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Home> Encyclopedia >Antineoplastic Agents>Pharmaceutical Intermediates>Organic Intermediate
Raltitrexed structure
Raltitrexed structure

Raltitrexed

Iupac Name:(2S)-2-[[5-[methyl-[(2-methyl-4-oxo-1H-quinazolin-6-yl)methyl]amino]
thiophene-2-carbonyl]amino]pentanedioic acid
CAS No.: 112887-68-0
Molecular Weight:458.48758
Modify Date.: 2022-11-22 17:09
Introduction: Tomudex was launched in Ireland, France, Luxembourg and the UK foradvanced colorectal cancer and it was prepared in a convergent manner (6 steps)from diethyl L-glutamate and 6-bromomethyi-2-methyl-quinazolin4(3H)-one.Tomudex is a highly selective inhibitor of thymidylate synthase (TS), the key enzymein the biochemical conversion of dUMP to dTMP. It enters the cell via the reducedfolatefmethotrexate cell membrane carrier and is converted to the polyglutamatespecies by folylpolyglutamate synthase within 4h where it then binds to the folatesubstrate site of TS. Clinically, it had a 29% response rate in patients with advancedcolorectal cancer. It is water soluble, can be administered as a single dose everythree weeks and had no hepto- or nephrotoxicity. View more+
1. Names and Identifiers
1.1 Name
Raltitrexed
1.2 Synonyms

(S)-2-(5-(METHYL((2-METHYL-4-OXO-3,4-DIHYDROQUINAZOLIN-6-YL)METHYL)AMINO)THIOPHENE-2-CARBOXAMIDO)PENTANEDIOIC ACID (s)-2-[(1-{5-[methyl-(2-methyl-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-amino]-thiophen-2-yl}-methanoyl)-amino]-pentanedioic acid D 1694 ICI-D 1694 ICI-D-1694 L-Glutamic acid, N-[[5-[[(1,4-dihydro-2-methyl-4-oxo-6-quinazolinyl)methyl]methylamino]-2-thienyl]carbonyl]- L-Glutamic acid, N-[[5-[[(3,4-dihydro-2-methyl-4-oxo-6-quinazolinyl)methyl]methylamino]-2-thienyl]carbonyl]- N-[[5-[[(1,4-Dihydro-2-methyl-4-oxo-6-quinazolinyl)methyl]methylamino]-2-thienyl]carbonyl]-L-glutamic Acid N-[[5-[[(3,4-Dihydro-2-methyl-4-oxo-6-quinazolinyl)methyl]methylamino]-2-thienyl]carbonyl]-L-glutamic acid TDX Tomudex ZD 1694 ZD-1694

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1.3 CAS No.
112887-68-0
1.4 CID
135400182
1.5 EINECS(EC#)
1533716-785-6
1.6 Molecular Formula
C21H22N4O6S (isomer)
1.7 Inchi
InChI=1S/C21H22N4O6S/c1-11-22-14-4-3-12(9-13(14)19(28)23-11)10-25(2)17-7-6-16(32-17)20(29)24-15(21(30)31)5-8-18(26)27/h3-4,6-7,9,15H,5,8,10H2,1-2H3,(H,24,29)(H,26,27)(H,30,31)(H,22,23,28)/t15-/m0/s1
1.8 InChIkey
IVTVGDXNLFLDRM-HNNXBMFYSA-N
1.9 Canonical Smiles
CC1=NC2=C(C=C(C=C2)CN(C)C3=CC=C(S3)C(=O)NC(CCC(=O)O)C(=O)O)C(=O)N1
1.10 Isomers Smiles
CC1=NC2=C(C=C(C=C2)CN(C)C3=CC=C(S3)C(=O)N[C@@H](CCC(=O)O)C(=O)O)C(=O)N1
2. Properties
2.1 Density
1.49 g/cm3
2.1 Melting point
176-1800C
2.1 Boiling point
°Cat760mmHg
2.1 Refractive index
1.638
2.1 Flash Point
°C
2.1 Precise Quality
458.12600
2.1 PSA
180.93000
2.1 logP
2.36810
2.1 Solubility
H2O: ≥10mg/mL
2.2 Appearance
off-white to light yellow
2.3 Storage
Hygroscopic, -20°C Freezer, Under Inert Atmosphere
2.4 Chemical Properties
Yellow Crystalline Powder
2.5 Color/Form
off-white to light yellow
2.6 pKa
3.50±0.10(Predicted)
2.7 Water Solubility
H2O: ≥10mg/mL
2.8 StorageTemp
<0°C
3. Use and Manufacturing
3.1 Usage
Folate-based inhibitor of thymidylate synthase; rapidly and extensively metabolized to its more potent polyglutamate derivatives. Antineoplastic
4. Safety and Handling
4.1 Hazard Codes
Xi
4.1 Risk Statements
R36/38
4.1 Safety Statements
S26;S37/39
4.1 Hazard Class
8
4.1 Hazard Declaration
H341
4.1 RIDADR
UN 2811 6.1 / PGIII
4.1 Caution Statement
P201, P202, P281, P308+P313, P405, P501
4.1 WGK Germany
3
4.1 Safety

Hazard Codes:? Xi
Risk Statements:
36/38: Irritating to eyes and skin?
The Safety Statements information of? Raltitrexed:
37/39: Wear suitable gloves and eye/face protection

4.2 Specification

? Raltitrexed , with CAS number of 112887-68-0, can be called L-glutamic acid, N-[[5-[[(1,4-dihydro-2-methyl-4-oxo-6-quinazolinyl)methyl]methylamino]-2-thienyl]carbonyl]- ; L-glutamic acid, N-[[5-[[(3,4-dihydro-2-methyl-4-oxo-6-quinazolinyl)methyl]methylamino]-2-thienyl]carbonyl]- ; N-(5-[N-(3,4-dihydro-2-methyl-4-oxoquinazolin-6-ylmethyl)-N-methylamino]-2-thenoyl)-L-glutamic acid ; N-[(5-{Methyl[(2-methyl-4-oxo-3,4-dihydroquinazolin-6-yl)methyl]amino}-2-thienyl)carbonyl]-L-glutamic acid , it is a yellow crystalline powder. It is a?Folate-based inhibitor of thymidylate synthase; rapidly and extensively metabolized to its more potent polyglutamate derivatives.

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Germ cell mutagenicity, Category 2

Reproductive toxicity, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Warning

Hazard statement(s)

H341 Suspected of causing genetic defects

H361 Suspected of damaging fertility or the unborn child

Precautionary statement(s)
Prevention

P201 Obtain special instructions before use.

P202 Do not handle until all safety precautions have been read and understood.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

Response

P308+P313 IF exposed or concerned: Get medical advice/ attention.

Storage

P405 Store locked up.

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

8. Other Information
8.0 Chemical Properties
Yellow Crystalline Powder
8.1 Uses
Folate-based inhibitor of thymidylate synthase; rapidly and extensively metabolized to its more potent polyglutamate derivatives. Antineoplastic
8.2 Brand name
Tomudex (Zeneca).
9. Computational chemical data
  • Molecular Weight: 458.48758g/mol
  • Molecular Formula: C21H22N4O6S
  • Compound Is Canonicalized: True
  • XLogP3-AA: 1.4
  • Exact Mass: 458.12600561
  • Monoisotopic Mass: 458.12600561
  • Complexity: 790
  • Rotatable Bond Count: 9
  • Hydrogen Bond Donor Count: 4
  • Hydrogen Bond Acceptor Count: 9
  • Topological Polar Surface Area: 177
  • Heavy Atom Count: 32
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
  • CACTVS Substructure Key Fingerprint: AAADceB7uABAAAAAAAAAAAAAAAAAASAAAAAwQAAAAAAAAACBwAAAHgQQCAAADCjB2AQzyYPAAgisAifyfACDAIFlChhJiJmYZMgKIDrg3bGEYYhklgD4yce8r0COCAACAAACAAAQAAQAAAQAAAAAAAAAAA==
10. Question & Answer
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