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Diabetic complication	5A2Y	Withdrawn from market	[1]
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Therapeutic Class

Hypoglycemic Agents

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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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: CHEBI:8064
CAS Number: 114-86-3
DrugBank ID: DB00914
TTD ID: D07XPE
VARIDT ID: DR00561
INTEDE ID: DR1273

Combinatorial Drugs (CBD)

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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]

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Drug Transporter (DTP)

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

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 2D6 (CYP2D6)_{Main DME}	DECB0K3	CP2D6_HUMAN	Substrate	[7]

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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]
Hypoxia-inducible factor 1-alpha (HIF1A)	OTADSC03	HIF1A_HUMAN	Gene/Protein Processing	[10]
NAD-dependent protein deacetylase sirtuin-1 (SIRT1)	OTAYZMOY	SIR1_HUMAN	Gene/Protein Processing	[10]

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Molecular Interaction Atlas (MIA)

MIA Detail

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.
10	The epigenetic regulation of HIF-1 by SIRT1 in MPP(+) treated SH-SY5Y cells. Biochem Biophys Res Commun. 2016 Feb 5;470(2):453-459. doi: 10.1016/j.bbrc.2016.01.013. Epub 2016 Jan 6.