Details of the Drug

General Information of Drug (ID: DMB7WYM)

Drug Name
ATOSIBAN
Synonyms
Atosiban; Tractocile; 90779-69-4; Atosiban acetate; Antocin; UNII-081D12SI0Z; Rwj 22164; Orf-22164; RWJ-22164; CHEMBL382301; 1-Deamino-2D-tyr-(OEt)-4-thr-8-orn-oxytocin; dTVT; 081D12SI0Z; 1-Deamino-2-D-Tyr-(O-ethyl)-4-Thr-8-ornoxytocin; 1-(3-Mercaptopropanoic acid)-2-(O-ethyl-D-tyrosine)-4-L-threonine-8-L-ornithineoxytocin; NCGC00165718-01; Atosibanum [INN-Latin]; ORF 22164; deTVT; Atosibanum; Antocin II; Atosiban [USAN:INN:BAN]; RWJ22164; 1-(3-Mercaptopropionic acid)-2-(3-(p-ethoxyphenyl)-D-alanine)-4-L-threonine-8-L-ornithineox
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 4 Molecular Weight (mw) 994.2
Topological Polar Surface Area (xlogp) -1.9
Rotatable Bond Count (rotbonds) 18
Hydrogen Bond Donor Count (hbonddonor) 11
Hydrogen Bond Acceptor Count (hbondacc) 15
ADMET Property
Clearance
The clearance of drug is 41.8 L/h [1]
Half-life
The concentration or amount of drug in body reduced by one-half in 0.21 hours (alpha), and 1.7 hours (beta) [1]
Metabolism
The drug is metabolized via prior cleavage of the disulfide bridge [1]
Vd
The volume of distribution (Vd) of drug is 41.8 L [1]
Chemical Identifiers
Formula
C43H67N11O12S2
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
Canonical 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
InChI
InChI=1S/C43H67N11O12S2/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/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)/t23-,24+,27-,28+,29-,30-,31-,35-,36-/m0/s1
InChIKey
VWXRQYYUEIYXCZ-OBIMUBPZSA-N
Cross-matching ID
PubChem CID
5311010
ChEBI ID
CHEBI:135899
CAS Number
90779-69-4
DrugBank ID
DB09059
TTD ID
D0D8XY

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Oxytocin receptor (OTR) TTSCIUP OXYR_HUMAN Inhibitor [2]
Vasopressin V1a receptor (V1AR) TT4TFGN V1AR_HUMAN Inhibitor [3]
Vasopressin V1b receptor (V1BR) TTL9MHW V1BR_HUMAN Inhibitor [3]
Vasopressin V2 receptor (V2R) TTK8R02 V2R_HUMAN Inhibitor [3]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Vasopressin V1b receptor (V1BR) DTT AVPR1B 5.14E-01 -0.03 -0.15
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 EMA: Tractocile Product Information
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12 Antibody-mediated disruption of the interaction between PCSK9 and the low-density lipoprotein receptor. Biochem J. 2009 May 1;419(3):577-84.
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16 Post-translational import of protein into the endoplasmic reticulum of a trypanosome: an in vitro system for discovery of anti-trypanosomal chemical entities. Biochem J. 2009 Apr 15;419(2):507-17.
17 Tetrahydroquinoline sulfonamides as vasopressin 1b receptor antagonists. Bioorg Med Chem Lett. 2009 Nov 1;19(21):6018-22.
18 Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800030285)
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20 Mapping peptide-binding domains of the human V1a vasopressin receptor with a photoactivatable linear peptide antagonist. J Biol Chem. 1997 Oct 17;272(42):26536-44.
21 Peptide and non-peptide agonists and antagonists for the vasopressin and oxytocin V1a, V1b, V2 and OT receptors: research tools and potential therapeutic agents. Prog Brain Res. 2008;170:473-512.
22 Investigational vasopressin receptor modulators in the pipeline. Expert Opin Investig Drugs. 2009 Aug;18(8):1119-31.
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28 The effect of barusiban, a selective oxytocin antagonist, in threatened preterm labor at late gestational age: a randomized, double-blind, placebo-controlled trial. Am J Obstet Gynecol. 2009 Jun;200(6):627.e1-10.
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