Arg8-Vasopressin

Vasopressin structure

(Arg8)-Vasopressin

4077849

What is vasopressin?

(Arg8)-Vasopressin or argipressin is an antidiuretic peptide hormone (ADH) that plays a key role in regulating the body’s retention of water by affecting the function of the kidneys, as well as regulating blood pressure and maintaining plasma osmolarity.

The peptide gets released from the posterior pituitary gland and promotes renal tubular reabsorption of water. In high concentration, it also raises blood pressure by inducing moderate vasoconstriction. Additionally, vasopressin is involved in the control of circadian rhythm, thermoregulation, and ACTH release in the brain.

Vasopressin function

Vasopressin mechanism of action

Vasopressin is a G-protein coupled receptor (GPCR) ligand acting on V1A, V1B and V2 receptors.

In the vascular system, vasopressin acts on V1a receptors located on vascular smooth muscle cells. Activation of these receptors leads to vasoconstriction, resulting in an increase in peripheral vascular resistance and blood pressure. This vasoconstrictive effect is particularly important in situations of hypovolemia or low blood volume, where vasopressin helps maintain adequate blood pressure by narrowing blood vessels.

Vasopressin’s action on V2 receptors in the renal collecting ducts is pivotal in regulating water reabsorption. By binding to V2 receptors, vasopressin stimulates the insertion of aquaporin-2 channels into the luminal membrane of collecting duct cells. This process enhances water permeability, facilitating water reabsorption from urine and concentrating the urine. Consequently, the reabsorption of water helps maintain water balance in the body, preventing excessive fluid loss and dehydration.

As an endogenous hormone, vasopressin has a very short half-life, between 16 and 24 minutes.

Vasopressin clinical uses:

Vasopressin has a number of applications, such as:

  • Variceal bleeding – By constricting blood vessels, it reduces blood flow to the bleeding site, helping to control hemorrhage.
  • Vasoconstrictor in local anesthetic injections – The localized vasoconstrictive effort works to enhance the efficacy, precision, and duration of anesthesia. It can also help to prolong the duration of the pain relief and minimize bleeding.
  • Central diabetes insipidus (DI) – Central DI comes from a deficiency of ADH and means the kidneys cannot retain water. Administering exogeneous vasopression (or desmopressin – a synthetic analog), water reabsorption is enhanced.

    How is vasopressin produced?

    Vasopressin is typically produced via solid-phase peptide synthesis (SPPS). The process begins with the attachment of the C-terminal amino acid to a solid resin, followed by iterative coupling and deprotection steps. The protecting groups are selectively removed, and the fully protected peptide is cleaved from the resin.

    Purification is then done via high-performance liquid chromatography (HPLC) to isolate pure vasopressin. The synthesis and subsequent purification processes are subject to stringent quality and regulatory standards due to the medical applications of vasopressin.

    Who manufactures vasopressin?

    There is more to creating generic APIs than simply following a recipe. How you make them makes a difference – the support around the molecule is key.

    Bachem is a leading, innovation-driven company specializing in the development and manufacture of peptides and oligonucleotides. With over 50 years of experience, Bachem has a reputation as a reliable GMP manufacturer and offers a full range of technical and regulatory support.

     

    Bachem is your partner of choice for manufacturing vasopressin API, we:

    • tackle challenges together with you
    • simplify the complex to make it easier for you
    • understand your need for a guaranteed, sustained supply
    • are committed to operating sustainably

    List of impurities and related products:

    Product numberNameSequence
    4012215(Arg⁸)-VasopressinH-Cys-Tyr-Phe-Gln-Asn-Cys-Pro-Arg-Gly-NH₂
    4039551Biotinyl-(Arg⁸)-VasopressinBiotinyl-Cys-Tyr-Phe-Gln-Asn-Cys-Pro-Arg-Gly-NH₂
    4005475(Arg⁸)-Vasopressin (free acid)H-Cys-Tyr-Phe-Gln-Asn-Cys-Pro-Arg-Gly-OH

    Bachem Regulatory Documentation

    DMF

    Vasopressin synonyms

    Argipressin; AVP; Arginine Antidiuretic Hormone; Leiormone

    Vasopressin sequence

    H-Cys-Tyr-Phe-Gln-Asn-Cys-Pro-Arg-Gly-NH₂ (Disulfide bond)

    Molecular Information

    Molecular Formula

    C46H65N15O12S2

    Relative Molecular Mass

    1084.25 g/mol

    CAS-Number

    113-79-1 (net)

    Long-term Storage

    -20 ± 5°C

    In need of a guaranteed, sustained supply of vasopressin API?

    Reach out to our knowledgeable sales representatives today to find out why we are your partner of choice. 

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