Procarbazine free base | CAS#671-16-9

MedKoo Cat#: 526634 | Name: Procarbazine free base

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Procarbazine is an antineoplastic chemotherapy drug for the treatment of Hodgkin's lymphoma and certain brain cancers (such as glioblastoma multiforme). It is a member of a group of medicines called alkylating agents. The drug is metabolized and activated in the liver. It also inhibits MAO thus increasing the effects of sympathomimetics, TCAs, and tyramine. It gained FDA Approved in July 1969. It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system.

Chemical Structure

Procarbazine free base

CAS#671-16-9 (free base)

Theoretical Analysis

MedKoo Cat#: 526634

Name: Procarbazine free base

CAS#: 671-16-9 (free base)

Chemical Formula: C12H19N3O

Exact Mass: 221.1528

Molecular Weight: 221.30

Elemental Analysis: C, 65.13; H, 8.65; N, 18.99; O, 7.23

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Related CAS #

671-16-9 (free base) 366-70-1 (HCl) 18969-59-0 (HBr)

Synonym

CB 400-497; NSC-77213; Ro 4-6467; Ro 4-6467/1; Procarbazine; Procarbazine free base

IUPAC/Chemical Name

4-[(2-Methylhydrazinyl)methyl]-N-propan-2-ylbenzamide

InChi Key

CPTBDICYNRMXFX-UHFFFAOYSA-N

InChi Code

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)

SMILES Code

O=C(NC(C)C)C1=CC=C(CNNC)C=C1

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Procarbazine is an orally active alkylating agent, with anticancer activity.

In vitro activity:

TBD

In vivo activity:

PCZ (procarbazine) treatment displayed significant reduction in sperm number, sperm motility, percentage normal sperm cells, and daily sperm production rate. Meanwhile the activities of testicular enzymes: gamma-glutamyl transferase, acid phosphatase, and lactate dehydrogenase were significantly altered in the PCZ group compared to control. Furthermore, PCZ caused a significant reduction in levels of glutathione and ascorbic acid as well as activities superoxide dismutase, catalase, glutathione peroxidase, and glutathione S-transferase in the testes of PCZ-treated rats. Reference: Porto Biomed J. 2018 Aug 3;4(1):e28. https://pubmed.ncbi.nlm.nih.gov/31595255/

Preparing Stock Solutions

The following data is based on the product molecular weight 221.30 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Olayinka ET, Ore A, Adeyemo OA, Ola OS. The role of flavonoid antioxidant, morin in improving procarbazine-induced oxidative stress on testicular function in rat. Porto Biomed J. 2018 Aug 3;4(1):e28. doi: 10.1016/j.pbj.0000000000000028. PMID: 31595255; PMCID: PMC6750247. 2. Revollo J, Bhalli JA, Tebbe C, Noteboom J, Thomas D, McKinzie P, Felton N, Pearce MG, Dobrovolsky VN. Spectrum of Pig-a mutations in T lymphocytes of rats treated with procarbazine. Mutagenesis. 2017 Dec 31;32(6):571-579. doi: 10.1093/mutage/gex032. PMID: 29237063.

In vitro protocol:

TBD

In vivo protocol:

1: Revollo J, Bhalli JA, Tebbe C, Noteboom J, Thomas D, McKinzie P, Felton N, Pearce MG, Dobrovolsky VN. Spectrum of Pig-a mutations in T lymphocytes of rats treated with procarbazine. Mutagenesis. 2017 Dec 8. doi: 10.1093/mutage/gex032. [Epub ahead of print] PubMed PMID: 29237063. 2: Schiff D. Low-grade Gliomas. Continuum (Minneap Minn). 2017 Dec;23(6, Neuro-oncology):1564-1579. doi: 10.1212/CON.0000000000000537. PubMed PMID: 29200111. 3: Nayak L, Reardon DA. High-grade Gliomas. Continuum (Minneap Minn). 2017 Dec;23(6, Neuro-oncology):1548-1563. doi: 10.1212/CON.0000000000000554. PubMed PMID: 29200110. 4: Kobe C, Dietlein M, Hellwig D. PET/CT for Lymphoma Post-therapy Response Assessment in Hodgkin Lymphoma and Diffuse Large B-cell Lymphoma. Semin Nucl Med. 2018 Jan;48(1):28-36. doi: 10.1053/j.semnuclmed.2017.09.003. Epub 2017 Sep 19. Review. PubMed PMID: 29195615. 5: Lin AJ, Campian JL, Hui C, Rudra S, Rao YJ, Thotala D, Hallahan D, Huang J. Impact of concurrent versus adjuvant chemotherapy on the severity and duration of lymphopenia in glioma patients treated with radiation therapy. J Neurooncol. 2017 Nov 16. doi: 10.1007/s11060-017-2668-5. [Epub ahead of print] PubMed PMID: 29143923. 6: Eichenauer DA, Plütschow A, Kreissl S, Sökler M, Hellmuth JC, Meissner J, Mathas S, Topp MS, Behringer K, Klapper W, Kuhnert G, Dietlein M, Kobe C, Fuchs M, Diehl V, Engert A, Borchmann P. Incorporation of brentuximab vedotin into first-line treatment of advanced classical Hodgkin's lymphoma: final analysis of a phase 2 randomised trial by the German Hodgkin Study Group. Lancet Oncol. 2017 Dec;18(12):1680-1687. doi: 10.1016/S1470-2045(17)30696-4. Epub 2017 Nov 10. PubMed PMID: 29133014. 7: Radhakrishnan V, Dhanushkodi M, Ganesan TS, Ganesan P, Sundersingh S, Selvaluxmy G, Swaminathan R, Rama R, Sagar TG. Pediatric Hodgkin Lymphoma Treated at Cancer Institute, Chennai, India: Long-Term Outcome. J Glob Oncol. 2016 Nov 9;3(5):545-554. doi: 10.1200/JGO.2016.005314. eCollection 2017 Oct. PubMed PMID: 29094094; PubMed Central PMCID: PMC5646877. 8: Borchmann P, Goergen H, Kobe C, Lohri A, Greil R, Eichenauer DA, Zijlstra JM, Markova J, Meissner J, Feuring-Buske M, Hüttmann A, Dierlamm J, Soekler M, Beck HJ, Willenbacher W, Ludwig WD, Pabst T, Topp MS, Hitz F, Bentz M, Keller UB, Kühnhardt D, Ostermann H, Schmitz N, Hertenstein B, Aulitzky W, Maschmeyer G, Vieler T, Eich H, Baues C, Stein H, Fuchs M, Kuhnert G, Diehl V, Dietlein M, Engert A. PET-guided treatment in patients with advanced-stage Hodgkin's lymphoma (HD18): final results of an open-label, international, randomised phase 3 trial by the German Hodgkin Study Group. Lancet. 2017 Oct 20. pii: S0140-6736(17)32134-7. doi: 10.1016/S0140-6736(17)32134-7. [Epub ahead of print] PubMed PMID: 29061295. 9: Lakomý R, Kazda T, Poprach A, Pospíšil P, Jančálek R, Šlampa P. [The Role of Chemotherapy in the Treatment of Low-grade Gliomas]. Klin Onkol. 2017 Fall;30(5):343-348. doi: 10.14735/amko2017343. Czech. PubMed PMID: 29031036. 10: Kazda T, Lakomý R, Poprach A, Pospíšil P, Jančálek R, Šlampa P. [Controversy in the Postoperative Treatment of Low-grade Gliomas]. Klin Onkol. 2017 Fall;30(5):337-342. doi: 10.14735/amko2017337. Czech. PubMed PMID: 29031035. 11: Izquierdo C, Joubert B, Ducray F. Anaplastic gliomas in adults: an update. Curr Opin Oncol. 2017 Nov;29(6):434-442. doi: 10.1097/CCO.0000000000000409. Review. PubMed PMID: 28901965. 12: Krul IM, Opstal-van Winden AWJ, Aleman BMP, Janus CPM, van Eggermond AM, De Bruin ML, Hauptmann M, Krol ADG, Schaapveld M, Broeks A, Kooijman KR, Fase S, Lybeert ML, Zijlstra JM, van der Maazen RWM, Kesminiene A, Diallo I, de Vathaire F, Russell NS, van Leeuwen FE. Breast Cancer Risk After Radiation Therapy for Hodgkin Lymphoma: Influence of Gonadal Hormone Exposure. Int J Radiat Oncol Biol Phys. 2017 Nov 15;99(4):843-853. doi: 10.1016/j.ijrobp.2017.07.016. Epub 2017 Jul 18. PubMed PMID: 28888722. 13: Yasuda T, Nitta M, Komori T, Kobayashi T, Masui K, Maruyama T, Sawada T, Muragaki Y, Kawamata T. Gliosarcoma arising from oligodendroglioma, IDH mutant and 1p/19q codeleted. Neuropathology. 2017 Aug 15. doi: 10.1111/neup.12406. [Epub ahead of print] PubMed PMID: 28812310. 14: Hattori K, Sakata-Yanagimoto M, Okoshi Y, Kato T, Kurita N, Yokoyama Y, Obara N, Takano S, Ishikawa E, Yamamoto T, Matsumura A, Hasegawa Y, Chiba S. A single institutional retrospective evaluation for younger patients with primary central nervous lymphomas on a modified R-MPV regimen followed by radiotherapy and high dose cytarabine. J Clin Exp Hematop. 2017 Oct 12;57(2):41-46. doi: 10.3960/jslrt.17012. Epub 2017 Aug 4. PubMed PMID: 28781291. 15: Parasramka S, Talari G, Rosenfeld M, Guo J, Villano JL. Procarbazine, lomustine and vincristine for recurrent high-grade glioma. Cochrane Database Syst Rev. 2017 Jul 26;7:CD011773. doi: 10.1002/14651858.CD011773.pub2. Review. PubMed PMID: 28744879. 16: Qian Y, Maruyama S, Kim H, Pollom EL, Kumar KA, Chin AL, Harris JP, Chang DT, Pitt A, Bendavid E, Owens DK, Durkee BY, Soltys SG. Cost-effectiveness of radiation and chemotherapy for high-risk low-grade glioma. Neuro Oncol. 2017 Nov 29;19(12):1651-1660. doi: 10.1093/neuonc/nox121. PubMed PMID: 28666368; PubMed Central PMCID: PMC5716167. 17: van den Bent MJ, Smits M, Kros JM, Chang SM. Diffuse Infiltrating Oligodendroglioma and Astrocytoma. J Clin Oncol. 2017 Jul 20;35(21):2394-2401. doi: 10.1200/JCO.2017.72.6737. Epub 2017 Jun 22. Review. PubMed PMID: 28640702. 18: Atilla PA, Atilla E, Bozdag SC, Yuksel MK, Toprak SK, Topcuoglu P, Demirer T, Ilhan O, Arslan O, Gurman G, Ozcan M. Treatment with methotrexate, rituximab, and cytosine arabinoside followed by autologous stem cell transplantation in primary central nervous system lymphoma: A single-center experience. Hematol Oncol Stem Cell Ther. 2017 Jun 15. pii: S1658-3876(17)30085-7. doi: 10.1016/j.hemonc.2017.05.030. [Epub ahead of print] PubMed PMID: 28633037. 19: van Eggermond AM, Schaapveld M, Janus CP, de Boer JP, Krol AD, Zijlstra JM, van der Maazen RW, Kremer LC, van Leerdam ME, Louwman MW, Visser O, De Bruin ML, Aleman BM, van Leeuwen FE. Infradiaphragmatic irradiation and high procarbazine doses increase colorectal cancer risk in Hodgkin lymphoma survivors. Br J Cancer. 2017 Jul 25;117(3):306-314. doi: 10.1038/bjc.2017.177. Epub 2017 Jun 20. PubMed PMID: 28632726; PubMed Central PMCID: PMC5537493. 20: Cernadas JR. Reactions to cytostatic agents in children. Curr Opin Allergy Clin Immunol. 2017 Aug;17(4):255-261. doi: 10.1097/ACI.0000000000000381. PubMed PMID: 28622171.