Synonym
Cipemastat; Trocade; Ro 32-3555; Ro 32 3555; Ro 323555
IUPAC/Chemical Name
(2R,3R)-3-(cyclopentylmethyl)-N-hydroxy-4-oxo-4-(piperidin-1-yl)-2-((3,4,4-trimethyl-2,5-dioxoimidazolidin-1-yl)methyl)butanamide
InChi Key
GFUITADOEPNRML-SJORKVTESA-N
InChi Code
InChI=1S/C22H36N4O5/c1-22(2)20(29)26(21(30)24(22)3)14-17(18(27)23-31)16(13-15-9-5-6-10-15)19(28)25-11-7-4-8-12-25/h15-17,31H,4-14H2,1-3H3,(H,23,27)/t16-,17+/m1/s1
SMILES Code
O=C(N1C[C@H](C(NO)=O)[C@H](C(N2CCCCC2)=O)CC3CCCC3)C(C)(C)N(C)C1=O
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
436.55
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: Ordonez AA, Pokkali S, Sanchez-Bautista J, Klunk MH, Urbanowski ME, Kübler A, Bishai WR, Elkington PT, Jain SK. Matrix Metalloproteinase Inhibition in a Murine Model of Cavitary Tuberculosis Paradoxically Worsens Pathology. J Infect Dis. 2019 Jan 29;219(4):633-636. doi: 10.1093/infdis/jiy373. PMID: 29920600; PMCID: PMC6601699.
2: Urbanowski ME, Ihms EA, Bigelow K, Kübler A, Elkington PT, Bishai WR. Repetitive Aerosol Exposure Promotes Cavitary Tuberculosis and Enables Screening for Targeted Inhibitors of Extensive Lung Destruction. J Infect Dis. 2018 Jun 5;218(1):53-63. doi: 10.1093/infdis/jiy127. PMID: 29554286; PMCID: PMC5989619.
3: Jayatilaka H, Umanzor FG, Shah V, Meirson T, Russo G, Starich B, Tyle P, Lee JSH, Khatau S, Gil-Henn H, Wirtz D. Tumor cell density regulates matrix metalloproteinases for enhanced migration. Oncotarget. 2018 Aug 24;9(66):32556-32569. doi: 10.18632/oncotarget.25863. PMID: 30220965; PMCID: PMC6135685.
4: Liechti FD, Grandgirard D, Leppert D, Leib SL. Matrix metalloproteinase inhibition lowers mortality and brain injury in experimental pneumococcal meningitis. Infect Immun. 2014 Apr;82(4):1710-8. doi: 10.1128/IAI.00073-14. Epub 2014 Feb 3. Erratum in: Infect Immun. 2014 Oct;82(10):4435. PMID: 24491581; PMCID: PMC3993388.
5: Yin Z, Sada AA, Reslan OM, Narula N, Khalil RA. Increased MMPs expression and decreased contraction in the rat myometrium during pregnancy and in response to prolonged stretch and sex hormones. Am J Physiol Endocrinol Metab. 2012 Jul 1;303(1):E55-70. doi: 10.1152/ajpendo.00553.2011. Epub 2012 Apr 10. PMID: 22496348; PMCID: PMC3404560.