PIMELAUTIDE

Details

Stereochemistry	MIXED
Molecular Formula	C29H52N6O9
Molecular Weight	628.758
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 4
E/Z Centers	0
Charge	0
Stereo Comments	DL-LYSINE; THREO CARBAMOYL

SHOW SMILES / InChI

Structure Search

SMILES

CCCCCCCCCCCC(=O)N[C@@H](C)C(=O)N[C@H](CCC(=O)NC(CCCC(NC(=O)CN)C(N)=O)C(O)=O)C(O)=O

InChI

InChIKey=BGGBQBAMDUCKFN-ZGJBTBESSA-N

InChI=1S/C29H52N6O9/c1-3-4-5-6-7-8-9-10-11-15-23(36)32-19(2)27(40)35-22(29(43)44)16-17-24(37)34-21(28(41)42)14-12-13-20(26(31)39)33-25(38)18-30/h19-22H,3-18,30H2,1-2H3,(H2,31,39)(H,32,36)(H,33,38)(H,34,37)(H,35,40)(H,41,42)(H,43,44)/t19-,20?,21?,22+/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2776860 | https://www.ncbi.nlm.nih.gov/pubmed/3791952 | Elks, J. (2014) The Dictionary of Drugs: Chemical Data, page 981, retrieved from: https://books.google.ru/books?id=0vXTBwAAQBAJ

Pimelautide is the immunomodulating lipopeptides lauroyl-L-Ala-gamma-D-Glu-LL-A2pmNH2-Gly. Pimelautide is an immunostimulant active on macrophages, polymorphonuclear leukocytes, T-lymphocytes, and NK cells, which in mice enhances delayed type hypersensitivity reactions, antibody production and resistance to bacterial infections. It was found to protect mice against the hepatotoxicity of paracetamol, which is due to cytochrome P-450 dependent formation of toxic metabolites and radicals. It decreased the amount of hepatic microsomal cytochrome P-450, and the level of CCl4-induced lipid peroxidation.

Approval Year

PubMed

Title	Date	PubMed
Pimelautide or trimexautide as built-in adjuvants associated with an HIV-1-derived peptide: synthesis and in vivo induction of antibody and virus-specific cytotoxic T-lymphocyte-mediated response.	1995-02-03	7853339
In vivo effects of immunostimulating lipopeptides on mouse liver microsomal cytochromes P-450 and on paracetamol-induced toxicity.	1989-09-15	2776860
Synthetic immunostimulants (excluding sulfur-containing compounds).	1986	3791952

Name

Type

Language

THREO-6-CARBAMOYL-N(SUP 2)-(N-(N-LAUROYL-L-ALANYL)-D-.GAMMA.-GLUTAMYL)-N(SUP 6)-GLYCYL-DL-LYSINE

Preferred Name

English

PIMELAUTIDE

Official Name

English

pimelautide [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C308