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Procarbazine hydrochloride

Catalog No. T1488   CAS 366-70-1
Synonyms: NSC-77213 HCl, Procarbazine HCl

Procarbazine hydrochloride (NSC-77213 HCl) is the hydrochloride salt of a methylhydrazine derivative with antineoplastic and mutagenic activities. Although the exact mode of cytotoxicity has not been elucidated, procarbazine, after metabolic activation, appears to inhibit the trans-methylation of methionine into transfer RNA (t-RNA), thereby preventing protein synthesis and consequently DNA and RNA synthesis. This agent may also undergo auto-oxidation, resulting in the formation of cytotoxic free radicals which damage DNA through an alkylation reaction.

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Procarbazine hydrochloride Chemical Structure
Procarbazine hydrochloride, CAS 366-70-1
Pack Size Availability Price/USD Quantity
50 mg In stock $ 30.00
100 mg In stock $ 39.00
1 mL * 10 mM (in DMSO) In stock $ 43.00
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Purity: 85.01%
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Biological Description
Chemical Properties
Storage & Solubility Information
Description Procarbazine hydrochloride (NSC-77213 HCl) is the hydrochloride salt of a methylhydrazine derivative with antineoplastic and mutagenic activities. Although the exact mode of cytotoxicity has not been elucidated, procarbazine, after metabolic activation, appears to inhibit the trans-methylation of methionine into transfer RNA (t-RNA), thereby preventing protein synthesis and consequently DNA and RNA synthesis. This agent may also undergo auto-oxidation, resulting in the formation of cytotoxic free radicals which damage DNA through an alkylation reaction.
In vitro Procarbazine plus Cu(II) induce piperidine-labile and formamidopyrimidine-DNA glycosylase-sensitive lesions at the 5'-ACG-3' sequence, complementary to a hotspot of the p53 gene, and the 5'-TG-3' sequence. Procarbazine causes DNA damage through non-enzymatic formation of the Cu(I)-hydroperoxo complex and methyl radicals. [1] Procarbazine has a strong clastogenic effect in hematopoietic cells and is mutagenic in a variety organs after high dose treatment. [2]
In vivo Procarbazine causes significant decrease in testicular and epididymal weight and a drastic reduction in haploid cells and spermatogenic arrest, demonstrating variation among the test golden hamster. [3] Procarbazine produces a dose-dependent potentiation of MAO A in brown adipose tissue, the elevation being more pronounced following monomethylhydrazine, with activity rising to 350% of that in control homogenates in rats. Procarbazine or monomethylhydrazine reduces metabolism of this amine by a similar degree as had been determined ex-vivo in blood vessel homogenates. [4] Procarbazine is mutagenic, clastogenic and teratogenic in a wide range of test systems of varying complexity and a wide-spectrum carcinogen in rodents and monkeys, causing tumours of the haemopoietic system, the mammary gland, the lung and the nervous system. Procarbazine in vivo undergoes a complex series of metabolic changes that result in the generation of a number of chemically reactive species, including methylating agents and free radicals. [5]
Synonyms NSC-77213 HCl, Procarbazine HCl
Molecular Weight 257.76
Formula C12H19N3O·HCl
CAS No. 366-70-1

Storage

Powder: -20°C for 3 years | In solvent: -80°C for 1 year

Solubility Information

H2O: 48 mg/mL (186.2 mM)

DMSO: 42 mg/mL(162.9 mM)

Ethanol: 22 mg/mL(85.4 mM)

TargetMolReferences and Literature

1. Ogawa K, et al. Mutat Res,2003, 539(1-2), 145-155. 2. Suzuki T, et al. Mutat Res,1999, 444(2), 269-281. 3. Weissenberg R, et al. Arch Androl,2002, 48(2), 91-100. 4. Holt A, et al. J Pharm Pharmacol,1995, 47(10), 837-845. 5. Pletsa V, et al. Carcinogenesis,1997, 18(11), 2191-2196.

Related compound libraries

This product is contained In the following compound libraries:
Anti-Cancer Approved Drug Library Anti-Cancer Drug Library Anti-Cancer Active Compound Library Anti-Cancer Clinical Compound Library FDA-Approved Drug Library Clinical Compound Library Chemotherapy Drug Library Bioactive Compounds Library Max Drug-Fragment Library Approved Drug Library

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Keywords

Procarbazine hydrochloride 366-70-1 Cell Cycle/Checkpoint DNA Damage/DNA Repair DNA/RNA Synthesis DNA Alkylator/Crosslinker NSC-77213 HCl Procarbazine HCl Inhibitor Procarbazine Hydrochloride Hodgkin's disease anticancer activity inhibit L1210 Procarbazine inhibitor

 

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