Atosiban

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Atosiban are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Atosiban?

The molecule Atosiban presents a molecular formula of C43H67N11O12S2 and its IUPAC name is (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.

Atosiban is a synthetic peptide molecule that is used to inhibit the action of oxytocin, a hormone that plays a role in labor and delivery. Atosiban is used to delay or stop preterm labor, which is labor that occurs before the 37th week of pregnancy. Preterm labor can be associated with serious complications for both the mother and the baby, and it is a leading cause of neonatal morbidity and mortality..

Atosiban works by inhibiting the binding of oxytocin to its receptors on the smooth muscle cells of the uterus. This action helps to relax the uterine muscles and reduce contractions, which can delay or stop preterm labor. Atosiban is typically administered intravenously or subcutaneously, and it is usually used in combination with other medications to delay or stop preterm labor..

Atosiban has been shown to be effective in delaying or stopping preterm labor in some patients, but it is not a cure for preterm labor and it does not prevent the recurrence of preterm labor. In addition, atosiban may not be effective in all patients and it may not be suitable for use in certain situations, such as when the cervix is already dilated or when the baby is in distress..

The most common side effects of atosiban include nausea, vomiting, headache, and dizziness. More serious side effects, such as allergic reactions and bleeding, have also been reported. Atosiban should not be used in patients who are allergic to the drug or its components, and it should be used with caution in patients with certain medical conditions, such as liver or kidney disease..

Summary

From all the above, this molecule is a synthetic peptide molecule that is used to inhibit the action of oxytocin and delay or stop preterm labor. It is typically administered intravenously or subcutaneously and is usually used in combination with other medications. Atosiban has been shown to be effective in some patients, but it is not a cure for preterm labor and it may not be suitable for use in all patients. The most common side effects of atosiban include nausea, vomiting, headache, and dizziness, and more serious side effects have also been reported..

3D structure

Cartesian coordinates

Geometry of Atosiban in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Atosiban VWXRQYYUEIYXCZ-OBIMUBPZSA-N chemical compound 2D structure molecule svg
Atosiban

 

Molecule descriptors

 
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
InChI codeInChI=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
InChI KeyVWXRQYYUEIYXCZ-OBIMUBPZSA-N
SMILESCCOc1ccc(C[C@H]2NC(=O)CCSSC[C@@H](C(=O)N3CCC[C@H]3C(=O)N[C@@H](CCCN)C(=O)NCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H]([C@@H](C)CC)NC2=O)cc1

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (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-pentaazacycloicosan-4-yl]carbonyl}pyrrolidin-2-yl]formamido}-N-(carbamoylmethyl)pentanamide
  • (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-(1-hydroxyethyl)-6,9,12,15,18-pentaoxo1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]pyrrolidine-2-carboxamide
  • (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
  • 081D12SI0Z
  • 1-(3-Mercaptopropionic acid)-2-(3-(p-ethoxyphenyl)-D-alanine)-4-L-threonine-8-L-ornithineoxytocin
  • 1-Deamino-2D-tyr-(OEt)-4-thr-8-orn-oxytocin
  • 79A694
  • 90779-69-4
  • A14334
  • Antocile
  • Antocin
  • Antocin II
  • Atosiban
  • Atosibanum
  • BDBM50177595
  • C77085
  • CAP-440
  • CAP-449
  • CAP-476
  • CAP-581
  • CCG-270604
  • ChEMBL_332615
  • DB09059
  • DSSTox_CID_28917
  • DSSTox_GSID_48991
  • DSSTox_RID_83184
  • F-314
  • FT-0652583
  • GLYCINAMIDE, O-ETHYL-N-(3-MERCAPTO-1-OXOPROPYL)-D-TYROSYL-L-ISOLEUCYL-L-THREONYL-L-ASPARAGINYL-L-CYSTEINYL-L-PROLYL-L-ORNITHYL-, CYCLIC (1->5)-DISULFIDE
  • GTPL2213
  • HS-2003
  • NCGC00165718-01
  • NCGC00165718-02
  • ORF 22164
  • ORF22164
  • Orf-22164
  • Oxytocin, 1-(3-mercaptopropanoic acid)-2-(O-ethyl-D-tyrosine)-4-L-threonine-8-L-ornithine-
  • RW-22164
  • RWJ-22164
  • Rwj 22164
  • Tractocile
  • dTVT
  • d[D-Tyr(Et)2,Thr4,Orn8]vasotocin
  • d[D-Tyr(Et)2,Thr4]OVT
  • deTVT
  • tractocil

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC169362009
  • CAS-90779-69-4
  • UNII-081D12SI0Z
  • AKOS015994643
  • DTXSID8048991
  • CHEMBL382301
  • CHEBI:135899
  • Tox21_113474
  • SCHEMBL34316

Physico-Chemical properties

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
Molecular formulaC43H67N11O12S2
Molecular weight994.189
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity274.38
LogP1.4
Topological polar surface area416.3

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.