WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 100730
CAS#: 54-91-1
Description: Pipobroman (trade names Vercite, Vercyte) is an anti-cancer drug that probably acts as an alkylating agent. It is marketed by Abbott Laboratories. Pipobroman (PB) has well documented clinical activity in polycythemia vera (PV) and essential thrombocythemia (ET).
MedKoo Cat#: 100730
Name: Pipobroman
CAS#: 54-91-1
Chemical Formula: C10H16Br2N2O2
Exact Mass: 353.95785
Molecular Weight: 356.05
Elemental Analysis: C, 33.73; H, 4.53; Br, 44.88; N, 7.87; O, 8.99
Synonym: NSC25154; Pipobroman; Trade names Vercite Vercyte.
IUPAC/Chemical Name: 1,1'-(piperazine-1,4-diyl)bis(3-bromopropan-1-one)
InChi Key: NJBFOOCLYDNZJN-UHFFFAOYSA-N
InChi Code: InChI=1S/C10H16Br2N2O2/c11-3-1-9(15)13-5-7-14(8-6-13)10(16)2-4-12/h1-8H2
SMILES Code: O=C(N1CCN(C(CCBr)=O)CC1)CCBr
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, not in water
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
The following data is based on the product molecular weight 356.05 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 |
1: Kiladjian JJ, Chevret S, Dosquet C, Chomienne C, Rain JD. Treatment of polycythemia vera with hydroxyurea and pipobroman: final results of a randomized trial initiated in 1980. J Clin Oncol. 2011 Oct 10;29(29):3907-13. doi: 10.1200/JCO.2011.36.0792. Epub 2011 Sep 12. PubMed PMID: 21911721.
2: Tsamaloukas AG. Pipobroman gets regulatory approval outside Germany. Dtsch Arztebl Int. 2008 Jan;105(4):71-2; author reply 72. doi: 10.3238/arztebl.2008.0071d. Epub 2008 Jan 25. PubMed PMID: 19633773; PubMed Central PMCID: PMC2696734.
3: Tchen T, Durlach A, Bernard P, Grange F. [Multiples squamous cell carcinomas during treatment with pipobroman]. Ann Dermatol Venereol. 2007 Jun-Jul;134(6-7):570-1. French. PubMed PMID: 17657187.
4: Kiladjian JJ, Rain JD, Bernard JF, Briere J, Chomienne C, Fenaux P. Long-term incidence of hematological evolution in three French prospective studies of hydroxyurea and pipobroman in polycythemia vera and essential thrombocythemia. Semin Thromb Hemost. 2006 Jun;32(4 Pt 2):417-21. Review. PubMed PMID: 16810617.
5: Orlandi E, Bernasconi P, Boni M, Calatroni S, Lazzarino M. Cytogenetic response to pipobroman in Philadelphia-positive chronic myeloid leukemia with thrombocythemic onset. Ann Hematol. 2005 Feb;84(2):127-8. Epub 2004 Sep 15. PubMed PMID: 15378276.
6: Passamonti F, Rumi E, Malabarba L, Arcaini L, Orlandi E, Brusamolino E, Pascutto C, Cazzola M, Lazzarino M. Long-term follow-up of young patients with essential thrombocythemia treated with pipobroman. Ann Hematol. 2004 Aug;83(8):495-7. Epub 2004 Jun 3. PubMed PMID: 15175894.
7: De Sanctis V, Mazzucconi MG, Spadea A, Alfò M, Mancini M, Bizzoni L, Peraino M, Mandelli F. Long-term evaluation of 164 patients with essential thrombocythaemia treated with pipobroman: occurrence of leukaemic evolution. Br J Haematol. 2003 Nov;123(3):517-21. PubMed PMID: 14617017.
8: Passamonti F, Lazzarino M. Treatment of polycythemia vera and essential thrombocythemia: the role of pipobroman. Leuk Lymphoma. 2003 Sep;44(9):1483-8. Review. PubMed PMID: 14565648.
9: Kiladjian JJ, Gardin C, Renoux M, Bruno F, Bernard JF. Long-term outcomes of polycythemia vera patients treated with pipobroman as initial therapy. Hematol J. 2003;4(3):198-207. PubMed PMID: 12764352.
10: Sironi M, Bertola G, Lodato A, Spinelli M, Sciariada L. Transition of essential thrombocythemia to megakaryoblastic leukemia after long-term therapy with sequential busulfan, pipobroman and hydroxyurea. Acta Haematol. 2003;109(3):161-2. PubMed PMID: 12714827.
11: Bernasconi P, Boni M, Cavigliano PM, Calatroni S, Brusamolino E, Passamonti F, Volpe G, Pistorio A, Giardini I, Rocca B, Caresana M, Lazzarino M, Bernasconi C. Acute myeloid leukemia (AML) having evolved from essential thrombocythemia (ET): distinctive chromosome abnormalities in patients treated with pipobroman or hydroxyurea. Leukemia. 2002 Oct;16(10):2078-83. PubMed PMID: 12357360.
12: Passamonti F, Malabarba L, Orlandi E, Pascutto C, Brusamolino E, Astori C, Baratè C, Canevari A, Corso A, Bernasconi P, Cazzola M, Lazzarino M. Pipobroman is safe and effective treatment for patients with essential thrombocythaemia at high risk of thrombosis. Br J Haematol. 2002 Mar;116(4):855-61. PubMed PMID: 11886392.
13: Triffet A, Straetmans N, Ferrant A. Bone marrow aplasia after pipobroman: an immune-mediated mechanism? Br J Haematol. 2001 Dec;115(3):713-4. Review. PubMed PMID: 11736962.
14: Najean Y, Rain JD, Lejeune F, Echard M, Fermand JP, Gruyer P, Brahimi S. [Treatment of polycythemia. II.--Comparison of hydroxyurea with pipobroman in 294 patients less than 65 years of age]. Ann Med Interne (Paris). 1998 Mar;149(2):94-100. French. PubMed PMID: 11490531.
15: Passamonti F, Brusamolino E, Lazzarino M, Baraté C, Klersy C, Orlandi E, Canevari A, Castelli G, Merante S, Bernasconi C. Efficacy of pipobroman in the treatment of polycythemia vera: long-term results in 163 patients. Haematologica. 2000 Oct;85(10):1011-8. PubMed PMID: 11025590.
16: Petti MC, Spadea A, Avvisati G, Spadea T, Latagliata R, Montefusco E, Cosenza M, Malagnino F. Polycythemia vera treated with pipobroman as single agent: low incidence of secondary leukemia in a cohort of patients observed during 20 years (1971-1991). Leukemia. 1998 Jun;12(6):869-74. PubMed PMID: 9639413.
17: Najean Y, Rain JD. Treatment of polycythemia vera: the use of hydroxyurea and pipobroman in 292 patients under the age of 65 years. Blood. 1997 Nov 1;90(9):3370-7. PubMed PMID: 9345019.
18: Messora C, Bensi L, Vanzanelli P, Temperani P, Carotenuto M, Sacchi S. Myelodysplastic transformation in a case of essential thrombocythemia treated with pipobroman. Haematologica. 1996 Jan-Feb;81(1):51-3. PubMed PMID: 8900853.
19: Paitel JF, Trechot P, Stockemer V, Dorvaux V, Lederlin P. [Acute liver disease during treatment with pipobroman and allopurinol]. Presse Med. 1995 Mar 4;24(9):460. French. PubMed PMID: 7746823.
20: Boivin P. Indications, procedure and results for the treatment of polycythaemia vera by bleeding, pipobroman and hydroxyurea. Nouv Rev Fr Hematol. 1993;35(5):491-8. PubMed PMID: 8295823.
Pipobroman was approved in German. Pipobroman is an antineoplastic agent. Specifically it is a piperazine derivative with a chemical structure close to that of many DNA alkylating agents. Pipobroman has well documented clinical activity against polycythemia vera and essential thrombocythemia. According to drugbank, pipobroman was indicated for the treatment of polycythaemia vera and refractory chronic myeloid leukaemia.
The mechanism of action is uncertain but pipobroman is thought to alkylate DNA leading to disruption of DNA synthesis and eventual cell death.
