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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
Molecular Weight:
170.19
MDL Number:
MFCD03854445
MOL File:
6112-76-1.mol
Last updated:2023-09-12 17:26:57

6-Mercaptopurine monohydrate Properties

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)
EWG's Food Scores 2
NCI Dictionary of Cancer Terms mercaptopurine
FDA UNII E7WED276I5
NCI Drug Dictionary mercaptopurine
ATC code L01BB02
Proposition 65 List Mercaptopurine
EPA Substance Registry System Mercaptopurine monohydrate (6112-76-1)

Pharmacokinetic data

Protein binding 20%
Excreted unchanged in urine 7%
Volume of distribution 0.1-1.7(L/kg)
Biological half-life 1-1.5 / -

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS06,GHS08
Signal word  Danger
Hazard statements  H301-H341-H361fd
Precautionary statements  P201-P202-P264-P270-P280-P301+P310
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
NFPA 704
1
2 0

6-Mercaptopurine monohydrate price More Price(55)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 852678 6-Mercaptopurine monohydrate 98% 6112-76-1 1g $53.5 2024-03-01 Buy
Sigma-Aldrich 852678 6-Mercaptopurine monohydrate 98% 6112-76-1 5G $94 2024-03-01 Buy
Sigma-Aldrich 1392002 Mercaptopurine United States Pharmacopeia (USP) Reference Standard 6112-76-1 500mg $436 2024-03-01 Buy
Sigma-Aldrich BP762 Mercaptopurine impurity standard British Pharmacopoeia (BP) Reference Standard 6112-76-1 25MG $221 2023-06-20 Buy
TCI Chemical M0063 6-Mercaptopurine Monohydrate >98.0%(HPLC)(T) 6112-76-1 1g $24 2024-03-01 Buy
Product number Packaging Price Buy
852678 1g $53.5 Buy
852678 5G $94 Buy
1392002 500mg $436 Buy
BP762 25MG $221 Buy
M0063 1g $24 Buy

6-Mercaptopurine monohydrate Chemical Properties,Uses,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

antihypertensive, ACE inhibitor

Uses

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

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).

Synthesis_6112-76-1

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.]

87-42-3
17356-08-0
6112-76-1
Synthesis of 6-Mercaptopurine monohydrate from 6-Chloropurine and Carbamimidothioic acid

6-Mercaptopurine monohydrate Preparation Products And Raw materials

Raw materials

Preparation Products

Global( 358)Suppliers
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View Lastest Price from 6-Mercaptopurine monohydrate manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
C5H6N4OS·H2O pictures 2023-09-12 C5H6N4OS·H2O
6112-76-1
US $0.00 / kg 1kg USP28/BP2000 20tons Hebei Yanxi Chemical Co., Ltd.
6-Mercaptopurine monohydrate pictures 2023-04-27 6-Mercaptopurine monohydrate
6112-76-1
US $5.00-2.00 / KG 1KG 99% 10000kg Hebei Guanlang Biotechnology Co,.LTD
6-Mercaptopurine monohydrate pictures 2022-09-30 6-Mercaptopurine monohydrate
6112-76-1
US $0.00-0.00 / KG 1KG 98% 1ton Henan Aochuang Chemical Co.,Ltd.
  • C5H6N4OS·H2O pictures
  • C5H6N4OS·H2O
    6112-76-1
  • US $0.00 / kg
  • USP28/BP2000
  • Hebei Yanxi Chemical Co., Ltd.
1,7-dihydro-6h-purin-6-thion,monohydrat 1,7-dihydro-6h-purine-6-thionemonohydrate 1,7-dihydro-6h-purine-6-thionmonohydrate 6h-purin-6-thion,monohydrat 6-merkaptopurin,monohydrat 3,7-Dihydro-purine-6-thione Monohydrate 6-MERCAPTOPURINE extrapure 6-Purinethiol, 6-Thiohypoxanthine 3,7Ddihydropurine-6-thione hydrate 6H-Purine-6-thione, 1,7-dihydro-, monohydrate Purin-6-thiol, monohydrate 6-MERCAPTOPURINE monohydrate (6SP) 6-Mercaptopurine monohydrate ,99% Mercaptopurine (500 mg) 6-Mercaptopurine mon 6-Mercaptopurine Monohydrat 6-Mercaptopurine  6-Mercaptopurine Monohydrate, 99.5+% 25GR 6-Mercaptopurine Monohydrate, 99.5+% 5GR 6-Mercaptopurine API DMF available USP, EP 6-Mercaptopurine Monohydrate, 98.5% 1,7-Dihydro-6H-purine-6-thione hydrate mercaptopurine hydrate purin-6-thiol,monohydrat MERCALEUKIN MONOHYDRATE MERCAPTOPURINE, MONOHYDRATE MERCAPTOPURINE MONOHYDRATE, 6- LEUKERIN MONOHYDRATE 6-PURINETHIOL MONOHYDRATE 6-thiohypoxanthine monohydrate 6-MERCAPTOPURINE HYDRATE 6-MERCAPTOPURINE MONOHYDRATE 6MP H2O 6MP MONOHYDRATE PURINE-6-THIOL, MONOHYDRATE 6-MERCAPTOPURIN HYDRAT 99% 6-Mercaptopurine monohydrate, 99.5+% 3,7-Dihydro-purine-6-thione Monohydrat MERCAPTOPURINE,MONOHYDRATE,USP 6-Mercaptopurinemonohydrate,98% 6-Mercaptopurine (6-MP) Monohydrate 6-Mercaptopurine monohydrate, 98.5%, a DNA/RNA synthesis inhibitor 6-MP(6-Mercaptopurine monohydrate) mercaptopurine impurity standard 6-MercaptopurineMonohydrate> Azathioprine BP Impurity B 6-Mercaptopurine monohydrate USP/EP/BP 6-Mercaptopurine 1-hydrate 6-Mercaptopurine HydrateQ: What is 6-Mercaptopurine Hydrate Q: What is the CAS Number of 6-Mercaptopurine Hydrate Q: What is the storage condition of 6-Mercaptopurine Hydrate C5H6N4OS·H2O 6-Mercaptopurine monohydrate,caS:6112-76-1 6-Mercaptopurine Monohydrate extrapure, 99% Mercaptopurine (1392002) MERCAPTOPURINE 7H-PURINE-6-THIOL HYDRATE Azathioprine Impurity B as Monohydrate