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MedKoo Cat#: 326895 | Name: Selfotel
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Description:

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

Selfotel, also known as CGS-19755 and CPDD 0027, is a competitive NMDA antagonist. Selfotel directly competes with glutamate for binding to the receptor. Initial studies showed it to have anticonvulsant, anxiolytic, analgesic and neuroprotective effects, and it was originally researched for the treatment of stroke, but subsequent animal and human studies showed phencyclidine-like effects, as well as limited efficacy and evidence for possible neurotoxicity under some conditions, and so clinical development was ultimately discontinued.

Chemical Structure

Selfotel
CAS#110347-85-8

Theoretical Analysis

MedKoo Cat#: 326895

Name: Selfotel

CAS#: 110347-85-8

Chemical Formula: C7H14NO5P

Exact Mass: 223.0610

Molecular Weight: 223.16

Elemental Analysis: C, 37.67; H, 6.32; N, 6.28; O, 35.85; P, 13.88

Price and Availability

Size Price Availability Quantity
10mg USD 450.00
20mg USD 750.00
50mg USD 1,500.00
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Related CAS #
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Synonym
CGS-19755; CGS 19755; CGS19755; CPDD 0027; CPDD-0027; CPDD0027; Selfotel
IUPAC/Chemical Name
(2R,4S)-4-(phosphonomethyl)piperidine-2-carboxylic acid
InChi Key
LPMRCCNDNGONCD-NTSWFWBYSA-N
InChi Code
InChI=1S/C7H14NO5P/c9-7(10)6-3-5(1-2-8-6)4-14(11,12)13/h5-6,8H,1-4H2,(H,9,10)(H2,11,12,13)/t5-,6+/m0/s1
SMILES Code
O=C(O)[C@H]1C[C@@H](CP(O)(O)=O)CCN1
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
Product Data
Product Data
Certificate of Analysis
View CoA: current batch, Lot# T22O01R12
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Biological target:
Selfotel is a selective and competitive antagonist at N-methyl-D-aspartate (NMDA)-preferring receptor. Selfotel inhibits the binding of [3H]-3-(2-carboxypiperazin-4-yl)propyl-1-phosphonic acid to NMDA-type receptors with an IC50 of 50 nM.
In vitro activity:
This study investigated selfotel’s NMDA antagonist activity. Selfotel effectively inhibited NMDA-evoked [3H] acetylcholine release in rat striatum slices, indicating a competitive interaction with NMDA-type receptors. Selfotel inhibited the binding of [3H]-3-(2-carboxypiperazin-4-yl)propyl-1-phosphonic acid to NMDA-type receptors (IC50 = 50 nM). Selfotel exhibited high selectivity, lacking interaction with 23 other receptor types, including excitatory amino acid receptors. Reference: J Pharmacol Exp Ther. 1988 Jul;246(1):65-75. https://pubmed.ncbi.nlm.nih.gov/2899170/
In vivo activity:
Selfotel disrupted recovery following cerebellar lesions. Limb hyperflexion, wide-based locomotion, side falls, tremor, and body tilt were prevalent, indicating a "decompensation" triggered by selfotel. In control rats, selfotel slightly affected postural patterns and significantly worsened motor skills requiring coordination and balance. However, in cerebellectomized and hemicerebellectomized rats, the cerebellar symptomatology dramatically worsened, resembling behaviors immediately post-surgery. Reference: Restor Neurol Neurosci. 2006;24(1):1-7. https://pubmed.ncbi.nlm.nih.gov/16518022/
Solvent mg/mL mM comments
Solubility
Water 5.6 25.00
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 223.16 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
Formulation protocol:
1. Lehmann J, Hutchison AJ, McPherson SE, Mondadori C, Schmutz M, Sinton CM, Tsai C, Murphy DE, Steel DJ, Williams M, et al. CGS 19755, a selective and competitive N-methyl-D-aspartate-type excitatory amino acid receptor antagonist. J Pharmacol Exp Ther. 1988 Jul;246(1):65-75. PMID: 2899170. 2. Federico F, Leggio MG, Mandolesi L, Petrosini L. The NMDA receptor antagonist CGS 19755 disrupts recovery following cerebellar lesions. Restor Neurol Neurosci. 2006;24(1):1-7. PMID: 16518022. 3. Davis SM, Lees KR, Albers GW, Diener HC, Markabi S, Karlsson G, Norris J. Selfotel in acute ischemic stroke : possible neurotoxic effects of an NMDA antagonist. Stroke. 2000 Feb;31(2):347-54. doi: 10.1161/01.str.31.2.347. PMID: 10657404.
In vitro protocol:
1. Lehmann J, Hutchison AJ, McPherson SE, Mondadori C, Schmutz M, Sinton CM, Tsai C, Murphy DE, Steel DJ, Williams M, et al. CGS 19755, a selective and competitive N-methyl-D-aspartate-type excitatory amino acid receptor antagonist. J Pharmacol Exp Ther. 1988 Jul;246(1):65-75. PMID: 2899170.
In vivo protocol:
1. Federico F, Leggio MG, Mandolesi L, Petrosini L. The NMDA receptor antagonist CGS 19755 disrupts recovery following cerebellar lesions. Restor Neurol Neurosci. 2006;24(1):1-7. PMID: 16518022. 2. Davis SM, Lees KR, Albers GW, Diener HC, Markabi S, Karlsson G, Norris J. Selfotel in acute ischemic stroke : possible neurotoxic effects of an NMDA antagonist. Stroke. 2000 Feb;31(2):347-54. doi: 10.1161/01.str.31.2.347. PMID: 10657404.
1: Dziuganowska ZA, Ślepokura K, Volle JN, Virieux D, Pirat JL, Kafarski P. Structural Analogues of Selfotel. J Org Chem. 2016 Jun 17;81(12):4947-54. doi: 10.1021/acs.joc.6b00220. Epub 2016 Jun 1. PubMed PMID: 27187758. 2: Davis SM, Lees KR, Albers GW, Diener HC, Markabi S, Karlsson G, Norris J. Selfotel in acute ischemic stroke : possible neurotoxic effects of an NMDA antagonist. Stroke. 2000 Feb;31(2):347-54. PubMed PMID: 10657404. 3: Juul N, Morris GF, Marshall SB, Marshall LF. Intracranial hypertension and cerebral perfusion pressure: influence on neurological deterioration and outcome in severe head injury. The Executive Committee of the International Selfotel Trial. J Neurosurg. 2000 Jan;92(1):1-6. PubMed PMID: 10616075. 4: Morris GF, Bullock R, Marshall SB, Marmarou A, Maas A, Marshall LF. Failure of the competitive N-methyl-D-aspartate antagonist Selfotel (CGS 19755) in the treatment of severe head injury: results of two phase III clinical trials. The Selfotel Investigators. J Neurosurg. 1999 Nov;91(5):737-43. PubMed PMID: 10541229. 5: Ananda A, Morris GF, Juul N, Marshall SB, Marshall LF. The frequency, antecedent events, and causal relationships of neurologic worsening following severe head injury. Executive Committee of the international Selfotel Trial. Acta Neurochir Suppl. 1999;73:99-102. PubMed PMID: 10494350. 6: Morris GF, Juul N, Marshall SB, Benedict B, Marshall LF. Neurological deterioration as a potential alternative endpoint in human clinical trials of experimental pharmacological agents for treatment of severe traumatic brain injuries. Executive Committee of the International Selfotel Trial. Neurosurgery. 1998 Dec;43(6):1369-72; discussion 1372-4. PubMed PMID: 9848851. 7: Yenari MA, Bell TE, Kotake AN, Powell M, Steinberg GK. Dose escalation safety and tolerance study of the competitive NMDA antagonist selfotel (CGS 19755) in neurosurgery patients. Clin Neuropharmacol. 1998 Jan-Feb;21(1):28-34. PubMed PMID: 9579282. 8: Knoche B, Milosavljev S, Gropper S, Brunner LA, Powell ML. Enantioselective determination of selfotel in human urine by high-performance liquid chromatography on a chiral stationary phase after derivatization with 9-fluorenylmethyl chloroformate. J Chromatogr B Biomed Sci Appl. 1997 Aug 1;695(2):355-63. PubMed PMID: 9300872. 9: Davis SM, Albers GW, Diener HC, Lees KR, Norris J. Termination of Acute Stroke Studies Involving Selfotel Treatment. ASSIST Steering Committed. Lancet. 1997 Jan 4;349(9044):32. PubMed PMID: 8999265. 10: Pérez-Pinzón MA, Steinberg GK. CGS 19755 (Selfotel): A Novel Neuroprotective Agent Against CNS Injury. CNS Drug Rev. 1996 Sep 1;2(3):257-268. PubMed PMID: 23766625; PubMed Central PMCID: PMC3678965. 11: Grotta J, Clark W, Coull B, Pettigrew LC, Mackay B, Goldstein LB, Meissner I, Murphy D, LaRue L. Safety and tolerability of the glutamate antagonist CGS 19755 (Selfotel) in patients with acute ischemic stroke. Results of a phase IIa randomized trial. Stroke. 1995 Apr;26(4):602-5. PubMed PMID: 7709405.

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