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MedKoo Cat#: 581343 | Name: Etoprine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Etoprine has the contraceptive effects The antifertility action of etoprine may be related to its capacity to inhibit testicular DHFR and its high degree of lipophilicity.

Chemical Structure

Etoprine
Etoprine
CAS#18588-57-3

Theoretical Analysis

MedKoo Cat#: 581343

Name: Etoprine

CAS#: 18588-57-3

Chemical Formula: C12H12Cl2N4

Exact Mass: 282.0439

Molecular Weight: 283.16

Elemental Analysis: C, 50.90; H, 4.27; Cl, 25.04; N, 19.79

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Etoprine; DDEP; Ethodichlorophen;
IUPAC/Chemical Name
2,4-Diamino-5-(3,4-dichlorophenyl)-6-ethylpyrimidine
InChi Key
PXLPCZJACKUXGP-UHFFFAOYSA-N
InChi Code
InChI=1S/C12H12Cl2N4/c1-2-9-10(11(15)18-12(16)17-9)6-3-4-7(13)8(14)5-6/h3-5H,2H2,1H3,(H4,15,16,17,18)
SMILES Code
CCC1=C(C2=CC=C(Cl)C(Cl)=C2)C(N)=NC(N)=N1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 283.16 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Han XM, Lee G, Hefner C, Maher JJ, Correia MA. Heme-reversible impairment of CYP2B1/2 induction in heme-depleted rat hepatocytes in primary culture: translational control by a hepatic alpha-subunit of the eukaryotic initiation factor kinase? J Pharmacol Exp Ther. 2005 Jul;314(1):128-38. Epub 2005 Mar 15. Erratum in: J Pharmacol Exp Ther. 2005 Nov;315(2):970. PubMed PMID: 15769864. 2: McNamee JP, Jurima-Romet M, Kobus SM, Marks GS. cDNA-expressed human cytochrome P450 isozymes. Inactivation by porphyrinogenic xenobiotics. Drug Metab Dispos. 1997 Apr;25(4):437-41. PubMed PMID: 9107543. 3: Pills, shots, implants, vaccines: can the elusive sperm be reined in? Male contraceptive research extremely slow, but promising. Contracept Technol Update. 1995 Aug;16(8):93-8. PubMed PMID: 12290717. 4: Malik NS, Matlin SA, Fried J, Pakyz RE, Consentino MJ. The contraceptive effects of etoprine on male mice and rats. J Androl. 1995 Mar-Apr;16(2):169-74. PubMed PMID: 7559148. 5: Kennedy CH, Mason RP. A reexamination of the cytochrome P-450-catalyzed free radical production from a dihydropyridine. Evidence of trace transition metal catalysis. J Biol Chem. 1990 Jul 15;265(20):11425-8. PubMed PMID: 2164003. 6: Sugiyama K, Yao K, Rettie AE, Correia MA. Inactivation of rat hepatic cytochrome P-450 isozymes by 3,5-dicarbethoxy- 2,6-dimethyl-4-ethyl-1,4-dihydropyridine. Chem Res Toxicol. 1989 Nov-Dec;2(6):400-10. PubMed PMID: 2519730. 7: Rosowsky A, Freisheim JH, Hynes JB, Queener SF, Bartlett M, Smith JW, Lazarus H, Modest EJ. Tricyclic 2,4-diaminopyrimidines with broad antifolate activity and the ability to inhibit Pneumocystis carinii growth in cultured human lung fibroblasts in the presence of leucovorin. Biochem Pharmacol. 1989 Aug 15;38(16):2677-84. PubMed PMID: 2788420. 8: Lee JS, Jacobsen NE, Ortiz de Montellano PR. 4-alkyl radical extrusion in the cytochrome P-450-catalyzed oxidation of 4-alkyl-1,4-dihydropyridines. Biochemistry. 1988 Oct 4;27(20):7703-10. PubMed PMID: 3207701. 9: Chow SA, Rickert DE, Fischer LJ. Evidence that drug metabolites are involved in cyproheptadine-induced loss of pancreatic insulin. J Pharmacol Exp Ther. 1988 Jul;246(1):143-9. PubMed PMID: 3292756. 10: Correia MA, Litman DA, Lunetta JM. Drug-induced modulations of hepatic heme metabolism. Neurological consequences. Ann N Y Acad Sci. 1987;514:248-55. PubMed PMID: 3442388. 11: Serano RD, Sigel CW, Nichol CA, Bigner DD. Evaluation of the lipid-soluble diaminopyrimidines, metoprine and etoprine, in the avian sarcoma virus rat glioma model. Cancer Treat Rep. 1982 Jan;66(1):99-106. PubMed PMID: 6272992. 12: Cavallito JC, Nichol CA, Brenckman WD Jr, Deangelis RL, Stickney DR, Simmons WS, Sigel CW. Lipid-soluble inhibitors of dihydrofolate reductase. I. Kinetics, tissue distribution, and extent of metabolism of pyrimethamine, metoprine, and etoprine in the rat, dog, and man. Drug Metab Dispos. 1978 May-Jun;6(3):329-37. PubMed PMID: 26555. 13: Laszlo J, Fyfe MJ, Swedwick D, Lee L, Brown O. Comparison of metoprine (DDMP) and etoprine (DDEP) by measuring the inhibition of deoxyuridine incorporation into the DNA of human leukemic cells 1,2,3. Cancer Treat Rep. 1978 Mar;62(3):341-4. PubMed PMID: 274177. 14: Nichol CA, Cavallito JC, Woolley JL, Sigel CW. Lipid-soluble diaminopyrimidine inhibitors of dihydrofolate reductase. Cancer Treat Rep. 1977 Jul;61(4):559-64. PubMed PMID: 301777.