137281-23-3,MFCD00902635
Catalog No.:AA0012YZ

137281-23-3 | Pemetrexed

Pack Size
Purity
Availability
Price(USD)
Quantity
  
1g
95%
in stock  
$59.00   $41.00
- +
5g
98% +(contains <4%EtOH)(Loss on drying≤6%)
in stock  
$123.00   $86.00
- +
  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
Technical Information
Catalog Number:
AA0012YZ
Chemical Name:
Pemetrexed
CAS Number:
137281-23-3
Molecular Formula:
C20H21N5O6
Molecular Weight:
427.4106
MDL Number:
MFCD00902635
SMILES:
OC(=O)CC[C@@H](C(=O)O)NC(=O)c1ccc(cc1)CCc1c[nH]c2c1c(=O)[nH]c(n2)N
NSC Number:
698037
Properties
Computed Properties
 
Complexity:
748  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Heavy Atom Count:
31  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
6  
Rotatable Bond Count:
9  
XLogP3:
0.2  

Upstream Synthesis Route

[1]Patent:US2016/214987,2016,A1,.Locationinpatent:Paragraph0081

[2]Patent:US2008/45711,2008,A1,.Locationinpatent:Page/Pagecolumn11

[1]Patent:US2016/214987,2016,A1,

Downstream Synthesis Route
1310-73-2    137281-23-3   
pemetrexeddisodium 

[1]Patent:US2008/45711,2008,A1.Locationinpatent:Page/Pagecolumn12

[2]Patent:US2008/45711,2008,A1.Locationinpatent:Page/Pagecolumn12

pemetrexeddisodium 
  137281-23-3 

[1]Patent:US2008/45711,2008,A1.Locationinpatent:Page/Pagecolumn10

[2]Patent:US2008/45711,2008,A1.Locationinpatent:Page/Pagecolumn10

[3]Patent:US2011/172424,2011,A1.Locationinpatent:Page/Pagecolumn4

[4]Patent:EP2351755,2011,A1.Locationinpatent:Page/Pagecolumn6

[5]Patent:CN104817563,2017,B.Locationinpatent:Paragraph0029-0032;0038-0039;0044-0045;0049-0050;0055

[1]Patent:US2016/214987,2016,A1.Locationinpatent:Paragraph0081

[2]Patent:US2008/45711,2008,A1.Locationinpatent:Page/Pagecolumn11

67-56-1    137281-23-3   
pemetrexeddisodium 

[1]Patent:US6013828,2000,A

Literature

Title: Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.

Journal: Chemical research in toxicology 20150518

Title: Proteomic identification of differentially expressed proteins associated with the multiple drug resistance in methotrexate-resistant human breast cancer cells.

Journal: International journal of oncology 20140701

Title: KRAS mutation status is associated with enhanced dependency on folate metabolism pathways in non-small cell lung cancer cells.

Journal: Molecular cancer therapeutics 20140601

Title: Pemetrexed downregulates ERCC1 expression and enhances cytotoxicity effected by resveratrol in human nonsmall cell lung cancer cells.

Journal: Naunyn-Schmiedeberg's archives of pharmacology 20131201

Title: Targeted agents in the third-/fourth-line treatment of patients with advanced (stage III/IV) non-small cell lung cancer (NSCLC).

Journal: Cancer treatment reviews 20130501

Title: Pemetrexed-based chemotherapy in patients with advanced, ALK-positive non-small cell lung cancer.

Journal: Annals of oncology : official journal of the European Society for Medical Oncology 20130101

Title: Pemetrexed alters folate phenotype and inflammatory profile in EA.hy 926 cells grown under low-folate conditions.

Journal: European journal of pharmacology 20121205

Title: Treatment paradigms for patients with metastatic non-small-cell lung cancer: first-, second-, and third-line.

Journal: Current oncology (Toronto, Ont.) 20120601

Title: Death receptor 5 and cellular FLICE-inhibitory protein regulate pemetrexed-induced apoptosis in human lung cancer cells.

Journal: European journal of cancer (Oxford, England : 1990) 20111101

Title: Establishment of pemetrexed-resistant non-small cell lung cancer cell lines.

Journal: Cancer letters 20111028

Title: Synthesis, biological, and antitumor activity of a highly potent 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolate inhibitor with proton-coupled folate transporter and folate receptor selectivity over the reduced folate carrier that inhibits β-glycinamide ribonucleotide formyltransferase.

Journal: Journal of medicinal chemistry 20111027

Title: Medical treatment of mesothelioma: anything new?

Journal: Current oncology reports 20110801

Title: Treatment of advanced non-small-cell lung cancer: Italian Association of Thoracic Oncology (AIOT) clinical practice guidelines.

Journal: Lung cancer (Amsterdam, Netherlands) 20110701

Title: Phase II study of pemetrexed and cisplatin, with chest radiotherapy followed by docetaxel in patients with stage III non-small cell lung cancer.

Journal: Journal of thoracic oncology : official publication of the International Association for the Study of Lung Cancer 20110501

Title: Anaplastic lymphoma kinase gene rearrangements in non-small cell lung cancer are associated with prolonged progression-free survival on pemetrexed.

Journal: Journal of thoracic oncology : official publication of the International Association for the Study of Lung Cancer 20110401

Title: Targeted therapies and other agents as first-line maintenance and beyond: particular benefit in pulmonary adenocarcinoma patients.

Journal: Current medicinal chemistry 20110101

Title: ABCC11/MRP8 confers pemetrexed resistance in lung cancer.

Journal: Cancer science 20101101

Title: Pemetrexed in advanced non-small-cell lung cancer.

Journal: Expert opinion on pharmacotherapy 20100601

Title: Cancer chemotherapy: targeting folic acid synthesis.

Journal: Cancer management and research 20100101

Title: Phase III study of pemetrexed plus carboplatin compared with etoposide plus carboplatin in chemotherapy-naive patients with extensive-stage small-cell lung cancer.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20091001

Title: Phase II study of pemetrexed and carboplatin plus bevacizumab with maintenance pemetrexed and bevacizumab as first-line therapy for nonsquamous non-small-cell lung cancer.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20090710

Title: Valproate, in combination with pemetrexed and cisplatin, provides additional efficacy to the treatment of malignant mesothelioma.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20090415

Title: A randomized, double-blind, phase II study of two doses of pemetrexed as first-line chemotherapy for advanced breast cancer.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20070615

Title: Changes in the status of p53 affect drug sensitivity to thymidylate synthase (TS) inhibitors by altering TS levels.

Journal: British journal of cancer 20070312

Title: Sequence-dependent administration of raloxifene and 5-fluorouracil/pemetrexed protects against pemetrexed cytotoxicity in human bone marrow.

Journal: Anticancer research 20070101

Title: [Pemetrexed: from preclinic to clinic].

Journal: Bulletin du cancer 20070101

Title: A semimechanistic-physiologic population pharmacokinetic/pharmacodynamic model for neutropenia following pemetrexed therapy.

Journal: Cancer chemotherapy and pharmacology 20060401

Title: Pemetrexed-associated urticarial vasculitis.

Journal: Lung cancer (Amsterdam, Netherlands) 20060201

Title: The inverse relationship between reduced folate carrier function and pemetrexed activity in a human colon cancer cell line.

Journal: Molecular cancer therapeutics 20060201

Title: Pemetrexed: a multitargeted antifolate.

Journal: Clinical therapeutics 20050901

Title: Human splicing factor SPF45 (RBM17) confers broad multidrug resistance to anticancer drugs when overexpressed--a phenotype partially reversed by selective estrogen receptor modulators.

Journal: Cancer research 20050801

Title: Cytotoxic effects of pemetrexed in gastric cancer cells.

Journal: Cancer science 20050601

Title: The multidrug resistance protein 5 (ABCC5) confers resistance to 5-fluorouracil and transports its monophosphorylated metabolites.

Journal: Molecular cancer therapeutics 20050501

Title: The roles of thymidylate synthase and p53 in regulating Fas-mediated apoptosis in response to antimetabolites.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20040515

Title: Accumulation of 5-phosphoribosyl-1-pyrophosphate in human CCRF-CEM leukaemia cells treated with antifolates.

Journal: The international journal of biochemistry & cell biology 20040301

Title: Thymidine rescue: an antidote for pemetrexed-related toxicity in the setting of acute renal failure.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20031101

Title: Pemetrexed (Alimta): a novel multitargeted antifolate agent.

Journal: Expert review of anticancer therapy 20030401

Title: Design, synthesis, and biological activities of classical N-[4-[2-(2-amino-4-ethylpyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-l-glutamic acid and its 6-methyl derivative as potential dual inhibitors of thymidylate synthase and dihydrofolate reductase and as potential antitumor agents.

Journal: Journal of medicinal chemistry 20030213

Title: Pemetrexed combination therapy in the treatment of non-small cell lung cancer.

Journal: Seminars in oncology 20020401

Title: A new route to 7-substituted derivatives of n-[4-(2-[2-amino-3,4-dihydro-4-oxo-7H-pyrrolo(2,3-d)pyrimidin-5-yl]ethyl)benzoyl]-L-glutamic acid [ALIMTA (LY231514, MTA)].

Journal: The Journal of organic chemistry 20010601

Title: Shih C, et al. LY231514, a pyrrolo,3-dpyrimidine-based antifolate that inhibits multiple folate-requiring enzymes. Cancer Res. 1997 Mar 15;57(6):1116-23.

Title: Anraku M, et al. Synergistic antitumor effects of regulatory T cell blockade combined with pemetrexed in murine malignantmesothelioma. J Immunol. 2010 Jul 15;185(2):956-66.

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SDS
Tags:137281-23-3 Molecular Formula|137281-23-3 MDL|137281-23-3 SMILES|137281-23-3 Pemetrexed
Catalog No.: AA0012YZ
137281-23-3,MFCD00902635
137281-23-3 | Pemetrexed
Pack Size: 1g
Purity: 95%
in stock
$59.00 $41.00
Pack Size: 5g
Purity: 98% +(contains <4%EtOH)(Loss on drying≤6%)
in stock
$123.00 $86.00
Quantity
- +
Add to Card
Order Now
bulk Quotation Request
Technical Information
Catalog Number: AA0012YZ
Chemical Name: Pemetrexed
CAS Number: 137281-23-3
Molecular Formula: C20H21N5O6
Molecular Weight: 427.4106
MDL Number: MFCD00902635
SMILES: OC(=O)CC[C@@H](C(=O)O)NC(=O)c1ccc(cc1)CCc1c[nH]c2c1c(=O)[nH]c(n2)N
NSC Number: 698037
Properties
Complexity: 748  
Covalently-Bonded Unit Count: 1  
Defined Atom Stereocenter Count: 1  
Heavy Atom Count: 31  
Hydrogen Bond Acceptor Count: 7  
Hydrogen Bond Donor Count: 6  
Rotatable Bond Count: 9  
XLogP3: 0.2  
Upstream Synthesis Route
165049-28-5    137281-23-3 

[1]Patent:US2016/214987,2016,A1,.Locationinpatent:Paragraph0081

[2]Patent:US2008/45711,2008,A1,.Locationinpatent:Page/Pagecolumn11

1118-89-4    137281-23-3 

[1]Patent:US2016/214987,2016,A1,

Downstream Synthesis Route
1310-73-2    137281-23-3   
pemetrexeddisodium 

[1]Patent:US2008/45711,2008,A1.Locationinpatent:Page/Pagecolumn12

[2]Patent:US2008/45711,2008,A1.Locationinpatent:Page/Pagecolumn12

pemetrexeddisodium 
  137281-23-3 

[1]Patent:US2008/45711,2008,A1.Locationinpatent:Page/Pagecolumn10

[2]Patent:US2008/45711,2008,A1.Locationinpatent:Page/Pagecolumn10

[3]Patent:US2011/172424,2011,A1.Locationinpatent:Page/Pagecolumn4

[4]Patent:EP2351755,2011,A1.Locationinpatent:Page/Pagecolumn6

[5]Patent:CN104817563,2017,B.Locationinpatent:Paragraph0029-0032;0038-0039;0044-0045;0049-0050;0055

165049-28-5    137281-23-3 

[1]Patent:US2016/214987,2016,A1.Locationinpatent:Paragraph0081

[2]Patent:US2008/45711,2008,A1.Locationinpatent:Page/Pagecolumn11

67-56-1    137281-23-3   
pemetrexeddisodium 

[1]Patent:US6013828,2000,A

Literature fold

Title: Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.

Journal: Chemical research in toxicology20150518

Title: Proteomic identification of differentially expressed proteins associated with the multiple drug resistance in methotrexate-resistant human breast cancer cells.

Journal: International journal of oncology20140701

Title: KRAS mutation status is associated with enhanced dependency on folate metabolism pathways in non-small cell lung cancer cells.

Journal: Molecular cancer therapeutics20140601

Title: Pemetrexed downregulates ERCC1 expression and enhances cytotoxicity effected by resveratrol in human nonsmall cell lung cancer cells.

Journal: Naunyn-Schmiedeberg's archives of pharmacology20131201

Title: Targeted agents in the third-/fourth-line treatment of patients with advanced (stage III/IV) non-small cell lung cancer (NSCLC).

Journal: Cancer treatment reviews20130501

Title: Pemetrexed-based chemotherapy in patients with advanced, ALK-positive non-small cell lung cancer.

Journal: Annals of oncology : official journal of the European Society for Medical Oncology20130101

Title: Pemetrexed alters folate phenotype and inflammatory profile in EA.hy 926 cells grown under low-folate conditions.

Journal: European journal of pharmacology20121205

Title: Treatment paradigms for patients with metastatic non-small-cell lung cancer: first-, second-, and third-line.

Journal: Current oncology (Toronto, Ont.)20120601

Title: Death receptor 5 and cellular FLICE-inhibitory protein regulate pemetrexed-induced apoptosis in human lung cancer cells.

Journal: European journal of cancer (Oxford, England : 1990)20111101

Title: Establishment of pemetrexed-resistant non-small cell lung cancer cell lines.

Journal: Cancer letters20111028

Title: Synthesis, biological, and antitumor activity of a highly potent 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolate inhibitor with proton-coupled folate transporter and folate receptor selectivity over the reduced folate carrier that inhibits β-glycinamide ribonucleotide formyltransferase.

Journal: Journal of medicinal chemistry20111027

Title: Medical treatment of mesothelioma: anything new?

Journal: Current oncology reports20110801

Title: Treatment of advanced non-small-cell lung cancer: Italian Association of Thoracic Oncology (AIOT) clinical practice guidelines.

Journal: Lung cancer (Amsterdam, Netherlands)20110701

Title: Phase II study of pemetrexed and cisplatin, with chest radiotherapy followed by docetaxel in patients with stage III non-small cell lung cancer.

Journal: Journal of thoracic oncology : official publication of the International Association for the Study of Lung Cancer20110501

Title: Anaplastic lymphoma kinase gene rearrangements in non-small cell lung cancer are associated with prolonged progression-free survival on pemetrexed.

Journal: Journal of thoracic oncology : official publication of the International Association for the Study of Lung Cancer20110401

Title: Targeted therapies and other agents as first-line maintenance and beyond: particular benefit in pulmonary adenocarcinoma patients.

Journal: Current medicinal chemistry20110101

Title: ABCC11/MRP8 confers pemetrexed resistance in lung cancer.

Journal: Cancer science20101101

Title: Pemetrexed in advanced non-small-cell lung cancer.

Journal: Expert opinion on pharmacotherapy20100601

Title: Cancer chemotherapy: targeting folic acid synthesis.

Journal: Cancer management and research20100101

Title: Phase III study of pemetrexed plus carboplatin compared with etoposide plus carboplatin in chemotherapy-naive patients with extensive-stage small-cell lung cancer.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology20091001

Title: Phase II study of pemetrexed and carboplatin plus bevacizumab with maintenance pemetrexed and bevacizumab as first-line therapy for nonsquamous non-small-cell lung cancer.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology20090710

Title: Valproate, in combination with pemetrexed and cisplatin, provides additional efficacy to the treatment of malignant mesothelioma.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research20090415

Title: A randomized, double-blind, phase II study of two doses of pemetrexed as first-line chemotherapy for advanced breast cancer.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research20070615

Title: Changes in the status of p53 affect drug sensitivity to thymidylate synthase (TS) inhibitors by altering TS levels.

Journal: British journal of cancer20070312

Title: Sequence-dependent administration of raloxifene and 5-fluorouracil/pemetrexed protects against pemetrexed cytotoxicity in human bone marrow.

Journal: Anticancer research20070101

Title: [Pemetrexed: from preclinic to clinic].

Journal: Bulletin du cancer20070101

Title: A semimechanistic-physiologic population pharmacokinetic/pharmacodynamic model for neutropenia following pemetrexed therapy.

Journal: Cancer chemotherapy and pharmacology20060401

Title: Pemetrexed-associated urticarial vasculitis.

Journal: Lung cancer (Amsterdam, Netherlands)20060201

Title: The inverse relationship between reduced folate carrier function and pemetrexed activity in a human colon cancer cell line.

Journal: Molecular cancer therapeutics20060201

Title: Pemetrexed: a multitargeted antifolate.

Journal: Clinical therapeutics20050901

Title: Human splicing factor SPF45 (RBM17) confers broad multidrug resistance to anticancer drugs when overexpressed--a phenotype partially reversed by selective estrogen receptor modulators.

Journal: Cancer research20050801

Title: Cytotoxic effects of pemetrexed in gastric cancer cells.

Journal: Cancer science20050601

Title: The multidrug resistance protein 5 (ABCC5) confers resistance to 5-fluorouracil and transports its monophosphorylated metabolites.

Journal: Molecular cancer therapeutics20050501

Title: The roles of thymidylate synthase and p53 in regulating Fas-mediated apoptosis in response to antimetabolites.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research20040515

Title: Accumulation of 5-phosphoribosyl-1-pyrophosphate in human CCRF-CEM leukaemia cells treated with antifolates.

Journal: The international journal of biochemistry & cell biology20040301

Title: Thymidine rescue: an antidote for pemetrexed-related toxicity in the setting of acute renal failure.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology20031101

Title: Pemetrexed (Alimta): a novel multitargeted antifolate agent.

Journal: Expert review of anticancer therapy20030401

Title: Design, synthesis, and biological activities of classical N-[4-[2-(2-amino-4-ethylpyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-l-glutamic acid and its 6-methyl derivative as potential dual inhibitors of thymidylate synthase and dihydrofolate reductase and as potential antitumor agents.

Journal: Journal of medicinal chemistry20030213

Title: Pemetrexed combination therapy in the treatment of non-small cell lung cancer.

Journal: Seminars in oncology20020401

Title: A new route to 7-substituted derivatives of n-[4-(2-[2-amino-3,4-dihydro-4-oxo-7H-pyrrolo(2,3-d)pyrimidin-5-yl]ethyl)benzoyl]-L-glutamic acid [ALIMTA (LY231514, MTA)].

Journal: The Journal of organic chemistry20010601

Title: Shih C, et al. LY231514, a pyrrolo,3-dpyrimidine-based antifolate that inhibits multiple folate-requiring enzymes. Cancer Res. 1997 Mar 15;57(6):1116-23.

Title: Anraku M, et al. Synergistic antitumor effects of regulatory T cell blockade combined with pemetrexed in murine malignantmesothelioma. J Immunol. 2010 Jul 15;185(2):956-66.

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