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[ CAS No. 65-82-7 ] {[proInfo.proName]}

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Chemical Structure| 65-82-7
Chemical Structure| 65-82-7
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Product Citations

Product Citations

Behymer, Matthew M. ; Mo, Huaping ; Fujii, Naoaki , et al. DOI: PubMed ID:

Abstract: The development of rapidly acting cyanide countermeasures using i.m. injection (IM) represents an unmet medical need to mitigate toxicant exposures in mass casualty settings. Previous work established that cisplatin and other platinum(II) or platinum(IV)-based agents effectively mitigate cyanide toxicity in zebrafish. Cyanide′s in vivo reaction with platinum-containing materials was proposed to reduce the risk of acute toxicities. However, cyanide antidote activity depended on a formulation of platinum-chloride salts with DMSO (DMSO) followed by dilution in phosphate-buffered saline (PBS). A working hypothesis to explain the DMSO requirement is that the formation of platinum-sulfoxide complexes activates the cyanide scavenging properties of platinum. Preparations of isolated NaPtCl5-DMSO and Na (NH3)2PtCl-DMSO complexes in the absence of excess DMSO provided agents with enhanced reactivity toward cyanide in vitro and fully recapitulated in vivo cyanide rescue in zebrafish and mouse models. The enhancement of the cyanide scavenging effects of the DMSO ligand could be attributed to the activation of platinum(IV) and (II) with a sulfur ligand. Unfortunately, the efficacy of DMSO complexes was not robust when administered IM. Alternative Pt(II) materials containing sulfide and amine ligands in bidentate complexes show enhanced reactivity toward cyanide addition The cyanide addition products yielded tetracyanoplatinate(II), translating to a stoichiometry of 1:4 Pt to each cyanide scavenger. These new agents demonstrate a robust and enhanced potency over the DMSO-containing complexes using IM administration in mouse and rabbit models of cyanide toxicity. Using the zebrafish model with these Pt(II) complexes, no acute cardiotoxicity was detected, and dose levels required to reach lethality exceeded 100 times the ED. Data are presented to support a general chem. design approach that can expand a new lead candidate series for developing next-generation cyanide countermeasures.

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Product Details of [ 65-82-7 ]

CAS No. :65-82-7 MDL No. :MFCD00064441
Formula : C7H13NO3S Boiling Point : -
Linear Structure Formula :CH3SC2H4CH(NHCOCH3)CO2H InChI Key :XUYPXLNMDZIRQH-LURJTMIESA-N
M.W : 191.25 Pubchem ID :448580
Synonyms :
N-Acetylmethionine
Chemical Name :Ac-Met-OH

Calculated chemistry of [ 65-82-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.71
Num. rotatable bonds : 6
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 48.13
TPSA : 91.7 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.43 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.32
Log Po/w (XLOGP3) : 0.05
Log Po/w (WLOGP) : 0.33
Log Po/w (MLOGP) : 0.19
Log Po/w (SILICOS-IT) : 0.32
Consensus Log Po/w : 0.44

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -0.66
Solubility : 41.7 mg/ml ; 0.218 mol/l
Class : Very soluble
Log S (Ali) : -1.53
Solubility : 5.66 mg/ml ; 0.0296 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.0
Solubility : 19.1 mg/ml ; 0.1 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.4

Safety of [ 65-82-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 65-82-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 65-82-7 ]

[ 65-82-7 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 67-56-1 ]
  • [ 65-82-7 ]
  • [ 35671-83-1 ]
Reference： [1] Journal of the American Chemical Society, 1958, vol. 80, p. 1465,1468
[2] Journal of the American Chemical Society, 1982, vol. 104, # 6, p. 1612 - 1616
[3] Canadian Journal of Chemistry, 2002, vol. 80, # 6, p. 633 - 639
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A1268183[ 1217457-61-8 ]

N-Acetyl-L-methionine-15N

Reason: Stable Isotope

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