Antipain

Source: Wikipedia, the free encyclopedia.
This article is about the protease inhbitor. For the article about pain relief, see analgesic.
Antipain
Names
IUPAC name
N2-{[(1S)-1-carboxy-2-phenylethyl]carbamoyl}-N5-(diaminomethylidene)-L-ornithyl-N-{(2S)-5-[(diaminomethylidene)amino]-1-oxopentan-2-yl}-L-valinamide
Identifiers
3D model (
JSmol
)
ChemSpider
UNII
  • InChI=1S/C27H44N10O6/c1-16(2)21(23(40)34-18(15-38)10-6-12-32-25(28)29)37-22(39)19(11-7-13-33-26(30)31)35-27(43)36-20(24(41)42)14-17-8-4-3-5-9-17/h3-5,8-9,15-16,18-21H,6-7,10-14H2,1-2H3,(H,34,40)(H,37,39)(H,41,42)(H4,28,29,32)(H4,30,31,33)(H2,35,36,43)/t18-,19-,20-,21-/m0/s1 checkY
    Key: SDNYTAYICBFYFH-TUFLPTIASA-N checkY
  • InChI=1/C27H44N10O6/c1-16(2)21(23(40)34-18(15-38)10-6-12-32-25(28)29)37-22(39)19(11-7-13-33-26(30)31)35-27(43)36-20(24(41)42)14-17-8-4-3-5-9-17/h3-5,8-9,15-16,18-21H,6-7,10-14H2,1-2H3,(H,34,40)(H,37,39)(H,41,42)(H4,28,29,32)(H4,30,31,33)(H2,35,36,43)/t18-,19-,20-,21-/m0/s1
    Key: SDNYTAYICBFYFH-TUFLPTIABE
  • O=C[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)N[C@H](C(=O)O)Cc1ccccc1)CCC/N=C(\N)N)C(C)C)CCC/N=C(\N)N
Properties
C27H44N10O6
Molar mass 604.713 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Antipain is an

ureylene group.[2] Antipain can aid in prevention of coagulation in blood. It is an inhibitor of serine and cysteine proteases.[3]

It has been crystallized in complexes with carboxypeptidase, which is obtained from wheat,[4] and Leishmania major oligopeptidase B.[5] In both cases, the backbone carbonyl of the terminal arginine of antipain forms a covalent bond to the active site serine in the protease.

A study was performed for information on the effect of antipain on the quality of post-thawed ram semen.[6] The results from this experiment concluded that antipain aided in the quality of ram semen by maintaining the sperm mobility.[6] Antipain includes the function to inhibit a degrading enzyme, called plasmin, permitting this substance to be able to improve the resistance of membrane disruption by freezing temperatures.[6]

Antipain Y, a similar chemical compound that is an

analog of antipain, which was isolated from a species of Streptomyces, inhibits the release of neurotransmitters in rat dorsal root ganglion neurons.[7]

References

  1. PMID 4559651
    .
  2. PMID 5052959
    .
  3. ISBN 9780199549351
    .
  4. PMID 8636973
    .
  5. PMID 20926390
    .
  6. ^
    S2CID 51629940
    .
  7. PMID 19911027
    .
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