Proguanil

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Proguanil are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Proguanil?

The molecule Proguanil presents a molecular formula of C11H16ClN5 and its IUPAC name is (1E)-1-[amino-(4-chloroanilino)methylidene]-2-propan-2-ylguanidine.

Proguanil, also known as chlorguanide and chlorproguanil, is a medication used to treat and prevent malaria. It is often used together with other antimalarial medications such as chloroquine or artemisinin. Proguanil is typically taken by mouth..

Common side effects include abdominal pain, diarrhea, headache, and nausea. Serious side effects may include allergic reactions and Stevens-Johnson syndrome. Use in pregnancy appears to be safe for the baby. Proguanil is in the biguanide class of medications. It works by interfering with the metabolism of folate in the parasite..

Proguanil was first made in 1945 and came into medical use in 1949. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. The wholesale cost in the developing world is about US$0.04 to 1.60 per day. In the United States it costs between 25 and 50 USD per course as of 2015..

3D structure

Cartesian coordinates

Geometry of Proguanil in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Proguanil SSOLNOMRVKKSON-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Proguanil

 

Molecule descriptors

 
IUPAC name(1E)-1-[amino-(4-chloroanilino)methylidene]-2-propan-2-ylguanidine
InChI codeInChI=1S/C11H16ClN5/c1-7(2)15-10(13)17-11(14)16-9-5-3-8(12)4-6-9/h3-7H,1-2H3,(H5,13,14,15,16,17)
InChI KeySSOLNOMRVKKSON-UHFFFAOYSA-N
SMILESCC(C)NC(=N)N/C(N)=N\c1ccc(Cl)cc1

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (4-chlorphenyl)-5-isopropylbiguanid
  • (hydrochloride)
  • 1-(4-Chlorophenyl)-3-(N-isopropylcarbamimidoyl)guanidine
  • 1-(4-chlorophenyl)-5-isopropylbiguanide;N1-(4-Chlorophenyl)-N5-isopropylbiguanide
  • 1-(p-Chlorophenyl)-5-isopropylbiguanide
  • 1-Isopropyl-5-(4-chlorophenyl)biguanide
  • 500-92-5
  • A901482
  • AB00053776
  • AB00053776_05
  • BDBM50227829
  • BIDD:GT0576
  • BIGUANIDE, 1-(p-CHLOROPHENYL)-5-ISOPROPYL-
  • BPBio1_001207
  • BRN 2811599
  • BSPBio_001097
  • BSPBio_003417
  • Bigumal
  • C07631
  • CS-12345
  • CS-6234
  • Chlorguanid
  • Chlorguanide
  • Chloroguanide
  • D08428
  • DB01131
  • Diguanyl (hydrochloride)
  • DivK1c_006763
  • Drinupal (hydrochloride)
  • HY-B0806
  • Imidodicarbonimidic diamide, N-(4-chlorophenyl)-N'-(1-methylethyl)-
  • KBio1_001707
  • KBio2_002068
  • KBio2_004636
  • KBio2_007204
  • KBio3_002637
  • KBioGR_001204
  • KBioSS_002068
  • M-4888 (hydrochloride)
  • MFCD00866201
  • N'-4-chlorophenyl-n5-isopropylbiguanide
  • N-(4-Chlorophenyl)-N'-(1-methylethyl)imidodicarbonimidic diamide
  • N-(4-Chlorophenyl)-N'-(isopropyl)-imidodicarbonimidic diamide
  • N-(4-chlorophenyl)-N'-(propan-2-yl)imidodicarbonimidic diamide
  • N1-(4-Chlorophenyl)-N5-isopropylbiguanide
  • N1-p-Chlorophenyl-N5-isopropylbiguanide
  • NCGC00016528-01
  • NCGC00016528-02
  • NCGC00016528-03
  • NSC12977
  • Paludrin
  • Paludrine
  • Paludrine (hydrochloride)
  • Palusil (hydrochloride)
  • Prestwick0_000999
  • Prestwick1_000999
  • Prestwick2_000999
  • Prestwick3_000999
  • Proguanil
  • Proguanil (INN)
  • Proguanile
  • Proguanilum
  • S61K3P7B2V
  • SBI-0052839.P002
  • SN-12837 (hydrochloride)
  • SpecPlus_000667
  • Tirian (hydrochloride)
  • proguanil
  • s5927

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • CAS-637-32-1
  • UNII-S61K3P7B2V
  • BRD-K28183345-003-05-6
  • BRD-K28183345-003-07-2
  • DTXSID3022794
  • CHEMBL1377
  • CHEBI:8455
  • EINECS 207-915-6
  • SPBio_001029
  • SPBio_002988
  • SCHEMBL45726
  • SCHEMBL16894670
  • SCHEMBL17300525
  • Spectrum_001588
  • Spectrum2_001135
  • Spectrum3_001659
  • Spectrum4_000622
  • Spectrum5_001384

Physico-Chemical properties

IUPAC name(1E)-1-[amino-(4-chloroanilino)methylidene]-2-propan-2-ylguanidine
Molecular formulaC11H16ClN5
Molecular weight253.731
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity71.79
LogP3.4
Topological polar surface area86.3

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.