Conivaptan hydrochloride Chemical Properties

Melting point:

>250°

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

color 

White to Off-White

InChI

InChI=1S/C32H26N4O2.ClH/c1-21-33-28-19-20-36(29-14-8-7-13-27(29)30(28)34-21)32(38)23-15-17-24(18-16-23)35-31(37)26-12-6-5-11-25(26)22-9-3-2-4-10-22;/h2-18H,19-20H2,1H3,(H,33,34)(H,35,37);1H

InChIKey

BTYHAFSDANBVMJ-UHFFFAOYSA-N

SMILES

C12=CC=CC=C1N(CCC1N=C(C)NC2=1)C(=O)C1=CC=C(NC(=O)C2C=CC=CC=2C2=CC=CC=C2)C=C1.Cl

Conivaptan hydrochloride Usage And Synthesis

Description

Arginine vasopressin is intimately involved in volume homeostasis, and elevated levels of arginine vasopressin are responsible for the pathogenesis and progression of diseases with an imbalance of sodium and water, particularly congestive heart failure. To restore homeostasis, antagonism of vasopressin receptors is a practical solution. As such, conivaptan has been developed and launched as a dual V1a and V2 vasopressin receptor antagonist. As a competitive, reversible inhibitor of both subtypes, conivaptan can modulate systemic vascular resistance through the V1a receptor (Ki ? 0.48 nM) distributed in vascular smooth muscle cells, cardiomyocytes, hepatocytes, and platelets and blocks the renal V2 receptor (Ki ? 3.04 nM) resulting in enhanced diuresis, thereby increasing serum sodium concentration and reducing total body volume. Currently, the drug is approved for the management of refractory hyponatremia and potentially lifethreatening sodium and water imbalance, but it has shown promise as a potential treatment option for other diseases, such as congestive heart failure, syndrome of antidiuretic hormone, diabetes insipidus, and liver cirrhosis.

Description

Conivaptan is an antagonist of the arginine vasopressin (AVP) receptors V_1A and V₂ (K_is = 0.48 and 3.04 nM for rat liver V_1A and kidney V₂, respectively). It also competitively inhibits oxytocin binding to rat uterine oxytocin receptors (K_i = 44 nM) but has no effect on AVP binding to anterior pituitary V_1B receptors at concentrations up to 100 μM in a radioligand binding assay. Conivaptan suppresses AVP-induced increases in intracellular calcium in vascular smooth muscle cells (VSMCs) in vitro and the pressor response in pithed rats. Conivaptan (0.01-0.3 mg/kg, i.v.) increases urine output and decreases urine osmolality in dehydrated conscious rats in a dose-dependent manner. It also reduces brain edema and blood-brain barrier disruption in a mouse experimental stroke model.

Chemical Properties

White to Off-White Solid

Originator

Yamanouchi (Japan)

Uses

Used in treatment of congestive heart failure.

Uses

Conivaptan is a non-peptide inhibitor of antidiuretic hormone (vasopressin receptor antagonist).

Definition

ChEBI: The hydrochloride salt of conivaptan. It is an antagonist for two of the three types of arginine vasopressin (AVP) receptors, V1a and V2, and is used for the treatment of hyponatraemia (low blood sodium levels) cau ed by syndrome of inappropriate antidiuretic hormone (SIADH).

brand name

Vaprisol (Astellas).

storage

Desiccate at RT

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