Panipenem

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MedKoo CAT#: 461483

CAS#: 87726-17-8

Description: Panipenem is a carbapenem antibiotic used in combination with betamipron.


Price and Availability

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Pricing updated 2020-07-10. Prices are subject to change without notice.

Panipenem is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 461483
Name: Panipenem
CAS#: 87726-17-8
Chemical Formula: C15H21N3O4S
Exact Mass: 339.1253
Molecular Weight: 339.41
Elemental Analysis: C, 53.08; H, 6.24; N, 12.38; O, 18.86; S, 9.45


Synonym: Panipenem; CS 533; CS-533; CS533; RS 533; RS-533; RS533;

IUPAC/Chemical Name: (5R,6S)-6-((R)-1-hydroxyethyl)-3-(((S)-1-(1-iminoethyl)pyrrolidin-3-yl)thio)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

InChi Key: TYMABNNERDVXID-DLYFRVTGSA-N

InChi Code: InChI=1S/C15H21N3O4S/c1-7(19)12-10-5-11(13(15(21)22)18(10)14(12)20)23-9-3-4-17(6-9)8(2)16/h7,9-10,12,16,19H,3-6H2,1-2H3,(H,21,22)/t7-,9+,10-,12-/m1/s1

SMILES Code: O=C(C(N12)=C(S[C@@H]3CN(C(C)=N)CC3)C[C@]2([H])[C@@H]([C@H](O)C)C1=O)O


Technical Data

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:
>3 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:
2934.99.03.00


References

1: Kato A, Ueyama J, Abe F, Hotta K, Tsukiyama I, Oshima T, Kondo F, Saito H, Hasegawa T. Panipenem does not alter the pharmacokinetics of the active metabolite of irinotecan SN-38 and inactive metabolite SN-38 glucuronide (SN-38G) in rats. Anticancer Res. 2011 Sep;31(9):2915-22. PubMed PMID: 21868538.

2: Nakagawa Y, Suzuki K, Ohta K, Hino M, Ohyashiki K, Kanamaru A, Tamura K, Urabe A, Masaoka T; Japan Febrile Neutropenia Study Group. Prospective randomized study of cefepime, panipenem, or meropenem monotherapy for patients with hematological disorders and febrile neutropenia. J Infect Chemother. 2013 Feb;19(1):103-11. doi: 10.1007/s10156-012-0466-8. Epub 2012 Sep 5. PubMed PMID: 22948387.

3: Suzuki H, Tokuda Y, Shichi D, Hitomi S, Ishikawa H, Maeno T, Nakamura H. A retrospective cohort study of panipenem/betamipron for adult pneumococcal bacteremia at three teaching hospitals in Japan. J Infect Chemother. 2013 Aug;19(4):607-14. doi: 10.1007/s10156-012-0525-1. Epub 2012 Dec 1. PubMed PMID: 23203218.

4: Ji J, Du X, Chen Y, Fu Y, Wang H, Yu Y. In vitro activity of sulbactam in combination with imipenem, meropenem, panipenem or cefoperazone against clinical isolates of Acinetobacter baumannii. Int J Antimicrob Agents. 2013 Apr;41(4):400-1. doi: 10.1016/j.ijantimicag.2012.12.014. Epub 2013 Feb 12. PubMed PMID: 23410789.

5: Clinical Trial Research Group on Panipenem-betamipron. [The clinical efficacy and safety of panipenem-betamipron in treatment of moderate to severe pulmonary infection]. Zhonghua Nei Ke Za Zhi. 2012 Jul;51(7):547-50. Chinese. PubMed PMID: 22943829.

6: Goa KL, Noble S. Panipenem/betamipron. Drugs. 2003;63(9):913-25; discussion 926. Review. PubMed PMID: 12678575.

7: Kimura T, Sunakawa K, Matsuura N, Kubo H, Shimada S, Yago K. Population pharmacokinetics of arbekacin, vancomycin, and panipenem in neonates. Antimicrob Agents Chemother. 2004 Apr;48(4):1159-67. PubMed PMID: 15047516; PubMed Central PMCID: PMC375245.

8: Ohashi N, Uematsu T, Nagashima S, Kanamaru M, Tajima N, Togawa A, Hishida A. Pharmacokinetics of panipenem/betamipron in patients with end-stage renal disease. J Infect Chemother. 2005 Feb;11(1):24-31. PubMed PMID: 15729484.

9: Kwon KT, Cheong HS, Rhee JY, Wi YM, Ryu SY, Heo ST, Moon CS, Ki HK, Kim KH, Jung CW, Peck KR, Song JH. Panipenem versus cefepime as empirical monotherapy in adult cancer patients with febrile neutropenia: a prospective randomized trial. Jpn J Clin Oncol. 2008 Jan;38(1):49-55. doi: 10.1093/jjco/hym151. Epub 2008 Jan 17. PubMed PMID: 18203711.

10: Kojima S, Nadai M, Kitaichi K, Wang L, Nabeshima T, Hasegawa T. Possible mechanism by which the carbapenem antibiotic panipenem decreases the concentration of valproic acid in plasma in rats. Antimicrob Agents Chemother. 1998 Dec;42(12):3136-40. PubMed PMID: 9835504; PubMed Central PMCID: PMC106012.

11: Tajima N, Ishizuka H, Naganuma H. Population pharmacokinetic analysis of panipenem/betamipron in patients with various degrees of renal function. Chemotherapy. 2006;52(5):245-53. Epub 2006 Jul 25. PubMed PMID: 16864999.

12: Li JJ, Jia YQ, Cui X, Huang J, He C. [Preliminary clinical evaluations of panipenem-betamipron in the treatment of hematological malignancy infections]. Zhonghua Yi Xue Za Zhi. 2012 Feb 21;92(7):452-5. doi: 10.3760/cma.j.issn.00376-2491-2012.07.006. Chinese. PubMed PMID: 22490964.

13: Ito N, Suzuki M, Kusai A, Takayama K. Effect of initial concentration on stability of panipenem in aqueous solution. Chem Pharm Bull (Tokyo). 2005 Mar;53(3):323-7. PubMed PMID: 15744107.

14: Fukuoka T, Ohya S, Narita T, Katsuta M, Iijima M, Masuda N, Yasuda H, Trias J, Nikaido H. Activity of the carbapenem panipenem and role of the OprD (D2) protein in its diffusion through the Pseudomonas aeruginosa outer membrane. Antimicrob Agents Chemother. 1993 Feb;37(2):322-7. PubMed PMID: 8452364; PubMed Central PMCID: PMC187661.

15: Kaku M. [Adequate use of parenteral antibacterial agents: panipenem/betamipron (discussion)]. Jpn J Antibiot. 2012 Apr;65(2):99-110. Japanese. PubMed PMID: 22970633.

16: Kimura T, Kokubun H, Nowatari M, Matsuura N, Sunakawa K, Kubo H. Population pharmacokinetics of panipenem in neonates and retrospective evaluation of dosage. J Antimicrob Chemother. 2001 Jan;47(1):51-9. PubMed PMID: 11152431.

17: Kurihara A, Hisaoka M, Mikuni N, Kamoshida K. Neurotoxicity of panipenem/betamipron, a new carbapenem, in rabbits: correlation to concentration in central nervous system. J Pharmacobiodyn. 1992 Jul;15(7):325-32. PubMed PMID: 1447679.

18: Shimada J, Kawahara Y. Overview of a new carbapenem, panipenem/betamipron. Drugs Exp Clin Res. 1994;20(6):241-5. PubMed PMID: 7758396.

19: Tajima N, Soma M, Ishizuka H, Naganuma H. Quantitative evaluation of effect of renal failure on the pharmacokinetics of panipenem in rats. Biol Pharm Bull. 2005 Nov;28(11):2170-2. PubMed PMID: 16272714.

20: Hayakawa M, Ito Y, Fujita I, Iseki K, Gando S. Pharmacokinetics and the most suitable regimen of panipenem/beta mipron in critically ill patients receiving continuous renal replacement therapy: a pilot study. ASAIO J. 2006 Jul-Aug;52(4):398-403. PubMed PMID: 16883119.