Cycloguanil

HCID 9049CAS 516-21-2
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Basic information

Standard SMILES
CC1(C)N=C(N)N=C(N)N1c1ccc(Cl)cc1
InChIKey
QMNFFXRFOJIOKZ-UHFFFAOYSA-N
Molecular formula
C11H14ClN5
Average molar mass
251.71 g/mol
Monoisotopic mass
251.09377313

Overview

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 antiinfective agent, an antiparasitic agent, an antiprotozoal drug, an antimalarial, an EC 1.5.1.3 (dihydrofolate reductase) inhibitor and an antifolate.

Names & identifiers

Preferred name
Cycloguanil
IUPAC
1-(4-chlorophenyl)-6,6-dimethyl-1,3,5-triazine-2,4-diamine
English name
Cycloguanil
Molecular formula
C11H14ClN5
Molecular weight
251.72

Names & synonyms

Cycloguanil516-21-2CycloguanylChlorguanide triazine1-(4-chlorophenyl)-6,6-dimethyl-1,6-dihydro-1,3,5-triazine-2,4-diamineWR 54731-(4-chlorophenyl)-6,6-dimethyl-1,3,5-triazine-2,4-diamineBN241026RM326WVN1-(p-Chlorophenyl)-4,6-diamino-2,2-dimethyl-1,2-dihydro-s-triazineDTXSID9022867CHEBI:135029
Show more names
WR-5473ChlorazinAids007020Aids-007020Cycloguanil-d6Cycloguanil HClCYCLOCHLOROGUANIDE
cycloquanilRefChem:129488DTXCID4028671-(4-chlorophenyl)-1,6-dihydro-6,6-dimethyl-1,2,5-triazine-2,4-diamineChlorcycloguanilCHEMBL7471-(4-Chlorophenyl)-1,6-dihydro-6,6-dimethyl-1,3,5-triazine-2,4-diamineCYCLOGUANIL [WHO-DD]

Database identifiers

CAS
516-21-2
PubChem CID
9049
DTXSID
DTXSID9022867
ChEMBL
CHEMBL747、CHEMBL92583
ChEBI
CHEBI:135029
UNII
26RM326WVN
Nikkaji
J6.306A

Properties

Computed structural properties

XLogP
1
Topological polar surface area
80 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
1
Rotatable bonds
1
Heavy atoms
17

Experimental & physicochemical properties

DrugsPharmaceuticals -> Metabolite of Proguanil

Physicochemical properties

Melting point
146 ° · 146°
Boiling point
397.13 °C · 397.13°C (rough estimate)
Density
1.2332 · 1.2332 (rough estimate)
refractive index
1.611 · 1.6110 (estimate)
storage temp.
-20 °C · Store at -20°C
solubility
Soluble in DMSO

Safety & regulation

Safety data

Signal word
Warning
Symbol(GHS)
GHS07
Hazard statements
H315-H319
Precautionary statements
P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Chemistry & industry

Pharmacology

Metabolism/MetabolitesCycloguanil is a known human metabolite of Proguanil.
MeSH Pharmacological Classification · 2 items

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)

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)

Tissue LocationsKidney
Cellular LocationsCytoplasm

Applications

UsesAntimalarial.

Suppliers22 total

上海毕得医药科技股份有限公司400-1647117 13681763483 · [email protected]
陕西缔都化学有限公司029-029-81123119 17391733320 · [email protected]
玺标（上海）科技有限公司18512111473 18512111473 · [email protected]
梯尔希（南京）药物研发有限公司18012923235 · [email protected]
上海一研生物科技有限公司021-69985186 13611928337 · [email protected]
Additional notes · 1 item

DefinitionChEBI: 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.

Related reactions

2 records
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Linked notes

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