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
- MOL File:
- 6112-76-1.mol
- Modify Date:
- 2024/4/25 17:59:01
| 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) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |   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 |
|
6-Mercaptopurine monohydrate price More Price(13)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | 852678 | 6-Mercaptopurine monohydrate 98% | 6112-76-1 | 1G | ₹2100.05 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | PHR1611 | Mercaptopurine Pharmaceutical Secondary Standard; Certified Reference Material | 6112-76-1 | 1G | ₹20621.63 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 852678 | 6-Mercaptopurine monohydrate 98% | 6112-76-1 | 5G | ₹6430.05 | 2022-06-14 | Buy |
| ALFA India | ALF-A12197-14 | 6-Mercaptopurine monohydrate, 98% | 6112-76-1 | 25g | ₹29155 | 2022-05-26 | Buy |
| TCI Chemicals (India) | M0063 | 6-Mercaptopurine Monohydrate | 6112-76-1 | 1G | ₹2100 | 2022-05-26 | 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
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.
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.
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
| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| PANCHSHEEL ORGANICS LTD | +91-9821053955 +91-9324201019 | Mumbai, India | 82 | 58 | Inquiry |
| Aventus Labs | +91-7021872517 +91-9324342304 | Maharashtra, India | 168 | 58 | Inquiry |
| Mekong pharmaceuticals pvt ltd | +91-4035163894 +91-8008212221 | Telangana, India | 129 | 58 | Inquiry |
| Apicore Pharmaceuticals Pvt Ltd | +91-2662267177 +91-2662267166 | Gujarat, India | 181 | 58 | Inquiry |
| HiMedia Laboratories | 91-22-61471919 | Maharashtra, India | 1843 | 58 | Inquiry |
| Pharma Affiliates | 172-5066494 | Haryana, India | 6761 | 58 | Inquiry |
| Srini Pharmaceuticals Limited | 091 | Hyderabad, India | 11 | 58 | Inquiry |
| Pharmaffiliates Analytics and Synthetics P. Ltd | +91-172-5066494 | Haryana, India | 6773 | 58 | Inquiry |
| SynZeal Research Pvt Ltd | +1 226-802-2078 | Gujarat, India | 6522 | 58 | Inquiry |
| Triveni chemicals | 08048762458 | New Delhi, India | 6093 | 58 | Inquiry |
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