| Identification | More | [Name]
Raltitrexed | [CAS]
112887-68-0 | [Synonyms]
RALTITREXED
(s)-2-[(1-{5-[methyl-(2-methyl-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-amino]-thiophen-2-yl}-methanoyl)-amino]-pentanedioic acid
ICI-D-1694
N-[[5-[[(1,4-Dihydro-2-methyl-4-oxo-6-quinazolinyl)methyl]methylamino]-2-thienyl]carbonyl]-L-glutamic Acid
Tomudex
ZD-1694
L-Glutamic acid, N-[[5-[[(3,4-dihydro-2-methyl-4-oxo-6-quinazolinyl)methyl]methylamino]-2-thienyl]carbonyl]-
(S)-2-[(1-{5-[Methyl-(2-methyl-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-amino]-thiophen-2-yl}-methanoyl)-amino]-pentanedioic acid
(S)-2-(5-(METHYL((2-METHYL-4-OXO-3,4-DIHYDROQUINAZOLIN-6-YL)METHYL)AMINO)THIOPHENE-2-CARBOXAMIDO)PENTANEDIOIC ACID
4-nitro-2-thiohenic acid
(2S)-2-[5-[N-Methyl-N-[[(3,4-dihydro-2-methyl-4-oxoquinazolin)-6-yl]methyl]amino]-2-thienylcarbonylamino]glutaric acid
(S)-2-[5-[N-Methyl-N-[[(3,4-dihydro-2-methyl-4-oxoquinazolin)-6-yl]methyl]amino]-2-thienylcarbonylamino]glutaric acid
ZEN-D-1694 | [EINECS(EC#)]
652-997-2 | [Molecular Formula]
C21H22N4O6S | [MDL Number]
MFCD00864168 | [Molecular Weight]
458.49 | [MOL File]
112887-68-0.mol |
| Chemical Properties | Back Directory | [Appearance]
Yellow Crystalline Powder | [Melting point ]
176-1800C | [density ]
1.49±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
H2O: ≥10mg/mL | [form ]
solid | [pka]
3.50±0.10(Predicted) | [color ]
off-white to light yellow | [Usage]
Folate-based inhibitor of thymidylate synthase; rapidly and extensively metabolized to its more potent polyglutamate derivatives. Antineoplastic | [InChIKey]
IVTVGDXNLFLDRM-HNNXBMFYSA-N | [CAS DataBase Reference]
112887-68-0(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/38:Irritating to eyes and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection . | [RIDADR ]
UN 2811 6.1 / PGIII | [WGK Germany ]
2 | [HS Code ]
2934.99.4700 |
| Hazard Information | Back Directory | [Description]
Tomudex was launched in Ireland, France, Luxembourg and the UK for
advanced 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 enzyme
in the biochemical conversion of dUMP to dTMP. It enters the cell via the reduced
folatefmethotrexate cell membrane carrier and is converted to the polyglutamate
species by folylpolyglutamate synthase within 4h where it then binds to the folate
substrate site of TS. Clinically, it had a 29% response rate in patients with advanced
colorectal cancer. It is water soluble, can be administered as a single dose every
three weeks and had no hepto- or nephrotoxicity. | [Chemical Properties]
Yellow Crystalline Powder | [Originator]
Zeneca (UK) | [Uses]
Folate-based inhibitor of thymidylate synthase; rapidly and extensively metabolized to its more potent polyglutamate derivatives. Antineoplastic | [Definition]
ChEBI: ICI D1694 is a N-acyl-amino acid. | [Brand name]
Tomudex (Zeneca). | [Biochem/physiol Actions]
Raltitrexed is a folate-based inhibitor of thymidylate synthase (TS) that is rapidly and extensively metabolized to its more potent polyglutamate derivatives. By inhibiting the formation of precursor pyrimidine nucleotides, raltitrexed prevents the formation of DNA and RNA, which are required for the growth and survival of both normal cells and cancer cells. | [Clinical Use]
Treatment of colorectal cancer when fluorouracil and
folinic acid cannot be used | [Drug interactions]
Potentially hazardous interactions with other drugs
Antipsychotics: avoid with clozapine, increased risk
of agranulocytosis.
Folic and folinic acid: impairs cytotoxic action -
avoid. | [Metabolism]
Raltitrexed is actively transported into cells and
metabolised to active polyglutamate forms.
The remainder of a dose is not metabolised and is
excreted unchanged, about 50% of a dose appearing in the
urine, and about 15% in the faeces. | [storage]
Store at -20°C |
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