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Oncology and immunology drugs

Pemetrexed

Also known as Pemfexy, N-(4-(2-(2-Amino-3,4-dihydro-4-oxo-7H-pyrrolo(2,3-d)pyrimdin-5-yl)ethyl)benzoyl)glutamic acid, N-{4-[2-(2-amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamic acid

CAS 137281-23-3Formula C20H21N5O6Molar mass 427.42 g/molEC 680-625-9
GHS signal word: Danger. Pictograms: Harmful or irritant, Serious health hazard 70 suppliers listed Drug substance
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Pemetrexed chemical structure, C20H21N5O6, CAS 137281-23-3
2D chemical structure

Key facts

What buyers check first

All properties
CAS number
137281-23-3
Formula
C20H21N5O6
Molar mass
427.42 g/mol
Appearance
Crystals from 50% methanol/methylene chloride
HS code
293359
Category
Oncology and immunology drugs
Illustrative photo, closed white HDPE bottles and amber jars on a laboratory bench
Typical packagingIllustrative packaging image, not the actual product

What is Pemetrexed?

Plain description, key identifiers and synonyms

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 antimetabolite, an antineoplastic agent, an EC 1.5.1.3 (dihydrofolate reductase) inhibitor, an EC 2.1.1.45 (thymidylate synthase) inhibitor and an EC 2.1.2.2 (phosphoribosylglycinamide formyltransferase) inhibitor. It is a N-acyl-L-glutamic acid and a pyrrolopyrimidine. It is a conjugate acid of a pemetrexed(2-).

Identifiers

Registry numbers, names and line notations, tap to copy

IUPAC name
(2S)-2-[[4-[2-(2-amino-4-oxo-3,7-dihydropyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]amino]pentanedioic acid
CAS number
137281-23-3 CAS number cross-checkedOther or deprecated CAS: 1006872-74-7
EC number
680-625-9
Molecular formula
C20H21N5O6
UNII
04Q9AIZ7NO
MDL number
MFCD19105065
InChIKey
WBXPDJSOTKVWSJ-ZDUSSCGKSA-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-/m0/s1
Canonical SMILES
Nc1nc2[nH]cc(CCc3ccc(C(=O)NC(CCC(=O)O)C(=O)O)cc3)c2c(=O)[nH]1
Isomeric SMILES
C1=CC(=CC=C1CCC2=CNC3=C2C(=O)NC(=N3)N)C(=O)N[C@@H](CCC(=O)O)C(=O)O

Synonyms

  • Pemfexy
  • N-(4-(2-(2-Amino-3,4-dihydro-4-oxo-7H-pyrrolo(2,3-d)pyrimdin-5-yl)ethyl)benzoyl)glutamic acid
  • N-{4-[2-(2-amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamic acid
  • Pemetrexed Sodium
  • L-Glutamic acid, N-(4-(2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo(2,3-d)pyrimidin-5-yl)ethyl)benzoyl)-
  • pemetrexedum
  • N-(4-(2-(2-amino-4-oxo-4,7-dihydro-1H-pyrrolo(2,3-d)pyrimidin-5-yl)ethyl)benzoyl)-L-glutamic acid
  • AXTLE
  • Multitargeted Antifolate
  • Pemetrexed for injection
  • (2R)-2-((4-(2-(2-amino-4-oxo-1,7-dihydropyrrolo(4,5-e)pyrimidin-5-yl)ethyl)benzoyl)amino)pentanedioic acid
  • 231514, LY
  • LY-231,514
  • 231,514, LY
  • L-Glutamic Acid, N-(4-(2-(2-Amino-4,7-dihydro-4-oxo-1H-pyrrolo(2,3-d)pyrimidin-5-yl)ethyl)benzoyl)
  • Alimta
  • (S)-2-(4-(2-(2-Amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzamido)pentanedioic acid
  • N-[4-[2-(2-amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid
  • 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
  • Pemetrexed (INN)
  • (2S)-2-[[4-[2-(2-amino-4-oxo-3,7-dihydropyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]amino]pentanedioic acid
  • 2-{4-[2-(2-Amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)-ethyl]-benzoylamino}-pentanedioic acid
  • N-[4-[2-(2-amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamicacid
  • (2S)-2-{[4-(2-{2-amino-4-oxo-3H,4H,7H-pyrrolo[2,3-d]pyrimidin-5-yl}ethyl)phenyl]formamido}pentanedioic acid
Show all 35 synonyms
  • LYA
  • 1juj
  • Pemetrexed Hydrate
  • Pemetrexed (TN)
  • (S)-2-[4-[2-(2-Amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzamido]pentanedioic Acid
  • 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
  • N-(4-[2-(2-amino-4,7-Dihydro-4-Oxo-1H-Pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl)-L-Glutamic Acid
  • Pemfexy (TN)
  • Pemetrexed (Standard)

Physical and chemical properties

Measured values and descriptors computed from the structure

Physical and chemical properties

Measured values, check the supplier specification for your grade

Appearance
Crystals from 50% methanol/methylene chlorideexp.
Vapour pressure
6 × 10⁻²¹ mm Hg at 25 °C at 25 °C /Estimated/exp.

Values vary by grade. Ask suppliers for the COA or TDS of the batch you buy.

Computed descriptors

Calculated from the structure, useful for screening and formulation

Molecular weight
427.42 g/molcalc.
Exact mass
427.1492 Dacalc.
LogP (octanol/water)
0.67calc.
Topological polar surface area
191.3 Ųcalc.
Hydrogen bond donors
6calc.
Hydrogen bond acceptors
6calc.
Rotatable bonds
9calc.
Heavy atoms
31calc.
Rings
3calc.
Aromatic rings
3calc.
Fraction sp3 carbons
0.25calc.
Formal charge
0calc.
Stereocentres
1calc.
Lipinski rule of five
Passes (1 violation)calc.

Calculated for screening. Confirm critical figures with the supplier.

Murcko scaffold

The ring system that remains when every side chain is removed

Murcko scaffold of this chemical, O=c1nc[nH]c2[nH]cc(CCc3ccccc3)c12

O=c1nc[nH]c2[nH]cc(CCc3ccccc3)c12

3 rings, 18 atoms.

37 other chemicals share this scaffold

Safety and hazards

GHS classification summary, not a safety data sheet

GHS signal word
Danger
GHS07: Harmful or irritant
Harmful or irritant
GHS08: Serious health hazard
Serious health hazard

Hazard statements

  • H302Harmful if swallowed.
  • H341Suspected of causing genetic defects.
  • H351Suspected of causing cancer.
  • H360May damage fertility or the unborn child.
Precautionary statements (9)
  • P203Obtain, read and follow all safety instructions before use.
  • P264Wash skin thoroughly after handling.
  • P270Do not eat, drink or smoke when using this product.
  • P280Wear protective gloves, protective clothing, eye protection and face protection.
  • P301 + P317If swallowed: Get medical help.
  • P318If exposed or concerned, get medical advice.
  • P330Rinse mouth.
  • P405Store locked up.
  • P501Dispose of contents and container in accordance with local regulations.

GHS classification summary, not a safety data sheet (SDS). Classifications can differ by supplier, grade and concentration. Always check the supplier's SDS.

Full safety data and first aid

Pemetrexed suppliers

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Where suppliers are based

70 suppliers in 16 countries

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Pemetrexed price

Indicative price range per kg from live supplier offers

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Uses and applications

What the substance is used for, by industry and function

Medication: Antineoplastic.

Pharmacological actions

  • Antineoplastic Agents
  • Enzyme Inhibitors
  • Folic Acid Antagonists
  • Nucleic Acid Synthesis Inhibitors

Roles

  • antifibrotic agent
  • antifolate
  • antimetabolite
  • antineoplastic agent
  • enzyme inhibitor
  • pharmaceutical

Pharmacology

Pemetrexed is a Folate Analog Metabolic Inhibitor. The mechanism of action of pemetrexed is as a Folic Acid Metabolism Inhibitor.

How it is made

Preparation: E.C. Taylor et al., EP 432677, idem, US 5344932 (1991, 1994 both to Trustees Princeton University)

Regulatory status

Inventories, regulations and trade controls that list this substance

Health and food

  • Active ingredient in FDA approved drug labels

HS code and trade data

Customs classification and reported world trade statistics

Global trade

World import and export statistics for the HS code Pemetrexed is traded under.

HS 2933.59Indicative HS code

Compounds containing a pyrimidine ring (whether or not hydrogenated) or piperazine ring, other

World exports in 2024
$18.4B
+10.5% vs 2023, imports $24.8B
2019 to 2024
Top exporters
  1. Ireland43.6%
  2. Switzerland * partner reported26.3%
  3. China7.9%
Top importers
  1. Slovenia30.3%
  2. United States30.1%
  3. Germany15.3%

* Partner reported figures, a lower bound.

Reported customs values in USD, not prices.Full trade data

The HS code shown for Pemetrexed is indicative (it was assigned by structure rules). Confirm the classification with your customs broker before shipping.

Frequently asked questions

Quick answers about Pemetrexed, based on the data on this page

What is Pemetrexed?

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).

What is the CAS number of Pemetrexed?

The CAS registry number of Pemetrexed is 137281-23-3. Other or deprecated CAS numbers: 1006872-74-7.

What is the molecular formula and weight of Pemetrexed?

The molecular formula of Pemetrexed is C20H21N5O6 and its molar mass is 427.42 g/mol.

What is Pemetrexed used for?

Medication: Antineoplastic.

Is Pemetrexed hazardous?

Pemetrexed carries the GHS signal word "Danger". Main hazards: harmful if swallowed, suspected of causing genetic defects, suspected of causing cancer. This summary is not an SDS, always read the supplier safety data sheet.

What is the HS code of Pemetrexed?

Pemetrexed is usually classified under HS code 293359 (Compounds containing a pyrimidine ring (whether or not hydrogenated) or piperazine ring…). This is indicative, confirm it with your customs broker before shipping.

Where can I buy Pemetrexed?

CompoundList lists 70 suppliers of Pemetrexed in United States, China, United Kingdom, Germany and 12 more. Send one free request to get and compare quotes. Your contact details stay private until you accept a quote.

What is the price of Pemetrexed?

Suppliers quote Pemetrexed on request because prices depend on grade, purity, quantity and destination. A free request on CompoundList gets you several quotes to compare.

Guides for buyers

Practical guides that help when you source, ship or handle Pemetrexed

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Data last updated 7 Oct 2026. Details may have changed, please confirm them with the supplier. Report an error on this page
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