LYPRESSIN ACETATE

Synonyms. Lypressin Acetate; (8-Lysine)vasopressin; 8-L-Lysine vasopressin; 8-L-Lysinevasopressin; Diapid; L-Cysteinyl-L-tyrosyl-L-phenylalanyl-L-glutaminyl-L-asparaginyl-L-cysteinyl-L-prolyl-L- lysylglycinamide cyclic (1-6)-disulfide; L-Lysine vasopressin; Lipresina; Lipressina; Lypressine; Lypressinum; Lysine pitressin; Lysine vasopressin; Lysine-vasopressin; Pitressin; Postacton; Syntopressin; Vasophysin; Vasopressin- 8-lysine; N-(6-Amino-1-((2-amino-2-oxoethyl)amino)-1-oxohexan- 2-yl)-1 -(16-amino-4- (2-amino-2- oxoethyl)-7- (3-amino-3-oxopropyl)-10-benzyl-13-((4-hydroxyphenyl)methyl)- 3,6,9,12,15- pentaoxo-18, 19-dithia- 2,5,8,11, 14-pentazacycloicosane-1-carbonyl) pyrrolidine-2- carboxamide;

LYPRESSIN

 

PRODUCT IDENTIFICATION

CAS RN

50-57-7

EINECS RN

200-050-5

FORMULA

C46H65N13O12S2

MOLE WEIGHT

1056.22

H.S CODE

 2933.99.9700

SMILES

 N1([C@@H](C(N[C@@H](C(NCC(N)=O)=O)CCCCN)=O) CCC1)C([C @@H]1 NC([C@@H](NC([C@@H](NC([C@@H](Cc2ccccc2)NC ([C@@H](NC( [C@@ H](CSSC1)N)=O) Cc1ccc(O)cc1 )=O)=O)CCC(N)=O)=O)CC(N)=O)=O)=O

CLASSIFICATION

Antidiuretic, Cardiovascular agent, Coagulant, Hematologic, Natriuretic, Vasoconstrictor

EXTRA NOTES

 The porcine antidiuretic hormone (vasopressins). It is a cyclic nonapeptide that differs from arg-vasopressin by one amino acid, containing an lysine at residue 8 instead of an arginine. Lys-vasopressin is used to treat diabetes insipidus or to improve vasomotor tone and blood pressure.

 

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE.

white powder

MELTING POINT

 

BOILING POINT

 

DENSITY

 

SOLUBILITY IN WATER

 

SOLVENT SOLUBILITY  

VAPOR DENSITY

 

log P(octanol-water)

  

VAPOR PRESSURE

  

AUTOIGNITION TEMP

  
pH

 

REFRACTIVE INDEX

 

FLASH POINT

 

 
STABILITY AND REACTIVITY
STABILITY Stable under normal conditions.

INCOMPATIBLE MATERIALS

Strong acids, Strong bases

POLYMERIZATION

Has not been reported

NFPA RATINGS

Health: 2,Flammability:0, Reactivity: 0

 

EXTERNAL LINKS & GENERAL DESCRIPTION

Vasopressin: abbr. VP. This protein is called also Antidiuretic hormone (ADH), Adiuretin, Vasotocin, Pituitrin P and Pitressin. It is a cyclic nonapeptide (1,6 disulfide bridge) synthesized in the hypothalamus and stored in the posterior lobe of the pituitary from which it is released into the circulation as necessary. AVP has been found also in other tissues, including testis, ovary, uterus, adrenal gland, superior cervical ganglion, and thymus (Clements and Funder, 1986).  The term Arginine vasopressin (Arg-Vasopressin, abbr. AVP or ARVP) refers to the presence of an arginine residue at position 8 (which can be occupied also by lysine (Lysine vasopressin, abbr. LVP); residues 3 and 4 have been shown also to be variable. Desmopressin (1-Desamino-8-D-Arginine vasopressin; abbr. DDAVP) is a synthetic analog of arginine vasopressin that is well tolerated after systemic administration. The human vasopressin gene encodes a larger protein product (termed AVP-NpII, arginine-vasopressin-neurophysin II, vasopressin-neurophysin 2-copeptin) (Sausville et al, 1985). Vasopressin is derived from exon 1 of the gene. A protein designated neurophysin or neurophysin-2 (exon 2) functions as a carrier protein (Brownstein et al, 1980). A third glycoprotein, termed copeptin, is encoded by exon 3 (Land et al, 1982; Ivell and Burbach, 1991). Mutations in the Vasopressin gene have been found in rats with hereditary diabetes insipidus (Brattleboro rats). These animals are deficient in synthesis of both arginine vasopressin and one species of neurophysin (Sunde and Sokol, 1975; Schmale et al, 1984). Mutations have been found also in human patients with familial autosomal dominant neurohypophyseal diabetes insipidus (Ito et al, 1997; Rittig et al, 1996). Ito et al (1997) have suggested that the cellular toxicity in familial neurohypophyseal diabetes insipidus may be caused by the intracellular accumulation of mutant precursor proteins. (http://www.copewithcytokines.de/)

Argipressin (also known as ADH -antidiuretic hormone and as AVP - arginine vasopressin): a structural analogue of vasopressin, having arginine at position 8. This is a human hormone and most other mammals. This hormone  is mainly released when the body is low on water.

Lypressin (also known as LVP - lysine vasopressin): a very similar substance with Argipressin, in having lysine instead of arginine. This is the antidiuretic hormone of the pig family.

These hormones are stored in the posterior part of the pituitary gland to be released into the blood stream and into the brain. The synthetic preparations of these hormones are used as antidiuretics to treat central diabetes insipidus when desmopressin is too potent. They are used to improve vasomotor tone and blood pressure.

Terlipressin is an inactive prodrug progressively converted to lypressin in the body. It is not used in the treatment of diabetes insipidus but in that of digestive hemorrhages by rupture of esophageal varices because of its vasoconstrictive effect on the portal circulation. ((http://www.pharmacorama.com/)

Pharmacological Actions

  • Antidiuretic
  • Cardiovascular
  • Coagulant
  • Hematologic
  • Natriuretic
  • Vasoconstrictor

 

SALES SPECIFICATION

APPEARANCE

 white to slightly yellowish powder
IDENTIFICATION

pass (HPLC)

PURITY

98.0% min
AMINO ACID ±10% (theoretical Composition)

RELATED SUBSTANCES

2.0% max (total impurity), 1.0% max (Individual impurity)
PEPTIDE CONTENT
80.0% min (N determination)
ACETATE CONTENT

15.0% max
WATER CONTENT 6.0% max
OPTICAL ROTATION -72.0° ~ -82.0°(c=1, 1% HAc)
BACTERIAL ENDOTOXINS 50EU/mg max

 

TRANSPORT & REGULATORY INFORMATION

UN NO.

Not known

HAZARD CLASS

  
PACKING GROUP  

 

SAFETY INFORMATION

HAZARD OVERVIEW

Target Organ Effect. Target Organs: Kidney, Cardiovascular system., Smooth muscle.

GHS

  

SIGNAL WORD

Warning

PICTOGRAMS

HAZARD STATEMENTS

H332

P STATEMENTS

P201-P308 + P313

EC DIRECTIVES

 

HAZARD CODES

RISK PHRASES

 20

SAFETY PHRASES

 36

 

PACKING