4-[(2-methylhydrazin-1-yl)methyl]-N-(propan-2-yl)benzamide

• ChemBase ID: 1039
• Molecular Formular: C12H19N3O
• Molecular Mass: 221.29876
• Monoisotopic Mass: 221.15281224
• SMILES: O=C(NC(C)C)c1ccc(CNNC)cc1
• Canonical SMILES: CNNCc1ccc(cc1)C(=O)NC(C)C
• InChI: InChI=1S/C12H19N3O/c1-9(2)15-12(16)11-6-4-10(5-7-11)8-14-13-3/h4-7,9,13-14H,8H2,1-3H3,(H,15,16)
• InChIKey: CPTBDICYNRMXFX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(2-methylhydrazin-1-yl)methyl]-N-(propan-2-yl)benzamide
• IUPAC Traditional name: procarbazine
• Brand Name: Matulane; Nathulane; Natulan; Natulan hydrochloride; Natulanar; Natunalar
• Synonyms: Ibenzmethyzine hydrochloride; Ibenzmethyzine; Ibenzmethyzin; IBZ; MBH; MIH; MIH Hydrochloride; PCB; PCB hydrochloride; Procarbazin [German]; Procarbazina [INN-Spanish]; Procarbazine hydrochloride; Procarbazinum [INN-Latin]; PCX; Procarbazin; Procarbazine

Database IDs

• CAS Number: 671-16-9
• PubChem SID: 46507706; 160964502
• PubChem CID: 4915
• ATC CODE: L01XB01
• CHEMBL: 1321
• Chemspider ID: 4746
• DrugBank ID: DB01168
• KEGG ID: D08423
• Unique Ingredient Identifier: 35S93Y190K
• Wikipedia Title: Procarbazine
• Medline Plus: a682094

CALCULATED PROPERTIES

JChem

• Acid pKa: 15.032636
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 0.6326173
• LogD (pH = 7.4): 0.97892106
• Log P: 0.9857342
• Molar Refractivity: 86.9783 cm^3
• Polarizability: 25.215479 Å^3
• Polar Surface Area: 53.16 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.53
• LOG S: -2.99
• Solubility (Water): 2.28e-01 g/l

PROPERTIES

Physical Property

• Solubility: 1420 mg/L
• Hydrophobicity(logP): 2.6

Pharmacology Properties

• Admin Routes: Oral (Gel Capsule), intravenous
• Excretion: Renal
• Half Life: 10 minutes
• Metabolism: Hepatic, Renal
• Legal Status: Rx-only
• Pregnancy Category: D (Australia); D (US)

DETAILS

DrugBank - DB01168

• Drug Groups: approved
• Description: An antineoplastic agent used primarily in combination with mechlorethamine, vincristine, and prednisone (the MOPP protocol) in the treatment of Hodgkin's disease. [PubChem]
• Indication: For use with other anticancer drugs for the treatment of stage III and stage IV Hodgkin's disease.
• Pharmacology: Procarbazine is an antineoplastic in the class of alkylating agents and is used to treat various forms of cancer. Alkylating agents are so named because of their ability to add alkyl groups to many electronegative groups under conditions present in cells. They stop tumor growth by cross-linking guanine bases in DNA double-helix strands - directly attacking DNA. This makes the strands unable to uncoil and separate. As this is necessary in DNA replication, the cells can no longer divide. In addition, these drugs add methyl or other alkyl groups onto molecules where they do not belong which in turn inhibits their correct utilization by base pairing and causes a miscoding of DNA. Procarbazine is cell-phase specific for the S phase of cell division.
• Toxicity: LD₅₀=785 mg/kg (orally in rats)
• Affected Organisms: Humans and other mammals
• Biotransformation: Procarbazine is metabolized primarily in the liver and kidneys. The drug appears to be auto-oxidized to the azo derivative with the release of hydrogen peroxide. The azo derivative isomerizes to the hydrazone, and following hydrolysis splits into a benzylaldehyde derivative and methylhydrazine. The methylhydrazine is further degraded to CO₂ and CH₄ and possibly hydrazine, whereas the aldehyde is oxidized to N-isopropylterephthalamic acid, which is excreted in the urine.
• Absorption: Procarbazine is rapidly and completely absorbed.
• Half Life: 10 minutes
• External Links: Wikipedia; RxList; Drugs.com