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atosiban

Structure via PubChem · Public domain (PubChem)

EntityQ421322· pop 14· linked from 85 articles

atosiban

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Atosiban, sold under the brand name Tractocile among others, is an inhibitor of the hormones oxytocin and vasopressin. It is used as an intravenous medication as a labour repressant (tocolytic) to halt premature labor. It was developed by Ferring Pharmaceuticals in Sweden and first reported in the literature in 1985. Originally marketed by Ferring Pharmaceuticals, it is licensed in proprietary and generic forms for the delay of imminent preterm birth in pregnant adult women.

Key facts

Drug.Verifiedfields
changed
Drug.Watchedfields
changed
Drug.verifiedrevid
457801156
Drug.image
Atosiban SW.svg
Drug.image_class
skin-invert-image
Drug.width
275
Drug.tradename
Tractocile, Antocin, others
Drug.licence_EU
yes
Drug.routes_of_administration
Intravenous
Drug.ATC_prefix
G02
Drug.ATC_suffix
CX01
Drug.legal_AU
S4
Drug.legal_UK
POM
Drug.legal_EU
Rx-only
Drug.legal_status
Rx-only
Drug.CAS_number
90779-69-4
Drug.PubChem
5311010
Drug.IUPHAR_ligand
2213

via Wikipedia infobox

Chemical data

Formula
C43H67N11O12S2
Molecular weight
994.2 g/mol
IUPAC name
(2S)-N-[(2S)-5-amino-1-[(2-amino-2-oxoethyl)amino]-1-oxopentan-2-yl]-1-[(4R,7S,10S,13S,16R)-7-(2-amino-2-oxoethyl)-13-[(2S)-butan-2-yl]-16-[(4-ethoxyphenyl)methyl]-10-[(1R)-1-hydroxyethyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]pyrrolidine-2-carboxamide
SMILES
CC[C@H](C)[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CSSCCC(=O)N[C@@H](C(=O)N1)CC2=CC=C(C=C2)OCC)C(=O)N3CCC[C@H]3C(=O)N[C@@H](CCCN)C(=O)NCC(=O)N)CC(=O)N)[C@@H](C)O
InChIKey
VWXRQYYUEIYXCZ-OBIMUBPZSA-N
XLogP
-1.9
Polar surface area
416 Ų
H-bond donors
11
H-bond acceptors
15
Formal charge
0

via PubChem

Drug data · ChEMBL

Max clinical phase
Approved
Molecule type
Protein
First approval
2000
Admin. routes
parenteral
Indications
premature birth, endometriosis

via ChEMBL · EBI

Research

643 papers

via PubMed

Wikidata facts

Mass
993.441209
Has use
medication
Show 6 more facts
chemical formula
C₄₃H₆₇N₁₁O₁₂S₂
Commons category
Atosiban
subject has role
tocolytic uterine relaxants
isomeric SMILES
CC[C@H](C)[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CSSCCC(=O)N[C@@H](C(=O)N1)CC2=CC=C(C=C2)OCC)C(=O)N3CCC[C@H]3C(=O)N[C@@H](CCCN)C(=O)NCC(=O)N)CC(=O)N)[C@@H](C)O
defined daily dose
165
canonical SMILES
CCOc1ccc(CC2NC(=O)CCSSCC(C(=O)N3CCCC3C(=O)NC(CCCN)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(C(C)O)NC(=O)C(C(C)CC)NC2=O)cc1
Sources (2)

via Wikidata · CC0

~7 min read

Encyclopedic overview

13 sections
Contents
  • Medical uses
  • Pharmacology
  • Mechanism of action
  • Other uses
  • Atosiban use after assisted reproduction
  • Pharmacovigilance
  • Regulatory affairs
  • Systematic reviews
  • Clinical trials
  • Atosiban vs. nifedipine
  • Atosiban vs. ritodrine
  • References
  • External links

Atosiban, sold under the brand name Tractocile among others, is an inhibitor of the hormones oxytocin and vasopressin. It is used as an intravenous medication as a labour repressant (tocolytic) to halt premature labor. It was developed by Ferring Pharmaceuticals in Sweden and first reported in the literature in 1985. Originally marketed by Ferring Pharmaceuticals, it is licensed in proprietary and generic forms for the delay of imminent preterm birth in pregnant adult women.

The most commonly reported side effect is nausea.

Excerpted from Wikipedia’s “atosiban” article, available under the CC BY-SA 4.0 licence.

Available in 13 languages

via Wikidata sitelinks · CC0