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150399-23-8 molecular structure
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(2R)-2-{[4-(2-{2-amino-4-oxo-1H,4H,7H-pyrrolo[2,3-d]pyrimidin-5-yl}ethyl)phenyl]formamido}pentanedioic acid

ChemBase ID: 524
Molecular Formular: C20H21N5O6
Molecular Mass: 427.41064
Monoisotopic Mass: 427.14918342
SMILES and InChIs

SMILES:
O=c1nc([nH]c2[nH]cc(CCc3ccc(cc3)C(=O)N[C@H](CCC(=O)O)C(=O)O)c12)N
Canonical SMILES:
OC(=O)CC[C@H](C(=O)O)NC(=O)c1ccc(cc1)CCc1c[nH]c2c1c(=O)nc([nH]2)N
InChI:
InChI=1S/C20H21N5O6/c21-20-24-16-15(18(29)25-20)12(9-22-16)6-3-10-1-4-11(5-2-10)17(28)23-13(19(30)31)7-8-14(26)27/h1-2,4-5,9,13H,3,6-8H2,(H,23,28)(H,26,27)(H,30,31)(H4,21,22,24,25,29)/t13-/m1/s1
InChIKey:
WBXPDJSOTKVWSJ-CYBMUJFWSA-N

Cite this record

CBID:524 http://www.chembase.cn/molecule-524.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2R)-2-{[4-(2-{2-amino-4-oxo-1H,4H,7H-pyrrolo[2,3-d]pyrimidin-5-yl}ethyl)phenyl]formamido}pentanedioic acid
IUPAC Traditional name
alimta
pemetrexed
Brand Name
Alimta
Synonyms
LY231514
Pemetrexed Disodium
Pemetrexed
(S)-2-(4-(2-(2-Amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzamido)pentanedioic acid
CAS Number
150399-23-8
137281-23-3
MDL Number
MFCD19105065
PubChem SID
160963987
46505640
PubChem CID
60843

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Bide Pharmatech
BD146899 Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 3.341115  H Acceptors
H Donor LogD (pH = 5.5) -2.0354736 
LogD (pH = 7.4) -5.047953  Log P 1.4881234 
Molar Refractivity 109.4496 cm3 Polarizability 40.419224 Å3
Polar Surface Area 186.97 Å2 Rotatable Bonds
Lipinski's Rule of Five false 
Log P 0.11  LOG S -3.97 
Solubility (Water) 4.55e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Product Information Bioassay(PubChem)
Hydrophobicity(logP)
-1.5 expand Show data source
Purity
95+% expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00642 external link
Item Information
Drug Groups approved; investigational
Description Pemetrexed (brand name Alimta?) is a chemotherapy drug manufactured and marketed by Eli Lilly and Company. Its indications are the treatment of pleural mesothelioma as well as non-small cell lung cancer.
Indication Used in combination with cisplatin for the treatment of malignant pleural mesothelioma in adults whose disease is unresectable or who otherwise are not candidates for potentially curative surgery. Also used as a monotherapy for the treatment of locally advanced or metastatic non-small cell lung cancer (NSCLC) after prior chemotherapy
Pharmacology Preclinical studies have shown that pemetrexed inhibits the in vitro growth of mesothelioma cell lines (MSTO-211H, NCI-H2052). Studies with the MSTO-211H mesothelioma cell line showed synergistic effects when pemetrexed was combined concurrently with cisplatin.
Affected Organisms
Humans and other mammals
Biotransformation Metabolized by Cytochrome P450 Enzymes
Half Life 3.5 hours
Protein Binding 81%
Elimination Pemetrexed is not metabolized to an appreciable extent and is primarily eliminated in the urine, with 70% to 90% of the dose recovered unchanged within the first 24 hours following administration.
Distribution * 16.1 L
Clearance * 91.8 mL/min [Cancer patients with normal renal function receiving 0.2 to 838 mg/m2 infusion over a 10-minute period]
References
Rollins KD, Lindley C: Pemetrexed: a multitargeted antifolate. Clin Ther. 2005 Sep;27(9):1343-82. [Pubmed]
Lansiaux A, Lokiec F: [Pemetrexed: from preclinic to clinic] Bull Cancer. 2007;94 Spec No Actualites:S134-8. [Pubmed]
Fuld AD, Dragnev KH, Rigas JR: Pemetrexed in advanced non-small-cell lung cancer. Expert Opin Pharmacother. 2010 Jun;11(8):1387-402. [Pubmed]
Adjei AA: Pemetrexed (Alimta): a novel multitargeted antifolate agent. Expert Rev Anticancer Ther. 2003 Apr;3(2):145-56. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Rollins KD, Lindley C: Pemetrexed: a multitargeted antifolate. Clin Ther. 2005 Sep;27(9):1343-82. Pubmed
  • • Lansiaux A, Lokiec F: [Pemetrexed: from preclinic to clinic] Bull Cancer. 2007;94 Spec No Actualites:S134-8. Pubmed
  • • Fuld AD, Dragnev KH, Rigas JR: Pemetrexed in advanced non-small-cell lung cancer. Expert Opin Pharmacother. 2010 Jun;11(8):1387-402. Pubmed
  • • Adjei AA: Pemetrexed (Alimta): a novel multitargeted antifolate agent. Expert Rev Anticancer Ther. 2003 Apr;3(2):145-56. Pubmed
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PATENTS

PATENTS

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INTERNET

INTERNET

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