Atosiban acetateProduct ingredient for Atosiban

Name
Atosiban acetate
Drug Entry
Atosiban

Atosiban is an inhibitor of the hormones oxytocin and vasopressin. It is used intravenously to halt premature labor. Although initial studies suggested it could be used as a nasal spray and hence would not require hospital admission, it is not used in that form. Atobisan was developed by the Swedish company Ferring Pharmaceuticals. It was first reported in the literature in 1985. Atosiban is licensed in proprietary and generic forms for the delay of imminent pre-term birth in pregnant adult women.

Accession Number
DBSALT002637
Structure
Synonyms
Not Available
UNII
0P5DNO7CEF
CAS Number
914453-95-5
Weight
Average: 1054.25
Monoisotopic: 1053.462338358
Chemical Formula
C45H71N11O14S2
InChI Key
SVDWBHHCPXTODI-QIWYXCRTSA-N
InChI
InChI=1S/C43H67N11O12S2.C2H4O2/c1-5-23(3)35-41(63)53-36(24(4)55)42(64)50-29(20-32(45)56)38(60)51-30(43(65)54-17-8-10-31(54)40(62)49-27(9-7-16-44)37(59)47-21-33(46)57)22-68-67-18-15-34(58)48-28(39(61)52-35)19-25-11-13-26(14-12-25)66-6-2;1-2(3)4/h11-14,23-24,27-31,35-36,55H,5-10,15-22,44H2,1-4H3,(H2,45,56)(H2,46,57)(H,47,59)(H,48,58)(H,49,62)(H,50,64)(H,51,60)(H,52,61)(H,53,63);1H3,(H,3,4)/t23-,24+,27-,28+,29-,30-,31-,35-,36-;/m0./s1
IUPAC Name
(2S)-5-amino-2-{[(2S)-1-[(4R,7S,10S,13S,16R)-13-[(2S)-butan-2-yl]-7-(carbamoylmethyl)-16-[(4-ethoxyphenyl)methyl]-10-[(1R)-1-hydroxyethyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carbonyl]pyrrolidin-2-yl]formamido}-N-(carbamoylmethyl)pentanamide; acetic acid
SMILES
CC(O)=O.[H][C@]1(NC(=O)[C@@]([H])(NC(=O)[C@@H](CC2=CC=C(OCC)C=C2)NC(=O)CCSSC[C@H](NC(=O)[C@H](CC(N)=O)NC1=O)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCN)C(=O)NCC(N)=O)[C@@H](C)CC)[C@@H](C)O
KEGG Drug
D07475
ChemSpider
24603109
Predicted Properties
PropertyValueSource
Water Solubility0.0517 mg/mLALOGPS
logP-0.17ALOGPS
logP-4.6ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)11.28ChemAxon
pKa (Strongest Basic)9.59ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area365.67 Å2ChemAxon
Rotatable Bond Count18ChemAxon
Refractivity250.62 m3·mol-1ChemAxon
Polarizability101.5 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon