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Revision as of 03:36, 22 October 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{drugbox}} (changes to verified fields - updated 'ChEBI_Ref', 'CAS_number_Ref') per Chem/Drugbox validation (report errors or bugs)← Previous edit Latest revision as of 23:10, 1 April 2023 edit undoEntranced98 (talk | contribs)Extended confirmed users, Pending changes reviewers, Rollbackers174,388 edits Importing Wikidata short description: "Chemical compound"Tag: Shortdesc helper 
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{{Short description|Chemical compound}}
{{Drugbox {{Drugbox
⚫ | verifiedrevid = 470615984
| Verifiedfields = changed
⚫ | verifiedrevid = 414586053
| IUPAC_name = 5-methyl-6- quinazoline-2,4-diamine | IUPAC_name = 5-methyl-6- quinazoline-2,4-diamine
| image = Trimetrexate.svg | image = Trimetrexate.svg
| width = 250

<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename =
| Drugs.com = {{drugs.com|CDI|trimetrexate}} | Drugs.com = {{drugs.com|CDI|trimetrexate}}
| MedlinePlus = a694019 | MedlinePlus = a694019
| pregnancy_category = | pregnancy_category =
| legal_status = | legal_status =
| routes_of_administration = | routes_of_administration =

<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability = VD: 20-30 Liters | bioavailability = VD: 20-30 Liters
| protein_bound = | protein_bound =
| metabolism = Oxidative O-demethylation, followed by conjugation with glucuronide or sulfate | metabolism = Oxidative O-demethylation, followed by conjugation with glucuronide or sulfate
| elimination_half-life = 11 to 12 hours | elimination_half-life = 11 to 12 hours

<!--Identifiers--> <!--Identifiers-->
| IUPHAR_ligand = 7613
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 52128-35-5 | CAS_number = 52128-35-5
| ATC_prefix = P01 | ATC_prefix = P01
| ATC_suffix = AX07 | ATC_suffix = AX07
| ATC_supplemental = | ATC_supplemental =
| PubChem = 5583 | PubChem = 5583
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = APRD00268 | DrugBank = DB01157
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5381 | ChemSpiderID = 5381
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = UPN4ITI8T4 | UNII = UPN4ITI8T4
| KEGG_Ref = {{keggcite|changed|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D06238 | KEGG = D06238
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 119 | ChEMBL = 119

<!--Chemical data--> <!--Chemical data-->
| C=19 | H=23 | N=5 | O=3 | C=19 | H=23 | N=5 | O=3
| molecular_weight = 369.418 g/mol
| smiles = n3c1c(c(c(cc1)CNc2cc(OC)c(OC)c(OC)c2)C)c(nc3N)N | smiles = n3c1c(c(c(cc1)CNc2cc(OC)c(OC)c(OC)c2)C)c(nc3N)N
| InChI = 1/C19H23N5O3/c1-10-11(5-6-13-16(10)18(20)24-19(21)23-13)9-22-12-7-14(25-2)17(27-4)15(8-12)26-3/h5-8,22H,9H2,1-4H3,(H4,20,21,23,24)
| InChIKey = NOYPYLRCIDNJJB-UHFFFAOYAI
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C19H23N5O3/c1-10-11(5-6-13-16(10)18(20)24-19(21)23-13)9-22-12-7-14(25-2)17(27-4)15(8-12)26-3/h5-8,22H,9H2,1-4H3,(H4,20,21,23,24) | StdInChI = 1S/C19H23N5O3/c1-10-11(5-6-13-16(10)18(20)24-19(21)23-13)9-22-12-7-14(25-2)17(27-4)15(8-12)26-3/h5-8,22H,9H2,1-4H3,(H4,20,21,23,24)
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}} }}


'''Trimetrexate''' is a ] derivative. It is a ].<ref name="pmid1981548">{{cite journal |author=Wong BK, Woolf TF, Chang T, Whitfield LR |title=Metabolic disposition of trimetrexate, a nonclassical dihydrofolate reductase inhibitor, in rat and dog |journal=Drug Metab. Dispos. |volume=18 |issue=6 |pages=980–6 |year=1990 |pmid=1981548 |doi= |url=http://dmd.aspetjournals.org/cgi/pmidlookup?view=long&pmid=1981548}}</ref> '''Trimetrexate''' is a ] derivative. It is a ].<ref name="pmid1981548">{{cite journal |vauthors =Wong BK, Woolf TF, Chang T, Whitfield LR |title=Metabolic disposition of trimetrexate, a nonclassical dihydrofolate reductase inhibitor, in rat and dog |journal=Drug Metab. Dispos. |volume=18 |issue=6 |pages=980–6 |year=1990 |pmid=1981548 |url=http://dmd.aspetjournals.org/cgi/pmidlookup?view=long&pmid=1981548}}</ref>


==Uses== ==Uses==
It has been used with ] in treating ].<ref name="pmid2136905">{{cite journal |author=Sattler FR, Allegra CJ, Verdegem TD, ''et al.'' |title=Trimetrexate-leucovorin dosage evaluation study for treatment of Pneumocystis carinii pneumonia |journal=J. Infect. Dis. |volume=161 |issue=1 |pages=91–6 |year=1990 |month=January |pmid=2136905 |doi= |url=}}</ref> It has been used with ] in treating ].<ref name="pmid2136905">{{cite journal |vauthors=Sattler FR, Allegra CJ, Verdegem TD, etal |title=Trimetrexate-leucovorin dosage evaluation study for treatment of Pneumocystis carinii pneumonia |journal=J. Infect. Dis. |volume=161 |issue=1 |pages=91–6 |date=January 1990 |pmid=2136905 |doi= 10.1093/infdis/161.1.91}}</ref>


It has been investigated for use in treating ].<ref name="pmid11748990">{{cite journal |author=Smith HO, Blessing JA, Vaccarello L |title=Trimetrexate in the treatment of recurrent or advanced leiomyosarcoma of the uterus: a phase II study of the Gynecologic Oncology Group |journal=Gynecol. Oncol. |volume=84 |issue=1 |pages=140–4 |year=2002 |month=January |pmid=11748990 |doi=10.1006/gyno.2001.6482 |url=http://linkinghub.elsevier.com/retrieve/pii/S0090825801964820}}</ref> It has been investigated for use in treating ].<ref name="pmid11748990">{{cite journal |vauthors =Smith HO, Blessing JA, Vaccarello L |title=Trimetrexate in the treatment of recurrent or advanced leiomyosarcoma of the uterus: a phase II study of the Gynecologic Oncology Group |journal=Gynecol. Oncol. |volume=84 |issue=1 |pages=140–4 |date=January 2002 |pmid=11748990 |doi=10.1006/gyno.2001.6482 }}</ref>
It is a methotrexate (MTX) analog that is active against transport-deficient MTX-resistant tumor cells that overcome the acquired and natural resistance to methotrexate. Other uses include skin lymphoma. <ref>Trimetrexate in relapsed T-cell lymphoma with skin involvement. J Clin Oncol. 2002 Jun 15;20(12):2876-80.</ref> It is a ] (MTX) analog that is active against transport-deficient MTX-resistant tumor cells that overcome the acquired and natural resistance to methotrexate. Other uses include skin lymphoma. <ref>Trimetrexate in relapsed T-cell lymphoma with skin involvement. J Clin Oncol. 2002 Jun 15;20(12):2876-80.</ref>


==References== ==References==
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] ]
] ]
]
]
] ]
] ]

Latest revision as of 23:10, 1 April 2023

Chemical compound Pharmaceutical compound
Trimetrexate
Clinical data
AHFS/Drugs.comConsumer Drug Information
MedlinePlusa694019
ATC code
Pharmacokinetic data
BioavailabilityVD: 20-30 Liters
MetabolismOxidative O-demethylation, followed by conjugation with glucuronide or sulfate
Elimination half-life11 to 12 hours
Identifiers
IUPAC name
  • 5-methyl-6- quinazoline-2,4-diamine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H23N5O3
Molar mass369.425 g·mol
3D model (JSmol)
SMILES
  • n3c1c(c(c(cc1)CNc2cc(OC)c(OC)c(OC)c2)C)c(nc3N)N
InChI
  • InChI=1S/C19H23N5O3/c1-10-11(5-6-13-16(10)18(20)24-19(21)23-13)9-22-12-7-14(25-2)17(27-4)15(8-12)26-3/h5-8,22H,9H2,1-4H3,(H4,20,21,23,24)
  • Key:NOYPYLRCIDNJJB-UHFFFAOYSA-N
  (verify)

Trimetrexate is a quinazoline derivative. It is a dihydrofolate reductase inhibitor.

Uses

It has been used with leucovorin in treating pneumocystis pneumonia.

It has been investigated for use in treating leiomyosarcoma. It is a methotrexate (MTX) analog that is active against transport-deficient MTX-resistant tumor cells that overcome the acquired and natural resistance to methotrexate. Other uses include skin lymphoma.

References

  1. Wong BK, Woolf TF, Chang T, Whitfield LR (1990). "Metabolic disposition of trimetrexate, a nonclassical dihydrofolate reductase inhibitor, in rat and dog". Drug Metab. Dispos. 18 (6): 980–6. PMID 1981548.
  2. Sattler FR, Allegra CJ, Verdegem TD, et al. (January 1990). "Trimetrexate-leucovorin dosage evaluation study for treatment of Pneumocystis carinii pneumonia". J. Infect. Dis. 161 (1): 91–6. doi:10.1093/infdis/161.1.91. PMID 2136905.
  3. Smith HO, Blessing JA, Vaccarello L (January 2002). "Trimetrexate in the treatment of recurrent or advanced leiomyosarcoma of the uterus: a phase II study of the Gynecologic Oncology Group". Gynecol. Oncol. 84 (1): 140–4. doi:10.1006/gyno.2001.6482. PMID 11748990.
  4. Trimetrexate in relapsed T-cell lymphoma with skin involvement. J Clin Oncol. 2002 Jun 15;20(12):2876-80.

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