1.0 to 1.5 mg/kg of body weight per day Usual Adult Dose for Inflammatory Bowel Disease Oral: 1.0 to 1.5 mg/kg of body weight per day
Route of Administration: Oral
In Vitro Use Guide
Mercaptopurine (10-500 ug/ml) inhibits in a dose-dependent manner the production of PGE2, PGF2 alpha, 6-keto-PGF1 alpha and TXB2 by unseparated spleen cells as well as that of 6-keto-PGF1 alpha by adherent peritoneal macrophages.
Substance Class Chemical
Created
by admin
on Tue Mar 06 10:30:21 UTC 2018
Edited
by admin
on Tue Mar 06 10:30:21 UTC 2018
Record UNII
PKK6MUZ20G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MERCAPTOPURINE ANHYDROUS
WHO-DD  
Common Name English
MERCAPTOPURINE ANHYDROUS [WHO-DD]
Common Name English
AZATHIOPRINE IMPURITY B [EP]
Common Name English
6-MERCAPTOPURINE
MI  
Systematic Name English
1,9-DIHYDRO-6H-PURINE-6-THIONE
Systematic Name English
6-MERCAPTOPURINE [MI]
Common Name English
MERCAPTOPURINE [HSDB]
Common Name English
MERCAPTOPURINE [INN]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175595
Created by admin on Tue Mar 06 10:30:21 UTC 2018 , Edited by admin on Tue Mar 06 10:30:21 UTC 2018
NDF-RT N0000000233
Created by admin on Tue Mar 06 10:30:21 UTC 2018 , Edited by admin on Tue Mar 06 10:30:21 UTC 2018
Code System Code Type Description
CAS
50-44-2
Created by admin on Tue Mar 06 10:30:21 UTC 2018 , Edited by admin on Tue Mar 06 10:30:21 UTC 2018
PRIMARY
NCI_THESAURUS
C61832
Created by admin on Tue Mar 06 10:30:21 UTC 2018 , Edited by admin on Tue Mar 06 10:30:21 UTC 2018
PRIMARY
EVMPD
SUB22133
Created by admin on Tue Mar 06 10:30:21 UTC 2018 , Edited by admin on Tue Mar 06 10:30:21 UTC 2018
PRIMARY
ECHA (EC/EINECS)
200-037-4
Created by admin on Tue Mar 06 10:30:21 UTC 2018 , Edited by admin on Tue Mar 06 10:30:21 UTC 2018
PRIMARY
MESH
D015122
Created by admin on Tue Mar 06 10:30:21 UTC 2018 , Edited by admin on Tue Mar 06 10:30:21 UTC 2018
PRIMARY
INN
587
Created by admin on Tue Mar 06 10:30:21 UTC 2018 , Edited by admin on Tue Mar 06 10:30:21 UTC 2018
PRIMARY
PUBCHEM
667490
Created by admin on Tue Mar 06 10:30:21 UTC 2018 , Edited by admin on Tue Mar 06 10:30:21 UTC 2018
PRIMARY SWITZERF
DRUG BANK
DB01033
Created by admin on Tue Mar 06 10:30:21 UTC 2018 , Edited by admin on Tue Mar 06 10:30:21 UTC 2018
PRIMARY
LactMed
50-44-2
Created by admin on Tue Mar 06 10:30:21 UTC 2018 , Edited by admin on Tue Mar 06 10:30:21 UTC 2018
PRIMARY
RXCUI
1546028
Created by admin on Tue Mar 06 10:30:21 UTC 2018 , Edited by admin on Tue Mar 06 10:30:21 UTC 2018
PRIMARY RxNorm
EVMPD
SUB12149MIG
Created by admin on Tue Mar 06 10:30:21 UTC 2018 , Edited by admin on Tue Mar 06 10:30:21 UTC 2018
PRIMARY
MERCK INDEX
M7208
Created by admin on Tue Mar 06 10:30:21 UTC 2018 , Edited by admin on Tue Mar 06 10:30:21 UTC 2018
PRIMARY Merck Index
HSDB
50-44-2
Created by admin on Tue Mar 06 10:30:21 UTC 2018 , Edited by admin on Tue Mar 06 10:30:21 UTC 2018
PRIMARY
EPA CompTox
50-44-2
Created by admin on Tue Mar 06 10:30:21 UTC 2018 , Edited by admin on Tue Mar 06 10:30:21 UTC 2018
PRIMARY
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SUBSTANCE->BASIS OF STRENGTH
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