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Details

Stereochemistry ABSOLUTE
Molecular Formula C28H27Cl2N3O7S
Molecular Weight 620.501
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RELCOVAPTAN

SMILES

COC1=C(OC)C=C(C=C1)S(=O)(=O)N2[C@@H](C(=O)N3CCC[C@H]3C(N)=O)[C@](O)(C4=CC(Cl)=CC=C24)C5=C(Cl)C=CC=C5

InChI

InChIKey=CEBYCSRFKCEUSW-NAYZPBBASA-N
InChI=1S/C28H27Cl2N3O7S/c1-39-23-12-10-17(15-24(23)40-2)41(37,38)33-21-11-9-16(29)14-19(21)28(36,18-6-3-4-7-20(18)30)25(33)27(35)32-13-5-8-22(32)26(31)34/h3-4,6-7,9-12,14-15,22,25,36H,5,8,13H2,1-2H3,(H2,31,34)/t22-,25-,28+/m0/s1

HIDE SMILES / InChI

Description

Relcovaptan is a potent, orally active nonpeptide vasopressin V1a antagonist that was undergoing clinical development with Sanofi-Synthélabo (formerly Sanofi) in France. SR49059 is specifically and selectively antagonizes the effect of vasopressin on the V1a receptor in animals’ and in humans. The drug has been shown to have an excellent safety profile in single and repeated dose toxicological studies in animals. In the human uterus in vitro, SR49059 caused a dose-dependent inhibition of vasopressin V1a receptor-mediated activity of myometrial strips and isolated uterine arteries. In vivo in nonpregnant women, an inhibition of vasopressin-induced uterine activity has been observed.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
13.0 nM [IC50]
178.0 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
25, 75 or 200 mg
Route of Administration: Oral
In Vitro Use Guide
MDCK II cells were seeded on 12 multiwell filters (Costar) at a density of 150,000 cells/cm2 and grown for 3 days. Cells were subsequently treated with the antagonists for 16 h, followed by three washes with ice-cold phosphate-buffered saline containing 1 mM MgCl2 and 0.1 mM CaCl2 (PBS-CM). The cells were then incubated for 1 h on ice with [3H]AVP (PerkinElmer Life Sciences, Boston, MA) and the antagonist (Relcovaptan) diluted in PBS-CM. Cells were washed three times with ice-cold PBS-CM, followed by excision of the filters and counting of the radioactivity