ChemFOnt: Showing chemical card for Mercaptopurine (CFc000009462)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:36 UTC

Chemfont ID

CFc000009462

Molecule Identification

Common Name

Mercaptopurine

Definition

Mercaptopurine is only found in individuals that have used or taken this drug. It is an antimetabolite antineoplastic agent with immunosuppressant properties. It interferes with nucleic acid synthesis by inhibiting purine metabolism and is used, usually in combination with other drugs, in the treatment of or in remission maintenance programs for leukemia. [PubChem]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).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,7-Dihydro-6H-purine-6-thione	ChEBI
3H-Purine-6-thiol	ChEBI
6-MP	ChEBI
6-Thiohypoxanthine	ChEBI
Mercaptopurine anhydrous	Kegg
Purinethol	Kegg
6 MP	HMDB
6-Mercaptopurine	HMDB
Mercaptopurine monohydrate	HMDB
Mercapurin	HMDB
MP	HMDB
6 Mercaptopurine monohydrate	HMDB
6-Mercaptopurine monohydrate	HMDB
Puri-nethol	HMDB
6 Mercaptopurine	HMDB
GlaxoSmithKline brand OF 6 mercaptopurine	HMDB
Leupurin	HMDB
Wellcome brand OF 6-mercaptopurine	HMDB
6 Thiohypoxanthine	HMDB
6 Thiopurine	HMDB
Glaxo wellcome brand OF 6 mercaptopurine	HMDB
GlaxoSmithKline brand OF 6-mercaptopurine	HMDB
Puri nethol	HMDB
Wellcome brand OF 6 mercaptopurine	HMDB
6-Thiopurine	HMDB
Glaxo wellcome brand OF 6-mercaptopurine	HMDB
Mercaptopurina wellcome	HMDB
Purimethol	HMDB

Chemical Formula

C₅H₄N₄S

Average Molecular Weight

152.177

Monoisotopic Molecular Weight

152.015666838

IUPAC Name

6,7-dihydro-3H-purine-6-thione

Traditional Name

mercaptopurine

CAS Registry Number

50-44-2

SMILES

S=C1N=CNC2=C1NC=N2

InChI Identifier

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

InChI Key

GLVAUDGFNGKCSF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purinethiones. These are purines in which the purine moiety bears a thioketone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyrimidines

Sub Class

Purines and purine derivatives

Direct Parent

Purinethiones

Alternative Parents

Substituents

Purinethione
Pyrimidinethione
Pyrimidine
Heteroaromatic compound
Imidazole
Azole
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organosulfur compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aryl thiol (CHEBI:2208 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Organ

Liver (HMDB: HMDB0015167)
Kidney (HMDB: HMDB0015167)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015167)
Membrane (HMDB: HMDB0015167)

Source

Exogenous

Exogenous (HMDB: HMDB0015167)

Endogenous

Endogenous (HMDB: HMDB0015167)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Azathioprine Action Pathway (PathBank: SMP0000427)
Mercaptopurine Action Pathway (PathBank: SMP0000428)
Thioguanine Action Pathway (PathBank: SMP0000430)

Metabolic pathway

Mercaptopurine Metabolism Pathway (PathBank: SMP0000609)
Azathioprine Metabolism Pathway (PathBank: SMP0000645)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.74 g/L	ALOGPS
logP	-0.13	ALOGPS
logP	-0.12	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	9.5	ChemAxon
pKa (Strongest Basic)	2.99	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	53.07 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	43.6 m³·mol⁻¹	ChemAxon
Polarizability	14.04 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon