Raltitrexed

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

What is the Raltitrexed?

The molecule Raltitrexed presents a molecular formula of C21H22N4O6S and its IUPAC name is (2S)-2-[[5-[methyl-[(2-methyl-4-oxo-3H-quinazolin-6-yl)methyl]amino]thiophene-2-carbonyl]amino]pentanedioic acid.

Raltitrexed (ZD 1694) is a thymidylate synthase inhibitor. It is used in the treatment of cancer. It works by inhibiting the enzyme thymidylate synthase, which participes in the synthesis of DNA..

Raltitrexed was first synthesized in 1983 by scientists at Zeneca Pharmaceuticals (now AstraZeneca). It was approved for use in the United Kingdom in 1997 and in the United States in 1998..

Raltitrexed exists as a powder for injection and as a solution for infusion. It is typically given by intravenous infusion over 30 minutes every 3 weeks..

Common side effects of raltitrexed include nausea, vomiting, diarrhea, constipation, anorexia, fatigue, stomatitis, and alopecia. Serious side effects include myelosuppression, mucositis, and neuropathy..

Raltitrexed is contraindicated in patients with severe myelosuppression, severe mucositis, or severe neuropathy..

Raltitrexed has shown activity in a variety of solid tumors, including colorectal, gastric, breast, and ovarian cancer. It is typically used in the second- or third-line setting, after other agents have failed..

Raltitrexed has shown a response rate of 5-15% in clinical trials. The median overall survival is 8-12 months..

Raltitrexed is an important option for patients with cancer who have failed other treatments. It has shown activity in a variety of solid tumors and is typically used in the second- or third-line setting..

3D structure

Cartesian coordinates

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

2D drawing

 

Raltitrexed IVTVGDXNLFLDRM-HNNXBMFYSA-N chemical compound 2D structure molecule svg
Raltitrexed

 

Molecule descriptors

 
IUPAC name(2S)-2-[[5-[methyl-[(2-methyl-4-oxo-3H-quinazolin-6-yl)methyl]amino]thiophene-2-carbonyl]amino]pentanedioic acid
InChI codeInChI=1S/C21H22N4O6S/c1-11-22-14-4-3-12(9-13(14)19(28)23-11)10-25(2)17-7-6-16(32-17)20(29)24-15(21(30)31)5-8-18(26)27/h3-4,6-7,9,15H,5,8,10H2,1-2H3,(H,24,29)(H,26,27)(H,30,31)(H,22,23,28)/t15-/m0/s1
InChI KeyIVTVGDXNLFLDRM-HNNXBMFYSA-N
SMILESCc1nc(=O)c2cc(CN(C)c3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)s3)ccc2[nH]1

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)-2-[(5-{methyl[(2-methyl-4-oxo-1,4-dihydroquinazolin-6-yl)methyl]amino}thiophen-2-yl)formamido]pentanedioic acid
  • (S)-2-(5-(Methyl((2-methyl-4-oxo-3,4-dihydroquinazolin-6-yl)-methyl)amino)thiophene-2-carboxamido)pentanedioic acid
  • (S)-2-(5-(methyl((2-methyl-4-oxo-1,4-dihydroquinazolin-6-yl)methyl)amino)thiophene-2-carboxamido)pentanedioic acid
  • (S)-2-(5-(methyl((2-methyl-4-oxo-3,4-dihydroquinazolin-6-yl)methyl)amino)thiophene-2-carboxamido)pentanedioic acid
  • 112887-68-0
  • 1hvy
  • 1i00
  • 2kce
  • 2tsr
  • 887R680
  • AB00698356-05
  • AMY42113
  • BCP0726000267
  • BDBM18795
  • BDBM50027655
  • CCG-101075
  • CCG-221273
  • D 1694
  • D-1694
  • D01064
  • D16
  • D1694
  • DB00293
  • DSSTox_CID_26482
  • DSSTox_GSID_46482
  • DSSTox_RID_81653
  • FCB9EGG971
  • GTPL7403
  • HMS2052I03
  • HMS3715P08
  • HY-10821
  • ICI D1694
  • ICI-D-1694
  • ICI-D1694
  • J-524216
  • KS-5069
  • L-Glutamic acid, N-((5-(((1,4-dihydro-2-methyl-4-oxo-6-quinazolinyl)methyl)methylamino)-2-thienyl)carbonyl)-
  • L-Glutamic acid, N-[[5-[[(3,4-dihydro-2-methyl-4-oxo-6-quinazolinyl)methyl]methylamino]-2-thienyl]carbonyl]-
  • MFCD00864168
  • MLS001424225
  • MLS006010125
  • N-(5-(((3,4-Dihydro-2-methyl-4-oxo-6-quinazolinyl)methyl)methylamino)-2-thenoyl)-L-glutamic acid
  • N-(5-(N-(3,4-Dihydro-2-methyl-4-oxoquinazolin-6-ylmethyl)-N-methylamino)-2-thenoyl)-L-glutamic acid
  • N-(5-[N-(3,4-dihydro-2-methyl-4-oxoquinazolin-6-ylmethyl)-N-methylamino]-2-thenoyl)-L-glutamic acid
  • N-[(5-{methyl[(2-methyl-4-oxo-1,4-dihydroquinazolin-6-yl)methyl]amino}thiophen-2-yl)carbonyl]-L-glutamic acid
  • N-[[5-[[(1,4-dihydro-2-methyl-4-oxo-6-quinazolinyl)methyl]methylamino]-2-thienyl]carbonyl]-L-glutamic acid
  • NC00325
  • NCGC00229704-01
  • NCGC00263534-02
  • NCI60_013008
  • NSC-639186
  • NSC639186
  • Q15304877
  • R0208
  • Raltitrexed
  • Raltitrexed (JAN/USAN/INN)
  • Raltitrexed (Tomudex)
  • SMR000469217
  • SMR002529608
  • SR-01000763351
  • SR-01000763351-3
  • SW197705-2
  • Tomudex
  • ZD 1694
  • ZD-16
  • ZD-1694
  • ZD1694
  • ZD1694; Raltitrexed
  • ZN-D1694
  • s1192

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3832372
  • CAS-112887-68-0
  • UNII-FCB9EGG971
  • AKOS015894877
  • AKOS015994729
  • BRD-K89839824-001-01-2
  • DTXSID0046482
  • CHEMBL225071
  • CHEBI:5847
  • Tox21_112237
  • Tox21_112237_1
  • SCHEMBL7438

Physico-Chemical properties

IUPAC name(2S)-2-[[5-[methyl-[(2-methyl-4-oxo-3H-quinazolin-6-yl)methyl]amino]thiophene-2-carbonyl]amino]pentanedioic acid
Molecular formulaC21H22N4O6S
Molecular weight458.488
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity119.67
LogP2.4
Topological polar surface area180.9

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.