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

• ChemBase编号: 1039
• 分子式: C12H19N3O
• 平均质量: 221.29876
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 4-[(2-methylhydrazin-1-yl)methyl]-N-(propan-2-yl)benzamide
• IUPAC传统名: procarbazine
• 商标名: Matulane; Nathulane; Natulan; Natulan hydrochloride; Natulanar; Natunalar
• 别名: 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

登记号

• CAS号: 671-16-9
• PubChem SID: 160964502; 46507706
• PubChem CID: 4915
• ATC码: L01XB01
• CHEMBL: 1321
• Chemspider ID: 4746
• DrugBank ID: DB01168
• KEGG ID: D08423
• 美国药典/FDA物质标识码: 35S93Y190K
• 维基百科标题: Procarbazine
• Medline Plus: a682094

理论计算性质

JChem

• Acid pKa: 15.032636
• 质子受体: 3
• 质子供体: 3
• LogD (pH = 5.5): 0.6326173
• LogD (pH = 7.4): 0.97892106
• Log P: 0.9857342
• 摩尔折射率: 86.9783 cm^3
• 极化性: 25.215479 Å^3
• 极化表面积: 53.16 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 0.53
• LOG S: -2.99
• 溶解度: 2.28e-01 g/l

分子性质

理化性质

• 溶解度: 1420 mg/L
• 疏水性(logP): 2.6

药理学性质

• 给药途径: Oral (Gel Capsule), intravenous
• 排泄: Renal
• 半衰期: 10 minutes
• 代谢: Hepatic, Renal
• 法定药品分级: Rx-only
• 妊娠期药物分类: D (Australia); D (US)

详细说明

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