KETOTREXATE

Details

Stereochemistry	EPIMERIC
Molecular Formula	C21H27N7O6
Molecular Weight	473.4824
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1C(CCNC2=CC=C(C=C2)C(=O)N[C@@H](CCC(O)=O)C(O)=O)CNC3=C1C(=O)N=C(N)N3

InChI

InChIKey=KCPBTDJBDDCNQE-KZUDCZAMSA-N

InChI=1S/C21H27N7O6/c1-28-13(10-24-17-16(28)19(32)27-21(22)26-17)8-9-23-12-4-2-11(3-5-12)18(31)25-14(20(33)34)6-7-15(29)30/h2-5,13-14,23H,6-10H2,1H3,(H,25,31)(H,29,30)(H,33,34)(H4,22,24,26,27,32)/t13?,14-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C21H27N7O6
Molecular Weight	473.4824
Charge	0
Count

Stereochemistry	EPIMERIC
Additional Stereochemistry	No
Defined Stereocenters	1 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3312079 | https://www.ncbi.nlm.nih.gov/pubmed/6848202

KETOTREXATE is an antifolate developed to overcome methotrexate (MTX) resistance. However, it demonstrated such potential only in MTX-resistant sensitive L1210/FR8 leukemia cells and its clinical development was discontinued. Unlike MTX, KETOTREXATE exhibited minimal inhibition of purified dihydrofolate reductase, which implies that it does not act as a classical antifolate.

Approval Year

PubMed

Title	Date	PubMed
Disposition of 5-methyltetrahydrohomofolate in mice, dogs, and monkeys.	1979 Feb	109197
Disposition of 5-methyltetrahydrohomofolate and methotrexate in rats.	1981 Jan-Feb	7226160
Clinical pharmacokinetics of 5-methyltetrahydrohomofolate.	1983 Feb	6848202
5-Methyltetrahydrohomofolate.	1987	3312079

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:45:43 GMT 2023` Edited by `admin` on `Fri Dec 15 15:45:43 GMT 2023`
Record UNII	504RN634MM
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

KETOTREXATE

Official Name

English

N-(P-((2-(2-AMINO-1,4,5,6,7,8-HEXAHYDRO-5-METHYL-4-OXO-6-PTERIDINYL)ETHYL)AMINO)BENZOYL)-L-GLUTAMIC ACID

Common Name

English

N-(4-((2-(2-AMINO-1,4,5,6,7,8-HEXAHYDRO-5-METHYL-4-OXO-6-PTERIDINYL)ETHYL)AMINO)BENZOYL)GLUTAMIC ACID

Systematic Name

English

ketotrexate [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C511