Details of the Drug

General Information of Drug (ID: DMQ52JG)

Drug Name
Phenformin
Synonyms
Azucaps; Cronoformin; DBI; Debeone; Debinyl; Diabis; Dibein; Dibiraf; Dibotin; Dipar; Feguanide; Fenfoduron; Fenformin; Fenformina; Fenormin; Glukopostin; Glyphen; Insoral; Lentobetic; Meltrol; Normoglucina; Pedg; Phenethyldiguanide; Phenformine; Phenforminum; Phenformix; Phenylethylbiguanide; Retardo; D Bretard; DB Comb; DBI monohydrochloride; Phenformine HCl; Phenoformine hydrochloride; W 32; Beta-PEBG; Beta-Phenethybiguanide; Beta-Phenethylbiguanide; Db-retard; Debeone (TN); Fenformina [INN-Spanish]; Meltrol-50; N-Phenethylbiguanide hydrochloride; Phenformin (BAN); Phenformin [INN:BAN]; Phenformine [INN-French]; Phenforminum [INN-Latin]; N'-beta-Fenetilformamidiniliminourea; N'-beta-Fenetilformamidiniliminourea [Italian]; N'-beta-Phenethylformamidinylliminourea; N-(2-Phenylethyl)imidodicarbonimidic diamide; PHENFORMIN (SEE ALSO PHENFORMIN HYDROCHLORIDE 834-28-6); 1-(diaminomethylidene)-2-phenethylguanidine; 1-Phenethylbiguanide
Indication
Disease Entry ICD 11 Status REF
Diabetic complication 5A2Y Withdrawn from market [1]
Therapeutic Class
Hypoglycemic Agents
Affected Organisms
Humans and other mammals
ATC Code
A10BA01: Phenformin
A10BA: Biguanides
A10B: BLOOD GLUCOSE LOWERING DRUGS, EXCL. INSULINS
A10: DRUGS USED IN DIABETES
A: ALIMENTARY TRACT AND METABOLISM
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 205.26
Logarithm of the Partition Coefficient (xlogp) -0.8
Rotatable Bond Count (rotbonds) 4
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 1
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [2]
Bioavailability
55% of drug becomes completely available to its intended biological destination(s) [3]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 8.13584 micromolar/kg/day [4]
Chemical Identifiers
Formula
C10H15N5
IUPAC Name
1-(diaminomethylidene)-2-(2-phenylethyl)guanidine
Canonical SMILES
C1=CC=C(C=C1)CCN=C(N)N=C(N)N
InChI
InChI=1S/C10H15N5/c11-9(12)15-10(13)14-7-6-8-4-2-1-3-5-8/h1-5H,6-7H2,(H6,11,12,13,14,15)
InChIKey
ICFJFFQQTFMIBG-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
8249
ChEBI ID
CHEMBL170988
CAS Number
114-86-3
UNII
DD5K7529CE
DrugBank ID
DB00914
TTD ID
D07XPE
VARIDT ID
DR00561
INTEDE ID
DR1273
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
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Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
AMP-activated protein kinase (AMPK) TTLAFZV AAPK1_HUMAN ; AAKB1_HUMAN ; AAKG1_HUMAN Activator [5]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Organic cation transporter 1 (SLC22A1) DTT79CX S22A1_HUMAN Substrate [6]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 2D6 (CYP2D6)
Main DME 		DECB0K3 CP2D6_HUMAN Substrate [7]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Antithrombin-III (SERPINC1) OTDFATG0 ANT3_HUMAN Gene/Protein Processing [8]
Cyclin-dependent kinase inhibitor 1 (CDKN1A) OTQWHCZE CDN1A_HUMAN Gene/Protein Processing [9]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Drug information of Phenformin, 2008. eduDrugs.
2 BDDCS predictions, self-correcting aspects of BDDCS assignments, BDDCS assignment corrections, and classification for more than 175 additional drugs
3 Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
4 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
5 Complementary regulation of TBC1D1 and AS160 by growth factors, insulin and AMPK activators. Biochem J. 2008 Jan 15;409(2):449-59.
6 Identification of novel substrates and structure-activity relationship of cellular uptake mediated by human organic cation transporters 1 and 2. J Med Chem. 2013 Sep 26;56(18):7232-42.
7 Neuronal cytochrome P450IID1 (debrisoquine/sparteine-type): potent inhibition of activity by (-)-cocaine and nucleotide sequence identity to human hepatic P450 gene CYP2D6. Mol Pharmacol. 1991 Jul;40(1):63-8.
8 Sulfenamide and sulfonamide derivatives of metformin can exert anticoagulant and profibrinolytic properties. Chem Biol Interact. 2018 Mar 25;284:126-136. doi: 10.1016/j.cbi.2018.02.012. Epub 2018 Feb 16.
9 Effects of phenformin on the proliferation of human tumor cell lines. Life Sci. 2003 Dec 19;74(5):643-50. doi: 10.1016/j.lfs.2003.07.015.