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MedKoo Cat#: 463423 | Name: PAßN dihydrochloride
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Description:

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

PAßN dihydrochloride (Phe-Arg -naphthylamide) is an Efflux pump inhibitor (EPI). It acts on the major multidrug resistance efflux transporters of Gram-negative bacteria. Phe-Arg -naphthylamide lowers fluoroquinolone resistance in Pseudomonas aeruginosa.

Chemical Structure

PAßN dihydrochloride
PAßN dihydrochloride
CAS#100929-99-5 (dihydrochloride)

Theoretical Analysis

MedKoo Cat#: 463423

Name: PAßN dihydrochloride

CAS#: 100929-99-5 (dihydrochloride)

Chemical Formula: C25H32Cl2N6O2

Exact Mass: 518.1964

Molecular Weight: 519.47

Elemental Analysis: C, 57.80; H, 6.21; Cl, 13.65; N, 16.18; O, 6.16

Price and Availability

Size Price Availability Quantity
25mg USD 340.00 2 Weeks
250mg USD 1,070.00 2 Weeks
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Synonym
PAßN dihydrochloride; PAßN-dihydrochloride; PAssN 2HCl; PAssN-2HCl; MC-207110 2HCl; MC207110 2HCl; MC 207110 2HCl; Phe-Arg β-naphthylamide;
IUPAC/Chemical Name
(S)-2-((R)-2-amino-3-phenylpropanamido)-5-guanidino-N-(naphthalen-2-yl)pentanamide dihydrochloride
InChi Key
MRUMOHLDHMZGMS-ZZYOSWMOSA-N
InChi Code
InChI=1S/C25H30N6O2.2ClH/c26-21(15-17-7-2-1-3-8-17)23(32)31-22(11-6-14-29-25(27)28)24(33)30-20-13-12-18-9-4-5-10-19(18)16-20;;/h1-5,7-10,12-13,16,21-22H,6,11,14-15,26H2,(H,30,33)(H,31,32)(H4,27,28,29);2*1H/t21-,22+;;/m1../s1
SMILES Code
O=C([C@H](CCCNC(N)=N)NC([C@H](N)CC1=CC=CC=C1)=O)NC(C=C2)=CC3=C2C=CC=C3.Cl.Cl
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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 519.47 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.

Recalculate based on batch purity %
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: Kouitcheu Mabeku LB, Eyoum Bille B, Tepap Zemnou C, Tali Nguefack LD, Leundji H. Broad spectrum resistance in Helicobacter pylori isolated from gastric biopsies of patients with dyspepsia in Cameroon and efflux-mediated multiresistance detection in MDR isolates. BMC Infect Dis. 2019 Oct 22;19(1):880. doi: 10.1186/s12879-019-4536-8. PMID: 31640588; PMCID: PMC6806547. 2: Laudy AE, Kulińska E, Tyski S. The Impact of Efflux Pump Inhibitors on the Activity of Selected Non-Antibiotic Medicinal Products against Gram-Negative Bacteria. Molecules. 2017 Jan 11;22(1):114. doi: 10.3390/molecules22010114. PMID: 28085074; PMCID: PMC6155833. 3: Misra R, Morrison KD, Cho HJ, Khuu T. Importance of Real-Time Assays To Distinguish Multidrug Efflux Pump-Inhibiting and Outer Membrane-Destabilizing Activities in Escherichia coli. J Bacteriol. 2015 Aug 1;197(15):2479-88. doi: 10.1128/JB.02456-14. Epub 2015 May 11. PMID: 25962916; PMCID: PMC4518837. 4: Vargiu AV, Ruggerone P, Opperman TJ, Nguyen ST, Nikaido H. Molecular mechanism of MBX2319 inhibition of Escherichia coli AcrB multidrug efflux pump and comparison with other inhibitors. Antimicrob Agents Chemother. 2014 Oct;58(10):6224-34. doi: 10.1128/AAC.03283-14. Epub 2014 Aug 11. PMID: 25114133; PMCID: PMC4187987. 5: Fusté E, López-Jiménez L, Segura C, Gainza E, Vinuesa T, Viñas M. Carbapenem- resistance mechanisms of multidrug-resistant Pseudomonas aeruginosa. J Med Microbiol. 2013 Sep;62(Pt 9):1317-1325. doi: 10.1099/jmm.0.058354-0. Epub 2013 May 30. PMID: 23722434. 6: Huguet A, Pensec J, Soumet C. Resistance in Escherichia coli: variable contribution of efflux pumps with respect to different fluoroquinolones. J Appl Microbiol. 2013 May;114(5):1294-9. doi: 10.1111/jam.12156. Epub 2013 Feb 18. PMID: 23414263. 7: Kothary V, Scherl EJ, Bosworth B, Jiang ZD, Dupont HL, Harel J, Simpson KW, Dogan B. Rifaximin resistance in Escherichia coli associated with inflammatory bowel disease correlates with prior rifaximin use, mutations in rpoB, and activity of Phe-Arg-β-naphthylamide-inhibitable efflux pumps. Antimicrob Agents Chemother. 2013 Feb;57(2):811-7. doi: 10.1128/AAC.02163-12. Epub 2012 Nov 26. PMID: 23183443; PMCID: PMC3553721. 8: Gomes C, Pons MJ, Magallon-Tejada A, Durand D, Lluque A, Mosquito S, Riveros M, Mercado E, Prada A, Ochoa TJ, Ruiz J. In vitro development and analysis of Escherichia coli and Shigella boydii azithromycin-resistant mutants. Microb Drug Resist. 2013 Apr;19(2):88-93. doi: 10.1089/mdr.2012.0036. Epub 2012 Nov 23. PMID: 23176550. 9: Buyck JM, Plésiat P, Traore H, Vanderbist F, Tulkens PM, Van Bambeke F. Increased susceptibility of Pseudomonas aeruginosa to macrolides and ketolides in eukaryotic cell culture media and biological fluids due to decreased expression of oprM and increased outer-membrane permeability. Clin Infect Dis. 2012 Aug;55(4):534-42. doi: 10.1093/cid/cis473. Epub 2012 May 9. PMID: 22573850. 10: Maravić A, Skočibušić M, Sprung M, Samanić I, Puizina J, Pavela-Vrančić M. Occurrence and antibiotic susceptibility profiles of Burkholderia cepacia complex in coastal marine environment. Int J Environ Health Res. 2012;22(6):531-42. doi: 10.1080/09603123.2012.667797. Epub 2012 Mar 19. PMID: 22428949. 11: Balganesh M, Dinesh N, Sharma S, Kuruppath S, Nair AV, Sharma U. Efflux pumps of Mycobacterium tuberculosis play a significant role in antituberculosis activity of potential drug candidates. Antimicrob Agents Chemother. 2012 May;56(5):2643-51. doi: 10.1128/AAC.06003-11. Epub 2012 Feb 6. PMID: 22314527; PMCID: PMC3346595. 12: Schaible B, Taylor CT, Schaffer K. Hypoxia increases antibiotic resistance in Pseudomonas aeruginosa through altering the composition of multidrug efflux pumps. Antimicrob Agents Chemother. 2012 Apr;56(4):2114-8. doi: 10.1128/AAC.05574-11. Epub 2012 Jan 30. PMID: 22290986; PMCID: PMC3318321. 13: Pons MJ, Mensa L, Gascón J, Ruiz J. Fitness and molecular mechanisms of resistance to rifaximin in in vitro selected Escherichia coli mutants. Microb Drug Resist. 2012 Aug;18(4):376-9. doi: 10.1089/mdr.2011.0010. Epub 2011 Jun 28. PMID: 21711150. 14: Luo L, Jiang X, Wu Q, Wei L, Li J, Ying C. Efflux pump overexpression in conjunction with alternation of outer membrane protein may induce Acinetobacter baumannii resistant to imipenem. Chemotherapy. 2011;57(1):77-84. doi: 10.1159/000323620. Epub 2011 Feb 23. PMID: 21346352. 15: Arias A, Seral C, Gude MJ, Castillo FJ. Molecular mechanisms of quinolone resistance in clinical isolates of Aeromonas caviae and Aeromonas veronii bv. sobria. Int Microbiol. 2010 Sep;13(3):135-41. doi: 10.2436/20.1501.01.118. PMID: 20890847. 16: Bohnert JA, Karamian B, Nikaido H. Optimized Nile Red efflux assay of AcrAB- TolC multidrug efflux system shows competition between substrates. Antimicrob Agents Chemother. 2010 Sep;54(9):3770-5. doi: 10.1128/AAC.00620-10. Epub 2010 Jul 6. PMID: 20606071; PMCID: PMC2934970. 17: Daugelavicius R, Buivydas A, Sencilo A, Bamford DH. Assessment of the activity of RND-type multidrug efflux pumps in Pseudomonas aeruginosa using tetraphenylphosphonium ions. Int J Antimicrob Agents. 2010 Sep;36(3):234-8. doi: 10.1016/j.ijantimicag.2010.03.028. Epub 2010 May 21. PMID: 20488669. 18: Vecchione JJ, Alexander B Jr, Sello JK. Two distinct major facilitator superfamily drug efflux pumps mediate chloramphenicol resistance in Streptomyces coelicolor. Antimicrob Agents Chemother. 2009 Nov;53(11):4673-7. doi: 10.1128/AAC.00853-09. Epub 2009 Aug 17. PMID: 19687245; PMCID: PMC2772354. 19: Kvist M, Hancock V, Klemm P. Inactivation of efflux pumps abolishes bacterial biofilm formation. Appl Environ Microbiol. 2008 Dec;74(23):7376-82. doi: 10.1128/AEM.01310-08. Epub 2008 Oct 3. PMID: 18836028; PMCID: PMC2592912. 20: Nikravesh A, Dryselius R, Faridani OR, Goh S, Sadeghizadeh M, Behmanesh M, Ganyu A, Klok EJ, Zain R, Good L. Antisense PNA accumulates in Escherichia coli and mediates a long post-antibiotic effect. Mol Ther. 2007 Aug;15(8):1537-42. doi: 10.1038/sj.mt.6300209. Epub 2007 May 29. PMID: 17534267.

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