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Pemetrexed

Pemetrexed Structure
Pemetrexed structure
CAS No.
137281-23-3
Chemical Name:
Pemetrexed
Synonyms
(S)-2-(4-(2-(2-AMino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyriMidin-5-yl)ethyl)benzaMido)pentanedioic acid;Premetred;PEMETREXED;Pemetrexedum;Pemetrexed99%;Pemetrexedaci;(R)-Pemetrexed;PeMetrexed-15C5;PeMetrexed-13C5;PEMETREXED ACID
CBNumber:
CB4170583
Molecular Formula:
C20H21N5O6
Molecular Weight:
427.41
MDL Number:
MFCD00902635
MOL File:
137281-23-3.mol
MSDS File:
SDS
TDS File:
TDS
Last updated:2026-09-10 08:17:50
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Pemetrexed Properties

Density 1.59±0.1 g/cm3(Predicted)
storage temp. 2-8°C(protect from light)
solubility slightly sol. in Methanol
form powder to crystal
pka 3.58±0.10(Predicted)
color White to Blue
Merck 14,7077
Major Application pharmaceutical small molecule
InChIKey WBXPDJSOTKVWSJ-ZDUSSCGKSA-N
SMILES C(O)(=O)[C@H](CCC(O)=O)NC(=O)C1=CC=C(CCC2C3C(=O)NC(N)=NC=3NC=2)C=C1
CAS DataBase Reference 137281-23-3(CAS DataBase Reference)
FDA UNII 04Q9AIZ7NO
ATC code L01BA04
UNSPSC Code 12352200
NACRES NA.24

SAFETY

Risk and Safety Statements

Symbol(GHS)  Exclamation Mark (GHS07)
GHS07
Signal word  Warning
Hazard statements  H302-H315-H319-H332-H335
Precautionary statements  P261-P280-P305+P351+P338
WGK Germany  WGK 3
RTECS  LZ9950100
HS Code  2933.99.9701
Storage Class 11 - Combustible Solids
Hazardous Substances Data 137281-23-3(Hazardous Substances Data)

Pemetrexed price More Price(77)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
TCI Chemical P2288 Pemetrexed Hydrate >98.0%(HPLC)(T) 137281-23-3 250mg $80 2026-04-30 Buy
TCI Chemical P2288 Pemetrexed Hydrate >98.0%(HPLC)(T) 137281-23-3 1g $200 2026-04-30 Buy
Usbiological 287523 Pemetrexed Asreported 137281-23-3 100mg $326 2026-06-03 Buy
Usbiological 287523 Pemetrexed Asreported 137281-23-3 250mg $460 2026-06-03 Buy
Usbiological 287523 Pemetrexed Asreported 137281-23-3 500mg $602 2026-06-03 Buy
Product number Packaging Price Buy
P2288 250mg $80 Buy
P2288 1g $200 Buy
287523 100mg $326 Buy
287523 250mg $460 Buy
287523 500mg $602 Buy

Pemetrexed Chemical Properties, Uses, Production

Chemical Properties

N-[4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid disodium salt is Off-White Solid

Uses

Pemetrexed is used in the treatment of malignant pleural mesothelioma (MPM) and erectile dysfunction therapy.

Definition

ChEBI: Pemetrexed is an N-acylglutamic acid in which the N-acyl group is specified as 4-[2-(2-amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl. Inhibits thymidylate synthase (TS), 421 dihydrofolate reductase (DHFR), and glycinamide ribonucleotide formyltransferase (GARFT). It has a role as an antineoplastic agent, an antimetabolite, an EC 2.1.1.45 (thymidylate synthase) inhibitor, an EC 1.5.1.3 (dihydrofolate reductase) inhibitor and an EC 2.1.2.2 (phosphoribosylglycinamide formyltransferase) inhibitor. It is a pyrrolopyrimidine and a N-acyl-L-glutamic acid. It is a conjugate acid of a pemetrexed(2-).

brand name

Alimta (Lilly).

Side effects

The most common side effects for pemetrexed include fatigue, nausea, vomiting, anorexia, mucositis, myelosuppression ± infection, bleeding, rash, diarrhea and ↑ LFTs.
Severe myelosuppression is often dose-limiting for pemetrexed. Sepsis, in some cases fatal, have occurred in approximately 1% of patients in clinical trials. Prophylactic folic acid and intramuscular vitamin B12 supplements are necessary to reduce hematologic or non-hematologic toxicities.
Pemetrexed may cause serious and in some cases fatal dermatologic toxicities. Rarely, StevensJohnson syndrome and toxic epidermal necrolysis have been reported.

Synthesis

N-[4-[2-(2-Amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid 1,5-diethyl ester 4-methylbenzenesulfonate

165049-28-5

Pemetrexed

137281-23-3

The general procedure for the synthesis of pemetrexed disodium salt from (S)-2-(4-(2-(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzamido)pentanedioic acid diethyl ester 4-methylbenzenesulfonate is as follows: 1. Preparation of pemetrexedic acid (Eq. 2): a. Add 1 L of a 1N aqueous NaOH solution to the reactor and cool to 5-15°C. b. To the cooled NaOH solution, slowly add 143 g of the compound of Formula 3 prepared in Example 1, maintaining the temperature at 5-15°C. c. The reaction mixture was stirred at 5-15°C for 2 hours, followed by filtration (HPLC purity: 99.8%). d. 2L of EtOH was added to the filtrate followed by slow dropwise addition of 2N HCl aqueous solution at 5-15°C to adjust the pH to 3.0. e. The crystalline mixture formed was stirred at 40-50°C for 1 hr and then filtered at 40°C. f. The filtered product was washed with 2 L of pure water followed by 1 L of EtOH. g. Dissolve the washed product in 4L of EtOH/pure water (1:1, v/v) and stir at 40-50°C for 1 hour. h. Cool to room temperature and filter, wash with 2L of pure water and then with 1L of EtOH. i. The product was dried under vacuum at 40-45 °C for 16 h to give 88 g of pemetrexedic acid as a white solid (yield: 95%, HPLC purity: 99.9%, individual impurity content: not mentioned). ii.

storage

Store at +4°C

Mode of action

Pemetrexed is a pyrrolopyrimidine antifolate that exerts its antineoplastic activity by inhibiting thymidylate synthase (TS), glycinamide ribonucleotide formyltransferase (GARFT) and dihydrofolate reductase (DHFR), which are involved in folate metabolism and DNA synthesis, resulting in inhibition of purine and thymidine nucleotide synthesis.

References

[1] Patent: US2016/214987, 2016, A1. Location in patent: Paragraph 0081
[2] Patent: US2008/45711, 2008, A1. Location in patent: Page/Page column 11

Pemetrexed synthesis

165049-28-5
137281-23-3
Synthesis of Pemetrexed from N-[4-[2-(2-Amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid 1,5-diethyl ester 4-methylbenzenesulfonate

Pemetrexed Preparation Products And Raw materials

Raw materials

N-[4-[2-(2-Amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid 1,5-diethyl ester 4-methylbenzenesulfonate Sodium hydroxide Hydrochloric acid

Preparation Products

Pemetrexed Suppliers

Global Suppliers ( 394)
Supplier Tel Email Country ProdList Advantage
Guangzhou Tomums Life Science Co., Ltd. 020-31155029 18902330969 sales@tomums.cn China 4688 58
J & K SCIENTIFIC LTD. 18210857532 18210857532 jkinfo@jkchemical.com China 96815 76
Chemvon Biotechnology Co., Ltd 021-50790412 info@chemvon.com China 371 57
Chembest Research Laboratories Limited 021-20908456 sales@BioChemBest.com China 5996 61
TCI (Shanghai) Development Co., Ltd. 021-67121386 Sales-CN@TCIchemicals.com China 24512 81
Energy Chemical 400-0056266 sales8178@energy-chemical.com China 44850 61
Jia Xing Isenchem Co.,Ltd 0573-85285100 18627885956 isenchem@163.com China 9389 66
Adamas Reagent, Ltd. 400-6009262 15618770481 yhx@titansci.com China 14098 59
LGM Pharma 1-(800)-881-8210 inquiries@lgmpharma.com United States 2110 70
Shanghai Hanhong Scientific Co.,Ltd. 021-54306202 13764082696 info@hanhongsci.com China 42917 64
Supplier Advantage
Guangzhou Tomums Life Science Co., Ltd. 58
J & K SCIENTIFIC LTD. 76
Chemvon Biotechnology Co., Ltd 57
Chembest Research Laboratories Limited 61
TCI (Shanghai) Development Co., Ltd. 81
Energy Chemical 61
Jia Xing Isenchem Co.,Ltd 66
Adamas Reagent, Ltd. 59
LGM Pharma 70
Shanghai Hanhong Scientific Co.,Ltd. 64

View Latest Price from Pemetrexed manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Pemetrexed pictures 2026-09-10 Pemetrexed
137281-23-3
 $33.00-66.00 98.10% 10g TargetMol Chemicals Inc.
Pemetrexed pictures 2026-08-20 Pemetrexed
137281-23-3
 $33.00-66.00 98.10% 10g TargetMol Chemicals Inc.
PeMetrexed-13C5 pictures 2026-03-20 PeMetrexed-13C5
137281-23-3
 $9.90 1KG 99% 5tons Hebei Chuanghai Biotechnology Co., Ltd
  • Pemetrexed pictures
  • Pemetrexed
    137281-23-3
  • $33.00-66.00
  • 98.10%
  • TargetMol Chemicals Inc.
  • Pemetrexed pictures
  • Pemetrexed
    137281-23-3
  • $33.00-66.00
  • 98.10%
  • TargetMol Chemicals Inc.

Pemetrexed Spectrum

Pemetrexed(137281-23-3)1HNMR

137281-23-3 (Pemetrexed) Related Search:

Pemetrexed Disodium 2-Amino-5-methyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one Pemetrexed disodium hemipentahydrate Pemetrexed Pyrrolo[2,3-d]pyrimidin-4-ol
2-Amino-4-hydroxypyrrolo[2,3-d]pyrimidine CHEMBRDG-BB 9071517 CHEMBRDG-BB 9071952 CHEMBRDG-BB 9071469

1of2

PeMetrexed-13C5 PeMetrexed-15C5 N-[4-[2-(2-aMino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyriMidin-5-yl)ethyl]benzoyl]L-GlutaMic acid (PeMetrexed acid) N-[4-[2-(2-AMino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyriMidin-5-yl)ethyl]benzoyl]-L-glutaMic acid (S)-2-(4-(2-(2-Amino-4-oxo-4,7-dihydro-1H-pyrrolo-[2,3-d]pyrimidin-5-yl)ethyl)benzamido)pentanedi N-[4-[2-(2-Amino-4,7 (2R)-2-{[4-(2-{2-aMino-4-oxo-1H,4H,7H-pyrrolo[2,3-d]pyriMidin-5-yl}ethyl)phenyl]forMaMido}pentanedioic acid N-(4- 2-(2-AMino-4,7-Dihydro-4-oxo-1H-pyrrol... PeMetrexed disodiuM INT-6 (S)-2-(4-(2-(2-AMino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyriMidin-5-yl)ethyl)benzaMido)pentanedioic acid The sour sour of the United States Pemetrexed Hydrate Pemetrexed - Labeled 15N,13C5 (R)-Pemetrexed (S)-2-(4-(2-(2-Amino-4-oxo-4,7-dihydro-1H-pyrrolo-[2,3-d]pyrimidin-5-yl)ethyl)benzamido)pentan PEMETREXED ACID PEMETREXED N-(4-[2-(2-Amino-4,7-Dihydro-4-oxo-1H-pyrrolo)[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-Gluamic Acid Pemetrexed99% L-Glutamic acid, N-[4-[2-(2-amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]- N-[4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid disodium salt PEFLOXACINMESYLATE Premetred disodium Pemetrexedum Premetred PemetrexedHydrate> (S)-2-(4-(2-(2-Amino-4-oxo-4,7-dihydro-3H-pyrroL )benzamido)pentanedioic acid 3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid disodium salt N-[4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidi... PemetrexedQ: What is Pemetrexed Q: What is the CAS Number of Pemetrexed Q: What is the storage condition of Pemetrexed Q: What are the applications of Pemetrexed Pemetrexedaci Pemetrexed, 10 mM in DMSO Pemetrexed - Bio-X ? Pemetrexed (Standard) (S)-2-(4-(2-(2-AMino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyriMidin-5-yl)ethyl)benzaMido)pentanedioic acid 137281-23-3 C20H21N5O6xH2O Anti-cancer & immunity API CIALIS