Ombitasvir

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

What is the Ombitasvir?

The molecule Ombitasvir presents a molecular formula of C50H67N7O8 and its IUPAC name is methyl N-[(2S)-1-[(2S)-2-[[4-[(2S,5S)-1-(4-tert-butylphenyl)-5-[4-[[(2S)-1-[(2S)-2-(methoxycarbonylamino)-3-methylbutanoyl]pyrrolidine-2-carbonyl]amino]phenyl]pyrrolidin-2-yl]phenyl]carbamoyl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamate.

Ombitasvir (ABT-267) is a potent NS5A inhibitor with a half-life of approximately 40 hours. It is co-formulated with paritaprevir and ritonavir and is indicated for the treatment of chronic HCV genotype 1 infection in adults..

The safety and efficacy of ombitasvir were evaluated in clinical trials involving 1,339 treatment-naive and treatment-experienced adults with HCV genotype 1 infection. The most common adverse reactions (≥10%) were headache, fatigue, and nausea..

Ombitasvir is a substrate of P-gp and BCRP. Co-administration of ombitasvir with ritonavir (a P-gp inhibitor) and paritaprevir (a BCRP inhibitor) results in increased exposure to ombitasvir..

The recommended dose of ombitasvir is 25 mg (one tablet) taken orally once daily with food. Ombitasvir should be co-administered with paritaprevir/ritonavir and with or without ribavirin..

3D structure

Cartesian coordinates

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

2D drawing

 

Ombitasvir PIDFDZJZLOTZTM-KHVQSSSXSA-N chemical compound 2D structure molecule svg
Ombitasvir

 

Molecule descriptors

 
IUPAC namemethyl N-[(2S)-1-[(2S)-2-[[4-[(2S,5S)-1-(4-tert-butylphenyl)-5-[4-[[(2S)-1-[(2S)-2-(methoxycarbonylamino)-3-methylbutanoyl]pyrrolidine-2-carbonyl]amino]phenyl]pyrrolidin-2-yl]phenyl]carbamoyl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamate
InChI codeInChI=1S/C50H67N7O8/c1-30(2)42(53-48(62)64-8)46(60)55-28-10-12-40(55)44(58)51-35-20-14-32(15-21-35)38-26-27-39(57(38)37-24-18-34(19-25-37)50(5,6)7)33-16-22-36(23-17-33)52-45(59)41-13-11-29-56(41)47(61)43(31(3)4)54-49(63)65-9/h14-25,30-31,38-43H,10-13,26-29H2,1-9H3,(H,51,58)(H,52,59)(H,53,62)(H,54,63)/t38-,39-,40-,41-,42-,43-/m0/s1
InChI KeyPIDFDZJZLOTZTM-KHVQSSSXSA-N
SMILESCOC(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)Nc1ccc([C@@H]2CC[C@@H](c3ccc(NC(=O)[C@@H]4CCCN4C(=O)[C@@H](NC(=O)OC)C(C)C)cc3)N2c2ccc(C(C)(C)C)cc2)cc1)C(C)C

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.

  • 1258226-87-7
  • 2302768XJ8
  • ABT 267
  • ABT-267
  • ABT-267;ABT267;ABT 267
  • ABT267
  • AMY6935
  • BDBM50453112
  • C72037
  • CCG-270561
  • CS-5330
  • Carbamic acid, N,N'-(((2S,5S)-1-(4-(1,1-dimethylethyl)phenyl)-2,5-pyrrolidinediyl)bis(4,1-phenyleneiminocarbonyl-(2S)-2,1-pyrrolidinediyl((1S)-1-(1-methylethyl)-2-oxo-2,1-ethanediyl)))bis-, C,C'-dimethyl ester
  • D10576
  • DB09296
  • EX-A5846
  • GTPL11272
  • HY-13997
  • L-Prolinamide, 2,2'-[[(2S,5S)-1-[4-(1,1-dimethylethyl)phenyl]-2,5-pyrrolidinediyl]di-4,1-phenylene]bis[N-(methoxycarbonyl)-L-valyl-
  • L-Prolinamide,2,2'-(((2S,5S)-1-(4-(1,1-dimethylethyl)phenyl)-2,5-pyrrolidinediyl)di-4,1-phenylene)bis(N-(methoxycarbonyl)-L-valyl-
  • Methyl ((S)-1-((S)-2-((4-((2S,5S)-1-(4-(tert-butyl)phenyl)-5-(4-((S)-1-((methoxycarbonyl)-L-valyl)pyrrolidine-2-carboxamido)phenyl)pyrrolidin-2-yl)phenyl)carbamoyl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-yl)carbamate
  • NCGC00510316-01
  • NCGC00510316-02
  • OMBITASVIR COMPONENT OF VIEKIRAX
  • Ombitasvir
  • Ombitasvir (USAN)
  • Ombitasvir(ABT-267)
  • Q19598175
  • Technivie (ombitasvir + paritaprevir + ritonavir)
  • VIEKIRAX COMPONENT OMBITASVIR
  • dimethyl ([(2S,5S)-1-(4-tert-butylphenyl)pyrrolidine-2,5-diyl]bis{(4,1-phenylene)carbamoyl(2S)pyrrolidine-2,1-diyl[(2S)-3-methyl-1-oxobutane-1,2-diyl]})biscarbamate
  • methyl N-[(1S)-1-[(2S)-2-[[4-[(2S,5S)-1-(4-tert-butylphenyl)-5-[4-[[(2S)-1-[(2S)-2-(methoxycarbonylamino)-3-methyl-butanoyl]pyrrolidine-2-carbonyl]amino]phenyl]pyrrolidin-2-yl]phenyl]carbamoyl]pyrrolidine-1-carbonyl]-2-methyl-propyl]carbamate
  • methyl N-[(2S)-1-[(2S)-2-[[4-[(2S,5S)-1-(4-tert-butylphenyl)-5-[4-[[(2S)-1-[(2S)-2-(methoxycarbonylamino)-3-methylbutanoyl]pyrrolidine-2-carbonyl]amino]phenyl]pyrrolidin-2-yl]phenyl]carbamoyl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamate
  • s5403

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC150601177
  • UNII-2302768XJ8
  • DTXSID201027920
  • CHEMBL3127326
  • CHEBI:85183
  • SCHEMBL8542284

Physico-Chemical properties

IUPAC namemethyl N-[(2S)-1-[(2S)-2-[[4-[(2S,5S)-1-(4-tert-butylphenyl)-5-[4-[[(2S)-1-[(2S)-2-(methoxycarbonylamino)-3-methylbutanoyl]pyrrolidine-2-carbonyl]amino]phenyl]pyrrolidin-2-yl]phenyl]carbamoyl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamate
Molecular formulaC50H67N7O8
Molecular weight894.109
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity262.84
LogP8.6
Topological polar surface area178.7

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.