ChemicalBook > CAS DataBase List > (2(S)-[1-(3,5-Dichlorophenylsulfonyl)-L-prolylaMino]-4-[N-Methyl-N-[2-[4-[3-(2-Methylphenyl)ureido]phenyl]acetyl]-L-leucylaMino]butyric acid )

(2(S)-[1-(3,5-Dichlorophenylsulfonyl)-L-prolylaMino]-4-[N-Methyl-N-[2-[4-[3-(2-Methylphenyl)ureido]phenyl]acetyl]-L-leucylaMino]butyric acid )

Product Name
(2(S)-[1-(3,5-Dichlorophenylsulfonyl)-L-prolylaMino]-4-[N-Methyl-N-[2-[4-[3-(2-Methylphenyl)ureido]phenyl]acetyl]-L-leucylaMino]butyric acid )
CAS No.
327613-57-0
Chemical Name
(2(S)-[1-(3,5-Dichlorophenylsulfonyl)-L-prolylaMino]-4-[N-Methyl-N-[2-[4-[3-(2-Methylphenyl)ureido]phenyl]acetyl]-L-leucylaMino]butyric acid )
Synonyms
BIO 5192;AMD 15057;BIO-5192 (BIO5192);(2(S)-[1-(3,5-Dichlorophenylsulfonyl)-L-prolylaMino]-4-[N-Methyl-N-[2-[4-[3-(2-Methylphenyl)ureido]phenyl]acetyl]-L-leucylaMino]butyric acid );(S)-2-((S)-1-((3,5-dichlorophenyl)sulfonyl)pyrrolidine-2-carboxamido)-4-((S)-4-methyl-2-(N-methyl-2-(4-(3-(o-tolyl)ureido)phenyl)acetamido)pentanamido)butanoic acid;(2S)-2-[[[(2S)-1-[(3,5-Dichlorophenyl)sulfonyl]-2-pyrrolidinyl]carbonyl]amino]-4-[[(2S)-4-methyl-2-[methyl[2-[4-[[[(2-methylphenyl)amino]carbonyl]amino]phenyl]acetyl]amino]-1-oxopentyl]amino]butanoic acid;Butanoic acid, 2-[[[(2S)-1-[(3,5-dichlorophenyl)sulfonyl]-2-pyrrolidinyl]carbonyl]amino]-4-[[(2S)-4-methyl-2-[methyl[2-[4-[[[(2-methylphenyl)amino]carbonyl]amino]phenyl]acetyl]amino]-1-oxopentyl]amino]-, (2S)-
CBNumber
CB02641205
Molecular Formula
C38H46Cl2N6O8S
Formula Weight
817.78
MOL File
327613-57-0.mol
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(2(S)-[1-(3,5-Dichlorophenylsulfonyl)-L-prolylaMino]-4-[N-Methyl-N-[2-[4-[3-(2-Methylphenyl)ureido]phenyl]acetyl]-L-leucylaMino]butyric acid ) Property

Melting point:
134 - 136°C
Density 
1.380±0.06 g/cm3(Predicted)
storage temp. 
Hygroscopic, -20°C Freezer, Under inert atmosphere
solubility 
DMSO (Slightly)
form 
Solid
pka
3.52±0.10(Predicted)
color 
White to Off-White
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Tocris
Product number
5051
Product name
BIO5192
Purity
≥98%(HPLC)
Packaging
10
Price
$293
Updated
2021/12/16
Tocris
Product number
5051
Product name
BIO5192
Purity
≥98%(HPLC)
Packaging
50
Price
$1195
Updated
2021/12/16
Usbiological
Product number
254770
Product name
BIO 5192
Packaging
10mg
Price
$559
Updated
2021/12/16
TRC
Product number
B591713
Product name
BIO5192
Packaging
1mg
Price
$120
Updated
2021/12/16
TRC
Product number
B591713
Product name
BIO5192
Packaging
5mg
Price
$180
Updated
2021/12/16
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(2(S)-[1-(3,5-Dichlorophenylsulfonyl)-L-prolylaMino]-4-[N-Methyl-N-[2-[4-[3-(2-Methylphenyl)ureido]phenyl]acetyl]-L-leucylaMino]butyric acid ) Chemical Properties,Usage,Production

Uses

BIO 5192, is selective, potent inhibitor of integrin α4β1 with an IC50 value of 1.8 ± 0.7 nM. α4β1 regulates the migration of lymphocytes into inflamed tissues, and thus BIO 5192 cna act as an antiinflammatory agent.

Biological Activity

bio5192 is a small molecule inhibitor of integrin α4β1 with an ic50 value of 1.8 ± 0.7 nm [1].integrin α4β1 is important in inflammatory processes. in the inflammatory processes, α4β1 regulates the migration of lymphocytes into inflamed tissues [1].in assays using cells expressing α4β7, α9β1, α2β1, and αiibβ3, bio5192 showed high selectivity for α4β1. the affinity of bio5192 for α4β1 was 250- to 1000-fold higher than for α4β7 that shared many ligands the same as α4β1. bio5192 bound even less tightly to α2β1 and αiibβ3. a significant but low level (kd=140 nm) of binding was seen on α9β1 in buffer containing 1 mm mn2+ [1].after 24 h of bio5192 treatment, the lymphocyte count rose about 1.5-fold. half as many cells as when ta-2 was given were released into the circulation following the treatment with bio5192. data showed that bio5192 remained bound to 100% of the α4β1 receptors for 24 h and 50% for 48 h. rats treated with bio5192 at 30 mg/kg, s.c. showed a 1- to 2-day shift when dosed q.d. and a 3-day delay in the onset of disease eae when dosed b.i.d. compared with the control groups. the delay in the onset of eae in the bio5192-treated group was consistent with the finding that bound bio5192 would occupy α4β1 long beyond the point at which the bio5192 was no longer detected in blood [1].

in vivo

The combination of BIO5192 (1 mg/kg; i.v.) and Plerixafor (5 mg/kg; s.c.) exert an additive effect on progenitor mobilization[1].
BIO5192 (30 mg/kg; s.c; bid; during days 5 through 14) delays paralysis associated with EAE (experimental autoimmune encephalomyelitis)[2].
BIO5192 (1 mg/kg, i.v.) shows the terminal half-life is 1.1 hours. BIO5192 (3, 10, and 30 mg/kg; s.c.) shows half-lives of 1.7, 2.7, and 4.7 hours, respectively. The blood plasma curves show that the AUC for the s.c. route of administration increased about 2.5-fold from 5,460 h*ng/ml for the 3 mg/kg dose to 14,175 h*ng/ml for the 30 mg/kg[1].

Animal Model:C57BL/6J x 129Sv/J F1 mice[1]
Dosage:1 mg/kg (with Plerixafor: 5 mg/kg)
Administration:I.v.
Result:Exerted an additive effect on progenitor mobilization.
Animal Model:Healthy female Lewis rats weighing 150g[2]
Dosage:30 mg/kg
Administration:S.c; bid; during days 5 through 14
Result:Showed a 3-day delay in onset of disease.

IC 50

α4β1: 1.8 nM (IC50); α9β1: 138 nM (IC50); α2β1: 1053 nM (IC50); α4β7: >500 nM (IC50)

storage

Store at -20°C

References

[1]. leone dr, giza k, gill a, et al. an assessment of the mechanistic differences between two integrin α4β1 inhibitors, the monoclonal antibody ta-2 and the small molecule bio5192, in rat experimental autoimmune encephalomyelitis[j]. journal of pharmacology and experimental therapeutics, 2003, 305(3): 1150-1162.

(2(S)-[1-(3,5-Dichlorophenylsulfonyl)-L-prolylaMino]-4-[N-Methyl-N-[2-[4-[3-(2-Methylphenyl)ureido]phenyl]acetyl]-L-leucylaMino]butyric acid ) Preparation Products And Raw materials

Raw materials

Preparation Products

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(2(S)-[1-(3,5-Dichlorophenylsulfonyl)-L-prolylaMino]-4-[N-Methyl-N-[2-[4-[3-(2-Methylphenyl)ureido]phenyl]acetyl]-L-leucylaMino]butyric acid ) Suppliers

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327613-57-0, (2(S)-[1-(3,5-Dichlorophenylsulfonyl)-L-prolylaMino]-4-[N-Methyl-N-[2-[4-[3-(2-Methylphenyl)ureido]phenyl]acetyl]-L-leucylaMino]butyric acid )Related Search:


  • (2(S)-[1-(3,5-Dichlorophenylsulfonyl)-L-prolylaMino]-4-[N-Methyl-N-[2-[4-[3-(2-Methylphenyl)ureido]phenyl]acetyl]-L-leucylaMino]butyric acid )
  • (2S)-2-[[[(2S)-1-[(3,5-Dichlorophenyl)sulfonyl]-2-pyrrolidinyl]carbonyl]amino]-4-[[(2S)-4-methyl-2-[methyl[2-[4-[[[(2-methylphenyl)amino]carbonyl]amino]phenyl]acetyl]amino]-1-oxopentyl]amino]butanoic acid
  • AMD 15057
  • BIO 5192
  • BIO-5192 (BIO5192)
  • Butanoic acid, 2-[[[(2S)-1-[(3,5-dichlorophenyl)sulfonyl]-2-pyrrolidinyl]carbonyl]amino]-4-[[(2S)-4-methyl-2-[methyl[2-[4-[[[(2-methylphenyl)amino]carbonyl]amino]phenyl]acetyl]amino]-1-oxopentyl]amino]-, (2S)-
  • (S)-2-((S)-1-((3,5-dichlorophenyl)sulfonyl)pyrrolidine-2-carboxamido)-4-((S)-4-methyl-2-(N-methyl-2-(4-(3-(o-tolyl)ureido)phenyl)acetamido)pentanamido)butanoic acid
  • 327613-57-0
  • C38H46Cl2N6O8S