(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: 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

NAMES AND DATABASE IDS

Names

• 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

Database IDs

• CAS Number: 137281-23-3; 150399-23-8
• MDL Number: MFCD19105065
• PubChem SID: 160963987; 46505640
• PubChem CID: 60843

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.341115
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -2.0354736
• LogD (pH = 7.4): -5.047953
• Log P: 1.4881234
• Molar Refractivity: 109.4496 cm^3
• Polarizability: 40.419224 Å^3
• Polar Surface Area: 186.97 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 0.11
• LOG S: -3.97
• Solubility (Water): 4.55e-02 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): -1.5

Product Information

• Purity: 95+%

DETAILS

DrugBank - DB00642

• 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

• 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