Conivaptan

Conivaptan
Clinical data


Trade names	Vaprisol
AHFS/Drugs.com	Monograph
Pregnancy category	US: C (Risk not ruled out)
Routes of administration	intravenous
ATC code	C03XA02 (WHO)
Legal status
Legal status	US: ℞-only
Pharmacokinetic data
Bioavailability	N/A
Identifiers
IUPAC name N-(4-((4,5-dihydro-2-methylimidazo[4,5-d][1]benzazepin- 6(1H)-yl)carbonyl)phenyl)- (1,1'-biphenyl)-2-carboxamide
CAS Number	210101-16-9^Y
PubChem (CID)	151171
IUPHAR/BPS	2203
DrugBank	DB00872^Y
ChemSpider	133239^Y
UNII	0NJ98Y462X^Y
KEGG	D01236^N
ChEBI	CHEBI:681850^Y
ChEMBL	CHEMBL1755^Y
Chemical and physical data
Formula	C₃₂H₂₆N₄O₂
Molar mass	498.583 g/mol
3D model (Jmol)	Interactive image
SMILES O=C(c2ccccc2c1ccccc1)Nc3ccc(cc3)C(=O)N5c6c(c4nc(nc4CC5)C)cccc6
InChI InChI=1S/C32H26N4O2/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)^Y Key:IKENVDNFQMCRTR-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)

Conivaptan (YM 087, brand name Vaprisol) is a non-peptide inhibitor of antidiuretic hormone (vasopressin receptor antagonist). It was approved in 2004 for hyponatremia (low blood sodium levels) caused by syndrome of inappropriate antidiuretic hormone (SIADH), and there is some evidence it may be effective in heart failure. It is marketed by Cumberland Pharmaceuticals, Inc.

Conivaptan inhibits two of the three subtypes of the vasopressin receptor (V1a and V2). Effectively, it causes iatrogenic nephrogenic diabetes insipidus.

Conivaptan has not been approved by the FDA for the treatment of decompensated congestive heart failure. However, in theory, vasopressin receptor antagonism would be particularly useful in this setting, and an initial study shows that it has some promise.^[1]

References

↑ Udelson JE, Smith WB, Hendrix GH, et al. (November 2001). "Acute hemodynamic effects of conivaptan, a dual V(1A) and V(2) vasopressin receptor antagonist, in patients with advanced heart failure". Circulation. 104 (20): 2417–23. doi:10.1161/hc4501.099313. PMID 11705818.

Antihypertensives: diuretics (C03)

Sulfonamides
(and etacrynic acid)

CA inhibitors (at PT)	Acetazolamide

Loop (Na-K-Cl at AL)	Furosemide^# Bumetanide Etacrynic acid Etozolin Muzolimine Ozolinone Piretanide Tienilic acid Torasemide

Thiazides (Na-Cl at DCT, Calcium-sparing)	Altizide Bendroflumethiazide Chlorothiazide Cyclopenthiazide Cyclothiazide Epitizide Hydrochlorothiazide^# Hydroflumethiazide Mebutizide Methyclothiazide Polythiazide Trichlormethiazide

Thiazide-likes (primarily DCT)	Quinethazone Clopamide Chlortalidone Mefruside Clofenamide Metolazone Meticrane Xipamide Indapamide Clorexolone Fenquizone

Potassium-sparing (at CD)

ESC blockers	Amiloride^# Triamterene Benzamil

Aldosterone antagonists	Spirolactones: Spironolactone^# Eplerenone Potassium canrenoate Canrenone Non-steroidal: Finerenone

Osmotic diuretics (PT, DL)

Vasopressin receptor inhibitors
(DCT and CD)

Other

Ethanol, Isopropanol, 2M2B
mercurial diuretics (Chlormerodrin, Mersalyl, Meralluride)
Theobromine
Cicletanine

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Oxytocin and vasopressin receptor modulators

Oxytocin

Agonists: Peptide: Aspartocin
Carbetocin
Cargutocin
Demoxytocin
Lipo-oxytocin-1
Merotocin
Nacartocin
Oxytocin
PF-06478939
PF-06655075 (PF1)
TGOT
Vasotocin (argiprestocin); Non-peptide: TC OT 39
WAY-267464

Antagonists: Peptide: Atosiban
Tocinoic acid; Non-peptide: Barusiban
Epelsiban
Erlosiban
IX-01
L-368,899
L-371,257
L-372,662
Retosiban
SSR-126768
WAY-162720

Vasopressin

V_1A	Agonists: Felypressin Lypressin Ornipressin Selepressin Terlipressin Vasopressin (argipressin) Vasotocin (argiprestocin) Antagonists: Atosiban Conivaptan FR-218944 JNJ-17079166 JNJ-17308616 LY-307174 PF-184563 Relcovaptan RG7314 SRX246 SRX251 TC OT 39 WAY-267464 YM-218 YM-471 YM-35471

V_1B	Agonists: Desmopressin Felypressin Lypressin Ornipressin Terlipressin Vasopressin (argipressin) Vasotocin (argiprestocin) Antagonists: ABT-436 Nelivaptan ORG-52186

V₂	Agonists: Desmopressin Felypressin Lypressin Ornipressin TC OT 39 Terlipressin Vasopressin (argipressin) Vasotocin (argiprestocin) Antagonists: Conivaptan JNJ-17079166 Lixivaptan Mozavaptan RWJ-351647 Satavaptan Tolvaptan YM-471 YM-35471

Unsorted	Antagonists: Ribuvaptan RWJ-339489 VMAX-367 VMAX-372 VMAX-382 YM-222546 Other inhibitors: Demeclocycline Lithium (lithium carbonate)

Others

Carrier proteins: Neurophysin (I, II)

See also: Peptide receptor modulators

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