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Cycloguanil

Cycloguanil structure

Cycloguanil 

structure
  • CAS No:

    516-21-2

  • Formula:

    C11H14ClN5

  • Chemical Name:

    Cycloguanil

  • Synonyms:

    1,3,5-Triazine-2,4-diamine,1-(4-chlorophenyl)-1,6-dihydro-6,6-dimethyl-;s-Triazine,4,6-diamino-1-(p-chlorophenyl)-1,2-dihydro-2,2-dimethyl-;1-(4-Chlorophenyl)-1,6-dihydro-6,6-dimethyl-1,3,5-triazine-2,4-diamine;Chlorguanide triazine;Cycloguanil;4,6-Diamino-1-(p-chlorophenyl)-1,2-dihydro-2,2-dimethyl-s-triazine;1-(p-Chlorophenyl)-1,2-dihydro-2,2-dimethyl-4,6-diamino-s-triazine;1-(4-Chlorophenyl)-4,6-diamino-1,2-dihydro-2,2-dimethyl-1,3,5-triazine;Cycloguanyl;WR 5473;TCl;Chlorazin;M 10580;D 20;Chlorazine;1-(4-Chlorophenyl)-6,6-dimethyl-1,6-dihydro-1,3,5-triazine-2,4-diamine

Description

Cycloguanil is a triazine in which a 1,6-dihydro-1,3,5-triazine ring is substituted at N-1 by a 4-chlorophenyl group, at C-2 and -4 by amino groups and at C-6 by gem-dimethyl groups. A dihydrofolate reductase inhibitor, it is a metabolite of the antimalarial drug proguanil. It has a role as an EC 1.5.1.3 (dihydrofolate reductase) inhibitor, an antiinfective agent, an antiparasitic agent, an antimalarial, an antiprotozoal drug and an antifolate.|Cycloguanil is the active metabolite of [proguanil].

Cycloguanil Basic Attributes

251.718

251.72

26RM326WVN

DTXSID9022867

2933699090

Characteristics

80

1

1.2332 (rough estimate)

146 °C

400.7ºC at 760mmHg

196.1ºC

Drug Information

Inhibitors of the enzyme, dihydrofolate reductase (TETRAHYDROFOLATE DEHYDROGENASE), which converts dihydrofolate (FH2) to tetrahydrofolate (FH4). They are frequently used in cancer chemotherapy. (From AMA, Drug Evaluations Annual, 1994, p2033) (See all compounds classified as Folic Acid Antagonists.)|Agents used in the treatment of malaria. They are usually classified on the basis of their action against plasmodia at different stages in their life cycle in the human. (From AMA, Drug Evaluations Annual, 1992, p1585) (See all compounds classified as Antimalarials.)

Cycloguanil is a known human metabolite of Proguanil.

1,3,5-triazine-2,4-diamine, 1-(4-chlorophenyl)-1,6-dihydro-6,6-dimethyl-, hydrochloride (1:1)

Cycloguanil Use and Manufacturing

Uses

Antimalarial.

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:251.71
XLogP3:1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:251.0937732
Monoisotopic Mass:251.0937732
Topological Polar Surface Area:80
Heavy Atom Count:17
Complexity:355
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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