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.
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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
6. Synthesis Route
112887-68-0Total: 14 Synthesis Route
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
-
Raltitrexed is a chemical substance and a medication commonly used in clinical practice to treat colon or rectal cancer. It has remarkable therapeutic effects. However, to ensure its safe use, it is i..
-
Raltitrexed can be used as a first-line treatment for advanced colorectal cancer. It can be used as a monotherapy for patients who are not suitable for 5-Fu/calcium folinate combination chemotherapy. ..
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