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MedKoo Cat#: 527410 | Name: CPP-115 free base

Description:

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

CPP-115 is a GABA-aminotransferase inhibitor potentially for the treatment of infantile spasms and refractory complex partial seizures. CPP-115 is a high-affinity vigabatrin analogue developed to increase therapeutic potency and to limit retinal toxicity.

Chemical Structure

CPP-115 free base
CPP-115 free base
CAS#640897-20-7 (free base)

Theoretical Analysis

MedKoo Cat#: 527410

Name: CPP-115 free base

CAS#: 640897-20-7 (free base)

Chemical Formula: C7H9F2NO2

Exact Mass: 177.0601

Molecular Weight: 177.15

Elemental Analysis: C, 47.46; H, 5.12; F, 21.45; N, 7.91; O, 18.06

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
640897-20-7 (free base) 760947-97-5 (HCl)
Synonym
CPP-115; CPP115; CPP 115
IUPAC/Chemical Name
(1S,3S)-3-amino-4-(difluoromethylene)cyclopentane-1-carboxylic acid
InChi Key
CBSRETZPFOBWNG-UCORVYFPSA-N
InChi Code
InChI=1S/C7H9F2NO2/c8-6(9)4-1-3(7(11)12)2-5(4)10/h3,5H,1-2,10H2,(H,11,12)/t3-,5-/m0/s1
SMILES Code
O=C([C@@H]1C[C@H](N)/C(C1)=C(F)/F)O
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

Preparing Stock Solutions

The following data is based on the product molecular weight 177.15 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: Lee H, Doud EH, Wu R, Sanishvili R, Juncosa JI, Liu D, Kelleher NL, Silverman RB. Mechanism of inactivation of γ-aminobutyric acid aminotransferase by (1S,3S)-3-amino-4-difluoromethylene-1-cyclopentanoic acid (CPP-115). J Am Chem Soc. 2015 Feb 25;137(7):2628-40. doi: 10.1021/ja512299n. PubMed PMID: 25616005; PubMed Central PMCID: PMC4353033. 2: Briggs SW, Mowrey W, Hall CB, Galanopoulou AS. CPP-115, a vigabatrin analogue, decreases spasms in the multiple-hit rat model of infantile spasms. Epilepsia. 2014 Jan;55(1):94-102. doi: 10.1111/epi.12424. PubMed PMID: 24321005; PubMed Central PMCID: PMC4102583. 3: Doumlele K, Conway E, Hedlund J, Tolete P, Devinsky O. A case report on the efficacy of vigabatrin analogue (1S, 3S)-3-amino-4-difluoromethylenyl-1-cyclopentanoic acid (CPP-115) in a patient with infantile spasms. Epilepsy Behav Case Rep. 2016 Aug 21;6:67-9. doi: 10.1016/j.ebcr.2016.08.002. PubMed PMID: 27668180; PubMed Central PMCID: PMC5024311. 4: Pan Y, Gerasimov MR, Kvist T, Wellendorph P, Madsen KK, Pera E, Lee H, Schousboe A, Chebib M, Bräuner-Osborne H, Craft CM, Brodie JD, Schiffer WK, Dewey SL, Miller SR, Silverman RB. (1S, 3S)-3-amino-4-difluoromethylenyl-1-cyclopentanoic acid (CPP-115), a potent γ-aminobutyric acid aminotransferase inactivator for the treatment of cocaine addiction. J Med Chem. 2012 Jan 12;55(1):357-66. doi: 10.1021/jm201231w. PubMed PMID: 22128851; PubMed Central PMCID: PMC3257419. 5: Silverman RB. The 2011 E. B. Hershberg award for important discoveries in medicinally active substances: (1S,3S)-3-amino-4-difluoromethylenyl-1-cyclopentanoic acid (CPP-115), a GABA aminotransferase inactivator and new treatment for drug addiction and infantile spasms. J Med Chem. 2012 Jan 26;55(2):567-75. doi: 10.1021/jm201650r. PubMed PMID: 22168767; PubMed Central PMCID: PMC3266980. 6: Lee H, Le HV, Wu R, Doud E, Sanishvili R, Kellie JF, Compton PD, Pachaiyappan B, Liu D, Kelleher NL, Silverman RB. Mechanism of Inactivation of GABA Aminotransferase by (E)- and (Z)-(1S,3S)-3-Amino-4-fluoromethylenyl-1-cyclopentanoic Acid. ACS Chem Biol. 2015 Sep 18;10(9):2087-98. doi: 10.1021/acschembio.5b00212. PubMed PMID: 26110556; PubMed Central PMCID: PMC4575653. 7: Yuan H, Silverman RB. Structural modifications of (1S,3S)-3-amino-4-difluoromethylenecyclopentanecarboxylic acid, a potent irreversible inhibitor of GABA aminotransferase. Bioorg Med Chem Lett. 2007 Mar 15;17(6):1651-4. PubMed PMID: 17267220; PubMed Central PMCID: PMC1853296. 8: Cid J, Escolar G, Galan A, López-Vilchez I, Molina P, Díaz-Ricart M, Lozano M, Dumont LJ. In vitro evaluation of the hemostatic effectiveness of cryopreserved platelets. Transfusion. 2016 Mar;56(3):580-6. doi: 10.1111/trf.13371. PubMed PMID: 26450525. 9: Buccellati C, Rossoni G, Bonazzi A, Berti F, Maclouf J, Folco G, Sala A. Nitric oxide modulation of transcellular biosynthesis of cys-leukotrienes in rabbit leukocyte-perfused heart. Br J Pharmacol. 1997 Mar;120(6):1128-34. PubMed PMID: 9134226; PubMed Central PMCID: PMC1564560.

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