ChemicalBook > CAS DataBase List > 6-Mercaptopurine monohydrate

6-Mercaptopurine monohydrate

Product Name
6-Mercaptopurine monohydrate
CAS No.
6112-76-1
Chemical Name
6-Mercaptopurine monohydrate
Synonyms
MERCAPTOPURINE;7H-PURINE-6-THIOL HYDRATE;USP, EP;6MP H2O;C5H6N4OS·H2O;DMF available;6MP MONOHYDRATE;6-Mercaptopurine mon;6-Mercaptopurine API;LEUKERIN MONOHYDRATE
CBNumber
CB7337963
Molecular Formula
C5H6N4OS
Formula Weight
170.19
MOL File
6112-76-1.mol
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6-Mercaptopurine monohydrate Property

Melting point:
>300 °C(lit.)
storage temp. 
2-8°C
solubility 
INSOLUBLE
form 
Fine Powder
color 
Yellow
Water Solubility 
INSOLUBLE
Merck 
14,5871
BRN 
4012091
BCS Class
4
Stability:
Stable. Incompatible with strong oxidizing agents, acids, strong bases. Light sensitive.
CAS DataBase Reference
6112-76-1(CAS DataBase Reference)
EPA Substance Registry System
Mercaptopurine monohydrate (6112-76-1)
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Safety

Hazard Codes 
Xn,Xi
Risk Statements 
22-36/37/38-63-20/21/22
Safety Statements 
22-36/37/39-45-36/37
RIDADR 
UN 2811 6.1 / PGIII
WGK Germany 
3
RTECS 
UP0400000
HS Code 
29335995
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H301Toxic if swalloed

H341Suspected of causing genetic defects

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
852678
Product name
6-Mercaptopurine monohydrate
Purity
98%
Packaging
1g
Price
$53.5
Updated
2024/03/01
Sigma-Aldrich
Product number
852678
Product name
6-Mercaptopurine monohydrate
Purity
98%
Packaging
5G
Price
$94
Updated
2024/03/01
Sigma-Aldrich
Product number
1392002
Product name
Mercaptopurine
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
500mg
Price
$436
Updated
2024/03/01
Sigma-Aldrich
Product number
BP762
Product name
Mercaptopurine impurity standard
Purity
British Pharmacopoeia (BP) Reference Standard
Packaging
25MG
Price
$221
Updated
2023/06/20
TCI Chemical
Product number
M0063
Product name
6-Mercaptopurine Monohydrate
Purity
>98.0%(HPLC)(T)
Packaging
1g
Price
$24
Updated
2024/03/01
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6-Mercaptopurine monohydrate Chemical Properties,Usage,Production

Description

6-Mercaptopurine (6-MP) is an inhibitor of purine synthesis and interconversion. It is rapidly converted to 6-mercaptopurine ribonucleoside-5''-monophosphate, which inhibits phosphoribosyl pyrophosphate (PRPP) amidotransferase, the rate-limiting enzyme in purine synthesis. It also inhibits the conversion of IMP to adenylosuccinic acid and xanthylic acid and blocks AMP formation in vitro. 6-MP (30 mg/kg) inhibits growth of sarcoma 180, adenocarcinoma E 0771, and adenocarcinoma 755 tumors and reduces the size of leukemia L1210 subcutaneous growths in mice. It also decreases delayed-type hypersensitivity and thyroid inflammation in a guinea pig model of thyroiditis when administered pre- or post-disease onset. Formulations containing mercaptopurine have been used for maintenance therapy in patients with acute lymphoblastic leukemia.

Chemical Properties

white to light yellow crystal powder

Uses

An immunosuppressive drug used to treat leukemia. It is also used for pediatric non-Hodgkin lymphoma, polycythemia vera, and psoriatic arthritis

Uses

An immunosuppressive drug used to treat leukemia. It is also used for pediatric non-Hodgkin’s lymphoma, polycythemia vera, and psoriatic arthritis.

Uses

antihypertensive, ACE inhibitor

Indications

Mercaptopurine (Purinethol) is an analogue of hypoxanthine and was one of the first agents shown to be active against acute leukemias. It is now used as part of maintenance therapy in acute lymphoblastic leukemia. Mercaptopurine must be activated to a nucleotide by the enzyme HGPRTase. This metabolite is capable of inhibiting the synthesis of the normal purines adenine and guanine at the initial aminotransferase step and inhibiting the conversion of inosinic acid to the nucleotides adenylate and guanylate at several steps. Some mercaptopurine is also incorporated into DNA in the form of thioguanine. The relative significance of these mechanisms to the antitumor action of mercaptopurine is not clear.
Resistance to mercaptopurine may be a result of decreased drug activation by HGPRTase or increased inactivation by alkaline phosphatase.
The plasma half-life of an intravenous bolus injection of mercaptopurine is 21 minutes in children and 47 minutes in adults. After oral administration, peak plasma levels are attained within 2 hours. The drug is 20% bound to plasma proteins and does not enter the CSF. Xanthine oxidase is the primary enzyme involved in the metabolic inactivation of mercaptopurine.
Mercaptopurine is used in the maintenance therapy of acute lymphoblastic leukemia. It also displays activity against acute and chronic myelogenous leukemias.
The major toxicities of mercaptopurine are myelosuppression, nausea, vomiting, and hepatic toxicity.

Definition

ChEBI: Mercaptopurine hydrate is a hydrate. It contains a mercaptopurine.

brand name

Purinethol (Teva).

General Description

The drug is available as a 50-mg tablet for oral use. The primaryuses of mercaptopurine are in the treatment of lymphoblasticleukemia, acute lymphocytic leukemia, and Crohndisease. The mechanism of action includes incorporation ofmercaptopurine into DNA and RNA via the triphosphatemetabolite. This incorporation inhibits synthesis and functionof the resulting modified DNA or RNA. The parent drug isinactive and requires phosphorylation for activity. Resistancecan occur via decreased expression of the activating enzymesor increased expression of the major catabolic enzymes.Oral absorption is generally incomplete (about 50%) andthe drug does not enter the CNS in therapeutic quantities.Mercaptopurine is metabolized by methylation, and themethylated product has anticancer activity. Oxidation byxanthine oxidase yields inactive metabolites. The concurrentuse of xanthine oxidase inhibitors such as allopurinol can enhancethe potency of mercaptopurine by inhibiting its catabolicbreakdown. The toxicities for mercaptopurine includemyelosuppression, immunosuppression, nausea, vomiting,diarrhea, dry skin, urticaria, and photosensitivity.

General Description

Odorless light yellow to yellow crystalline powder. Becomes anhydrous at 284°F.

Air & Water Reactions

6-Mercaptopurine monohydrate is sensitive to light and oxidation. Insoluble in water.

Reactivity Profile

6-Mercaptopurine monohydrate reacts with strong oxidizing agents, strong bases and strong acids.

Fire Hazard

Flash point data for 6-Mercaptopurine monohydrate are not available. 6-Mercaptopurine monohydrate is probably combustible.

Mechanism of action

Because the major mechanism of action of mercaptopurine is inhibition of de novo purine nucleotide biosynthesis rather than apoptosis secondary to the incorporation of false nucleotides into DNA, there is a lower risk for mutagenesis and secondary malignancy compared to thioguanine.

Clinical Use

Mercaptopurine is used in the treatment of acute lymphatic and myelogenous leukemias.

Side effects

Bone marrow suppression is the major use-limiting toxicity, although the drug can be hepatotoxic in high doses. Dosage adjustments should be considered in the face of renal or hepatic impairment.

Synthesis

Mercaptopurine, 6-purinthiol, is made from uric acid (30.1.2.5), which is synthesized from barbituric acid (30.1.2.1). Barbituric acid (30.1.2.1) is easily made by condensing urea with malonic ester and then nitrosylating it with nitrous acid. The nitrosoderivative (30.1.2.2) is reduced by hydrogen (obtained in situ by reacting tin with hydrochloric acid) to an amine (uramil) (30.1.2.3), and then reacted with isocyanic acid, which forms pseudouric acid (30.1.2.4). This undergoes cyclization to uric acid (30.1.2.5) when heated in the presence of hydrochloric acid. Upon reacting phosphorous pentachloride with uric acid, 2,6,8-trichloropurine (30.1.2.6) is formed. The three chlorine atoms in trichloropurine differ significantly in terms of reactivity for nucleophilic substitution. The chlorine atom at C6 is much more active than the chlorine atom at C2, and this is more active than the chlorine atom at C8, which allows subsequent manipulation by them. Interaction of 2,6,8-trichloropurine (30.1.2.6) with sodium hydroxide allows to replace the chlorine atom at C6, forming the dichloro-derivative (30.1.2.7), which is then reduced by hydriodic acid to hypoxanthine (30.1.2.8). Upon reaction with phosphorous pentasulfide, hypoxanthine is transformed into mercaptopurine (30.1.2.9).

Drug interactions

Potentially hazardous interactions with other drugs
Allopurinol: decreased rate of metabolism of mercaptopurine - reduce dose of mercaptopurine to a quarter of normal dose.
Antibacterials: increased risk of haematological toxicity with co-trimoxazole and trimethoprim.
Anticoagulants: possibly reduced anticoagulant effect of coumarins.
Antipsychotics: avoid with clozapine (increased risk of agranulocytosis).
Febuxostat: avoid concomitant use.

Metabolism

It is available in an oral dosage form, but absorption can be erratic and is reduced by the presence of food. The drug is extensively metabolized on first pass and excreted by the kidneys.

Purification Methods

Crystallise 6-mercaptopurine from pyridine (30mL/g), wash it with pyridine, then triturate with water (25mL/g) and adjust to pH 5 by adding M HCl. Recrystallise it by heating, then cooling, the solution. Filter off the solid, wash it with water and dry it at 110o. It has also been crystallised from water (charcoal) as yellow crystals of the monohydrate which become anhydrous on drying at 140o. It has UV: at 230 and 312nm ( 14,000 and 19,600) in 0.1N NaOH; 222 and 327nm ( 9,2400 max and 21,300), and 216 and 329nm ( 8,740 and 19,300) in MeOH. It forms a 1:1 complex with Zn2+ , Pb2+ , Co2+, and Ni2+ in aqueous dioxan. It is an antineoplastic. [Albert & Brown J Chem Soc 2060 1954, IR: Brown & Mason J Chem Soc 682 1957, UV: Fox et al. J Am Chem Soc 80 1669 1958, UV: Mason J Chem Soc 2071 1954, Beilstein 26 III/IV 2097.]

6-Mercaptopurine monohydrate Preparation Products And Raw materials

Raw materials

6-Hydroxypurine Phosphorus pentasulfide Thiazole

Preparation Products

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View Lastest Price from 6-Mercaptopurine monohydrate manufacturers

HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
Product
6-Mercaptopurine monohydrate 6112-76-1
Price
US $100.00-75.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
5000Ton
Release date
2024-08-13
WUHAN FORTUNA CHEMICAL CO., LTD
Product
6-Mercaptopurine 6112-76-1
Price
US $0.00-0.00/Kg/Drum
Min. Order
1KG
Purity
98%min
Supply Ability
100KGS
Release date
2021-06-05
Hebei Yanxi Chemical Co., Ltd.
Product
C5H6N4OS·H2O 6112-76-1
Price
US $0.00/kg
Min. Order
1kg
Purity
USP28/BP2000
Supply Ability
20tons
Release date
2023-09-12

6112-76-1, 6-Mercaptopurine monohydrateRelated Search:

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