Structure via PubChem · Public domain (PubChem)
nesiritide
Sign in to saveNesiritide, sold under the brand name Natrecor, is the recombinant form of the 32 amino acid human B-type natriuretic peptide, which is normally produced by the ventricular myocardium. Nesiritide works to facilitate cardiovascular fluid homeostasis through counterregulation of the renin–angiotensin–aldosterone system, stimulating cyclic guanosine monophosphate, leading to smooth muscle cell relaxation.
Chemical data
- Formula
- C143H244N50O42S4
- Molecular weight
- 3464 g/mol
- IUPAC name
- (2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[(4R,10S,16S,19S,22S,25R,28S,31S,34S,37S,40S,43S,49R,52R)-52-[[2-[[(2S)-2-[[2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[[(2S)-1-[(2S)-2-amino-3-hydroxypropanoyl]pyrrolidine-2-carbonyl]amino]hexanoyl]amino]-4-methylsulfanylbutanoyl]amino]-3-methylbutanoyl]amino]-5-oxopentanoyl]amino]acetyl]amino]-3-hydroxypropanoyl]amino]acetyl]amino]-40-(4-aminobutyl)-49-benzyl-28-[(2S)-butan-2-yl]-31,43-bis(3-carbamimidamidopropyl)-34-(carboxymethyl)-16,19,22,25-tetrakis(hydroxymethyl)-10-(2-methylpropyl)-37-(2-methylsulfanylethyl)-6,9,12,15,18,21,24,27,30,33,36,39,42,45,48,51-hexadecaoxo-1,2-dithia-5,8,11,14,17,20,23,26,29,32,35,38,41,44,47,50-hexadecazacyclotripentacontane-4-carbonyl]amino]hexanoyl]amino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]-5-carbamimidamidopentanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-(4H-imidazol-4-yl)propanoic acid
- SMILES
- CC[C@H](C)[C@H]1C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)NCC(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@@H](C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)CCCNC(=N)N)CC(=O)O)CCSC)CCCCN)CCCNC(=N)N)CC2=CC=CC=C2)NC(=O)CNC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCCCN)NC(=O)[C@@H]3CCCN3C(=O)[C@H](CO)N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CC4C=NC=N4)C(=O)O)CC(C)C)CO)CO)CO)CO
- InChIKey
- KSFAMFKTRGJQKV-GXSIVEILSA-N
- XLogP
- -17.2
- Polar surface area
- 1610 Ų
- H-bond donors
- 55
- H-bond acceptors
- 55
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Protein
- First approval
- 2001
- Admin. routes
- parenteral
- Indications
- hypertension, heart failure, myocardial infarction, congestive heart failure
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Has use
- medication
Show 5 more facts
- chemical formula
- C₁₄₃H₂₄₄N₅₀O₄₂S₄
- defined daily dose
- 1.5
- NCI Thesaurus ID
- C47636
- permanent duplicated item
- brain natriuretic peptide
- Commons category
- Nesiritide
via Wikidata · CC0
~2 min read
Encyclopedic overview
6 sectionsContents
- Administration
- Controversy
- Side effects
- References
- Further reading
- External links
Nesiritide, sold under the brand name Natrecor, is the recombinant form of the 32 amino acid human B-type natriuretic peptide, which is normally produced by the ventricular myocardium. Nesiritide works to facilitate cardiovascular fluid homeostasis through counterregulation of the renin–angiotensin–aldosterone system, stimulating cyclic guanosine monophosphate, leading to smooth muscle cell relaxation.
Nesiritide was believed initially to be beneficial for acute decompensated congestive heart failure. It received approval from the United States' Food and Drug Administration for this purpose in 2001 after initial non-approval. In July 2011, the results of the largest study so far for nesiritide was published in The New England Journal of Medicine. The study failed to show a difference between nesiritide and placebo on mortality or re-hospitalizations.
Excerpted from Wikipedia’s “nesiritide” article, available under the CC BY-SA 4.0 licence.